The Exchanges

Q Final one for you, my friend. What one company sales strategy, culture do you, have you been most impressed by? Do you look up to? What would that be, that one other company, obviously outside of Figma?

A Oh man, that's a good question. I think one that I have a lot of respect for is Slack. I think their, Stuart's notorious for saying, oh, we're not going to build a sales team, right, early on. I think he even said that much on your show. And then what they did in a relatively short amount of time, they built A really impressive sales org. And of course had an amazing, you know, exit and outcome. A former boss of mine went over there to lead VP of sales and we've interviewed and hired a couple people there. And I talked to a lot of leaders that came from Slack. And I think that of the past few years, it's one of the companies that in that PLG group as well, which, which is what my background is and what Figma represents. I look up to Slack a lot. I think that a really, really strong culture, not in terms of just the people, customer expectations, But also results. You know, they were wildly successful, and so I hope that Figma can maybe even dethrone them in terms of not only culture, but results, but only time will tell.

AI assessment note: “I think one that I have a lot of respect for is Slack.”

Q Can I ask, sorry, I'm dumb. What would be an example of that?

A So, you know, for example, one thing is like, how do you set up your day? So if you're an AE, you could have sales development support. You could not have sales development support, but prospecting is one of those things that in an IC role as a salesperson can easily fall off the calendar. You can put all the fake blocks you want in the calendar. Oh, Kyle's going to go prospect for four hours this Friday. You know, you have a big Thursday night that falls off the calendar. You're catching up on emails, getting dopamine hits, checking slack, whatever it may be. But the best sales reps, they treat that as like a customer meeting. Right. I'm going to show up to that prospecting block at nine 30 at 10 o'clock. I'm going to put the hours in. I'm also going to come prepared. So I don't spend the 1:30 minutes saying, who am I going to go after? What message am I going to send? How am I going to email them? They've already done that preparation the day before whenever that time is. So that when they actually get into that block, it's straight output. And those people know, and they work with their managers and their leaders to come with this model that says, if I know that I'm reaching the right people, With the right message. And I touch, you know, X number of contacts or accounts over this four hour period, I can reliably generate this much pipeline. And so that's like one thing wher…

AI assessment note: “for example, one thing is like, how do you set up your day?”

Q I'm sure the stock options didn't make a difference if you joined a couple of years. Don't worry about it, my friend. I do want to start, though, with the core question that I always have, which is fundamentally, does the founder need to be the person who creates the first sales playbook, or can you outsource that to a head of sales or a sales rep? Help me, Kyle.

A Yeah, it's a good question. When I think of playbook, I think of something that's repeatable. It's codified across a number of salespeople as you start to build the sales org. So I don't think that it's a bad thing if the CEO wants to be involved in kind of shaping the framework for that playbook. I think it's a good thing to be involved, but does the CEO need to build the playbook? I don't think that's the best idea. I think that some of the best companies that I've seen, the CEO is very involved early on in selling those first deals. Understanding what's landing with customers. What pains are we uncovering? What is the narrative of like where we're going? You know, what is our story? What is our mission? Why should I give a Dan about what this company is doing? And so that passion, that conviction, and you know, the technical aptitude and exposure in terms of like what you're trying to do and go build. I think it's critical in getting whatever your first 500 K, your first two million ARR. I think it differs based on a company, but when you start thinking about even the concept of let's go build

AI assessment note: “does the CEO need to build the playbook? I don't think that's the best idea.”

Q If we double-click on that, then, when you are interviewing reps today, and thinking about our teams, What questions do you ask? What case studies do you give to determine that sales rep efficiency and that inquisitiveness to just be better and be more efficient?

A Yeah. Well, I think one thing that I always like to just ask is what have you learned in this role over the past couple of years? Like what is, you know, the playbook that you're taking away as a rep? I think we always talk about leaders and people building teams and orgs about, Hey, what is your playbook? But every good sales rep, they develop a playbook at that company, at that role. When they're hyper successful, it's not a fluke. They're extremely prepared, extremely diligent, of course motivated, but they have found what that playbook is, and of course it evolves as the business matures and changes, but I think the really best sales reps can tell you exactly what their secret sauce was, what they learned to drive success, not as a fluke, not one quarter, not one sales year, but consistently, time and time again.

AI assessment note: “one thing that I always like to just ask is what have you learned”

Q So I totally understand that perspective, but then the next logical question is, okay, do I hire a head of sales who will bring the team with them, or do I hire the reps and then layer on a head of sales in a year's time? How do you think about that? Head of sales or rep first approach?

A Yeah, very good question, and something I hear often from founders. I think that it really does depend. I think if you have hit some level of product market fit, you're seeing traction. You know that there is a market to go grab, and it's a speed game. And like, we need to go do it fast. And you're like, I think that we can support having five salespeople, even, you know, three salespeople, some number of salespeople where it's not just, Hey, let's hire one Renaissance rep, have them, you know, run down 500 yards, bring back some Intel, tell us what's working, what's not. And then, you know, we'll iterate and improve when you've got some conviction that, Hey, this is a motion that's going to require a sales team. I know that we've got capacity to hire at least let's call it three salespeople go and get That head of sales, go and get that frontline sales manager. Because I think that what I've seen again is when founders kind of give that away, staying close to it, staying very involved, of course, managing that person, they just see so much come to life in terms of someone who's built their career thus far in selling and leading and building sales teams and sales orgs, and just having experience. Most founders that come in, they don't have experience in building or growing sales teams. And the CEO gets to hand off a huge And I don't mean to say this negatively, but just like th…

AI assessment note: “capacity to hire at least let's call it three salespeople go and get That head of sales”

Q Can I ask, sorry, I'm dumb. What would be an example of that?

A So, you know, for example, one thing is like, how do you set up your day? So if you're an AE, you could have sales development support. You could not have sales development support, but prospecting is one of those things that in an IC role as a salesperson can easily fall off the calendar. You can put all the fake blocks you want in the calendar. Oh, Kyle's going to go prospect for four hours this Friday. You know, you have a big Thursday night that falls off the calendar. You're catching up on emails, getting dopamine hits, checking slack, whatever it may be. But the best sales reps, they treat that as like a customer meeting. Right. I'm going to show up to that prospecting block at nine 30 at 10 o'clock. I'm going to put the hours in. I'm also going to come prepared. So I don't spend the 1:30 minutes saying, who am I going to go after? What message am I going to send? How am I going to email them? They've already done that preparation the day before whenever that time is. So that when they actually get into that block, it's straight output. And those people know, and they work with their managers and their leaders to come with this model that says, if I know that I'm reaching the right people, With the right message. And I touch, you know, X number of contacts or accounts over this four hour period, I can reliably generate this much pipeline. And so that's like one thing wher…

AI assessment note: “one thing is like, how do you set up your day?”

Q What one piece of advice would you give to a new sales leader today, starting at a new company or starting in a new role, more importantly?

A It's a good question. I think come in and ask questions. The thing I've seen time and time again of sales leaders across my career, they come in, they say all the right things. Oh, I'm not going to copy the Playbook from blah, blah, blah, but then they don't ask questions and they just make a, you know, they have this like direction they're heading in and they're just bulldozing towards it. It's like what I've learned is sometimes this job is three steps back, one step forward, five steps back, 10 steps forward. It's not this directional line that we're just marching on. So ask questions, learn, and be open to adapting. Everything's changing in the world. I didn't plan to be a hybrid remote sales leader, but that's what I became. And that's what many people became. So ask questions, come in, challenge, And being open to trying something new because the market and the world is just changing so rapidly.

AI assessment note: “I think come in and ask questions.”

Q It is so good to chat again, but I want to start with a little on you and some context. You know, now obviously running sales at Figma, it's an incredible position, but how did you make your way into the world of tech and startups and really leading some of the world's most powerful sales orgs?

A Yeah, thank you, Harry. So I think not traditional, which I guess you probably get from a lot of people, but my background grew up In Southern California, in Long Beach, 30 minutes south of Los Angeles. Ended up going to school for finance out in Arizona and was a good student. I wouldn't say I was the best student, but, you know, I had good grade and the, you know, mid three to four GPA. I don't know if that's how you do it out in the UK, but when I graduated, I was a finance major, and I was starting to interview with companies and looking into analyst jobs. I'd always kind of enjoyed math growing up and was going to pursue this traditional finance path, but I graduated in I don't know if you remember that time, if you were in the workforce quite yet, maybe not, but the world was kind of ending, and it sure felt that way in the U.S., and so I actually got pretty close to getting this full-time position with Morgan Stanley, and then they pulled all offers, all of the financial opportunities were off the table, and so what did I do? A group of my four best friends in college and I went to India and Southeast Asia and actually up the coast of China and backpacks, you know, sleeping in airports, not much money to our name at all. It was not glamorous, but a lot of great memories came from From that trip. When I came back, I was actually living with my parents for a handful of mon…

AI assessment note: “I ended up getting a job, moving to San Francisco”

Q I'm sure the stock options didn't make a difference if you joined a couple of years. Don't worry about it, my friend. I do want to start, though, with the core question that I always have, which is fundamentally, does the founder need to be the person who creates the first sales playbook, or can you outsource that to a head of sales or a sales rep? Help me, Kyle.

A Yeah, it's a good question. When I think of playbook, I think of something that's repeatable. It's codified across a number of salespeople as you start to build the sales org. So I don't think that it's a bad thing if the CEO wants to be involved in kind of shaping the framework for that playbook. I think it's a good thing to be involved, but does the CEO need to build the playbook? I don't think that's the best idea. I think that some of the best companies that I've seen, the CEO is very involved early on in selling those first deals. Understanding what's landing with customers. What pains are we uncovering? What is the narrative of like where we're going? You know, what is our story? What is our mission? Why should I give a Dan about what this company is doing? And so that passion, that conviction, and you know, the technical aptitude and exposure in terms of like what you're trying to do and go build. I think it's critical in getting whatever your first 500 K, your first two million ARR. I think it differs based on a company, but when you start thinking about even the concept of let's go build

AI assessment note: “does the CEO need to build the playbook? I don't think that's the best idea.”

Q 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? Literally, 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?

A Yeah, so, By then, we've had baseline metrics in terms of number of discovery calls, so like initial call with the 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 how 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 with customers and help us demonstrate and spread the value. 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 Keep them motivated and excited about like where we're going. I think I connected you a long time with Natalie or the first salesperson we hired at Figma. And she'd only worked in large compa…

AI assessment note: “baseline metrics in terms of number of discovery calls... pipeline that you've been adding”

Q So I totally understand that perspective, but then the next logical question is, okay, do I hire a head of sales who will bring the team with them, or do I hire the reps and then layer on a head of sales in a year's time? How do you think about that? Head of sales or rep first approach?

A Yeah, very good question, and something I hear often from founders. I think that it really does depend. I think if you have hit some level of product market fit, you're seeing traction. You know that there is a market to go grab, and it's a speed game. And like, we need to go do it fast. And you're like, I think that we can support having five salespeople, even, you know, three salespeople, some number of salespeople where it's not just, Hey, let's hire one Renaissance rep, have them, you know, run down 500 yards, bring back some Intel, tell us what's working, what's not. And then, you know, we'll iterate and improve when you've got some conviction that, Hey, this is a motion that's going to require a sales team. I know that we've got capacity to hire at least let's call it three salespeople go and get That head of sales, go and get that frontline sales manager. Because I think that what I've seen again is when founders kind of give that away, staying close to it, staying very involved, of course, managing that person, they just see so much come to life in terms of someone who's built their career thus far in selling and leading and building sales teams and sales orgs, and just having experience. Most founders that come in, they don't have experience in building or growing sales teams. And the CEO gets to hand off a huge And I don't mean to say this negatively, but just like th…

AI assessment note: “go and get That head of sales, go and get that frontline sales manager”

Q It is so good to chat again, but I want to start with a little on you and some context. You know, now obviously running sales at Figma, it's an incredible position, but how did you make your way into the world of tech and startups and really leading some of the world's most powerful sales orgs?

A Yeah, thank you, Harry. So I think not traditional, which I guess you probably get from a lot of people, but my background grew up In Southern California, in Long Beach, 30 minutes south of Los Angeles. Ended up going to school for finance out in Arizona and was a good student. I wouldn't say I was the best student, but, you know, I had good grade and the, you know, mid three to four GPA. I don't know if that's how you do it out in the UK, but when I graduated, I was a finance major, and I was starting to interview with companies and looking into analyst jobs. I'd always kind of enjoyed math growing up and was going to pursue this traditional finance path, but I graduated in I don't know if you remember that time, if you were in the workforce quite yet, maybe not, but the world was kind of ending, and it sure felt that way in the U.S., and so I actually got pretty close to getting this full-time position with Morgan Stanley, and then they pulled all offers, all of the financial opportunities were off the table, and so what did I do? A group of my four best friends in college and I went to India and Southeast Asia and actually up the coast of China and backpacks, you know, sleeping in airports, not much money to our name at all. It was not glamorous, but a lot of great memories came from From that trip. When I came back, I was actually living with my parents for a handful of mon…

AI assessment note: “A good friend who'd went to school at Berkeley had gotten a job with ADP”

Q If we double-click on that, then, when you are interviewing reps today, and thinking about our teams, What questions do you ask? What case studies do you give to determine that sales rep efficiency and that inquisitiveness to just be better and be more efficient?

A Yeah. Well, I think one thing that I always like to just ask is what have you learned in this role over the past couple of years? Like what is, you know, the playbook that you're taking away as a rep? I think we always talk about leaders and people building teams and orgs about, Hey, what is your playbook? But every good sales rep, they develop a playbook at that company, at that role. When they're hyper successful, it's not a fluke. They're extremely prepared, extremely diligent, of course motivated, but they have found what that playbook is, and of course it evolves as the business matures and changes, but I think the really best sales reps can tell you exactly what their secret sauce was, what they learned to drive success, not as a fluke, not one quarter, not one sales year, but consistently, time and time again.

AI assessment note: “what have you learned in this role over the past couple of years?”

Q we find this candidate, we've gone through their calendar, we've asked them what they've learned. We're like, yeah, this is great. How do you structure a hiring process? Do you hire after one Zoom call? Do you hire after two? Where's the case study? How do you literally do it? How many meetings do Does it take to hire? When do you do certain things? What does that look like?

A Yeah, good question, and this is relevant. I think, again, just like the business changes and the role changes, how you hire and thinking about the candidate experience and then just what's happening in the world right now, it's all coming into play for us at Figma. So we're trying to think about the candidate experience being a positive one, even if you don't get the job. You know, you go and tell your friends, hey, this company is doing big things, and the people were great. All the leaders and the peers that I met on the slate were great. The second part is, like, you want to be efficient, both in terms of your team's time You have reps and managers joining on these interviews. You have directors and VPs and, you know, occasionally CEOs and the rest of the C-suite joining in on these interviews. You're not going to hire every person you meet. That's just not realistic, but can we be efficient? Can we make the best use of both our time internally, but of course the candidates time as well. And the last thing I think is just focus. We have things that we want to measure for. We got a methodology and a process to this. And so how do we know that we're testing for the right things? And we're doing so in a way that hopefully is somewhat enjoyable for the candidates. So for us, what that looks like is you've got a fit screen with the recruiter. Then that goes well. After a while, …

AI assessment note: “So for us, what that looks like is you've got a fit screen with the recruiter.”

Q You said there about kind of their communication with different parts of the org. I do want to get to the post-hire. You know, we've been through that process now. When we think about, say, the first month or two, what's the ideal onboarding process for new reps? How should I stage it? How do you stage it?

A 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 got to get things off the ground to prove you can bring in resources and additional headcount and other experts that know that area much, much 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 emotion that 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 and your knowledge base yet. You're literally defining it as you go. 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, shadow as man…

AI assessment note: “early on, shadow as many calls as you can. Here's all the documentation”

Q but, uh, let's roll with this. And we've decided the rep, but we're going back a bit, but the rep first approach, we know that's the right approach. I need to hire them now. When you were hiring and when you were advising me, what are the non-obvious characteristics, attitudes of the best sales reps? What did you and number one and two at ADP have? So the other three

A Yeah, no, it's a good question. This is something that the former COO at Dropbox kind of mentions when he talks about hiring me, and I don't remember it because I kind of, you know, the interview was intense, and you get out of those things, you're like, what happened? I asked him this question. I go, why did you hire me in that interview? You know, what stood out? I was at ADP, this huge corporate company selling payroll and HR services, and I come to this cloud storage company with forty-something employees looking to get a job here, and when he talked about, like, the leaderboard and what made people successful, and he asked me, why aren't you Number one. And my answer was like, these people that are number one and number two have been here for 10 years. They're lifers at this company and organization. And so I think what allowed me to be successful was tenacity, work ethic, and just always looking to get a little bit better. I would see little parts of every rep around me, things that they did well, things I heard on the phone, prospecting strategies, how to think about customer meetings once you actually set up the meetings. And I would have just tried and always Be genuine to who I was as an individual, what my sales style was, and incorporate that, and so keeping that growth mindset so that I could just get marginally better every day, every week, and I got to the point …

AI assessment note: “what allowed me to be successful was tenacity, work ethic, and just always looking”

Q I love that. Can I ask if it's potentially not working, how long do you give someone and what are the core signs that it's not working? Is it just that they haven't closed deals? What are the other signs that it's not working and you should be worried and how long do you give them?

A Yeah. So I think, you know, some of the canary in the coal mines are definitely just conversion rates early on. Say for example, you're doing a bunch of initial calls with Customers, but you're just converting at a much lower rate. That would be an indicator to me or someone on the management team that there's something going on here. So call recording software is big. Joining calls to shadow. I think sometimes that can feel a little having your manager on all the calls, both for the customer and the rep, of course. But I think with the call recording software, it's really nice because you can go and review. All right. So is he setting the agenda? Is he asking a lot of questions? Like what can we learn from that experience? I think that's really critical. And I think the other part is you start to see at a hyper growth company, can they move Fast enough. There's, of course, the sales skills. Are they good at the job? Are they putting in the work? Is conversion there? And then it's about speed. Can you be efficient? You can't take two hours every day to close out. You know, there's a bunch of clicks you got to do in these jobs. Convert this league, create an opportunity, put notes for your manager, do all these things. We don't do that just to, you know, for management sanity. It's for the entire organization. If Dylan wants to jump in Salesforce, which I don't think he does oft…

AI assessment note: “some of the canary in the coal mines are definitely just conversion rates early on”

Q Say you lose a big account. Do you do postmortems, and how do you structure them?

A We do, and we do lose accounts, so don't, you know, let me get off the topic here by saying this. We need to do more postmortems, but we do a lot of, Deal reviews. So we've got a biweekly deal review where we have a couple reps from all segments all the way to our strategic account segment down to mid market. And we're actually soon launching SMB, but we do deal reviews and we have kind of an outline that they follow and they bring it and they come and they talk with, you know, myself, our CRO, our sales ops and rev ops leaders, frontline managers. And we just have a good discussion on all of the different things that it's going to take. So I think we spend more time doing deal reviews on deals. We're trying to win not as many postmortems. And I guess, thankfully, We lose deals, but not as many where it makes sense to make that consistently part of the postmortem, but I think it's really valuable, and it's on my mind to keep doing more heading into twenty-twenty-two.

AI assessment note: “We need to do more postmortems, but we do a lot of, Deal reviews.”

Q Say you lose a big account. Do you do postmortems, and how do you structure them?

A We do, and we do lose accounts, so don't, you know, let me get off the topic here by saying this. We need to do more postmortems, but we do a lot of, Deal reviews. So we've got a biweekly deal review where we have a couple reps from all segments all the way to our strategic account segment down to mid market. And we're actually soon launching SMB, but we do deal reviews and we have kind of an outline that they follow and they bring it and they come and they talk with, you know, myself, our CRO, our sales ops and rev ops leaders, frontline managers. And we just have a good discussion on all of the different things that it's going to take. So I think we spend more time doing deal reviews on deals. We're trying to win not as many postmortems. And I guess, thankfully, We lose deals, but not as many where it makes sense to make that consistently part of the postmortem, but I think it's really valuable, and it's on my mind to keep doing more heading into twenty-twenty-two.

AI assessment note: “We need to do more postmortems, but we do a lot of, Deal reviews.”

Q I love that. Can I ask if it's potentially not working, how long do you give someone and what are the core signs that it's not working? Is it just that they haven't closed deals? What are the other signs that it's not working and you should be worried and how long do you give them?

A Yeah. So I think, you know, some of the canary in the coal mines are definitely just conversion rates early on. Say for example, you're doing a bunch of initial calls with Customers, but you're just converting at a much lower rate. That would be an indicator to me or someone on the management team that there's something going on here. So call recording software is big. Joining calls to shadow. I think sometimes that can feel a little having your manager on all the calls, both for the customer and the rep, of course. But I think with the call recording software, it's really nice because you can go and review. All right. So is he setting the agenda? Is he asking a lot of questions? Like what can we learn from that experience? I think that's really critical. And I think the other part is you start to see at a hyper growth company, can they move Fast enough. There's, of course, the sales skills. Are they good at the job? Are they putting in the work? Is conversion there? And then it's about speed. Can you be efficient? You can't take two hours every day to close out. You know, there's a bunch of clicks you got to do in these jobs. Convert this league, create an opportunity, put notes for your manager, do all these things. We don't do that just to, you know, for management sanity. It's for the entire organization. If Dylan wants to jump in Salesforce, which I don't think he does oft…

AI assessment note: “some of the canary in the coal mines are definitely just conversion rates early on”

Q we find this candidate, we've gone through their calendar, we've asked them what they've learned. We're like, yeah, this is great. How do you structure a hiring process? Do you hire after one Zoom call? Do you hire after two? Where's the case study? How do you literally do it? How many meetings do Does it take to hire? When do you do certain things? What does that look like?

A Yeah, good question, and this is relevant. I think, again, just like the business changes and the role changes, how you hire and thinking about the candidate experience and then just what's happening in the world right now, it's all coming into play for us at Figma. So we're trying to think about the candidate experience being a positive one, even if you don't get the job. You know, you go and tell your friends, hey, this company is doing big things, and the people were great. All the leaders and the peers that I met on the slate were great. The second part is, like, you want to be efficient, both in terms of your team's time You have reps and managers joining on these interviews. You have directors and VPs and, you know, occasionally CEOs and the rest of the C-suite joining in on these interviews. You're not going to hire every person you meet. That's just not realistic, but can we be efficient? Can we make the best use of both our time internally, but of course the candidates time as well. And the last thing I think is just focus. We have things that we want to measure for. We got a methodology and a process to this. And so how do we know that we're testing for the right things? And we're doing so in a way that hopefully is somewhat enjoyable for the candidates. So for us, what that looks like is you've got a fit screen with the recruiter. Then that goes well. After a while, …

AI assessment note: “for us, what that looks like is you've got a fit screen with the recruiter”

Q You said there about kind of their communication with different parts of the org. I do want to get to the post-hire. You know, we've been through that process now. When we think about, say, the first month or two, what's the ideal onboarding process for new reps? How should I stage it? How do you stage it?

A 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 got to get things off the ground to prove you can bring in resources and additional headcount and other experts that know that area much, much 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 emotion that 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 and your knowledge base yet. You're literally defining it as you go. 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, shadow as man…

AI assessment note: “shadow as many calls as you can. Here's all the documentation we have access to.”

Q So pipe is full. We've got our rep first approach, and they're closing customers, and things are looking really good. When is the right time to hire a head of sales to manage them, and then maybe be a more strategic lead, guiding sales moving forwards when you have those initial three to five reps?

A Yeah, and so say you go the route where you don't bring in a leader. I think the one thing to call out is it's the cheaper route. You're not going to give away as much equity. You're not going to be probably paying these people in very early stage, high amount of cash, and so if you can find people People that are really passionate about what you're doing and are energized about working with you and the broader team, then that's great. And that works for a lot of companies. I think you'll be able to get scrappy Renaissance reps who can do a little bit of everything. You know, they can't only be pure play blinders on sales reps. Like you'll see at a publicly traded company or a really late stage org. They need to be able to work really well, cross-functionally. You know, Harry, we've talked about this in the past, but if you bring someone in and they only worked in a really formulated environment, Where everything is given to them. They got enablement and they've got, you know, a good frontline manager who's in the trenches of them every single day. They need to be driven. They need to be pushed. Those kinds of people that aren't intrinsically motivated, they're just not going to do well. And so I think if you've got a few people that are in that role that are doing well, and it's getting to the point where all of a sudden the CEO is trying to manage other key executives across …

AI assessment note: “getting to the point where all of a sudden the CEO is trying to manage”

Q So pipe is full. We've got our rep first approach, and they're closing customers, and things are looking really good. When is the right time to hire a head of sales to manage them, and then maybe be a more strategic lead, guiding sales moving forwards when you have those initial three to five reps?

A Yeah, and so say you go the route where you don't bring in a leader. I think the one thing to call out is it's the cheaper route. You're not going to give away as much equity. You're not going to be probably paying these people in very early stage, high amount of cash, and so if you can find people People that are really passionate about what you're doing and are energized about working with you and the broader team, then that's great. And that works for a lot of companies. I think you'll be able to get scrappy Renaissance reps who can do a little bit of everything. You know, they can't only be pure play blinders on sales reps. Like you'll see at a publicly traded company or a really late stage org. They need to be able to work really well, cross-functionally. You know, Harry, we've talked about this in the past, but if you bring someone in and they only worked in a really formulated environment, Where everything is given to them. They got enablement and they've got, you know, a good frontline manager who's in the trenches of them every single day. They need to be driven. They need to be pushed. Those kinds of people that aren't intrinsically motivated, they're just not going to do well. And so I think if you've got a few people that are in that role that are doing well, and it's getting to the point where all of a sudden the CEO is trying to manage other key executives across …

AI assessment note: “say you go the route where you don't bring in a leader.”