20Sales: Slack, Atlassian, Dropbox: Five of the Biggest Lessons on Starting, Scaling and Managing Sales Teams from 25 Years Leading the Best with Kevin Egan, Global Head of Enterprise Sales at Atlassian

Kevin Egan is the Global Head of Enterprise Sales at Atlassian and brings more than 25 years of enterprise sales experience and leadership to the company. Prior to his current role, Kevin served as the Vice President of North America Sales at both Slack and Dropbox and has held various senior sales leadership positions at Salesforce. In Todays Episode With Kevin Egan We Discuss: 1. The Makings of a Truly Great Enterprise Sales Leader: How did Kevin first make his way into the world of enterprise sales? What does Kevin know now that he wishes he had known when he entered sales? What advice would Kevin give to a new sales leader today starting a new role? 2. The Sales Playbook: How does Kevin define "the sales playbook"? Does the founder have to be the one to create the sales playbook When is the right time to hire your first salespeople? Should they be senior or junior first? What are the different types of reps to hire in the early days? Should you hire two at a time? 3. PLG vs Enterprise: Does Kevin believe it is possible to run both PLG and enterprise playbook at the same time? How does one know when they are ready to scale from PLG into enterprise? What are the signs? What do companies need to change in the way their sales team, is structured to make the transition from PMG to enterprise sales? What are the single biggest mistakes Kevin sees founders make in the scaling from PLG to enterprise? 4. Hiring the Sales Team: What non-obvious characteristics and attitudes should we look for in sales reps? How does Kevin structure the hiring process for all new additions to sales and revenue teams? What makes good PLG sales leaders? How are they different from enterprise sales leaders? What questions and case studies are most revealing for you in identifying them? What have been some of Kevin's biggest lessons on comp structure for these early rep hires? 5. Making the Machine Work: How does Kevin build trust with his early sales rep hires? What works? What does not? How does Kevin balance hitting the quarterly revenue target with longer-term pipeline strategy? How does Kevin manage when a quarter is missed? What is the right approach? How does Kevin approach post-mortems and deal reviews? How often? What do the best entail?

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Speaker 00

  I do favor hiring two to three at a time if you can afford it. In a PLG world, rep effectiveness, the best companies out there are doing a lot of A/B testing. Early days of hiring reps, you're going to need Renaissance reps that have a very wide breadth of skill sets.

• 0:15Harry Stebbings?

  You are listening to 20 Sales with me, Harry Stebbings. Now, this is the monthly show where we sit down with the best sales leaders in the world to reveal their tips, tactics and strategies when it comes to scaling sales teams. Today, I'm so thrilled to be joined by Kevin Egan, Global Head of Enterprise Sales at Atlassian, and brings more than 25 years of enterprise sales experience and leadership to the company. And prior to his current role, Kevin served as the Vice President of North America Sales at both Slack and Dropbox, and has held various senior sales leadership positions at Salesforce. I'd also want to say a huge thank you to Maggie Hart, Kim Graves and Raynu Gupta for some fantastic question suggestions today. I so appreciated that. But before we move into the show today, you might remember in our amazing episode with Maggie Hart, she mentioned a tool she could not live without called Pocas. What is Pocas?

• 1:01Harry Stebbings?

  Well, Pocas is a revenue data platform that makes it easy for go-to-market teams to analyze, visualize and action data about their prospects and customers without needing engineers. Pocas helps companies like Miro, Webflow, Loom and Superhuman focus their sales and success teams on the highest priority opportunities by surfacing insights at the right moment so reps can take action quickly. Pocas gives you a 360-degree view into product usage, empowering you to act on insights and fill your funnel efficiently. Sales teams save 10-plus hours per week digging through data to surface millions of new revenue opportunities. Learn more about why top PLG businesses trust Pocas as their revenue data platform by visiting pocas.com/demo.

• 1:46Harry Stebbings?

  And SalesLoft is the leading sales engagement platform, helping sales teams drive more revenue with the modern revenue workspace. It's the one place sales teams can go to prospect, manage additive deals and get the insights they need, to coach seller performance, forecast with accuracy and find out what steps to take to close more deals. Some of the world's leading companies like Google, Shopify and Stripe all love a new SalesLoft. And so can you. It's the new way to sell. Find out more at salesloft.com. And finally, finding your next customer is hard, but it doesn't have to be. ZoomInfo is the answer. ZoomInfo handles the full revenue pipeline from marketing to sales, even ops, all based on the number one ranked business data. It's the single best way for B2B professionals to find their next customer,

• 2:31Harry Stebbings?

  close their next deal and streamline their operations. Best of all, it's all in one place so your revenue teams can collaborate easily and close deals faster. Customers include enterprises like Snowflake, Workday, PayPal, Unilever, and thousands of startup and growth companies, 30,000 customers and growing. ZoomInfo is making their go-to-market playbook available for free for anyone to try. So if you want to find out how you can use intent data to target key prospects or how to revive a stalled deal by expanding your buying committee outreach, head on over to zoominfo.com/20vc to see for yourself and sign up for a free trial of the ZoomInfo platform.

• 3:15Speaker 02

  You have now arrived at your destination.

• 3:18Harry Stebbings?

  Kevin, I am so excited for this. I have heard so many great things from Maggie, from Kim, from Rainu, but I want to start at the beginning. So hit me, how did you make your way into the world of sales first? Let's start there.

• 3:30Speaker 00

  So I was lucky to join Oracle in the mid 90s and I started in the data center at a technical support role and quickly made my way over to the sales engineering side of the house again at Oracle in the late 90s in their DMD organization, which was a fast-moving, fantastic place to learn.

• 3:48Harry Stebbings?

  I thought it'd be really cool if I started with a quickfire round because you've had some incredible companies where you've been a central part of their sales teams and often led them, Salesforce, Dropbox and Slack. And I thought there's going to be like one or two lessons from each that have really shaped how you think. And so I wanted to delve into each in a quickfire round. So if we take Salesforce, what was the biggest takeaway for you? And how did that shape how you think?

• 4:11Speaker 00

  Salesforce does not get enough credit for being one of the original product-led growth companies. If you look at Salesforce and what Benioff did in the early days, we were one of the First companies to ever allow companies for our potential clients to use a trial at no charge for 30 days. During that trial, the sales team was obsessed with what are the business problems that this customer is trying to solve? How do I could help configure the Salesforce service to help solve those business problems? And it led to incredible conversion rates. The idea that if we're going to put the product in our customers' hands, we got to give them help in terms of how they solve their problems. That was an amazing element of Salesforce and what I just don't think they got enough credit for.

• 4:49Harry Stebbings?

  Let's move to Dropbox. You then spent four years, a little over four years at Dropbox. What was the biggest takeaway for you from your time there? And how did it shape your mindset?

• 4:57Speaker 00

  My biggest takeaway from Dropbox was the importance of getting it right. How do we provide a product that end users really love, but that large enterprises can trust from a security and operations standpoint? So the balance between end user love and enterprise security posture is a really difficult one to strike. And I think Dropbox was one of the first companies to go from a B to C company into the B to B realm and really work hard to get the enterprise posture, the security and controls right, which is no small task. And it's somewhat of an unsexy pursuit, but it's much necessary in order for large companies to trust you and to bring you in and allow you to expand within their domain.

• 5:32Harry Stebbings?

  I mean, we're going to dive into that later. I'm going to pepper you with questions. Slack, such a hyper growth story that you're the core and central to. What was your biggest takeaway from your time at Slack? And how did that impact your mindset?

• 5:44Speaker 00

  If you think about Slack, the power of Slack comes, the bigger the team and the more employees you can get engaged on that platform, the more value they drive to their customers. So Slack from day one had an appetite to work with large teams and large customers, yet they had an incredibly engaging platform. So that ability to marry end user love with the enterprise posture right out of the gates, focus on large teams and all the security controls that were necessary there was something that was truly unique at the time and very enjoyable. It led to, as you said, hyper growth.

• 6:16Harry Stebbings?

  Now, I do want to start at the core crux of a lot of the discussions I have with founders, which is the sales playbook. And I just want to get some nomenclature right. How do you define sales playbook, Kevin?

• 6:26Speaker 00

  Well, that's an interesting question, Gary. I don't typically use the word playbook. Playbook to me seems like just a simple one, two, three, and you follow these steps and you're going to close the deal. I think it's more than that. When I think of a playbook, I actually just think of sales motions. I prefer the term sales motions, understanding who is the buyer, what's the user persona that we're selling to? What's the industry that they're in? What are the business problems that they're faced with? And how does our product uniquely solve that problem? Talking in terms of the unique solution to that problem is where I think strong sellers really shine. And not talking about product features, but really the solution that overall would drive a business value. So that's a motion more than it is a one, two, three playbook in my mind.

• 7:08Harry Stebbings?

  So when we think about that motion, is it the founder that needs to be the one who creates the different motions? Or are they able to hire a first sales leader, a first sales hire to create the motions for them?

• 7:20Speaker 00

  I think when you listen to a founder speak to their product and how it solves business problems, it's the job of the sales leader to pull from that and codify it and put it into writing and explain that these are our sales motions. So I think it's the CEO or the founder's job to provide the inspiration and the high level talking points and the kind of the idea matching as they're talking to other executives. But it's the sales VP's job to really nail it.

• 7:44Harry Stebbings?

  If we think about PLG versus enterprise, something that I see a lot of today, founders chasing PLG and enterprise kind of from day one. Can you do both at the same time, do you think, Kevin?

• 7:56Speaker 00

  I think you can, but I think it's extremely difficult. I think Slack was able to do it. I think they nailed PLG first and then enterprise, but they always had an eye towards enterprise. The reason why I say it's extremely difficult is to capture the end user's imagination, capture that end user love is one thing. But to build out the enterprise security set, the feature set and the enterprise posture, all the processes and controls that are necessary to really go big in enterprise takes many, many years. So I think if I had to pick a path, it's probably more sequential. PLG first, gathering that end user love, and then adding on the enterprise layers following that.

• 8:31Harry Stebbings?

  We're going to delve into that. I just have to ask, you mentioned Slack nailing PLG first there and then moving to enterprise. I just chatted to Kim before this show and she said, I have to ask, how did you know it was the right time to move into enterprise when you did with Slack?

• 8:45Speaker 00

  If you're a product that's generating enough end user value and it starts to spread within companies, you're going to get pulled in by those companies to enterprise. And you're going to get to user counts that are so significant, you're going to get on the radar procurement and legal. And they say, this many people are using this product. I want the right turns in place so that I can feel comfortable using the product. So you're going to feel a real pull if you're getting it right and that virality is happening within companies. And I think that's what happened at Slack. They had, in some cases, tens of thousands of users within single companies that said, hey, look, we need to come to the table and operate. You need to operate as more of a strategic partner than a Rome service that my end users love.

• 9:25Harry Stebbings?

  But then we come to that realization, we're getting pulled into enterprise, we're getting pulled into procurement. I think there's a maybe naivety sometimes around what needs to change when you move to enterprise. What are the biggest elements, Kevin, that need to change when you're scaling from a PLG motion to an enterprise motion?

• 9:41Speaker 00

  Well, I think number one is scale and reliability. They need to know that if this becomes business critical, you're going to be providing the SLAs and the 99.99 uptime. There's data geography requirements around data residency. If I'm going to use a service in Japan or if I'm going to use it in Europe, I need to know that you've got local data centers, process controls. You know, they want to know how your engineers control data, who has access to that data, what security protocols you use around that data. They have encryption requirements, data loss prevention requirements. It gets pretty deep, but I think the one thing to emphasize there is that there's no finish line. It's not like as a PLG company, you can dip your toe into enterprise and deliver these three or four features. It's a lifelong pursuit that you need to be in partnership with your customers.

• 10:26Speaker 00

  If you look at today and just the changes in the data requirements around GDPR, like that's a full-time job for somebody to be looking at that and saying, okay, well, how are we running our service and is it compliant in Europe? It's naive to think it's just a few features because in fact it is a lifelong pursuit to make sure that you're staying up with the most stringent requirements that are coming out of enterprises today.

• 10:45Harry Stebbings?

  I totally agree in corn dip your toe in. Those are the quite technical gnarly aspects of what needs to be done. There's also just the actual ability to move there in the first place. When you think about structuring your sales team as well, does the sales team carbon copy from PLG to enterprise? Should we change the structure? Should it be more formal from AE to SDR to you name it? Like, how does the structure of sales teams change when moving from PLG to enterprise?

• 11:13Speaker 00

  Well, I think at first, the sales team is obviously there for revenue growth, but almost even more importantly, providing customer feedback into the product group. Giving the product team that they're working with a sense for why do these people gravitate to this service? What business problem is it solving? How would you down the line translate this into ROI for the end user? Early days is creating a major feedback loop, which you can build that repeatability on. Once you have that repeatability, then you can start to build sales teams that are more traditional with the EDR, core sellers focused on just revenue numbers, supported by sales engineers and so forth.

• 11:48Harry Stebbings?

  Can I answer you a bit of a weird one? But like, when you're doing PLG, you kind of know if sales teams are good. Do you see very quickly the velocity that they close customers? The sales cycles are shorter, it's easier to tell effectiveness. When you're scaling into enterprise, sales cycles are longer, conversations take more time. How do you determine rep effectiveness when moving into enterprise?

• 12:09Speaker 00

  In a PLG world, rep effectiveness, the best companies out there are doing a lot of A B testing. Atlassian is famous for A B testing. What happens if I put this account in the hands of a rep versus my regular online channels? And I'd say the most effective way is that testing.

• 12:26Harry Stebbings?

  Should we test from the start? Should we layer the testing in? When we say like testing, if I'm a founder listening, test with what? A rep versus, what is the alternative to testing? Do you see what I mean? You need to have a.

• 12:38Speaker 00

  If you're doing an A B test, you have your marketing, you have your online channels. You've got chat, you've got your website and you've got your e-commerce engine and so forth. So that's one channel. And then the other would be sales rep handled, where you can kind of measure what they're doing through their activities and sales force and opportunities that are being created. So you simply have a cohort of customers that are managed through the web channels and another cohort that are managed through sales reps. And if you see outsized growth in the ones managed through sales reps, hopefully you do. And that'll tell you that you have strong effectiveness or you're on your way to effective sales channel.

• 13:11Harry Stebbings?

  One way to tell effectiveness is also like when you hire multiple at the same time. You can tell, do you agree with the hiring two or three at the same time? Or actually, do you think that's unnecessary?

• 13:21Speaker 00

  I do favor hiring two to three at a time if you can afford it. That is a great indicator of sales rep effectiveness. And the compares on the reps is very effective and will tell you. Number one, can my reps accelerate? And number two, within my sales rep base, who's really carrying the water up the hill and making it happen?

• 13:38Harry Stebbings?

  If we dive into that hiring process, I heard that you were incredible when it came to identifying talent. How do you structure the hiring process for new sales hires? And if I'm a founder that you've angel invested in, how would you advise me? I've never done it before and I need that help and guidance.

• 13:54Speaker 00

  I think hiring great salespeople is about process and it's about discipline. And when I was at Salesforce, I had the benefit of being a part of a process that came together that we really invested in. As Mark Benioff said, he wanted to see everybody have hiring fatigue. Everybody should be interviewing it all the time, whether it be for a job opening that you have today or one that you might have down the line. To hire well, you really need to put a multi-step process in to get to know the candidate, to get to know how they approach a customer, understand business problems, and then present to those business problems in a differentiated way. No hire that I've made at my past companies have gotten the job until they've presented a mock scenario around a fictitious company and a business problem that they're trying to solve.

• 14:36Speaker 00

  So we really put the rep on the spot, so to speak, to show how they deliver in the moment. We're talking to a customer about how they'll uniquely solve their business problem. By the time a rep gets a job with one of these companies, they should have met with five or six different people in five or six different steps. And that stand and deliver moment, I think, is important and tells you who can really command the conversation.

• 14:55Harry Stebbings?

  Kevin, help me out here. Mock scenario, what does that look like? So one, like often people either give like the mock scenario of the company where the rep's at now or the company that the hire is at, which is kind of biased, I find, in either direction. How do you think about which company that they should like sell against or like sell for? How long do you give them? Who's in that mock scenario meeting? What makes the best ones? Can you just help me understand? That looks like for me.

• 15:22Speaker 00

  Sure. So I could go either way on that. At Salesforce, we gave them a fictitious company, a business set of business problems that they resolve using Salesforce set of solutions. At Slack, we were comfortable with them positioning their own service. And so I think both have their advantages. I just think it's what's important is really to really lay out what the business problems are, how this rep is going to solve them, and how they're going to kind of command the room, so to speak, when they're trying to get over the finish line.

• 15:48Harry Stebbings?

  I struggle with that one. And you're the hailed business leader, so I'm like, you know, being very bold here. But if you have, you know, years at a company, I know back to front how to articulate my business solution. I know back to front every aspect of it. I can pull the wool over your eyes in seconds. If you give me a new company and say you've got 24 hours, sell me this pen. I've really got to think on my feet about different customer personas, different customer needs, how to position that in market competitive. I've really got to show my skill on the spot in real time, like sales leaders need to. Do you not think that actually it's a bit easier if you give them what they already know?

• 16:24Speaker 00

  Good question. I think if they're selling you what they already know, then the audience should be delivering much harder questions and harder objections. I think you can accommodate for that in terms of the tone that you take in that meeting and some of the mock question there.

• 16:39Harry Stebbings?

  What do we think about good versus great? How do the best do in these mock scenarios? And are there any red flags that you look for?

• 16:46Speaker 00

  The most curious part of the interview process is when they get through final interviews, and you're assuming that they're just going to crush the mock scenario. And sometimes they'll just come in and it'll be a flop. And you'll say, wow, I just never saw that coming. And that comes down to what's their comfort level being in front of a room, being in front of an audience that's going to throw up real objections. So sometimes you're surprised. Good versus great comes down to are they consistent throughout the whole process, right? Did they, did they crush the interviews and then just come in with a level of confidence during the mock scenario that just wins you over and makes a ton of sense? I'd say overall, it's consistency. When you start to see inconsistency across the different steps of the process, that's definitely a red flag.

• 17:24Harry Stebbings?

  Does the type of person that you need change, dependent on whether you're running a PLG or an enterprise motion cabin?

• 17:31Speaker 00

  I'm not sure I differentiate so much on enterprise versus PLG. To me, it's a little bit more about the timing of the company. How old is the company and where are they in their journey? Early days of hiring reps, you're going to need renaissance reps that have a very wide breadth of skill sets, who enjoy the building process. And as things go on and you start to scale your sales team, you're going to see reps that are there for, really to make a living and are more concerned with what's the paycheck and what's the quota. That's a different rep. So I think it's, to me, it's a little bit over time. How the reps change, a little bit less PLG versus enterprise. But certainly as you go into enterprise and you've been there longer, that rep that is going to be successful there has more experience and is more focused on what are my set of accounts and how do I crush my number?

• 18:16Harry Stebbings?

  Do you think it's a fair description that sales reps are coin operated? And is that a bad thing even? I hear founders sometimes say, oh, I'm a bit worried about how focused they are on the comp, on the OT, on the bonus. Is that a bad thing?

• 18:30Speaker 00

  Again, going back to diving, it does not pay to have coin operated sales reps in the early days. They're going to be overly focused on quotas and crushing their number to get to a certain outcome. The early days are really about who is creating the best connection between my developing product and my potential customer. But I think in the later years or as you build out your sales organization, well, I don't like the term coin operated. People do become more specialized as you get bigger as a company. And the specialization of the sales rep is to bring in customers and grow revenue and they need to make a living. And so I would be concerned about coin operated early days, but not later.

• 19:05Harry Stebbings?

  I hear a lot of founders say their biggest mistake they made when hiring sales teams was hiring for logos. My question to you is, how do you advise founders on the logo hires? So often I see startups and they go, oh, amazing name from big company, Microsoft, Oracle. And they say that's their big mistake. How do you advise on logo hires and what to look for?

• 19:27Speaker 00

  I could absolutely see where the big logo hire does not work out. I think, again, what you're looking for there is intellectual range and that often doesn't just show up from, by the fact that they worked at Microsoft or came from Google.

• 19:40Harry Stebbings?

  What do you mean by intellectual range, Kevin?

• 19:42Speaker 00

  What I mean by intellectual range is this person, this initial sales leader is going to have a lot on their plate. They're not going to have a big marketing team that they can outsource all of the writing and the messaging to. They're not going to have all the resourcing from product management and so forth. So they're going to need to do a lot of different things. And so they're going to need to have energy and range to do everything from writing to messaging to closing and providing that customer feedback, you know, the voice of the customer back in the product. So that range, as the companies become bigger and more specialized, starts to narrow, if you will. But in early days, it's really about how much stuff are you willing to take on? And that's sort of referred to when I talk about range.

• 20:20Harry Stebbings?

  Can I ask you, Kevin, you've hired some of the best across many different organizations. Comp packages are pretty hard to understand if it's your first time and to know what's good, what's fair. What have been some of your biggest lessons on effective comp package giving when hiring?

• 20:35Speaker 00

  I think when I'm closing a candidate, I'm interested if I'm giving them a fair comp plan, are they really interested in about the long-term journey at this company? Because this comp plan only represents this moment in time for the next year or two. If we're both successful, the company will increase in size, our jobs will be different, our jobs will be bigger. So what, how do they view the, oh, the long-term journey at this company? And are they excited about the company and the journey? Or is it about the comp plan? Sometimes it becomes too much about the comp plan, then that's a red flag. Because it's really about a total rewards element, which is you're joining a rocket ship. You love this job and it's going to really benefit your career overall. That's kind of what I'm looking for, but comp plans certainly need to be fair. If you're not providing a fair comp plan, you can't expect to hire the best.

• 21:16Harry Stebbings?

  One of my favorite mentors says, you're never wrong to do the right thing. And I always think back to that on fairness. Can I ask you though, you know, again, and we mentioned like working with amazing people. Again, spoke to so many that worked with you and they said, once you hired them, you were incredible when it came to trust building. And I wanted to ask you, how do you think about building trust with new hires? And then building trust in you both ways? What works?

• 21:43Speaker 00

  Well, I think on the journey of people joining a company, in the early days, they want to have clear expectations and you as a Leader need to be a little bit more directive on what are the expectations and how are you going to get there? And then as they become competent and ramped up in their job, it's a little bit more of a partnership. And here's what we're going to do. I want to hear more ideas from them on what they see as the next steps for the organization. So it goes from directive to more of a partnership. So I think that's an important element. The job and the manager employee relationship changes over time. So that's one thing I try to focus on.

• 22:17Harry Stebbings?

  How do you retain a sense of hierarchy? I think one thing that I've got wrong, Kevin, as a manager, honestly, I'm young. I tried to be people's friend and I'm not your friend. I am your boss at the end of the day and I know we don't like hierarchies or boss. You are someone's boss and everyone has a boss. How do you retain that hierarchy, but also trust and proximity?

• 22:37Speaker 00

  The term hierarchy is is an interesting one to get buy in from your employees. They need to appreciate their manager is contending with a lot more issues and has more on their plate, which is requiring a certain level of skill set and focus and hard work to get done. As I look at my boss, Cameron, he's got more on his plate than myself. And they need to appreciate that you've got a lot going on. And when you're with them, you're focused on in their world and what's important to them. They need to have a sense for if I was to take your job, here are the four or five things that I would need to ramp up to have a grasp on. If they feel like you're doing the same job as them, then you're in trouble and the hierarchy is going to break down.

• 23:18Speaker 00

  So I think it's about how much work, role and responsibility that we're putting at every level so that people can be their best. And how do we ramp them into the next job and do they have appreciation for that there is a ramp? If they do, then I think hierarchy works and there's an appreciation. Secondly, with hierarchy, I think you're not going to exercise hierarchy every day. But there are moments throughout the year where you had to be very direct with your employees on what the expectations are. If they're not meeting those expectations, you certainly need to. Deliver that when he was in plain speak and they need to know where they stand. So hierarchy also breaks down if the leader is not available or comfortable providing direct feedback.

• 23:57Harry Stebbings?

  I mean, I'm glad you said about direct feedback. I heard that you were very good at providing direct feedback, which again is something that I honestly struggle with. And I like to avoid conflict. What would you advise founders on how to provide effective direct feedback?

• 24:11Speaker 00

  When I think of direct feedback, I think of it in terms of a ratio. So there's the day to day work that we're trying to get done. There's the challenges that we're facing and we should be enjoying those challenges and having fun with it. But there's also times where we need to get better or we have our blinders on and we need to be thinking more broadly. And it's the job of the manager to to break that news, so to speak. But it is a portion of the relationship. It is not a constant feedback loop that's happening every day. It's a moment in time. People kind of sit up a little bit straighter, dust themselves off and off we go. We're back to more of a congenial, fun, working relationship. But again, you can't be afraid to provide that feedback. And I think the employees sense that and they are disappointed when they don't get feedback because it's something that everybody I've worked for is looking for.

• 24:57Harry Stebbings?

  What are the biggest mistakes sales leaders make with feedback?

• 25:00Speaker 00

  When I think of feedback, Liz Wiseman's book Multipliers really nailed it. Is the feedback diminishing and is it overbearing? And is it too frequent? Or is it just the right amount? And is it geared towards the priorities that we're trying to get after? So I think it's about frequency and making sure that it's not personal, but it's about how are we getting after it as a team?

• 25:19Harry Stebbings?

  In terms of how we're getting after it as a team, you need something to get after. How do you think about effective sales forecasting in 2023? A year of such uncertainty.

• 25:27Speaker 00

  In the year 2023, I think sales forecasting has gotten a little more difficult. Everything is on the table. Every company is looking for areas to trim or reasons not to spend. So as a rep or a sales team, you better be crystal clear on the business problem that your solution is solving and why the company would spend money on it and what are they expecting in terms of return? If you don't have those things, you may not have a deal that's forecastable.

• 25:51Harry Stebbings?

  How do you think about CFOs being in every deal now? The deal cycles have changed so significantly in my The buyers have changed so significantly. Everything about the way that we used to sell has changed with the complexity that now is inherent within cycles. Do you agree and how does that change your process?

• 26:08Speaker 00

  I think if the CFO is involved in your deal and they're spending time on that deal, that tells you that you are strategic to them. So your responsibility to respond to that is giving them the financial or the value engineering, as it's called, on the ROI. And that is the job of the sales team to do that. Maybe they have resources in a value engineering team, maybe they don't. But really giving the CFO a crystal clear picture of what's the return. I think if table stakes these days, I welcome it because it tells you that they're willing to lean in and work with his partner.

• 26:38Harry Stebbings?

  Speaking of kind of leaning in and working with you as a partner, when you think about like driving them home to actually closing, how do you think about quite a challenging element, which is balancing hitting quarterly revenue targets with longer term pipeline and sales strategy? How do you think about that balance?

• 26:54Speaker 00

  I think the balance between hitting the quarterly number and building long term pipeline. If it's an early stage company who absolutely needs that deal, you're probably going to need your leadership and executive support as a seller on your side to make it clear in the right tone to the prospect that this is an opportunity that would really help the company at that time. But it needs to be done in a tone that works for the customer. Jamming deals at the end of the quarter is always kind of obnoxious, but it happens and does work. But sometimes there is a detrimental effects to kind of cramming deals at the end of the quarter. So in all this, the best reps are creating ample pipeline throughout the year. They create enough pipeline that they're able to hit their quarterly numbers without doing anything unnatural to get those deals in.

• 27:38Speaker 00

  Because if one falls out, they've got another that comes in. So it's around really generating enough pipeline throughout the year so you don't put yourselves in that position. Now, is that possible every time? Probably not, but for the most part, over the long run, pipeline covers all sins.

• 27:52Harry Stebbings?

  Do you do discounting, my friend?

• 27:54Speaker 00

  We don't discount. We try to work on terms that work for our customer, but everything's programmatic. So if our customers were to speak with any other customer, they know that they're in the same boat and that we're transparent and fair. At other previous employers, yeah, we would discount, but that was something that worked well for both the company and the customer.

• 28:12Harry Stebbings?

  How do you do discounting well? Do you know what I mean? Like if I want to get it over the line, I don't want to seem desperate. I don't want to give away too much. How do I do discounting well? And do I need approvals to do discounting? I'm a rep on your team. Can I give a 20% discount? Can I give a 30% discount? All stages acceptable versus unacceptable.

• 28:29Speaker 00

  Good discounting should originate from the office of the CFO. Meaning the CFO knows the margins. They know what margins are willing to give away on products at what volumes. What should happen in most companies is CFO should provide a discount matrix that the rep might have a few points to give. The ref's manager might have a few more points to give based on volume. And then all the way up to the sales VP. And then at some level, the exception would come from the CFO. So it should be very well organized and it should be with an eye towards what can a company afford to give based on certain volumes. If it's distinct or not tied into CFO's office, then I think you're going to run in circles and have a lot of problems.

• 29:06Harry Stebbings?

  What are the biggest mistakes that you see startups and startup founders make when it comes to discounting?

• 29:11Speaker 00

  For most startups, if you're in with procurement and you're not selling through PLG and through the website and swiping credit cards, so to speak, and you're in with procurement. That procurement agent knows that you're a startup, knows that you are really keen on that revenue and that that revenue matters. And they're going to push you harder than they might other vendors. And what they're looking for is conviction on your side that you believe in the product, that you have an understanding of the business value and the ROI that it's going to provide. And they're looking for you to make a stand. So you'll face more pressure to discount, but I think procurement is looking for you to hold the line.

• 29:45Harry Stebbings?

  If you don't get a deal over the line, you do a deal review or you do deal reviews generally. But I just want to focus on that. How often do you do deal reviews? How do you structure them? Who's invited? Can you walk me through how you do deal reviews?

• 29:59Speaker 00

  A deal review is happening at different frequencies based on where you are in the organization. Sales reps having a deal review with their manager daily. I'm spending two to three hours a week just doing deal reviews. What separates good from great, I think great is organized using medic or med pick or some framework for how do we assess the deal, the people on the deal, the business value, and what are the drivers and how are we going to get across the finish line? And I think the best sales leaders that I've seen run deal reviews aren't so interested in why the deal is going to happen, but they're more focused on why the deal won't happen. So it's the job of the manager to see around the corner or see areas of weakness in that deal plan to really get the team to step up and cover any gaps. So it's about why it's not going to happen. Not all the good news about why it is going to happen.

• 30:42Harry Stebbings?

  Kevin, I'm on many boards and very often they say, ah, it just slipped to next quarter. Just slipped to next quarter. And I never quite know what to say. I'm like, you know, why? And well, we're not really sure. How do you respond when you hear the classic, oh, it slipped to next quarter?

• 30:58Speaker 00

  When I hear it slipped to next quarter, what I'm looking for is, did you commit it to this quarter? And did you tell the company that it was absolutely coming in? And it's actually slipped? Or was it something that you were pursuing that potentially you could pull into this quarter? Those are two very different things. If it was committed to the quarter and did not come in, then if I'm a startup, I would do a full deal review and understand why it didn't come in. And is it something around our pricing and our product? Or is it something around the sales execution? And I would be looking at those different sides of the equation to really dig into, where do I have a problem?

• 31:31Harry Stebbings?

  I do want to move into my favorite though, Kevin, which is a quick fire answer. I say a short statement and then you suggest a wonderful answer in about 60 seconds. So what sales tactics have not changed in the last five years?

• 31:43Speaker 00

  Great writing. Written communication that illustrates grasp of what the business problem is and how you're going to solve it, illustrates the fact that you've got a plan and you can drive according to that plan.

• 31:54Harry Stebbings?

  What sales tactics have died a death?

• 31:56Speaker 00

  The sales tactics that have died a death are really around withholding information. When I started at Oracle to get a white paper, you had to email the sales rep and to get any technical documentation and so forth. Over time, that has changed dramatically. So withholding information has died a death. I think transparency across the board is. The new normal.

• 32:15Harry Stebbings?

  What one piece of advice would you give to a new sales leader starting a new role? So imagine you the night before you joined Atlassian or Slack as a sales leader. What would you have called yourself up and said?

• 32:27Speaker 00

  I'd call myself and say every environment is different. Watch out for pattern matching from the previous company. Really get to know your peer group and the other side of the equation. That being probably the engineering leadership to understand how they view their product and how their product solves problems. So spending more time with the broader organization and not pattern matching.

• 32:48Harry Stebbings?

  What would you most like to change about the world of sales, Kevin?

• 32:50Speaker 00

  I think that there's an opportunity with AI to use technology to help every sales rep understand the best next step for their customers and to show up with more great idea for their customers. In terms of change, I'd like to see more adoption of AI to help us do that.

• 33:05Harry Stebbings?

  What would you most like to change or what's the hardest element of your role with Atlassian today?

• 33:10Speaker 00

  I think the hardest part of the job at Atlassian right now is helping our customers with an opinionated view on how to make them successful. And I don't think that's different than any other company. Jira has been out there a long time. How are we helping engineering teams at broader companies ship better products faster? And really getting into the weeds with them and providing an opinionated solution on how our services are helping them. I think is a pursuit that we're really turning up the investment on, but something that we're going to work every day to make happen.

• 33:38Harry Stebbings?

  What one company sales strategy, Kevin, final one? Do you most look up to, respect or impressed by recently? Where you literally go, that was a smart sales strategy. Well done.

• 33:48Speaker 00

  I would press by Snowflake from afar. I've not been a buyer of Snowflake technology, but my sense is that that company from the CEO on down has really great alignment and is customer centric. And again, I don't work there, but I think it's probably a pretty intense environment and they're making it happen every day. So that's a company that if you look at the last five years, they've really made hay and the hat's off to them in terms of how much progress they've made.

• 34:10Harry Stebbings?

  Kevin, listen, I've loved doing this. As I said, I had so many good things from Kim, from Rainu, from Maggie. So thank you so much for joining me today and I so appreciate the time.

• 34:19Speaker 00

  Harry, thanks so much for having me.

• 34:22Harry Stebbings?

  Such a great discussion with Kevin there. And if you want to see more from us behind the scenes, of course you can on YouTube with the full video available by searching for 20VC, that's 20 VC. But before we leave you today, you might remember in our amazing episode with Maggie Hott, she mentioned a tool she could not live without called Pocus. What is Pocus? Well, Pocus is a revenue data platform that makes it easy for go-to-market teams to analyse, visualise and action data about their prospects and customers without needing engineers. Pocus helps companies like Miro, Webflow, Loom and Superhuman focus their sales and success teams on the highest priority opportunities by surfacing insights at the right moment so reps can take action quickly.

• 35:03Harry Stebbings?

  Pocus gives you a 360-degree view into product usage, empowering you to act on insights and fill your funnel efficiently. Sales teams save 10-plus hours per week digging through data to surface millions of new revenue opportunities. Learn more about why top PLG businesses trust Pocus as their revenue data platform by visiting pocus.com/demo. And SalesLoft is the leading sales engagement platform, helping sales teams drive more revenue with the modern revenue workspace. It's the one place sales teams can go to prospect, manage active deals and get the insights they need to coach seller performance, forecast with accuracy and find out what steps to take to close more deals.

• 35:44Harry Stebbings?

  Some of the world's leading companies like Google, Shopify and Stripe all love and use SalesLoft and so can you. It's the new way to sell. Find out more at salesloft.com. And finally, finding your next customer is hard, but it doesn't have to be. ZoomInfo is the answer. ZoomInfo handles the full revenue pipeline from marketing to sales, even ops, all based on the number one ranked business data. It's the single best way for B2B professionals to find their next customer, close their next deal and streamline their operations. Best of all, it's all in one place so your revenue teams can collaborate easily and close deals faster. Customers include enterprises like Snowflake, Workday, PayPal, Unilever and thousands of startup and growth companies, 30,000 customers and growing.

• 36:28Harry Stebbings?

  ZoomInfo is making their go-to-market playbook available for free. For anyone to try. So if you want to find out how you can use intent data to target key prospects, or how to revive a stalled deal by expanding your buying committee outreach, head on over to zoominfo.com/20vc to see for yourself and sign up for a free trial of the ZoomInfo platform. Stay tuned for Friday's episode 20 VC we haven't saw a shield moan of co-founder at Better Tomorrow Ventures.