Pod Insights The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch 20Sales: Sierra: Inside Silicon Valley's Fastest Growing Sales Machine & How to Prospect, Outbound and Close Enterprise Deals in AI About this episode Reggie Marable is the Head of Global Sales at Sierra, a conversational AI platform for businesses. Sierra enables companies like ADT, Sonos, SiriusXM, and WeightWatchers to build AI agents that transform customer experiences. The company has rapidly become a hypergrowth leader in Silicon Valley, recently securing a funding round that values it at $4.5 billion. Before joining Sierra, Reggie was the Head of Sales in North America at Slack and the Area Vice President of Enterprise Sales at Salesforce. In Today’s Episode We Discuss: 02:50 “What I Learned from Failing Early as a CRO” 06:06 The Most Effective Sales Strategy and the BS Sales Methodology 06:55 How to Build Sales Processes from Scratch 12:28 When and How to do Verticalised Sales Teams 14:15 How to Become World Class as Sales Prospecting and Outbound 17:21 How to Use Proof of Concepts to Win Enterprise Deals 22:04 Enterprise vs. Self-Serve: Both or One and How 30:09 Building a Sales Team from Scratch 37:39 Structuring the Hiring Process 41:14 How Founders F*** Up Hiring in Sales 46:25 Handling Salary and Title Expectations 51:36 How to Run Effective Deal Cycles 57:06:07 How to do Onboarding for New Sales Hires 59:07:48 How to do Post Mortems in Sales Processes 01:04:24 Negotiating Enterprise Deals 01:08:04 Quick Fire Round: Sales Tactics and Strategies
Transcript 14,331 words · 2 speakers
Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.
0:00 Harry Stebbings? This is 20 Sales with me, Harry Stebbings. 20 Sales is the monthly show where I sit down with one of the best sales leaders to show you what truly great looks like and how the best sales teams work. Today, we have one of the best, Head of Global Sales for one of the fastest growing AI companies in the world, Sierra, founded by Brett Taylor and funded by Benchmark and Greeno's. Yes, I'm thrilled to welcome Reggie Marable. Now, before Sierra, Reggie was the Head of Sales in North America at Slack and Area Vice President of Enterprise Sales at Salesforce. But before we dive into the show today, if you're ready to leave rigid payment terms behind, Capchase is here to change the game. Capchase brings B2C buying convenience to B2B software and hardware purchases. Capchase offers your buyers the flexibility they demand on annual
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2:10 Harry Stebbings? Doesn't close deals. So Gong captures every customer interaction and gives you real time insights. So you can drive predictable growth. With Gong, you can power all your critical revenue workflows from prospecting to renewal on one AI platform. That's why go to market teams at LinkedIn, Snowflake, ADP, NASDAQ, Shopify, such incredible companies and thousands of others trust Gong. Masterclass even used it to assess and prioritize key areas of their sales pitch, ultimately leading to a forty four percent increase in win rates. Get started today at gong.io and unify your data, workflows and teams with AI to win more. You have now arrived at your destination. Reggie, I'm so looking forward to this, dude. I heard so many good things. I literally just got off a call with Frank Filmon.
2:56 Harry Stebbings? I spoke to many of the team from Slack and Salesforce. So thank you for joining me.
3:00 Speaker 01 It's an honor to be here. I've had admiration on the show. This is like a bucket list moment for me. There's been several of my mentors and heroes like Larry Shirts, Frank Filmon, AKA Frank Philly, Danny Hertzberg, Zach Lorick, Kevin Egan. So it's an honor to be here, especially we're doing it live in London. So.
3:17 Harry Stebbings? You said Filmon there. Filmon said that we should start with, you know, I always start with context and kind of a little bit of history. But Filmon said that we should start with the first attempt at leadership. And he said, actually, your first attempt at leadership was challenging and had ups and downs. And he said that that would be an interesting place to start and dig in on some lessons from that. Can we start there?
3:36 Speaker 01 Let's do it. So hopefully I won't, I won't like get emotional, but most of my career was in the telecom industry. I worked for Sprint and I started in customer service, worked my way all the way up to the sales organization. I was running their international wholesale business, big job, global experience. I left Sprint to be a CRO of a midsize media company that was trying to go all digital. And at the time, Harry, I was the smartest guy in the room. I had a big ego. I alienated people there that could help me because it was all about my career, my results. After a year, that's just a bad way to lead. I got fired. So this was maybe eight years ago. So I was unemployed for six months and part of the time I was a bartender.
4:15 Harry Stebbings? When you get fired and when you have a really hard moment like that, how do you mentally? Respond. What were you thinking when you left that office?
4:23 Speaker 01 Quite frankly, I broke down. I was in tears. I never failed in anything before. That was the first time I failed. But really, I did a lot of self-reflection on what true leadership is. Listening skills are really important. So I had to reinvent myself. And then I had a friend, his name was Ryan Radding. He's a senior executive at Salesforce. And at the time, he was the second line sales leader. And he was like, dude, you should come over to Salesforce. You know, the product, you would do really well here, but no one's going to hire you as a senior leader. You're going to have to come in and kind of prove yourself. So I had to swallow my pride. And I came into Salesforce eight years ago as a first line sales leader, all the way from a CRO to a first line sales leader. But this time, I came in with humility, with respect, listening, putting people first.
5:06 Speaker 01 And my career at Salesforce really flourished because I reinvented myself based on failing as a CRO with a big ego.
5:12 Harry Stebbings? So what did you change most significantly? You listen, you get down in the trenches. What did you change when you reflect back on that CRO to now first line sales at Salesforce?
5:24 Speaker 01 That's a great question. This is the last time I'm going to get a shot to reinvent myself at this stage of my career. So I had to do it right. And I love this quote from the great Dr. Cam with the Morehouse College. So Martin Luther King Jr. is one of my heroes. And he says, life's most persistent and urgent question is, what are you doing for others? And I kept that quote in front of me at all times. It was a reminder of putting people first, listening. And that's how you're going to be successful, especially in leadership.
5:49 Harry Stebbings? We go to Salesforce, a lot of expectation and pressure on us because as you said, that kind of, you don't get another shot at this also. And so you've got that moment. When you look back, what are your biggest takeaways on how Salesforce as an organization? Impacted how you think about what great sales and sales leadership is?
6:06 Speaker 01 Salesforce is one of the greatest companies in the world.
6:10 Harry Stebbings? What did you not take from Salesforce? And what I mean by that is, when you think about your role with Sierra State, what did you see at Salesforce and deliberately decide to not bring with you to your leadership at Sierra?
6:21 Speaker 01 I learned the hard way that coming to a new company with a playbook doesn't work. When I left, well, not left, but because Salesforce is in Slack. Or the same company. But when I went to Slack, what I didn't do is just take the Salesforce playbook and try to implement that at Slack. I went in and listened and learned, understood what made them successful. And then I figured out what could I take from my Salesforce experience to help enable Slack? Same thing when I, when I joined Sierra, which by the way, when I joined Sierra, I was employee number 23 last year. There was no sales team. I couldn't come in with the Salesforce playbook or the Slack playbook. I had to come in and figure out what was going to make Sierra successful. And I just took collections of my different experiences at Salesforce Slack and other companies. And that's kind of what we created at Sierra.
7:05 Harry Stebbings? Can I ask you a hard question, which is if every playbook, it needs to be different. It needs to change with each company. When you think about what you were inheriting at that point, was there a playbook? Was there a clear motion of what worked and what didn't?
7:17 Speaker 01 Yes and no. So I consider Brett, one of the, I call him the apex predator. He's one of the best salespeople I've ever been around.
7:25 Harry Stebbings? Why? What makes him so good at sales?
7:26 Speaker 01 Brett has the ability to articulate and connect the technology to actual business. And he makes it simple for people to understand and follow. And he's a great storyteller. They had a pretty strong process because we had design customers, a proof of concept, selling motion. So there were some things in place. But what I was able to do with our leadership team was take that to the next level and really define our sales process. And huge shout out to my sales methodologies like medic and the challenger sale. We've taken all of that. We call ours peer and that is partnerships, use case, ROI, and then I love this one, event comma compelling. So we've kind of elevated what we've learned at different experiences and created a new sales process, which we're executing.
8:08 Harry Stebbings? If we think about the partnership element, can we just break that one down? What does good look like in that realm?
8:13 Speaker 01 Partnership is, is really just mapping out your executive alignment. Who's the executive sponsor? Who's your champion? What executives of Sierra are getting involved in your deal cycle? So things of that nature is just figuring out like, what is your strategy to go deep and wide and build relationships across this account?
8:31 Harry Stebbings? How do you multi-thread effectively? I always find, you know, I'm a fundraiser, you know, for my firm. And it's very difficult to multi-thread without sounding like you're multi-threading because like, oh. I'd love to meet some of your team. So if you sod off, then I'm not screwed, basically. How do you do that effectively?
8:45 Speaker 01 It's a total team effort. It can't just be the account executive. It has to be leadership. It has to be folks from the technology team. So multi-threading is a team sport and everyone gets involved. That's kind of how I look at it.
8:57 Harry Stebbings? Okay, totally get you there. How do you know if someone actually is the buyer? A lot of people will pontificate and say that they have budget or say that they're the buyer. How do you know if they're actually the one who can spend the money?
9:08 Speaker 01 Great question. We've been very fortunate. We usually start in the C-suite. And then throughout the sales process, we'll identify who the champion is, who's the technology decision maker, who's the business decision maker, who owns the budget. I think just having intellectual curiosity, well, it definitely during the pandemic. During the pandemic, the CFO or the financial leader became the decision maker for all deals.
9:30 Harry Stebbings? And that became harder?
9:32 Speaker 01 Yeah, it became harder, but it forced you to really tighten up your craftsmanship. Make sure you had a powerful ROI. You had business value. You were actually solving a real problem. Because no projects during the pandemic were getting approved. If you weren't solving a problem, you weren't delivering results or you weren't delivering an ROI. So it forced really strong sellers to tighten their game up and really focus on craftsmanship.
9:54 Harry Stebbings? In the sales process, are you able to get access to their data? To show them the power, it's almost like a demo where you want to show them how great it could be. But they're not just going to give you access to their data pre-signing and pre-being a customer. How do you think about showing the value before actually being a vendor to them?
10:11 Speaker 01 One of the things that we do with Sierra is we do a proof of concept. It's a paid proof of concept and what that allows us to do is to partner with our clients, identify three or four journeys. Some very complex, so you can put us through our paces, some high volume and some easy. And then we will go build an agent and put that agent into live production in a proof of concept. So our clients can see the technology in action. And they can also get a feel for what it's like to partner with Sierra. Throughout that process, we also absorb all the integration work, all the implementation work. So it's low risk for our potential clients to test out Sierra and make sure the technology is going to work.
10:48 Harry Stebbings? And so that's kind of like a break. Even land. Is that kind of how you think about it? Like a break even trial for you?
10:54 Speaker 01 Well, yeah. Well, actually, the investment that you make in the proof of concept becomes a credit towards your long term contract. So it's not throwaway money, but also we deliver what you invest in the P O C. You'll get that back based on the the value that we're going to deliver in the containment rates and the resolution rates throughout the proof of concept.
11:11 Harry Stebbings? Has anyone ever not converted post P O C and why?
11:15 Speaker 01 I will knock on wood. Right now we're batting a thousand on our proof of concepts.
11:19 Harry Stebbings? Thank God. That would have been awkward. Okay, so we have that as a use case and use case articulation there. How do you advise founders when it is quite horizontal? And what I mean by that is, you know, you serve a wide variety of different customers. And so it's not like, hey, we sell to the insurance industry. Resolution rates for financial fraud in car insurance is quite broad. How do you think about like product marketing or selling effectively crafting that message? When it could be anything to anyone?
11:49 Speaker 01 Yeah, we're we're laser focused on seven key industries. Financial services, healthcare, telecoms, retail, media, consumer technology, and then travel tourism. Hospitality, if you think about it.
12:02 Harry Stebbings? That's a lot, right?
12:03 Speaker 01 When you interact with the brand, you need to call your financial services company. Healthcare, you need to talk to your doctor or your insurance company. So if you go down the list of where you live, work and play. That's where Sierra wants to be. That's where we can enable and power.
12:16 Harry Stebbings? But that's very horizontal. That's like, that's very broad. That's everyone from your bank to your radio station.
12:21 Speaker 01 But if you dig into each of those industries. We know exactly what the problems are and how our technology can help our clients solve these problems.
12:28 Harry Stebbings? That's really, I love verticalized sales teams because I think that domain knowledge is so powerful in messaging and conversion and speaking the language of the customer. Do you like verticalized sales teams and do you have them?
12:39 Speaker 01 So I believe that if you're verticalized, you understand the industry trends. You understand the different personas and what they care about and what they're interested in and how you can help. And all of your messaging is crafted toward that particular industry. So you can speak the client's language. You understand the industry. So you can really add more value. So I'm a big believer in verticalization.
12:58 Harry Stebbings? When do you think it's the right? Right time and should that be from day one or should it be post ten million ARR? How do you think about that?
13:06 Speaker 01 Most companies wait until they get more scale and more maturity. At Sierra, we made the decision to do it early because we know those are the industries where we can make the most impact. And we really want to show up right in those industries by understanding the trends and being able to speak the language. So we made the decision to do it very early in our journey.
13:22 Harry Stebbings? Are the sales cycles what you expected them to be when you joined?
13:26 Speaker 01 Well, yes and no. I mean, on average, because we're focused on the enterprise.
13:30 Harry Stebbings? Yeah. What is a sales cycle?
13:32 Speaker 01 Enterprise software, it's anywhere from, depending on the complexity of the client, what you're selling, anywhere from six months to two years.
13:38 Harry Stebbings? Wow.
13:39 Speaker 01 Yeah, it just in traditional software, but.
13:41 Harry Stebbings? But for you, it's not that.
13:42 Speaker 01 It's a little under a year.
13:43 Harry Stebbings? Yeah.
13:44 Speaker 01 Because we are doing a proof of concept, which you've got to deploy the technology, build trust. It's AI, so you have to go through the legal compliance, governance reviews. So it's about eight months from first meeting to actually closing a deal. I think that could get longer or more compressed depending on the complexity of the clients that you work with.
14:03 Harry Stebbings? I think brand can often help really reduce that. When you have customer validity, social validity and that brand drives an increased velocity, I think it can help. When you look now, what percent of customers net are inbound versus outbound?
14:17 Speaker 01 We are a enterprise driven sale, so we have a very aggressive, talented sales team that does a lot of outbound prospecting. I still prospect as the head of sales.
14:26 Harry Stebbings? You still prospect?
14:27 Speaker 01 I still prospect every single day, our co-founders prospect, so.
14:31 Harry Stebbings? So you will like cold message on LinkedIn, cold email?
14:34 Speaker 01 I will do whatever it takes to generate interest and help build our company.
14:37 Harry Stebbings? Do you think many heads of sales and people in your position with your experience still do?
14:41 Speaker 01 I can't speak for other heads of sales, but I know I will take out the trash and wash the dishes if it helps Sierra be successful. So I'm willing to do whatever it takes, which means I prospect. I still run deals, I still code call, I still put dishes in the dishwasher, whatever it takes, man.
14:56 Harry Stebbings? Do you think it has a higher hit rate when the founders or the heads of sale does it versus A's and BDRs and you name it?
15:02 Speaker 01 I think so, but I also think it comes down to messaging and timing. If you have a relevant message, I think that captures people's. Attention. I think everyone is trying to figure out AI, how to put AI to work and how to use AI to solve problems and reduce costs. So I think our message is resonating, but it's very competitive and it's hard. If you're consistent with it, you know, we now have customer stories. We had a lot of very successful customer stories, so we can lean into that as well. But at the end of the day, you have to be the one to initiate the conversation. And I think that's why I'm aggressive and I'm making cold calls and prospecting myself.
15:36 Harry Stebbings? I love that in terms of the willingness to take the trash out. It's a great quote, by the way. When you think about relevant messaging, it's really hard. I mean, outbound today is harder than ever, but there is infinite supply of providers that will, you know, write the message for you and everything in between. How do you think about what it takes to send the right, relevant message today and making it resonate with that reader the first time they consume it?
15:58 Speaker 01 I think it goes back down to craftsmanship and researching who you're targeting. And then if it's an industry relevant message, making sure that it's short, sweet, straight to the point and impactful. And I think if it's short, sweet, straight to the point impactful, people will pick it up and read it. I'm very fortunate. I've got, we have a very strong marketing team. Shout out to Ally Johnson and Emily Vince who've really helped us with our industry messaging. But I think if the, once again, if it's short, sweet, straight to the point and it's impactful, I like to think people would respond.
16:28 Harry Stebbings? Do you know what I think is also amazing is the lack of attention or awareness that people show to consistent engagement. And what I mean by that is you post, I don't know, 10 times a month on LinkedIn, just say. And actually me putting up awesome, want to see this Reggie, thumbs up in the next one. Or I love this post, such a great one, sending to my team. And you as the author will consistently see that across seven to 10 posts. And then when I send you a LinkedIn message a month later, you're like, I know this guy. He's the one that keeps on connecting with my posts. Do you know what I mean?
17:01 Speaker 01 Absolutely.
17:02 Harry Stebbings? I find that so, so important. So when we think about that, you do then outbound and we have like first calls. How do we think about progression through funnel? Because the thing that worries me is this really kind of difficult moment of handoff. When you get to the P O C and it's like, and now I'm gone. How do you do handoff effectively between the sales team and then the inevitable C S integrations implementations?
17:25 Speaker 01 So we have what we call a forward deployed engineering model. So in all of our engagements, we don't just get you in a POC and walk away. It's a full service solution where we provide a dedicated agent product manager. Think of like ex-Google MBA from Stanford and then a dedicated agent engineer that's integrated. It becomes part of your team.
17:46 Harry Stebbings? Do they actually like become part of your team?
17:47 Speaker 01 Absolutely. They become part of the team. They're integrated with your IT, your technology, and then your business team to understand what are the goals you want to accomplish with the proof of concept? What are the journeys we need to build? What are the systems we need to integrate with? We have a weekly meeting. We have a Slack channel. We're constantly collaborating because once we put the agent in production, we want the agent to improve over time. So we're coaching the agent to improve, get better, and then we're adding on more use cases. So you've got to be deeply integrated with the team and your client and partner with them.
18:18 Harry Stebbings? I love that in terms of like, I mean, having the internal messenger for you is so powerful. How do you think about having a really tight feedback loop and communication with the fully deployed engineer when you are a sales team that could really benefit from the information that they give you and have?
18:35 Speaker 01 Well, the sales team and the agent engineer and the agent PM, they're all one team. They're all integrated. They collaborate. They're always talking. They're always communicating. Once again, we're collaborating with our clients through Slack. We actually have a what's called an experience manager. It's a platform that they can go in and give us feedback. They can coach the agent themselves. They can do self-serve. But we're collaborating in that platform. We're collaborating on Slack. We have a weekly touch point. So we're constantly getting feedback from our clients and we're implementing that.
19:02 Harry Stebbings? Can I ask, how do FDEs, what's the relationship between them and customer success? Because if you think about them building, learning the solutions and in the construction phase, so to speak, how do you think about who's driving engagement? Who's driving usage? Who's driving activity within the team? And how does CS relate to FDEs?
19:22 Speaker 01 The key person on that account team is the agent product manager. They're a project manager. They're a product manager. They're also technical, but they're kind of running the show in partnership with the sales professional. And also the agent engineer, they're coordinating, they're kind of leading and they're partnering with the client. So they're kind of the face of the engagement. And these are some, some of our like super, super sharp people that we've been able to attract to work at Sierra. Some of these are going to be, you know, the next wave of Brett Taylors are going to be some of these agent product managers.
19:52 Harry Stebbings? How important is time to value? Once you're in these P O Cs and you've got your fully deployed engineers in these organizations, how important is it to be showing to the customer, hey, here's the ROI, I'm driving value, I'm driving value versus being a little bit slower?
20:07 Speaker 01 It's important because people are investing time. They have a little skin in the game, but we're taking on a lot of risk by doing these proof of concepts. So we are highly incented to deliver immediate value. Not only value with the technology working, resolving cases, high C sat scores, solving problems, but also being responsive and building trust with the client that we can actually take on this engagement and handle it. So it's critically important because we are proving our value in that proof of concept. And if we don't execute that, we don't deliver value, there's no incentive for them to continue partnering with us.
20:38 Harry Stebbings? Do you agree what the larger enterprise contract will be pre P O C? In other words, when you sign the P O C, do you say if we hit X goals, we will sign Y contract?
20:50 Speaker 01 No, it's somewhat fluid. I mean, we have, I think the client in our team, we have an idea of what the potential could be. But in order for us to even get to the potential, talk about the potential, we need to execute in the proof of concept based on the journeys that we're going to build and the results that they want to see. But we do have somewhat of an idea of kind of potentially where this could be. And our vision is to be the front door of their experience, be their concierge, put their best sales professional, their best customer service agent in front of their customers 24 seven. But we've got to earn our right to be able to, to be the front door of the experience by executing in the proof of concept.
21:24 Harry Stebbings? Can I ask, with the commoditization of software, with software increasing in terms of its abilities and ease of implementation and integration, over time, do you lose the fully deployed engineer and it become a much less bluntly cumbersome integration for clients?
21:39 Speaker 01 We're actually partnering with clients with different levels of the white glove service. Some of our customers want us to take on On everything, full white glove. Some, they want us to give us the keys to the car. They want to, we certify their engineers to build and develop on our platform. And then there's also self-serve. They want to do it themselves. So we've got different flavors of the model. And I think that will continue to evolve over time. As customers want to take on more or they want us to be the full, you know, one stop shop.
22:04 Harry Stebbings? I always have founders ask the question that you mentioned the word self-serve. And then obviously enterprise is kind of really the bread and butter. I always have founders ask me, Harry, can I do self-serve PLG and enterprise at the same time? Or are they two fundamentally opposing motions to running in collaboration? How would you advise an early stage founder who's debating that?
22:24 Speaker 01 I'm not a technologist and this is my first time in a startup. But in my humble opinion, I would say you would need to focus on one or the other. In my humble opinion, right now, we are purely focused on the enterprise. Working with the biggest brands of the world. And I think you have to have that hands-on service versus self-serve, which is more downstream. I think over time, we'll probably get there with the evolution of our platform. But right now, we're focused on working with the largest brands in the world.
22:49 Harry Stebbings? And you have outcome-based pricing, which is a very different structure of pricing to traditional SaaS, which has always been seat-based pricing. Now, I always worry that when you are introducing something new, it is uncertain and people need educating. How has the process been in terms of introducing really a relatively new pricing mechanism to traditional enterprise customers who aren't used to it?
23:12 Speaker 01 This is the most fun I've had as a sales leader in my entire career. Because I'm selling a business model that people get immediately. They no longer have to pay for the right to use software. They don't pay for seats, they don't pay for consumption, they pay for outcomes. Did our agent solve a problem? Did our agent convert a sale? Did it make the right product recommendation? If so, we get paid. And oh, by the way, it's a fraction of what you're paying human beings to do this work. So people get it. We don't charge implementation fees or any integration work. We absorb all of that. So when you partner with Sierra, you're paying for outcomes, you're paying for results. And it's just a fun model that people get and it's fun to be in the space. And we're creating a brand new category of software and the way we price it and the way people consume it. It's really fun.
23:55 Harry Stebbings? It's so funny. When I was young, you you watched kind of trash TV and they would have adverts for like lawyers for car crashes or whatever insurance stuff. And they would be like, no win, no fee. And you're like, well, great. Like, and that's like win and get money. Like, I'm not paying you. And it's like the most obvious win win for the customers.
24:15 Speaker 01 Exactly. The software today, the power of this technology, it actually delivers results. So you actually can pay for the results that you receive.
24:22 Harry Stebbings? Is there a challenge in terms of contention around attribution? And what I mean by that is, say, you prevent a churn of a customer. And then one of the CS reps actually goes, well, not really. I actually went for dinner with Reggie last night and I saved the deal. It wasn't really Sierra doing that work. It was me going for dinner with them on a Saturday evening to reassure them. How do you think about ambiguity in resolution?
24:47 Speaker 01 It's fairly simple. I mean, it's a fairly simple definition that it's possibly different for each client, but we partner with our clients of what the definition of a resolution is. And then how we measure it. And we get alignment with our clients. So we're both fully aligned when we go into a long term contract.
25:02 Harry Stebbings? How do you think about the volume of resolutions? In other words, we're 90% of resolutions or 85%, whatever it is, versus we solve the really, really difficult ones.
25:13 Speaker 01 Our vision for all of our clients is to be the front door and the concierge of their experience. So we can handle the easy stuff, but we can also, where we really, really thrive and and shine and excel is the really complex things. Like, for example, if you're a Sonos customer and your Sonos system stops working, our agent is sophisticated enough to figure out, is it your Wi-Fi? Is it the software on the speaker or is it the hardware? So it's got the ability to handle that kind of complexity. If you're a serious XM customer, not only can we tell you what station Shade 45 hip hop music is playing on, but we can also, if your radio stops working in your car, our agent will call the satellite and resend the encryption keys back to your car to get your satellite radio working.
25:55 Speaker 01 So this technology, it can handle very, very sophisticated things. So our job, our goal is to put, once again, your best sales rep, your best customer service agent in front of your customers 24
26:05 Harry Stebbings? And so that take then on outcome based ticketing pricing, whatever we want to call it, it must differ dramatically because different customers are worth different amounts in different fields. A financial services customer is worth a lot versus in maybe media, they're worth less if they churn. How do you think about how your take varies by sector?
26:24 Speaker 01 It depends on what the client wants to accomplish, what use cases they want us to handle. We can customize our outcome based pricing to fit their needs. We have one customer that actually pays us a commission when we upsell someone's membership, or we get paid when we prevent you from cancelling. Some customers, we do a revenue share with them on, you know, preventing from someone from cancelling their service. So there's different models that we can implement and partner with our clients on. But at the end of the day, once again, people want to pay for outcomes. They don't want to pay for the right to use software. And that's the fun thing about partnering with the Sierra is we can customize our outcome based pricing to meet your needs.
27:01 Harry Stebbings? Do you think we will have per seat pricing in three to five years?
27:04 Speaker 01 If I had to look at my crystal ball, not sure. The expectations of clients are going to change. And I think outcome based pricing is a way to catch on to the new wave where people really want to pay for results and they don't want to pay for the right to use the software. But I can't predict the future, but if I had to guess, I would say I think that's going to change.
27:21 Harry Stebbings? Do you think the sales teams will get dramatically smaller with the increasing advancement of sales tooling, which means you can bundle so much intelligence into one sales rep, that actually you don't need teams of AEs, BDRs, SDRs, and actually one is just a superhero that has amazing tooling? How do you think about how the structure of sales teams change?
27:42 Speaker 01 If I had to look at my crystal ball, I would say salespeople are going to be better and more efficient because they're going to be using the technology to help them work smarter. Is it going to decrease the number of salespeople and BDRs and SDRs? Not really sure yet. I still think there's always going to be a place for a salesperson and human interaction, but what that looks like in the future, I'm not really sure.
28:01 Harry Stebbings? Has the way that you lead in sales changed in a world of AI in terms of the tooling that you use, how you use ChatGPT or any of the models to actually write emails, write monthly updates, write sales forecasts? Has how you work changed with AI?
28:17 Speaker 01 Absolutely. I pretty much stay in ChatGPT all day long. I try to use, and I, and I think our teams, one of our mantras at Sierra is use the technology to make the way we operate better. So helping me executive briefings, it used to take hours to do that. Now it takes less than a few minutes.
28:36 Harry Stebbings? Can I ask, I know it's weird, but we have so many people who literally really listen with notepads. What do you put in a prompt for an executive briefing?
28:43 Speaker 01 I'm going to talk to the Nobu collection of hotels. I would just put in there, going to meet with XYZ executive at Nobu. Please tell me about the company, their business, their challenges. What is this particular executive interested in? And valuation, revenue, and then three minutes later, it's got this beautiful executive briefing that used to take me or someone on my team hours to create. It's now taking minutes, so that time can be reallocated to do something else. And by the way, this information is really accurate. It's really good.
29:15 Harry Stebbings? Oh dude, it's unbelievable. Honestly, when I click deep research and then I love it when it like goes away and shows you all the different sources. And you're just like, wow. I used it the other day for an incredible show that I did. And it went back to a show that the guest did in 2017 in French.
29:29 Speaker 01 Wow, that's amazing.
29:30 Harry Stebbings? And I was like, well, that's better than I could ever, I ever have dreamed of. Okay. So we use it for executive briefing. Anything else where it's really cool?
29:37 Speaker 01 I also like the fact that I use it a lot for email. Like I like, still like writing my own emails, but I use it for just making it shorter, more concise, crafting it. That's another good use case. And then we use it to help with like the way we run our business, with some of the forecasting that we do. It's pervasive throughout Slack. Just being able to use the technology to move faster and then take that time and reallocate it more to being in front of customers, but.
30:01 Harry Stebbings? Has the way that you use Salesforce changed over time? And when you look at today, do you use Salesforce with Sierra?
30:07 Speaker 01 Still, absolutely.
30:08 Harry Stebbings? Okay. People say that it is a data repository and you just kind of throw the data in and blech respectfully. I know, I know that that's an insulting thing in some terms. Do you think that the relationship with Salesforce changes with it potentially becoming a data repository that agents just crawl over?
30:24 Speaker 01 Possibly. We still. Live in Salesforce quite quite a bit. Yeah, I mean, I just part of my DNA from, you know, running our forecast.
30:30 Harry Stebbings? Do the reps like it?
30:32 Speaker 01 Yeah, yeah. I mean, I think if you set clear expectations and then you tell them what information we need to be inputted in there. And a lot of a lot of our team, most sales organizations use Salesforce. If you do it right and you make it simple and easy for people to use, people will like love using it. But we we pretty much use it frequently the way we run our business.
30:51 Harry Stebbings? So I want to go back to you joining and you're employee number 23 and you're tasked with building out a sales team, correct? What were the hardest elements of building out the sales team at Sierra when you joined as employee number 23?
31:03 Speaker 01 Well, when you join a startup and you come from a, you know, traditional company, there's this thing called a pay cut. So so one of the jobs that one of the the challenges I had was convincing.
31:13 Harry Stebbings? A pay cut significant?
31:15 Speaker 01 Very significant. Convincing highly compensated, super talented people that were successful in other companies to take a pay cut and come join our pirate ship.
31:23 Harry Stebbings? So Jason Lampkin, a dear friend of mine, says, don't do it. It's not possible. A question that I have for you is, are you a unique situation respectfully? Because you're Brett Taylor and the team is so stellar. If you're like a normal team with great founders, but you're 25, you're 30, whatever. Do you think this is an isolated incident where basically you can get people like you because of who the founders are?
31:46 Speaker 01 The Brett and Clay factor obviously definitely helps, but I still think it's a startup and there's a lot of uncertainty, a lot of unknown. And what I sell, I don't sell, I just try to teach people what the vision of where this could go. And in my heart and soul, I believe Sierra is going to be one of the most important companies in AI. And I tell people that you have an opportunity to be on the ground floor of one of the most important technology companies in the world. And also, this is an opportunity to create real generational wealth for your family if we execute. And then also, I look at it too. The reason, one of the reasons I came is like, I want to be a legend, man. I want to be a trailblazer. I want to help, you know, make Sierra a generational company and then open up doors for other, you know, minorities to get these kind of opportunities
32:28 Speaker 01 and take these kind of risks. And I always go back to this quote from Muhammad Ali. If your dreams don't scare you, they're not big enough. So the most important decisions I've made in my career is when it's scary and when it's uncomfortable. If you can convince people to see where potentially this company is going to go, then it's much easier to recruit them.
32:47 Harry Stebbings? You mentioned generational wealth there. Often, sales reps teams are suggested to be coin operated.
32:54 Harry Stebbings? Mercenary than other functions. To what extent do you find salespeople, and I know it's generalist, so forgive me for it, but it's a podcast, mission driven versus money driven?
33:06 Speaker 01 It's a great question. That's like the million dollar question about sales. Obviously, everyone wants to go into sales. People want to make money because there is unlimited compensation. But I also think people like being part of something special. I think people like being creators and trailblazers and helping to build something. So I think that's an aspect. People love recognition. You get into sales for recognition. But I think also people get into sales because they're intellectually curious. They love how companies make money. They want to help these companies be successful. So there's a lot of other reasons why people get into sales. I also find that a lot of former athletes get into sales like myself. I was a former, I played college American football and I played.
33:42 Harry Stebbings? No way, dude, you look so small.
33:44 Speaker 01 I still try to stay in shape. But I also think sales, professional sales is one of the most competitive things you can do. It's wins and losses. It's accountability. It's what have you done for me lately? And I think a lot of people like being in those environments because you get rewarded for it.
34:00 Harry Stebbings? I totally agree with you. Do you think we demonize the money chasing? I think it's great. If you want to make money and you're like, I want to make a lot of money and I'm here to crush it. I'm like, great. But I think a lot of people go, oh, they're not here for the mission and they're not here to have impact. Fine.
34:15 Speaker 01 It's quite okay to want to, you know, make a lot of money. But I think it's more of what I try to do when I interview people is connect. Like, what is your why? Like, what motivates you every day? Why do you get up and why do you get after it every single day? And what you'll find, it's not the money, it's what the money can do. It's like providing a better life for your family, sending your kids to college or private school, or being able to get on a flight and travel first class. I think it's not just about the cash. It's about what the cash can do. So I always try to connect with people's why and what's motivating them.
34:45 Harry Stebbings? I totally get you. I think that's so important. That's a very good addition. When we just go a step back in the hiring process, where do you find the best candidates come from? Is it network? Is it outbound where you're very targeted in wanting a specific type of person? Is it from old companies that you've worked with before? You find the best sales talent comes from when you look at who you've hired.
35:08 Speaker 01 Referrals all day long.
35:10 Harry Stebbings? Really?
35:10 Speaker 01 The best hires I've ever made is either through my network or my colleagues' networks or my friends' networks. Obviously, you're looking for the certain things like intellectual curiosity, hustle, grit, proven track record of success, you know, energy, swag. But you want to be able to have someone that knows that's someone that can vouch for that person. This is a good person. They're a humble person. They're a great teammate. They're going to come in and add like value to the company. So the only way you can really do that is through referrals.
35:38 Harry Stebbings? I completely agree, and I also think you can never short circuit years of experience working with someone. And so when someone says, I worked with Reggie for six years. He was incredible in here, here, here, and here. Versus someone else where it's like, I met them and they seemed credible. Great, but six years against someone I really trust who worked with them, it's a no brainer. So we have that referrals is where we get our best candidates from. How do we structure hiring processes? Again, you had to build out your team. We have them in. Do we first meeting, it's all personal? Second meeting, it's about sales? How do you structure that process?
36:10 Speaker 01 Well, first of all, we have a phenomenal recruiting team that's led by this gentleman named Greg Marsh. So they usually do the qualification first and then we'll have them talk to one or two of our sales leaders. And if there's mutual agreement to move forward, then we'll have them come visit our company for half a day where they do a presentation and they meet senior leadership. And then if all that checks out, then I have a one on one with that particular candidate.
36:32 Harry Stebbings? The presentation, sorry, just to dive in there. Are they about Sierra or are they about a company they've worked with before? How do you choose which material to give them?
36:40 Speaker 01 It's a general prompt and it's really explain who are you? Tell me about your background, you know, walk me through a deal that you closed. And then how do you think about, you know, certain things that we're looking for? We have corporate values that we really hone in on. And we try to evaluate like their craftsmanship, their track record of success, what kind of teammate they're going to be, how they think about their sales principles, how they execute deals. What's the complexity of the deals that they sold? And I think if you throughout that process, you'll figure out if this person's a right fit for for the company or not.
37:11 Harry Stebbings? When someone doesn't get it, what's the most common? Area where they fall down.
37:16 Speaker 01 Craftsmanship.
37:17 Harry Stebbings? In what way?
37:18 Speaker 01 It's the way that they show up. It's the way that, you know, are they concise? Are they compelling in their verbal communication? And I think when someone does a sales presentation, do they have like errors on the slides or the slides formatted correctly? Are they a storyteller? I think you can find out a lot about someone, but their craftsmanship by how they prepare for the interview process. And I think that manifests. If you're not going to put the time and effort into delivering a really nice presentation, how can I trust you to do that when you actually become part of the company?
37:46 Harry Stebbings? Spelling in slides is the worst. When I see that on my slide two and you're like, really? Really? That that's what you came up with?
37:53 Speaker 01 Spell check, right?
37:54 Harry Stebbings? This was like, dude, just like OpenAI, like ChatGPT this now. This is just lazy. So I totally agree with you. Do you have hiring panels?
38:01 Speaker 01 We do.
38:02 Harry Stebbings? Do you find them helpful?
38:03 Speaker 01 Very helpful. I'm very fortunate to work with some incredible sales leaders like Mandy St. Ledger, Kylie Maddox, Lily Skolnick, Lee Wafer. I could go on and on and on. Scott Townsend, Matt Joshie. And these folks have an innate ability to identify talent. So you may be able to fool me and I get happier sometimes, but throughout the process, these are some really sharp evaluators of talent. You're not going to be able to get past these folks.
38:29 Harry Stebbings? Do you need consensus?
38:30 Speaker 01 Absolutely.
38:31 Harry Stebbings? Do you not think the best people are often spiky or controversial? So like in venture, often the best deals or investments are non-obvious and right, which means that three out of five want to do it, but two don't want to do it. In people, do you find consensus-driven decision-making is best?
38:48 Speaker 01 I think so. Over Mike, if I look at the statistics of folks that I've taken chances on that didn't work out, I always go back and look. I remember debating in that room and there was two people that were like, I'm not sure. And we still did it anyways and it came back to bite us. So I think at least now I really rely on the team. We make decisions on consensus. Now, if someone hears, so if someone is really passionate and they're an outlier, we'll listen and we'll take that into consideration. But we try our best to do it by consensus.
39:15 Harry Stebbings? When you review your hiring mistakes, what did you not see most often that you should have seen?
39:21 Speaker 01 Well, we saw that, we saw things, we just overlooked them.
39:25 Harry Stebbings? What did you see?
39:26 Speaker 01 Craftsmanship issues, communication issues.
39:29 Harry Stebbings? And you overlook them because?
39:31 Speaker 01 They had, they were stronger in certain other areas, or someone, they had a great referral, that someone I trusted, hey, give this person a shot, or they were really, really strong at one particular prospecting, and at the time, we really focused on that, solving that particular problem. But I think your gut and your instincts and your heart always tells you the truth, and you should listen to it. And I think a lot of times, I've had instincts like, that person's not gonna make it, but let's give them a shot. And it's usually, you always end up being correct with your initial instincts.
39:59 Harry Stebbings? So let's give them a shot, right? Let's do it. And there's two parts where I find really telling of a candidate in terms of how they think, which is salary and title. How do you learn about the candidate from salary and title? So is it bad if I come in and say, I wanna be a VP of Sales?
40:16 Speaker 01 At Sierra, what we do is everyone comes in as an individual contributor for a certain period, even if you're in leadership, like myself included. Once again, as I said before, when I started, there was no sales team. So I was an AE, I was an SDR, I was a BDR, took the trash out, I kinda like earned my right to kinda lead a team. And all of the sales leaders that we brought into Sierra, they came in for a period of time to be an IC. And that takes humility. I mean, you've gotta like master your craft, you've gotta learn how to prospect, you've gotta learn how to run a deal, you've gotta learn how to negotiate a deal. And I think that's important and powerful. So when you do start running a team, you know how to lead your team, especially when this is a brand new category of software, we're a new company. So I think it's important for people to come in and kinda earn, earn their leadership. And Michael Jordan says, like, earn your leadership every day. I still
41:00 Speaker 01 feel like I'm earning my leadership every day. But that's just how we approach it. Now, over time, that may change.
41:05 Harry Stebbings? Do you find it bad then, if people are very, very focused on a title?
41:08 Speaker 01 I think so. For a startup, you need to be focused on the mission, on building something. And one of the cool things I love about our company, no titles, no egos, everyone's aligned on this mission of building an amazing company, everyone's humble and hardworking. I think that's really important.
41:22 Harry Stebbings? What about the focus on money, the salary? Hey, listen, Reggie, I know you want me, but I'm at Okta now, and actually, I'm paid like, you know, two Base and you're paying me one seventy five like come on dude, I need you to help me out here.
41:36 Speaker 01 If you have the vision to see that this is going to be one of the most important companies ever in software. And you believe in yourself and you believe in our team and you believe in what we're doing. There is unlimited commission, so you can make as much money as you want, but you have to come in and earn that. But once again, I'm looking for mission driven people that want to help us build something special. But they have to be able to take risks because they can make that pay cut back in commission if they execute. But they have to be able to believe in themselves and see the vision of what we're building.
42:03 Harry Stebbings? Don't laugh. It's a bit of a stupid question, but you know, I'm British and a podcaster, so it's kind of within my rights. You said unlimited commission there. If you were to really crush it as a salesperson at Sierra, really crush it. How much could one make? Is it like five million dollars?
42:19 Speaker 01 It's quite a bit. How about that? How about that? I won't get into the specific numbers of what people are making, but I would just say if you have aspirations and you're an A player and you want to make a ton of money, there's room for you at Sierra to help us build an amazing company, make lots of money.
42:33 Harry Stebbings? Why do you think athletes make such good salespeople?
42:36 Speaker 01 Discipline, work ethic, being part of a team, being coachable, mastering your craft. All those things and just having like a never can say die attitude, holding yourself accountable. I think all those things that make athletes successful translate well into into professional sales.
42:52 Harry Stebbings? I think it's also like the willingness to do a lot of work for no perceived obvious gain. You know, you're in the gym and it's like you can train for a week really hard. There's no gain at all. There's none. Two weeks, sometimes three weeks. And slowly, slowly you start to see the gains, but you have to at the start not get anything for it. That's a hard mindset.
43:11 Speaker 01 Yeah, especially when you start out and you've got a prospect, you've got to build your business from scratch. That goes into like the discipline, the work ethic. And I think about like Mark Cuban's quote. Work like there's someone working 24 hours a day to take it all away from you. You've got to have that mentality as an athlete and you've got to have that mentality as a professional seller. And I think professional sellers, I consider them athletes.
43:31 Harry Stebbings? You said there about kind of learning to run deals. What are the biggest mistakes you see team members or other professionals make when it comes to running a deal well? What should we watch out?
43:41 Speaker 01 I think great enterprise sellers are leaders. They're natural leaders. They know how to galvanize like resources to get them excited about working their deal. I think it's listening to your team, directing your team, including like the co-founders and the executives. You're the quarterback of the deal cycle. And I think if you're running a tight deal cycle, you're learning more about the client than know about themselves. You're asking great questions. You're deploying your resources. You're giving them guidance and instruction about your strategy. I think that's how people succeed in enterprise sales.
44:10 Harry Stebbings? Should AEs be responsible for demand gen? Or should they be fed by marketing?
44:15 Speaker 01 AEs, in my humble opinion, should be responsible for their own pipe gen. And I'm going to quote one of my sales leaders, Matt Joshi. He says, pipeline is lifeline. I think marketing can help you. BDRs can help you, but at the end of the day, the sales professional is accountable to generating their own leads.
44:31 Harry Stebbings? I always say like, you know what? It's like ice cream with sprinkles, hundreds and thousands. That's like the marketing, what they can give you, but you need to be doing the ice cream. Do you batch time or do you advise your team members to batch time for outreach, prospecting, filling pipe? Or is it much more natural throughout the week?
44:48 Speaker 01 No, I think in my humble, I try to tell my team, put it on your calendar like it's a customer meeting. Put like an hour, two hours a day on your calendar for prospecting. Every Friday, we have like a quote unquote, old school, like prospecting blitz where the team will block off a couple of hours. They'll do it together as a team to go out and prospect and try new, new strategies.
45:07 Harry Stebbings? Can you just take me to that? What's a prospecting blitz? How do you guys work together in this time? What does that look like?
45:13 Speaker 01 Buy lunch. Everybody get, because we're, obviously we're a global company. We have folks in here in London, all over the East Coast, Central, West Coast. And we just pick a time and, you know, we'll buy lunch and we'll come up with a theme that everyone will just, they'll come up with a list of what they're going to target that day. It's more fun because like prospecting is hard here. You know, like you're getting your teeth kicked in, you're getting rejected. But when you do it as a collective group, it's fun. You kind of exchange war stories. You find out what's working. You share information. We've been doing that consistently and it actually really works and people look forward to it. Do you record your sales calls? Not yet. Why not? Not yet. Uh, we're, we're going to probably invest in some technology to do so. We have a Done that yet, but in previous roles, obviously, yeah, we used all types of different.
45:54 Harry Stebbings? Did you find it helpful, understanding what worked, what didn't work, the messaging, you could go back over your old calls. Ah, it wasn't so good there and that was where I fell apart. Do you find it or not really, we overemphasize it?
46:05 Speaker 01 Yeah, I think it works. Yeah, I think it works. Like I would go back, even presentations, I'm a perfectionist, I'm going to go back and watch this podcast and see what I did well or not. But I think recording yourself like is just helping you master your craft and get better, especially when you hear and see yourself.
46:18 Harry Stebbings? We also airbrush, wonderfully helpful. I listened to it after my brilliant editing team have done it and I'm like, wow, I'm so good. And then I hear the roar and I'm like, oh shit. So yes, I totally get you there. You mentioned that global company, team around the world. Well done on London, thrilled about the team here. I don't believe that remote sales teams work as efficiently. How do you think about that versus the rah rah of having people in person?
46:42 Speaker 01 We're in office culture and right now we have a large office in San Francisco where our corporate headquarters is, we have a big op, we just opened a big office in Midtown Atlanta. And then we obviously just opened an office in Soho, we're going to open an office in New York. We have an in-office culture, I think. Being in the office together, collaborating, sharing information, I think it's really important and it's, it builds community, it builds culture. Now, we do have offices that are people that work from home that don't live in those major cities, but I bring the sales team together once a month.
47:11 Harry Stebbings? Oh, wow.
47:11 Speaker 01 Yeah, and we do team building, we do a customer event and then we do like some training, some enablement, but I try my best as we get bigger and bigger. And we have a more dispersed team to get everybody together so they can meet their teammates, they can build relationships, they can collaborate and share information. And I think that's the power of having a strong sales culture is when people like know each other, trust each other and they collaborate.
47:33 Harry Stebbings? So you've hired me, right? I've finally found gain for employment after a decade. My mother will be thrilled.
47:38 Speaker 01 I'd love, I'd love for you to come over.
47:40 Harry Stebbings? That's very kind of you. I do care about salary. I'm not taking your pay card.
47:45 Speaker 01 I'll give you the commission.
47:46 Harry Stebbings? That's so kind of you. I'm not that good a seller. My question to you is, when you think about knowing how good someone is quickly, how quickly do you know if I'm good versus I made a mis-hire?
47:58 Speaker 01 Within a few weeks.
47:59 Harry Stebbings? Is it really?
47:59 Speaker 01 Yeah, within a few weeks. And then we have a certification process that you have to go through and you have to present.
48:04 Harry Stebbings? What does my first week look like?
48:05 Speaker 01 First week, we usually have all of our new hires come out to San Francisco and we have a curated first week where you kind of go through, somewhat of a bootcamp where you learn about like our sales process, our technology, our platform, our products, our sales process. You also learn like the technology. We have like a, we call it an agent bootcamp where you kind of learn how to build an agent. So it's a first week, you get a chance to meet the team, meet the co-founders, meet the entire everybody in San Francisco. It's a good vibe. We do some team building and then within a few weeks, we actually have you certify, present to us the first call deck. And I think after a couple of weeks, you know, if you've made a hiring mistake or if someone's good.
48:40 Harry Stebbings? When you've made a hiring mistake, what does show up? In other words, what are the signals that they're not a good fit?
48:46 Speaker 01 I always go back to the same, guess where I'm going to go, Harry?
48:49 Harry Stebbings? Craftsmanship?
48:49 Speaker 01 Craftsmanship, yeah, craftsmanship.
48:51 Harry Stebbings? And you see that pretty clearly?
48:52 Speaker 01 Very clearly. It's something we truly believe in at Sierra is craftsmanship. The way you show up, the way you prepare, the way you communicate, the way you show up to customer meetings, the way you engage with clients, your teammates.
49:03 Harry Stebbings? How quickly do you get me on calls with customers?
49:05 Speaker 01 First week.
49:06 Harry Stebbings? Really?
49:06 Speaker 01 Yeah, well, actually you're not going to run a call, but we'll have you shadow teammates. And what's really cool is our co-founder Brett and Clay, they are heavily involved in like meeting with customers. So they get a chance to see how Brett and Clay interact with clients, how I do it, how our sales leaders like Manny and Kylie do it, how our solutions engineers do it. So they get a wide variety of different people. And then within a few weeks, they certify and they're off and running. But we're trying to hire the best talent in the world. So a lot of these folks have great instincts. They just need to learn how to sell our products.
49:37 Harry Stebbings? I totally get you, but it's still pretty cool to have that exposure to see a founder sell as early in your journey as that. So that's amazing. So fantastic. Can I ask you then, when we have these deal cycles and we're in a team setting, how do we do postmortems? What do they look like? How are they structured? It's a difficult thing to do well.
49:55 Speaker 01 Yeah, they're pretty impromptu. We always usually collaborate immediately after calls, whether they went well or they-
50:01 Harry Stebbings? So we'll do it in real time-
50:02 Speaker 01 Real time.
50:03 Harry Stebbings? -not got you.
50:03 Speaker 01 Real time. Whether if we're in person, it's in person, I mean, we'll just huddle right after, or if it's virtual, we'll just jump on a Slack huddle and do it. But we do it quick, and we provide each other feedback, good, bad, and ugly. And it's two-way. It's not like sales leadership is giving you feedback. You're also giving us feedback. Hey, Reggie, didn't like how you positioned that. You know, next time, do it this way. It's a total team effort, and we share-
50:24 Harry Stebbings? Do you have any lessons? I find this hard, actually, as a leader today. Do you have any lessons in how to give feedback that's hard, but in a way that doesn't discourage some moving forwards and kind of make sure they leave inspired with their head up?
50:36 Speaker 01 Yeah. So it starts off with, I think, the leadership style and your principles. So I start off with, I'm open, I'm honest, I'm transparent, I lead from the front, I treat people with respect. I would never ask someone to do something I wouldn't do myself, but I also have high expectations and I'm very clear about what's expected. So I think if you lead with that type of energy, if people know what to expect, so I think delivering feedback, because you're doing it quite often, is pretty easy. As long as you're respectful, but you're honest, and you also are open to receiving feedback, people will accept your feedback, and they'll also listen and action your feedback. If you're willing, you do it in a respectful way, but you're also open to getting feedback back. I get lots of feedback, not only from my colleagues, but also my wife and my children.
51:20 Harry Stebbings? Your wife is always right, is the answer. Just never, ever push back on that one.
51:24 Speaker 01 Amen, sir.
51:25 Harry Stebbings? Listen, I'm so sorry, Reggie. The deal just fell through. I wasn't expecting it, or it slipped to next quarter. I'm sorry, dude. Happens a lot. I've sit on many boards where big deals, they just slipped to next quarter. What do we say as a sales leader, or me as a board member, when I hear it slipped to next quarter?
51:44 Speaker 01 I have the mantra of, good news should, and I got this from one of my mentors, Scotty Warren Wick, who's a superstar at Salesforce. Learned a lot from him. He says, good news should travel fast, bad news should travel faster. And what I try to do is create an environment where people feel okay telling the truth and letting us know in advance if there's an issue, so we can also jump in the boat and try to help them salvage a deal from slipping. But when it does slip, we just want to understand how it happened, what can we do differently so it doesn't happen again. It's not like to beat someone up. It's just to learn. Is there something wrong with the product? There's something wrong with your approach? Something wrong with our process? What can we learn from this, so it doesn't happen again?
52:21 Harry Stebbings? We mentioned running deals and then you said about negotiating deals and negotiating is where deals can slip and where deals can not happen. What are your biggest lessons on how to and how not to negotiate large enterprise deals?
52:36 Speaker 01 That's great. There's different variations of enterprise sales negotiations, but it really comes back to are you delivering value? Are you solving a problem? Are you talking to the right people? Have you done your homework? Have you built business value in or return on investments so the client can see the technology they're investing in? What are they going to get out of it? And then are you talking to the right people? Are you leveraging the power of your of Sierra? Are you getting me involved? Are you getting Elliot Greenwald, our co-founders involved? Like, are you loading up the boat to make sure you have the right people helping you negotiate these deals? Where are you weak? Does someone else better at like negotiating like this, the financial structure of the deal? Let's get them in the boat with you. So do we need to get our general counsel, Jonathan Millard, involved? Like, use all the resources, all these talented people to get help you get your deal across,
53:21 Speaker 01 but just know where your strengths and weaknesses are and then know where to fill those gaps.
53:24 Harry Stebbings? What's an acceptable reason to lose a deal? What's an unacceptable reason?
53:28 Speaker 01 Unacceptable reason is you're not talking to the right people. You didn't deliver value, or it was a craftsmanship issue where we didn't follow up on something, we didn't do something right. We didn't control the controllables. What I think where it's out of our control, like there's some type of financial issue with the company, there's some-
53:47 Harry Stebbings? Companies IPOing, they're not buying anything new for them. Three months while they're going through regulatory-
53:51 Speaker 01 Pandemic, whatever it may be. Like, I think those are things that are out of our control, but what I can't accept is you did not execute the controllables. You didn't leverage the power of Sierra. You didn't get the right people involved in your deal. I can't accept that.
54:05 Harry Stebbings? I totally agree with you there. What's the hardest thing for you today about being a sales leader? There's so many challenging elements, there's so many shifting parts. What's the hard part today?
54:14 Speaker 01 Right now, we are in hypergrowth stage. We have right product, right time, incredible co-founders. We've got really talented, smart people. We have a product that delivers the best quality agents. So we have a tremendous amount of demand and we're growing fast. My challenge is hiring, hiring fast, hiring smart, maintaining the awesome sales culture that we've created.
54:35 Harry Stebbings? A lot of founders ask me, they go, "Hey, Harry, I know everyone says, oh, wait till you get that perfect hire. I need bums on seats. I need to hit targets, Harry. It's a luxury to wait for the perfect hire." What would you say to them?
54:48 Speaker 01 I would say if you hire fast and you don't hire smart, you end up having to fire fast. I don't use the word fire, but usually have an issue. So I think you have to be measured, you have to be aggressive, and you have to move with urgency, but you need to be smart about it because I think hiring the wrong people causes more problems than it's worth. So I think just being aggressive, but being measured and doing it smart.
55:10 Harry Stebbings? How do sales cultures break down in hypergrowth? You've seen huge scale sales teams across different organizations. Now you're scaling one in real time, fast. What cracks could appear that you're aware of and looking out for?
55:25 Speaker 01 I think it's making sure people are part of an environment where they feel trusted, they feel respected, they feel supported, they know who their teammates are, they know where to go to get things done, they are supported and ramped up fast. I think if you bring people on and there's no structure there, there's no environment, there's no support, there's no help, I think that causes problems. I think if you don't really focus on building like a culture and building a really strong team, I think people feel isolated and disconnected. So those are two things that I really focus on is, one, hiring the right people and then creating a really positive environment where they feel trusted, supported, and they feel like they have the support they need to be successful.
56:04 Harry Stebbings? What do you advise on competition? You do have competitors, every space does, that's worth something, really. How do you advise founders on how to think about competition? And also just how to message about competition in sales cycles?
56:16 Speaker 01 We are in a ultra competitive environment. We're competing with big tech. We're competing with startups. We're competing with, I can build this myself. We're competing with, I'm too scared to put AI in front of my customers. So there's lots of competition, but I just think it is basically understanding your message, understanding how to combat what your competitor is going to throw against you. Understanding your competition, respecting your competition. Don't take your competition for granted, but know your strengths of how you can beat your competition and just making sure your team is enabled on that. And not, don't be scared to compete. I love to compete. I love waking up every day and knowing that every client that I'm chasing, someone else is chasing that client too, and I need to show up better, stronger, faster, more craftsmanship, make sure my product, you know, we have an awesome product to sell.
57:01 Speaker 01 So that's kind of how I think about competition. I love it. It's always going to be there, especially in AI. But just understanding your competition, respect your competition and know how to sell against them.
57:09 Harry Stebbings? Which competitors do you respect the most?
57:11 Speaker 01 I respect all competitors. I don't take anyone for granted.
57:14 Harry Stebbings? You don't?
57:15 Speaker 01 Do not. All these competitors we're competing with, by the way, they all have strengths. So we need to respect those strengths and just be aware of that and not be scared to compete. But I respect all the competitors out there.
57:25 Harry Stebbings? I'm going to push you, but not a name because names always tough and tricky. You don't want to single people out. Do you think incumbents with distribution are more threatening than startups with speed and agility?
57:37 Speaker 01 I know this is like a vague answer. I think they're both incredibly formidable. Startups, they're unique, they're fast, they're nimble, they're aggressive. And the large incumbents, you know, the big tech companies, they have scale. They have marketing muscle. They have massive distribution. They have strong, powerful customer relationships. They're respected brands. So they're formidable, just like the startups are.
58:00 Harry Stebbings? Dude, I could talk to you all day. I'd love to move into a quick fire answer. I say a short statement and you give me your immediate thoughts. Does that sound okay?
58:05 Speaker 01 Let's do it.
58:06 Harry Stebbings? What sales tactic has not changed over the last five years?
58:10 Speaker 01 Prospecting, going out, generating interest, getting meetings. And I call that corporate swag. Having the ability to get a busy, important person to give you 30 minutes of their time that they don't have. That's never going to change.
58:23 Harry Stebbings? You mentioned cold calling earlier. Do you actually cold call?
58:26 Speaker 01 Yeah, absolutely. It's a combination of emails, phone calls, messaging on social media, but also inviting people to events.
58:34 Harry Stebbings? Does that work well?
58:35 Speaker 01 I think so.
58:36 Harry Stebbings? Yeah. What has died a death?
58:38 Speaker 01 A lot of the administrative tasks have changed because of the power of technology like ChatGPT, building executive briefs. I think that that's changed. Like, I can do that in three minutes now versus spending hours creating stuff like that. I think a lot of the administrative tasks have been changed with automation. And I think if people aren't taking advantage of the technology that are disadvantaged.
58:57 Harry Stebbings? Which I think is great because it just means you have so much more time to be creative and think about how you can prove your differentiation in a more creative way. Do you know what I mean?
59:06 Speaker 01 Focus on prospecting.
59:07 Harry Stebbings? Yeah, like briefing, like it's not that creative in many ways. So totally. Talk to me about a deal you've closed where you've had to do something, I love this one, out of the box, creative to get it over the line.
59:18 Speaker 01 I'll think about this company, one of the largest IT companies in the world. And one of my colleagues, one of the best sales professionals I've ever worked with, Mandy St. Ledger, and I worked together along with Brett and this guy named Andy Kofoid to close a deal when we were at Salesforce. They were Microsoft's number one reseller, which usually means that they have to buy Microsoft's technology. So we were in a very, very competitive environment. And what we did unique was we sold the vision of creating their own SI practice where they could resell Salesforce and be an implementation partner, which is high revenue, high margin. And that was how we were able to navigate the Microsoft reseller compete. And they saw the vision, not only was our, at the time, you know, I felt our technology platform was better,
1:00:03 Speaker 01 but we also had this unique way that they could be a partner, not just a vendor relationship where they can actually resell Salesforce and add value there. So that was a pretty unique approach that we took and it was a very successful, it was a fun deal to work.
1:00:16 Harry Stebbings? Wow. Is that the biggest deal that you've worked on?
1:00:18 Speaker 01 At Salesforce, yes, but I think based on the power of what we can do for clients at Sierra, I'm hopeful that we'll have much bigger transactions.
1:00:27 Harry Stebbings? I'm sure you will, my friend. What one piece of advice would you give to a sales leader starting a new role today? I'm starting tomorrow in my new position, name the company. What would you say to me?
1:00:38 Speaker 01 I would ask you, or the advice I'd give you are three things. Hire the right people. Build a powerful culture where people feel trusted, respected, and they love coming to work. And then three, lead from the front. Be willing to get your hands dirty, be willing to jump in and work deals and not like lead from a glass tower, but lead from like be in the trenches with your team.
1:00:56 Harry Stebbings? How do you maintain morale when goals are missed? It's really hard. You have that team meeting and people are deflated if something hasn't gone. How do you maintain morale?
1:01:05 Speaker 01 What I do is I focus on inspirational leadership, making sure people always stay connected to their why. Like what gets them out of the bed every day? Why are they showing up to work? Why are they in sales? And it's usually something, some type of financial thing, or it's something with their family or something personal where they want recognition or to advance their career. So I keep people connected to their why through tough times and I come up with a motivational quote every week.
1:01:28 Harry Stebbings? You're very good with quotes.
1:01:30 Speaker 01 Thank you, thank you.
1:01:31 Harry Stebbings? I think it's important actually, because in the hard times you kind of draw on them.
1:01:34 Speaker 01 Yeah, and I think the sales leader is critically important because you're the only thing between the sale, the sales professional and the fire. And the fire is the rejection, you know, the tough part of being in sales. And it's your responsibility not only to be in the fire with them, but to keep them motivated to continue to run out into the fire.
1:01:52 Harry Stebbings? What's your favorite quote?
1:01:53 Speaker 01 I have a lot of great quotes. There's this quote that I found that I used this week and it's from, I don't know if you're into American basketball. The quote is, "No one ever loses at anything as long as they don't quit." It's from the head coach of the Houston Cougars, Kelvin Sampson. I don't know if you watched. They played Duke University on Saturday night in the first game of the final four. Duke, bigger, stronger, more talented team. Three of their guys in their starting five are all going to be NBA lottery picks. Houston was down like 15 points late in the game. I turned it off. I mean, everyone thought that they were going to lose, but what this Coach did was he instilled grit, hustle, griminess into their culture. Never quitting and they they battled back and they actually beat Duke,
1:02:35 Speaker 01 who was the favorite and won the game. And I just that quote really resonated with me. No one ever loses at anything. As long as they don't quit. That's what you gotta have in sales.
1:02:44 Harry Stebbings? I totally agree. I love a talk General Admiral McRaven, which is the guy who says always make your bed in the morning. I don't know if you've seen this video. It's probably one of the best ones.
1:02:52 Speaker 01 I have seen that.
1:02:53 Harry Stebbings? Yeah, and he says never ring the bell, which is exactly that. Never quit, essentially.
1:02:58 Speaker 01 I'll give you one more. I got this from my dad. My dad was a thirty year full Colonel of the US Army, eighty second Airborne, Army Ranger, Green Beret. And one of the things that he embedded in my DNA is failure is not an option. If you're going to be part of this memorable family, failure is not an option. So I learned that and that's kind of how I approached life.
1:03:17 Harry Stebbings? Do you think that puts unnecessary pressure on children?
1:03:20 Speaker 01 No, it just sets expectations. And I go back to Nelson Mandela. I never lose. I either win or learn. So when he was teaching us that, it's like, you're gonna fail, but don't quit. Figure out what you did wrong, how you can get better. But the overall failure of quitting, that's failure, is giving up. And that's something that we don't do as Mirables.
1:03:39 Harry Stebbings? Love that. Final one. What one company sales strategy have you been most impressed by recently? Where have you been like, that was smart, other than Sierra?
1:03:48 Speaker 01 Can't be Sierra.
1:03:49 Harry Stebbings? If you want to do a Sierra and it's granular.
1:03:51 Speaker 01 I love the fact that we allow our potential clients to test out our technology before they make a long term commitment. I love that model. It forces us to be on top of our A game at all times and deliver results before, you know, customers make a long term investment in us. So it gives you the opportunity to earn your keep, earn your value and demonstrate the power of what we can do. And I love that model. I'm not saying that because I work at Sierra. It's just you get to compete every day. You get to compete and show customers the value that you can deliver.
1:04:20 Harry Stebbings? I totally agree. It reduces the risk for them. It reduces so much of the burden on them. I totally agree. Reggie, I so appreciate you taking the time. I'm thrilled that we could do it in person. As I said, I spoke to so many. Larry, Frank, we mentioned Danny. So you've been amazing and thank you for joining me, man.
1:04:36 Speaker 01 Thank you. It's a bucket list moment, especially live from London, too.
1:04:40 Harry Stebbings? My word, it was so great to have Reggie in the studio there in London. I'm so grateful to get to do these shows and meet just the best operators in their verticals. I hope you enjoyed the show. Let me know on Twitter at Harry Stebbings. But before we leave you today, if you're ready to leave rigid payment terms behind, Capchase is here to change the game. Capchase brings B2C buying convenience to B2B software and hardware purchases. Capchase offers your buyers the flexibility they demand on annual and multi-year contracts while you get paid upfront every time. This means faster closings, higher deal sizes and a streamlined process without the hassle of discounts or collections. Over 2,000 companies already use Capchase to accelerate their sales and secure predictable revenue. It's time to unlock your team's full potential.
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1:06:05 Harry Stebbings? practical advice, including hands-on demos of cutting-edge AI tools from ZoomInfo, the go-to-market intelligence platform that makes every seller your best seller. Learn more and subscribe to be the first to know when registration opens at zoominfo.com/20vc. And if you want to turn insight into action, Gong has you covered. Gong is the number one revenue AI platform that's changing the way sales teams win. You know guesswork doesn't close deals, so Gong captures every customer interaction and gives you real-time insights so you can drive predictable growth. With Gong, you can power all your critical revenue workflows from prospecting to renewal on one AI platform. That's why go-to-market teams at LinkedIn, Snowflake, ADP...
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1:07:10 Speaker 01 As always, I so appreciate all your support and stay tuned for an incredible episode coming on Monday next week. We have an exclusive, a very special news announcement.
Previous 20VC: Why Fund Returners Are Not Enough Anymore | Why Sequoia Had the Best Strategy at the Worst Time | What it Takes to Be Good at Series A and B Today | Benchmark Leads Manus Round: Should US Funds Invest in Chinese AI Next 20VC Exclusive: Why Mega Platforms Will Win in VC | Why You Cannot Do VC If You Do Not Do Pre-Seed | Why Market Sizing is BS | Where Will Foundation Models Build/Buy Apps vs Where Will They Not with Bucky Moore Page updated September 29, 2026 · transcript and summary are machine-generated
