20 Sales: The Ultimate Guide to Sales Onboarding for New Sales Reps and Sales Leaders, The Biggest Red Flags in the First 30 Days & What Can Be Done to Set Them Up for Success with Leaders from Figma, Dropbox, Miro and more.

Oliver Jay (OJ) is one of the most successful sales leaders of the last decade. Most recently, OJ spent 6 years as CRO @ Asana and grew the team from 20 to over 450, becoming a master in sales onboarding in the process. Before Asana, OJ spent 4 years at Dropbox, where OJ was Head of APAC & LATAM. Jordan Van Horn is a Revenue Leader @ Monte Carlo. Prior to this role, Jordan spent 4 years at Segment as VP of Sales, leading a sales team of 50+ Account Executives. Before Segment, Jordan was at Dropbox for 4 years leading enterprise sales for Dropbox Business. Dannie Herzberg is a Partner @ Sequoia Capital and before Sequoia, Dannie spent 4 years at Slack as their Head of Enterprise Sales, growing the business from $100M – $1B in revenue. Before Slack, Dannie spent over 5 years at Hubspot building sales teams. Zhenya Loginov is the CRO @ Miro. At Miro, Zhenya runs the go-to-market team of 700+ people across. Prior to Miro, Zhenya was the COO @ Segment where he built and ran the global go-to-market team of 200+ people. Pre-Segment, Zhenya led a 100-person team at Dropbox across different functional areas. Lauren Schwartz is VP of Enterprise Sales at Fivetran, where she has scaled the team to nearly 100, while more than tripling enterprise revenues. Previously, Lauren spent close to 4 years at Segment where she started as the first female AE and ultimately built and led sales teams in enterprise and growth. Kyle Parrish is VP Sales @ Figma, where he built the sales engine from scratch to today, with over 100 in sales. Before Figma, Kyle spent over 5 years at Dropbox in numerous different roles including Head of Sales, and Global Partnerships lead, responsible for growing Dropbox’s partner ecosystem. In Todays Episode on Sales Onboarding We Discuss: 1.) How should the onboarding process for all new sales reps be structured? 2.) How should the onboarding process for a new sales leader be structured? 3.) What specific things can leaders do to set both reps and leaders best up for success? 4.) What are the single biggest red flags in the first 30 days that a rep is not going to work out? 5.) What tools and software can be used to improve this process of ramping new reps?

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

• 0:00Harry Stebbings?

  This is 20 Sales with me, Harry Stebbings. Now, 20 Sales is the monthly show where we take you inside the minds of the best sales leaders to unpack their tips, tactics and strategies when it comes to scaling the best sales teams in the world. And today, we focus on sales team onboarding, an area where founders universally struggle. What does their first week look like in the role? How do we set them up for success? How do we measure their success? This and so much more in today's episode, and we're joined by the best from the likes of Figma, Notion, Loom, Zoom, Miro and more. And founders, if you have sales reps and you want to get the best out of them from day one, this is for you. Get out the notebook and enjoy this one. But before we dive into the show today, planning sales force capacity and successful quota management can define the trajectory of your business.

• 0:45Harry Stebbings?

  That's why you need Pigment. Pigment is an integrated planning platform that helps sales leaders bridge the gap between strategy and execution by promoting those golden conversations between your sales planning team and the leadership of the reps out in the field. From capacity planning and quota management to accurate territory plans and increased visibility on pipeline health, Pigment's intuitive interface lets you focus on what matters, driving that revenue. Integrate all your sales data, your CRM, HRIS and financial data into a single platform for trackable, predictable success. Introducing an entirely new segment, unsure if your team is even set up for success this quarter?

• 1:25Harry Stebbings?

  Well, with Pigment, you can make changes in minutes and overcome the disruption that moving heads can have on your plans. That's why companies like Figma, Gong, Deliveroo, Carter and more trust Pigment. Visit gopigment.com/20vc to request a demo and grab a free copy of the report. What's more, if you use that link in the next 30 days, the team has promised me they'll run a personalized sales planning audit for you and you will get an exclusive discount on the product. And speaking of incredible products, Salesoft 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

• 2:10Harry Stebbings?

  What steps to take to close more deals? Some of the world's leading companies like IBM, 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, we have to talk about Chargebee. Chargebee is the subscription revenue and billing management platform that streamlines your revenue operations like never before. Chargebee automates the lead to ledger workflow across your revenue stack. So you can dream, deploy and enjoy the breeze while the MRR just keeps rolling in, baby. But don't worry, Chargebee goes so much further beyond just billing. One example, pricing alterations. They allow you the ability to change pricing models with one click. Grandfathering old pricing has never been so easy.

• 2:53Harry Stebbings?

  That and for hundreds of other reasons is why the likes of Freshworks, Opta and Envoy all love and use Chargebee. Head over to chargebee.com and find out more.

• 3:08Speaker 01

  You have now arrived at your destination.

• 3:11Harry Stebbings?

  And kicking us off today, we have Oliver Jay, one of the most successful sales leaders of the last decade. Most recently, OJ spent six years as CRO at Asana and grew the team from less than 20 to over 450. Before Asana, OJ spent four years at Dropbox where he was head of APAC and Latam. So Oliver, as a founder or a sales leader, how do I structure the onboarding for each new sales hire?

• 3:36Speaker 02

  We're talking about like you're still at early stage. So I would do a product first, market second and sales last. Product first, in the beginning, you're not going to have a full-fledged sales team where you have SEs, sales engineers who can handle the technical things. You may not even know what gotchas you have in your, whatever data model your company was built on. In the beginning, I think it's super important that whatever customer-facing people you hire, they have to play that role. They have to go two orders of magnitude deeper on the technical side of the product. Whether it's talking about the security, the infrastructure with like a CISO or CIO, then kind of your future A's. I think in the beginning, it's really important to build that product knowledge. A lot of times, the best way to do that is actually get the team exposed to you.

• 4:20Speaker 02

  Support because the tickets that you get coming in is basically a reflection of what your likely sales obstacles that you're gonna get. So you want to be able to talk about it, understand, number one.

• 4:30Harry Stebbings?

  Just so I get that right. So we put them with product, they sit with product for a week, a day? What sort of level of exposure? Just dumb question.

• 4:37Speaker 02

  I actually say it's less product in the beginning. You start with support because everyone's gonna be filing all your bugs. Then you as a A A go get some answers, understand like not just how we answer it. Go and find the engineer to understand why things are built a certain way. That's how I would actually have it is like figure out what will likely be your most more difficult product questions? And you go find the answers because we don't have a playbook yet.

• 5:02Harry Stebbings?

  Got you. Okay. So then we put them in support. They understand from the tickets and from the knowledge they get from the feedback. Then market, what do we do for market knowledge? How do we educate them there?

• 5:11Speaker 02

  That to me is at this point, probably going through your fundraising deck. Because at this point, you probably don't have a sales pitch. I remember at Asana when I joined it, when I joined Asana, we had 20 million in revenue mainly driven from our self-serve business. And we didn't have a sales deck. So it's very common that you don't. So at that point, you're probably taking your fundraising deck and you're just like educating on like, here are the players. Here's a competition. You're getting your one-on-one that way. Why I think is important to do a market first is I think I want to put the sales stuff last. Because that's the stuff that the team will hone in on forever. It's really hard to like, okay, you're in the middle, you're ramping, you're fully ramped to like, then suddenly come back and be like, let me just educate you on the market.

• 5:50Speaker 02

  Like you just, the absorption is not going to be there. Plus, I actually think that people are, will be higher performers if they actually understand broadly what's happening. What are the drivers? Because you want to educate them, not in terms of like your sales messaging and value articulation yet. But hey, just like, this is why we exist. What's the mission that we're trying to do? That's why.

• 6:07Harry Stebbings?

  And so we've got the kind of first area in customer support and they're in support. Second, they're going through the decks, understanding the market competition. Third being sales, the last component. What is involved in that third component being the sales orientation?

• 6:20Speaker 02

  My guess is if you're hiring your first couple of people, you're shadowing the founder on a couple of conversations. I think absolutely you go. Talk to your top 10 customers and you develop a relationship there. These are probably pretty friendly customers. And really ask like, hey, you can even ask customer like, we haven't written case study yet, but like, how would you quantify the value that we provided to you? You probably have to do that because no one had done that yet. So you basically shadow the founder for a little bit. And then what I knew is like, it culminates for me, absolutely. I want someone to demo the product at the end of whatever onboarding period. This is kind of like a, the equivalent of a PhD defending their thesis. Going in, you're going to present your demo of our product and we are going to actually role play.

• 7:03Speaker 02

  And I invite, it would be like, if I'm the founder, it would be a PM and like the other two, three people you have in the customer facing team. So it's high stakes. You can't even like present to your own team. You forget about customers. It ends up being a good forcing function to wrap up everything that someone has learned. And in that demo, someone plays a role of a, depending on you're buying, right? You're trying to role play. So like someone's like a CISO. Someone's a CIO, someone's the actual champion and you see how they act. And that's basically a certification process.

• 7:31Harry Stebbings?

  How long is this three-stage process number one? And when do we allow these new reps to speak to their first customers?

• 7:38Speaker 02

  I feel like two months is reasonable at this stage. To get to a point where like they're really, really solid with like a great demo. They have acquired all this knowledge. That doesn't mean that they can't talk to customers earlier. If you're a PLG company where you have a reasonable flow of inbound or you're an open source company where you can like start tapping to a community, I think within three weeks, they can start talking to customers. They may not need to be selling because again, I just want to hire some good customer facing people at first. So that in the beginning, they might just be talking to existing customers, just being like checking in. What do you love about the product? What do you only like about the product? What's your issues? It's like get more reps. I do think it's important to get reps, but just because you're talking to customers at that point, doesn't mean you're truly ready yet. So this is the different, one difference between PLG company and non PLG companies.

• 8:21Speaker 02

  You can actually start doing that and it helps with accelerating their ramp.

• 8:25Harry Stebbings?

  I just love the three-step structure that OJ outlines there. Now we're going to move to Jordan Van Horn, Revenue Leader at Monte Carlo. Now prior to this role, Jordan spent four years at Segment as VP of Sales, leading a sales team of over 50 account executives.

• 8:40Speaker 03

  Four segment, Jordan was at Dropbox for four years, including leading enterprise sales for Dropbox Business. What does an ideal onboarding process look like for you with new sales hires and how should we stage it? I always think that onboarding should reflect the stage and maturity of your company. I didn't create a super structured, rigorous onboarding program when we had five employees. Because it's not like you're going to be in this 30 day onboarding season, then you're going to move out. And like, everything's going to be hunky dory. You're walking into like a disaster and you're going to continue to be in a disaster. So you've got to figure it out. Early days, the onboarding was, hey, here's the information that you need. Go figure it out. I ain't got time. And then I'm going to give you a ton of feedback. I'm going to shadow you. I'm going to put time into you, but there's nothing structured.

• 9:20Speaker 03

  That works with like your first couple of sales hires. It needs to work with your first couple of sales hires because that's the reality of the company. Later on, as you're trying to go onboard, like what we're in right now, we're trying to onboard and hire people in the borders of magnitude of 10s and 20s. You have to get really, really disciplined and structured. Okay. What are the things that you need to know? When do you need to know them by? And how do we demonstrate that you've actually known them? We've put together a very rigorous onboarding program that checks off those competencies. And what are the levels associated with those competencies? And how do we know that that person's achieved those levels? I put onboarding at this phase into the hands of those frontline sales managers because it's their job to onboard and enable their people. Someday, when we have a thousand reps, there will be a field enablement or a field productivity function that will own that.

• 10:02Speaker 03

  But in the early days, it's your managers. And I think that's true for every function for what it's worth. It's incumbent on the manager to go spend a third of their time with new hires in the first month. What are the biggest mistakes that managers make onboarding from your perspective, do you think? First one is proximity. They're not close enough to the person's work. And they don't know how to break out whether the person actually has a weakness or they're new. Managers need to get really adept of what are the signals that someone just doesn't know something because they're new? Or what is the, hey, there's like an actual skill gap here. Maybe this person doesn't move fast enough. They struggle to actually like parse out those things. Unfortunately, the best way to solve it is through pattern matching and pattern recognition, but you don't necessarily have a lot of that. What I always say to managers is like, pick out one or two people that you think had the best onboarding.

• 10:44Speaker 03

  Get really disciplined about those two or three things that that person needs to have and know that inside and out and watch that. Like a hawk and support the heck out of them until they get there. And then you should know within 30 days about whether someone's going to be a fit or not.

• 10:55Harry Stebbings?

  Can I ask, what are the biggest or most common red flags you see when someone's not working out? What are the reasons it's obvious early?

• 11:04Speaker 03

  Impact. Everyone can make an impact in 30 days. Now, impact doesn't mean that I'm closing a six-figure deal with like JP Morgan Chase in my first month, but they're actually having an impact. Impact might look like they're on customer calls and they're having an impact on that customer. Or they're looking at the sales process and they're having an impact on that sales process. Or they're raising the bar on the onboarding process and they're getting there faster than the people before them. If you're not seeing that, but you're seeing maybe people are like, oh, I developed 5X pipeline coverage. Or all of these like very soft things that TBD you about whether they're high impacting or I put together like my book strategy. Ain't nobody got time for that. You need to come in, you need to have an impact immediately. And I think that you can tell pretty quickly whether or not someone's like actually jumping in and going in the right direction or they're flailing in the organization.

• 11:48Harry Stebbings?

  My word, that show with Jordan was so much fun. Now I'm very, very excited to move to Danny Hersberg, partner at Sequoia. And before Sequoia, Dannie spent four years at Slack as their head of enterprise sales, growing the business from a hundred million dollars to a billion dollars in revenue. And before Slack, Dannie spent over five years at HubSpot building sales teams. So let's start with sales leader and then move to rep. Fantastic.

• 12:11Speaker 04

  Okay, so month one as a sales leader is about listening and engaging. So a sales leader should go on a customer tour, ideally meeting some of the customers in person. And that person should wonder, where do they work? How does your tool get used in the wild? What do people love? What do they hate? And you are listening, listening, listening, codifying, and then communicating it back to the founder, back to the company. Note to founders, investing in sales should equate to creating a culture of understanding and serving the customer. And this listening tour of a sales leader is step one in that. And then on the rep side, the ideal onboarding, frankly, if I'm a rep onboarding and I would listen to as many recordings as possible of what it sounds like when someone sells.

• 12:55Speaker 04

  And I'm listening for customer engagement, customer questions, common objections.

• 13:00Speaker 04

  Competition come up and then I practice. The faster you dive in, the better. You can't just sit in that listening hole forever as a rep. So find a pool of discarded leads. Maybe the company focuses upmarket, but there's a bunch of SMBs who raise their hands and we don't bother selling to them. Take that pool of SMB leads, start calling them and just practice the discovery. Practice the pitch and that way you start working out the kinks and you show really, really good when a good one lands on your lap or when a good proactive opportunity makes its way into your pipeline.

• 13:28Harry Stebbings?

  You can also on the rep side, in particular with the rise of PLG. I just find reps no longer, they obviously it's not glamorous, but they don't want to do outbound. They don't want to have pavements really getting prospects through the door and just into the funnel in the first place. Everyone wants to do the call and the sell when they're educated and they've reached a certain qualification level. Do you find that in terms of this unwillingness to do outbound now in this rather luxurious world of product led growth and educated customers that we live in?

• 13:54Speaker 04

  Well, remember what we talked about as the number one trait of a 10x seller? They love to sell. Loving to sell does not mean sitting back in your chair and waiting for product qualified inbounds to fall into your lap. Yes, the beauty of being a sales professional at a PLG company is that you get to talk to customers who are already warmed up and teed up and hopefully effusive about the product, but you have to be really proactive. So a good seller within a PLG company is kind of like an extroverted user researcher. So they may have talked to 10 different users on the front lines who are effusive about the product. And then they're synthesizing those user interviews, putting those into some sort of an email that they're going to send up to the CIO

• 14:37Speaker 04

  saying, here's what I've learned about how your company operates. And here's a unique insight that you would have never gotten on your own that I'm serving to you. A carrot for a live conversation together.

• 14:47Harry Stebbings?

  Just in terms of rad flags, when you look at on the rep side and on the leader side for those first one or two months, what would be early signs of rad flag or caution for you that would make you a little bit wary and monitor more closely?

• 14:59Speaker 04

  In a product led growth company, a rep and a leader have to be very well versed in the product because prospects come to you very well versed in the product. They may have been using it for free for months. Years before you talk to them. So signal number one is actually in the interview process. A good candidate will use the product and perhaps deliver some of the interview unprompted by utilizing the product itself, just to show that they know how to geek out in there and that they've taken the time to understand the user journey. Once you're on the other side and red or yellow flags when you're onboarding a new rep or a new leader, it's kind of biased toward action. So I did talk about the listening tour for a leader. And on the leader's side, I would look to see whether they've developed a point of view about what are the one to two things that are most important to deliver on over the

• 15:43Speaker 04

  course of this year and what's their action plan for doing that. And that comes from a combination of learning from the founder during the interview process and hearing from customers directly. If a leader had not gotten in front of a customer, if he or she was sitting in virtual or physical conference rooms for their first two months and wasn't talking to one new customer at minimum every single week, that is a major flag for me about customer orientation and the health of the org that they were going to build. On the seller's side, you want someone who's going to jump in. You don't want someone who's doing research forever and looking for every product signal. You want someone who is diving in, like I was saying earlier, finding some users to interview, some leads to call upon, or manufacturing some proactive outbound opportunities

• 16:25Speaker 04

  and going in headfirst so that they can start working out the kinks and figuring out how to sell this thing.

• 16:29Harry Stebbings?

  I love the breakdown there between rep and leader onboarding. Now I'm very excited to move to Genea Loganov, CRO at Miro. Now at Miro, Genea runs the go-to-market team of over 700 people. Prior to Miro, Genea was the COO at Segment, where he built and ran the global go-to-market team of over 200 people. And pre-Segment, Genea led a 100-person team at Dropbox across many different functional areas. What does that onboarding process look like for this first head of sales?

• 16:57Speaker 05

  So what I try to do for every leadership hire that I make, I try to free up their first months as much as possible. I try to create a situation where they don't need to deliver anything in the first one months. I'm hiring them not for the next six months or 12 months. I'm hiring them for the next five years plus with the company. And I want them to build the foundation of being able to succeed in the company. And for me, that's understand the product, get to meet everybody in the company. Who you will need to work with and ideally you start from people who you will need to work with a year from now, not a month from now. So if you're a head of sales, you don't go and talk to your salesperson first. You go and talk to your head of engineering or key engineering product leaders. Because eventually as a head of sales, you are going to need to work with them for the company to be successful. If you miss the opportunity to build this personal connection in the first months, it's going to be really hard to do when you're six months into the role.

• 17:42Speaker 05

  So the first months, I tried to give them as much kind of direction to learn broadly about the company into seeing sales calls to just ingest everything that the company has built before they joined as possible. So that's step one. And then second, I'd like them to have one low hanging fruit in their area. I'd like them to do like one small project and it needs to be small, that delivers value to if you have sales, you either go and sell. Or you go and solve a particular problem for this small initial sales teams that you may already have. Or you will figure some other thing that people see that you are delivering value. Because as a new person, you also need to get a lot of buy in from the rest of the company that you're actually capable. And by delivering this first low hanging fruit, you get the credibility that allows you to then drive change on a larger scale.

• 18:24Harry Stebbings?

  Okay, so just pausing there, I'm the CEO. Do I say, Shania, you need to go meet the head of product, the head of engineering, da, da, da, and I make it happen? And do I need to give you the low hanging fruit to go get? Or do I drop you in and say, make it happen? Should I expect you to do it or should I give you the guidance?

• 18:41Speaker 05

  I think that like expecting me to do it, expecting your first sales hire to do it, it only makes sense if you're trying to test them more. But you've just interviewed them, you should have tested them to the extent that possible before they joined. I think after they join the company, it's your mutual job to make them successful. It's their job and it's your job. And if you have any ability to help them, do it. Go and reduce them to your board members, to your people who are their peers, sit down with them for like four hours, walk them through the intricacies of the product. I think investing as a hiring manager, as the CEO, as a founder, you need to invest a lot in your hires, especially in the first months to then see the investments fade back in the next several years.

• 19:17Harry Stebbings?

  This head of sales hire, one of the biggest signs in the first three months that I've fucked up this hire.

• 19:23Speaker 05

  If you don't see any results delivered in the first three months, if you see the person sitting and freaking out. One gold strategy and drawing charts and not meeting customers and not delivering any value for the early sales team in the first three months. That's a big red flag for me. So when we had new exec team or new leadership team members join segment and they asked how am I successful in this company, like the biggest beginning of the answer was you need to start delivering value on your month's number two or number three. And you need to ship something. So it's a small company. There's no time to wait and build plans. You need to deliver fast. You have this maybe beginning one months to or you are invested in, but then you need to start paying back big, quick.

• 20:03Speaker 05

  So I think that's the first one. The second one for me, which I've seen a couple of times was when your initial team starts to reject the person you just hired. You maybe have five salespeople and you're now hiring, they have sales or maybe you have, you know, customer success folks or somebody else. And on months two or months three, somebody from the team comes to you and says, I didn't know about this new guy. And your job as the CEO is actually to make sure that you go and practically ask them, ask all of your team members, how do they feel about the new hire? What is the value that the new hire is delivering already? How is the new hire helping them up level and do better in their job? If you're not getting a clear like, oh, this is awesome. We get so much value. We like the person so much. You need to dig deeper and figure out, can you enable this person to be more successful or do you need to part ways?

• 20:46Speaker 05

  So I've seen a lot of like early rejection and oftentimes it's not the quality of the candidate. Sometimes it's the approach that they take. I had an example of one hire who got significant kind of rejection after the first three months. But then when we sat down and resolved it and the person talked to the team, they are now much loved by their team.

• 21:03Harry Stebbings?

  Now moving from one segment alum to another, I'm thrilled to welcome Lauren Schwartz, VP of Enterprise Sales at Five Term, where she scaled the team to nearly a hundred while more than tripling enterprise revenues. Before Five Term, Lauren spent close to four years at Segment where she worked with Genia and was also the first female AE and ultimately built and led sales teams in enterprise and growth. How do we do onboarding? They turn up on day one? What now? What do we give them?

• 21:28Speaker 06

  Are we talking about first sales rep or just anyone that we're onboarding?

• 21:31Harry Stebbings?

  First and second sales rep.

• 21:33Speaker 06

  I was talking earlier about how valuable it was for me when I started at Segment to be getting those at bats. It helped accelerate my ramp. I think the most important thing you can do when you're starting your sales role is getting exposure to customers. So whether it's listening to recorded calls, whether it's joining the founder or the hiring manager on sales calls, taking a call that a BDR would normally take, so we can just get some at bats to get someone ramped, is something that I did back at Segment. It really helps because it's like lower risk, right? You don't want a new hire to take that call with First Republic. That's not the time when you're hiring people in enterprise. It's tough because it's like few and far between opportunities and each of those at bats in a long enterprise sales cycle is actually

• 22:13Speaker 06

  very high impact, high leverage. And so the onboarding process needs to be driven by three things. One is exposure to customers. They can really understand the impact and the value that we're having with customers. Two is exposure to what has worked and what hasn't worked so far.

• 22:30Harry Stebbings?

  What's right for us there? Because you're the sales leader. Have we recorded all of our sales calls? Do we have like deal review papers that they can go through? What materials can we give them to make sure that their ramp is easier?

• 22:41Speaker 06

  Yeah, recorded sales calls, having like a library of recorded calls is really valuable as people ramp. And then just capturing postmortems, lessons that we learned from a win, lessons that we learned from a loss. I'm really big on running deal reviews and making sure that we capture learnings that we can then amplify when people are joining the organization.

• 23:00Harry Stebbings?

  Okay, so we have talking to customers. We have the library of resources. When do we actually let them speak to customers? Because like day one, we can't let them speak to customers. They have to listen to like recorded calls, read the decks that we have from fundraises. Is it like two weeks in? Or is it like three months in? This is enterprise.

• 23:17Speaker 06

  You will have some of those early customers that are more than happy to talk with new hires, right? In terms of like a specific period of time. It really just depends on how quickly they ramp. So in a past life, we did practicing with the pitch and then you would go through a certification. Right now at Viprane, we have like a full 90 day plan of onboarding where you come in and you have like very structured. These are the things you're learning about the company. This is what you're learning about our pitch. This is what you're learning about our customers, our value drivers, et cetera. And then just depending on how quickly you can ramp up, we get you out in the wet.

• 23:50Harry Stebbings?

  I mean, if you don't know how to do onboarding after this show, I think it's a no hope case. Honestly, I've learned so much in this episode. So time for our final guest, Carl Parish, VP of Sales at Figma, where he built the sales engine from scratch to today with over 100 in sales. Now, before Figma, Carl spent over five years at Dropbox in numerous different roles, including Head of Sales and Global Partnerships Lead, responsible for growing Dropbox's partner ecosystem.

• 24:17Speaker 07

  Yeah, so what I'll say is when I joined Figma, for example, there was nobody in a customer facing role. And so I'm Sales Enablement, Sales Operations, Sales Finance, and I'm all of those things bad or mediocre at best. Because you just have to be, those roles and those functions don't exist. You gotta get things off the ground to prove you can bring in resources, additional headcount and other experts that know that area a bunch better than you do. So my happiest day is when we hired a Sales Ops Leader and then we hired someone to lead Enablement. And so I think early on, Enablement is about getting the team together and bonding as much as you can. So you've got a motion, it could be with one or two people, and you're trying a bunch of different things to see what sticks at the wall. You don't have a playbook, it's not sitting in some, you know, document in your knowledge base yet. You're literally defining it as you go.

• 25:02Speaker 07

  And so I think today, virtually, when I was at Figma, it was still primarily an in-office culture. But it was like, how can we keep everyone on the same page? And I don't want to create a meeting culture where we're meeting, you know, every other day. But we had a lot of meetings and some of them had structure and were formal. Others were like, what are you seeing out there? Like, we're trailblazers, we're learning this as we go. So early on, shout out as many calls as you can. Here's all the documentation I have access to. Here's how we think about the space, like let's talk about Figma, design, our competition, as previously mentioned, where we're going in terms of product roadmap, some of the history around design tooling and how we got. In this place. And then from a sales perspective, I was sitting in on a ton of calls, giving feedback. I mean, that's just like the nature of like the experience because even if you're a really good salesperson,

• 25:45Speaker 07

  you've never sold this product. And so I think how we communicate, how we ask questions, how we understand a new persona. For us, most people coming in, selling to design is a brand new persona. So the onboarding was a lot of kind of constant recollecting of what we were seeing out in the field, absorbing resources, spending time, learning, watching, listening. And then once you hit go mode as a sales rep, it's about that growth mindset and continuing to incorporate these things. But early on, I feel like it was a lot of kind of sidelining. You're on the bench, you're watching the players on the court play for only a couple of weeks. But that's the best thing for the business and for the customer in a lot of cases. Because if you put someone on the phone four days into the job, it's not a good look if they're not prepared. And it's, and it's not a good feeling if you're brand new to the job and you feel like, I gotta go get my first sale five days in.

• 26:28Speaker 07

  Like, we're hiring people to be here for the long haul. This isn't a flash in the pan, so we want you to be successful and consistently successful. Of course, ramp is something you continue to calculate and get better at over time. But early on, it was like, let's make sure that you are completely dialed in on our customer, our brand, the product, the space, and how to sell it effectively. And a lot of that starts with really good discovery.

• 26:49Harry Stebbings?

  Three months in, we have a review. We see good, we see bad. What do you want them to have done three months in when you're looking at that review? Initially, imagine this is a one-to-one feedback review. You're reviewing me as my manager. Like, Harry, I want you to have done this. And what are red flags that you see?

• 27:04Speaker 07

  Yeah. So by then, if you have baseline metrics in terms of number of discovery calls, so like initial call to customer that you expect, pipeline that you've been adding, and hopefully, at least at Figma, by three months, you've been closing deals, you've been bringing on revenue. And so we've got a body of work to review and we have some data to see how are you performing week over week? There's going to be some weeks where people don't hit their targets. But in aggregate, if you're tracking on a quarterly basis to your pipeline goal, of course, like revenue targets, that's all that matters. And so digging in, understanding both quantitatively and qualitatively, what is this person doing well? I think in early stage, you get a lot of feedback too that isn't just sales. It goes back to being very cross-functional. I'm hearing things from engineering. I'm hearing things from our designer advocates who work really close to customers and help us demonstrate and spread the value.

• 27:49Speaker 07

  And so I got all of these different pieces of information on top of the data, on top of me sitting on calls. And so my goal is just to give them direction, something tangible to work on, and ultimately keep them motivated and excited about like where we're going.

• 28:04Harry Stebbings?

  I have to say, I really learned so much from these compilation episodes. I'd love your thoughts and feedback. Let me know on Twitter @HarryStebbing or you can email me [email protected]. But before we leave you today. Planning sales force capacity and successful quota management can define the trajectory of your business. That's why you need Pigment. Pigment is an integrated planning platform that helps sales leaders bridge the gap between strategy and execution by promoting those golden conversations between your sales planning team and the leadership of the reps out in the field. From capacity planning and quota management to accurate territory plans and increased visibility on pipeline health, Pigment's intuitive interface lets you focus on what matters: driving that revenue.

• 28:48Harry Stebbings?

  Integrate all your sales data, your CRM, HRIS and financial data into a single platform for trackable, predictable success. Introduce an entirely new segment unsure if your team is even set up for success this quarter. Well, with Pigment, you can make changes in minutes and overcome the disruption that moving heads can have on your plans. That's why companies like Figma, Gong, Deliveroo, Carter and more trust Pigment. Visit gopigment.com/20vc to request a demo and grab a free copy of the report. What's more, if you use that link in the next 30 days, the team has promised me they'll run a personalized sales planning audit for you and you will get an exclusive discount on the product. And speaking of incredible products, SalesLoft is the leading sales engagement platform,

• 29:32Harry Stebbings?

  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. Some of the world's leading companies like IBM, 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, we have to talk about ChargeB. ChargeB is the subscription revenue and billing management platform that streamlines your revenue operations like never before. ChargeB automates the lead to ledger workflow across your revenue stack so you can dream, deploy and enjoy. Enjoy the breeze while the MRR just keeps rolling in baby.

• 30:17Harry Stebbings?

  But don't worry, Chargebee goes so much further beyond just billing. One example, pricing alterations. They allow you the ability to change pricing models with one click. Grandfathering old pricing has never been so easy. That and for hundreds of other reasons is why the likes of Freshworks, Okta and Envoy all love and use Chargebee. Head over to chargebee.com and find out more. As always, I so appreciate all your support and I cannot wait to beam you an incredible episode on Friday with the rising star in venture.