Pod Insights The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch 20 Sales: Why Founders Should Not Be The One To Create The Sales Playbook, How To Structure Each Interview in the Hiring Process For Sales Reps, How To Use an "Interview Panel" Effectively and more with Zhenya Loginov, CRO @ Miro About this episode Zhenya Loginov is the CRO @ Miro, the leading visual collaboration platform that helps bring teams together and meaningfully improves the way people work. At Miro, I run the go-to-market team of 700+ people across 11 global offices. Prior to Miro, Zhenya was the COO @ Segment where he built and ran the global go-to-market team of 200+ people, expanded the product-market fit into the Enterprise and grew revenue 6x, leading to their acquisition by Twilio for $3.2Bn. Finally, before Segment, Zhenya led a 100-person team at Dropbox across numerous different functional areas. In Today's Episode with Zhenya Loginov You Will Learn: 1.) Entry into Sales as an Outsider: How Zhenya made his way into sales as an outsider and came to be one of the most powerful revenue leaders today with Miro? What are 1-2 of the biggest takeaways for Zhenya from his time at Segment and Dropbox? How did they impact his mindset today? Why did Dropbox not win the enterprise when they had the chance? What mistakes did they make? 2.) The Sales Playbook: What, Why and How: What does "the sales playbook mean to Zhenya? Does the founder need to be the one to create the sales playbook? What are the signs that the founders needs to bring in their first sales hire? Should this sales hire be a sales leader or more junior sales rep? Is is possible to run a PLG and enterprise sales motion at the same time in the early days of the company? What do many founders misunderstand when contemplating adopting an enterprise sales strategy? 3.) Hiring the Team: How does Zhenya structure the interview process for new sales hires? Zhenya spends 5 hours with each candidate, what does he look to get out of each meeting? How does Zhenya break down the criteria for what he wants to see? What are some examples of this? How does Zhenya test to determine if the candidate has these criteria? What questions does he find to be most revealing? Why does Zhenya find case studies to not be useful? How does Zhenya use interview panels to ensure he makes the right hiring decision? Who is on the panel? At what stage do they meet the candidate? How does Zhenya like to use the panel? 4.) Laying the Groundwork: The Onboarding Process: What is the right way to structure the onboarding process for all new sales hires? What are some early signs that a new sales hire is not working? What can sales leaders do to ensure new reps get "early wins" on the board? What can leadership do to ensure the sales team has good cross-functional communication across the org? What works? What does not work? What are some of the biggest challenges of running a remote sales team?
Transcript 11,393 words · 4 speakers
Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.
0:00 Harry Stebbings? This is 20 Sales with me, Harry Stebbings. Now, 20 Sales is our monthly episode where we sit down with the leading sales leaders on the planet to unpack their tips, tactics and strategies to scaling sales teams. Today, I'm so thrilled to be joined by a master of their craft, Genia Loginov, Ciara Miro, the leading visual collaboration platform that helps bring teams together and meaningfully improves the way people work. At Miro, Genia runs the go-to-market team of 700-plus people across 11 global offices. Prior to Miro, Genia was the COO at Segment, where he built and ran the global go-to-market team of 200-plus people, expanded the product-market fit into the enterprise, and grew revenue 6X, leading to their acquisition by Twilio for $3.2 billion. Finally, before Segment, Genia led a 100-person-plus team
0:45 Harry Stebbings? at Dropbox across numerous different functional areas. And I want to say a huge thank you to Peter at Segment for some amazing questions and suggestions today, and then also Danny Hersberg at Sequoia for the intro which made this show possible. But before we dive into the episode today, walnut.io is the world's first interactive product demo platform. Walnut lets sales leaders easily create, share and analyze insightful sales demos, which are 100% tailor-made to their prospect needs. Walnut helps hundreds of customers, such as Adobe, Dell, Treasure Data, People AI and many more. Check out walnut.io if you want to generate much more revenue using their codeless demo platform. And what happens next? You need an incredible sales engagement platform. Welcome Sales Loft, helping sales
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2:51 Harry Stebbings? But that is enough from me. So now it's time for an incredible episode with Genea Loginov, CRO at Miro.
3:02 Speaker 01 You have now arrived at your destination.
3:05 Harry Stebbings? Genea, this is such a pleasure to do. I've wanted to do this one for a while. I heard so many great things from Peter and from Olga. So thank you so much for joining me today.
3:12 Speaker 02 Harry, it's a pleasure to be here. Thank you for inviting me.
3:15 Harry Stebbings? Not at all, but I want to unpack a little bit of the background because there's some incredible history here. So talk to me, how did you make your way into the world of tech? And then how did you come to lead some of the most powerful revenue and sales orgs, most recently with where we are today?
3:28 Speaker 02 Yeah, I think my upbringing and education probably prepared me for the world of tech. So in high school and college, I did a bunch of computer programming competitions, all Russian competitions and so on. But then eventually went instead of kind of becoming an engineer, which was the path that I think I was prepared for. I went into the business side and spent five years doing consulting and finance. And then eventually made it to tech by starting a company. So I saw friends of mine start their own companies. I thought that it's exciting, wanted to see what it's like and started a company in e-commerce space. And then found that I loved it. So eventually when I closed that company, made it to larger companies like eBay and then Dropbox and then Segment.
4:03 Harry Stebbings? I love the way you just kind of glossed over some of those companies because I want to unpack a couple of learnings. If we look at say Segment and Dropbox, if we were to isolate one to two learnings from your time there, what would you say are the one or two biggest takeaways from each? Can you unpack them for me?
4:18 Speaker 02 I think the biggest one for me from Dropbox was That you have to win the enterprise market. If your market kind of includes the enterprise, you have to figure out as a company how to win the enterprise market. I think at Dropbox when I left, my biggest learning was that we had an opportunity to be Dropbox for the enterprise and we sort of lost this opportunity to other companies. And I never wanted to be in this position again. So when I was joining Segment after Dropbox, one of my biggest things that I wanted to accomplish was take the company into the enterprise and make it a major enterprise player in that space.
4:47 Harry Stebbings? I just want to pause that. I'm too interested because I most often see founders and they say, we need to move into enterprise. And I always say to them, listen, SMB is deeper than you think it is and you can build a bigger business than you think you can staying there. Don't move there too soon. How do you think about that, given the need to also win enterprise?
5:05 Speaker 02 Yeah, I think the markets are different. So it really depends on where you are, how much competition you have and where, how do you see your market developing over the years? So if you have significant competition or if you see other people potentially jumping into the enterprise market for you, you have to try to win it and not miss the boat. If you have the time, if you are alone in your market, there are a few companies that are in this lucky position. Then yes, figuring out firstly PLG motion, SMB motion, market motion is a great thing to do. It's just one thing to know that enterprise takes multiple years to build. So even if you start today, it's not going to be until maybe three years, four years from now that you really figure out how to be a PLG plus enterprise company. So just you kind of need to plan for way ahead of time.
5:43 Harry Stebbings? Yeah, I totally agree. Do you think you can do them both at the same time at an early stage? Given it's expansive to enterprise and actually PLG is expensive too. It's a big investment in product teams. Do you think it's possible for early stage companies to do PLG and enterprise alongside each other in the early days?
6:00 Speaker 02 Yeah, I think in the long run, I think the best business model that you can have is PLG plus enterprise. But in the early days, I agree with you that if your resources are scarce, you need to focus on one. And if you have any opportunity to build a PLG business in your market, I would advise like first figure out PLG. I think that's a lot bigger add to your valuation, a lot bigger add to your future success if you figure out PLG. Go to market, you will also, you will always have the time for it. If your PLG motion is figured out, but the PLG if you miss it and if you build the sales teams too early. It's very hard to build later.
6:31 Harry Stebbings? I often have conversations with founders where they say like, this big enterprise is desperate to sign a contract with us. It's free money, we should take it. How do you advise those ones who are kind of getting pulled into enterprise by a large customer? But I always think there's a lot more to it than free money.
6:46 Speaker 02 Yeah, we've seen it, right? Every company. So it's a double edged sword, I suppose. On one hand, some of those early adopters will become your marquee customers who you will show to all of your other prospects for the next like two to three years. And every company, you know, Dropbox and Segment and Miro, we had those first few adopters that adopted the product very, very early and became large users. It really helped us go into the enterprise and figure out how to build the product there and figure out what are the requirements for the enterprise customers. On the other hand, if you know that you're gonna need to build a lot for this particular customer that is outside of your normal product roadmap and that would detract your engineering product resources from building the core product, I wouldn't do it. It's very hard to say no to a lot of money and the logo that you like, but I think if you know that it's gonna detract your resources, don't do it.
7:30 Harry Stebbings? If you analyze Dropbox, you said there about not winning. Why do you think you didn't win it?
7:34 Speaker 02 I think what I learned, I guess, from Dropbox is that going into the enterprise is commitment for the entire company that starts with the CEO and that needs to take the entire, not just the go to market teams and sales teams, but the entire like marketing and engineering and product and the entire like culture of the company needs to change a bit. And the whole company needs to believe that, that enterprise is good fundamentally, that it's not evil and that salespeople are not evil, but that it's great for your customers, it's great for bringing your product into the market. And I think this lack of that level of commitment early on, I think at Dropbox was what played us. We had wonderful, fantastic go to market leaders, but we just had them, each one came for a couple of years and then left. And we never had the full, full commitment to go full on and win the enterprise no matter what.
8:16 Harry Stebbings? I totally get you in terms of the commitment top down. What would you say was a big takeaway for you from Segment? It was an incredible journey there. What do you say is a big takeaway that impacted you from Segment?
8:25 Speaker 02 So like Segment for me, Segment was really the first place where I ran the sales teams, right? So I started about six years ago and I started as a head of customer success team at Segment. And then about a month in, Peter, the CEO, asked me to run sales and I told him, hey, There's so many people who know how to do this way better than I do. You can go and hire them and do you really want to do it? He said, well, yeah, you seem to be to understand how the go to market thing may work and go and try to run the sales team. And if you fail, we'll hire somebody. And so I've been at Segment ever since, like every six months increment is like, okay, let's trust another six months to Genie. And let's trust another six months to see how he can run sales team. So I think the biggest learning from Segment for me was this kind of pass of an outsider into the sales team
9:07 Speaker 02 in learning about the sales world and like I'm a kind of a mathematics nerd and an operations geek. And I think that I saw initially sales as maybe nothing other than building relationships and maybe knowing your product well. Over three years at Segment, I came to realize how fantastic and how deep the world of sales is, how much it has to master and to learn. And that it's sort of a separate field of knowledge, even like several different fields of knowledge. So before Segment, I think I respected salespeople because I saw that they can do kind of seemingly effortlessly what I couldn't see myself doing. But then after Segment, I respected them even more, knowing how much they have to learn and how much they need to do and excel in to be able to do things they do so easy.
9:47 Harry Stebbings? I totally agree with you in terms of the complexity in many ways of the sales role, especially today with the multiple different personas and the product knowledge required. It's, I think people consistently underestimate it. I want to start on something that people often talk about, but I think there's a little bit of a lost clarity around it, which is the sales playbook. Love the term. How do you think about the definition of what a sales playbook actually is?
10:09 Speaker 02 I feel like I think about sales playbook on three different levels. The customer level, team level and market level. So customer level for me is all about the problem and the solution. So the question is like, what problem are you solving? Who are you solving it for? And how are you solving this problem with your product? And the timeframe for this is somewhere between one single meeting and one deal cycle. The team level for me is about organizing the team to solve as many of those customer level problems as possible in a period of time effectively. So it's about hiring profiles. It's about how do you ramp and train salespeople? It's about the leaders that you hire into the team. What is the coverage model and who does what on the sales team and customer success team? And the timeframe here is maybe six to 12 months. And then the last level is the market level, which I think is all. About your plan to win the larger market in the long run.
10:53 Speaker 02 So it can be about moving from SMB to enterprise, which we talked about. It can be sort of moving from mid-level decision makers as buyers to C A O as a buyer or C level decision makers as a buyer. Moving from selling into one country to global sales team and covering the global market from sort of one set of competitors that are maybe small pure plays to entire different another set that may include the likes of like Microsoft and Google and so on. So and from original products to the long-term product vision and the timeframe for this is maybe five years or more.
11:19 Harry Stebbings? I love that breakdown of the three different stages. And when we think about those three different stages, who needs to own what part of the stage? Often founders are told you need to create and execute the sales playbook before you hire your first reps. When you look at those three stages, what does the founder need to do? And then what needs to be brought on at what stage there?
11:36 Speaker 02 I listened to some of your interviews with sales leaders before on the question of whether the founders should create their own first sales playbook. And I feel like we have a consensus here and I think that no, the founder shouldn't. And it's better that that they're not. So of course, the founder is the most often the first seller. I mean, and most often, and they need to link the sales playbook to the vision of the product and the company they want to build, right? It's very helpful for them to be deeply involved in creating this first sales playbook. But it's also very, very helpful if a sales professional is actually running the process. So coming back to my point about sales being like a very deep area of expertise. I think that some first time founders just don't realize it and don't realize how much they may not know about sales and about what's important for the sales rep. And how to create a playbook that would resonate with them and they would feel like it's their own.
12:20 Speaker 02 And I think one more important thing that I want to emphasize is I'm a big believer in enablement and empowerment. And I think if the founder sort of hires salespeople who he gives the playbook to that the founder developed, it's going to be less effective and less efficient than if founder brings in the person and lets them create something that they would feel ownership over and would feel empowered to go and execute.
12:40 Harry Stebbings? Okay, so I am clearly naive or dumb here bluntly because I disagree. And I think the founders should create the sales playbook. And my thinking around that also then leads me to my next question, which is if you don't think the founder should create the sales playbook, then you have to hire a head of sales first, not reps. Because you can't bring in bluntly low-level sales reps and expect To manage, create and execute on a new sales play, but that would be a lot to expect a young sales rep. Do you agree then that it's head of sales next? And if so, do any heads of sales want to join as the first salesperson in an org? And if they do, are they any good?
13:14 Speaker 02 Yeah, I think I agree that the head of sales is the best role to hire for instead of just reps. I think that if you can at all afford it, then I think go and hire your first head of sales. I think this stage is important, right? So if you don't know where your initial product market fit is, you should hire any salespeople, either reps or head of sales. They are not going to figure it out for you, like the founder is a lot more likely to figure out the initial product market fit. But after you closed either several deals or maybe you are up to maybe one million in revenue, it is time to hire your first head of sales. I think that the junior rep will consume bandwidth from the founder and the founder will need to spend time on those first few reps and to enable them, to support them, to show them what to do. And the head of sales will instead create bandwidth that the founder can use to go solve other problems, to go like build a product, to go hire a finance person to go do something else.
13:58 Speaker 02 So I'm a big believer in scaling yourself through hiring people who can do things independently of you.
14:03 Harry Stebbings? When we think about scaling yourself, PLG itself as a motion is a way to scale your sales motion very efficiently. We just had Oliver Jay from formerly Asana on the show and they got to 20 million in ARR without having a sales rep, I think it was because of the PLG motion. And I spoke to Paul, who obviously you know very well before the show. And he told me that you know everything that goes wrong and everything that goes right in PLG and you've applied it to Miro. So what are the most common things to go wrong in PLG and then we'll do what goes right?
14:32 Speaker 02 I'm a big fan of OJ from Asana, right? But I would argue actually that companies like Asana or Dropbox were a little too late into getting the enterprise motion on top of PLG. I think that's one of the reasons that OJ joined Asana was that Asana realized that they need to build the sales enabled motion and grow much faster than they did. So that to me is one maybe mistake. It's the question of sequencing, right? It's the question of when do you transition from a pure PLG to a combination of PLG and enterprise? So if you are too late, you may just miss the market. On the other hand, the other thing that we talked about is that doing enterprise too early and having hired a lot of salespeople without figuring out the fundamentals of your PLG motion just makes you into pure. Sales-led company and there sure are markets where purely sales-led company is the right way to go.
15:14 Speaker 02 But many, many, many markets allow for a combination of PLG and enterprise. And if you are too early into enterprise, you will miss the PLG, building the PLG engine that would actually help you in the long run. And then the third big kind of area of problems that I've seen is structuring your team in a way that creates conflicts between the PLG side of the company and the self-service side of the company and enterprise side of the company. So and where people don't optimize for the company overall and for customers overall, but optimize for their own thing that they own. So I've seen a couple of those. So actually a lot of. What do you mean optimize for the thing that they own? What does that mean? Sorry. So let's say that one bad way to organize this is to have two people. One is responsible for self-serve revenue, another one is responsible for high-tech revenue and they're only responsible for their own portion of revenue.
15:59 Speaker 02 And in a couple of months after that, the high-tech person will go and figure out, well, I can launch an SMB motion here and sell to small companies through a salesperson. And a self-serve person will come to the CEO and say, well, those guys are cannibalizing my self-serve revenue. And actually, they are deploying people resources where we should not deploy people resources where the customer eventually will grow. Maybe it will take them additional couple of months, but will grow to the same level that it would grow with a salesperson with no costs spent. And this creates a room for conflict and people are starting to spend time on things that are not productive for the whole company, but that would optimize for either self-serve or high-tech. What are the biggest resource conflicts you have today at Miro? I don't think that there is resourcing conflict. I think the biggest conflicts that can happen are alignment conflicts. What are your goals and what are the goals of the people around you?
16:44 Speaker 02 So for example, you asked me, right, like, how did I take into account all the mistakes and the ways to do things right when I joined Miro? And I think most of those things I took into account even before joining Miro. And you asked about the resource conflict. So one of the big things that I wanted to make sure happens before I joined Miro was that we don't have an internal conflict. So now I'm responsible for all revenue, all self-serve and high-tech. But the self-serve team doesn't report to me, which I also think is the right thing. I think the self-serve team is fundamentally a product team first and foremost, and it needs to be a product engineering team and sit within the product organization to be actually able to build the experiences for the customer. That enable PLG, but because I have this responsibility for all revenue, I actually don't care whether the revenue is self-serve with a customer, self-serve customer or high
17:28 Speaker 02 tech customer. So I don't have any incentive to build things that don't make sense for the end customer.
17:32 Harry Stebbings? You have the high-touch sales team going, hey, we need these products, we need these features for these customers and it's going to drive revenue and the product PLG team are not doing it fast enough. Genia, come on, help me. You get that?
17:44 Speaker 02 I don't think we do, actually. So I think the way that we build collaboration between the two teams, I think the entire sort of high-tech side of the company realizes that the PLG side is not about small customers, it's not about self-serve alone, it's about PLG motion for all of our customers. So within the PLG team, we actually have enterprise growth team, which is a product team that sits within our self-serve organization, self-serve product organization, and it helps mature customers to the enterprise level and it helps expand customers in the enterprise. So generally, when I joined, the thing that I saw as maybe mission or thing that I wanted to do most is kind of build the next iteration of the best-in-beat combination of PLG and enterprise and how the more they are connected everywhere, the better I think the overall motion is.
18:27 Harry Stebbings? I love that, actually, in terms of putting like enterprise product within the PLG motion. And I didn't actually know that, so that's awesome to hear. I do want to dive into the hiring process itself, because now we've identified, as you said, actually, that's hire the head of sales first. Okay, I've never done this before, Genia. You are an angel in my hypothetical company and my most trusted advisor. Tell me, if we think about before, like how to structure the process, like what we're actually looking for in the people, what are the non-obvious characteristics, traits, qualities that these incredible sales leaders, because we're going for the head of sales first, according to your advice, what am I looking for in terms of characteristics and traits that's non-obvious?
19:04 Speaker 02 Yeah, hiring is definitely my favorite part of the job. And mostly, I'm going to talk about general leadership hiring and maybe the first sales leader hiring, but also you can apply the same for anywhere from your head of engineering to head of marketing to anywhere else. I think first and foremost, I'm looking for people who have not done the job before. So usually, instead of hiring people who have the experience, who have done exactly the same role before, which sometimes is appropriate, but for most roles, especially in high-growth companies, I'm actually striving To look for somebody who knows seventy percent of the job, but is really, really passionate about getting the other thirty percent. And the only motivation I care about them having is to grow personally and professionally by succeeding in this next step in their career. So I give them the opportunity to take this next step. And I see the most amazing results when they have the passion and the skills to run it.
19:49 Speaker 02 I think the big trick here is to know exactly like what are the key, non-negotiable experiences that fall into this seventy percent? What can you not miss? And frankly, there is just about non-obvious characteristics of those people. My feeling is that there is no simple formula answer to this. And that your job as a hiring manager is to make those non-obvious things obvious to you by trying to deeply understand the role that you are filling before you are starting to interview the first people for the role. So if you're hiring your first head of sales and you have no idea how to hire a head of sales and what they should be doing, go and talk to ten heads of sales who you may possibly maybe not be able to hire much larger companies, right? For not looking for anything and just talk to them for an hour or two and understand like, what are they doing?
20:29 Harry Stebbings? Sorry, on that point, that's why I started these shows. Cause I wanted founders to be able to listen to you, to OJ, to Danny Hersberg and go, wow, these are the best sales leaders. This is what great looks like and it allows them to build a benchmark. And then they can take this conversation to their conversation and it democratizes access to you in a way that they may not have otherwise.
20:48 Speaker 02 Yeah, it makes total sense. I think what founders should learn from this is not necessarily only here's what the salespeople look like, right? But more, you can use the same approach for and should use the same approach for any role. If you are hiring your first, I don't know, CISO or CMO or your head of engineering or anybody else, go and figure out what the job is before you start talking to people about joining you for that role.
21:07 Harry Stebbings? Just one question, when you don't know, so say I'm not technical in terms of engineering managers or engineers, how do you advise people on hiring for roles where they really have no idea? Other than speaking to ten people in the space, is there anything else they can do? And also, are there any dangers or red flags of hiring someone who hasn't done the role before?
21:25 Speaker 02 So I think if you don't have the background in this, I think that's gonna be the most difficult situation. As a founder, you're hiring a lot of people who are gonna be professionals in their fields where you're not a professional in their field. You may be a professional one or two, but not ten others. So it's always gonna be the case and you have to. Learn it like it's very hard to say, hey, as a founder, I have, I don't want to deal with legal and finance and I'm gonna just find somebody and they're gonna take care of this and I'm never gonna be need to be involved. Well, you are gonna have to be involved. You're gonna have a bunch of things leading at least up to the IPO that you will need to learn even about that field, not even talking about engineering or sales or marketing. So I think to some extent, you need to always be sort of a scholar of different disciplines. The best way that I found that you can learn is really talk to people who have done that before.
22:05 Speaker 02 But you can read a bunch of books that is like you read maybe ten different sales books when I was starting to run sales. That's a segment to figure out what people wrote about this. So that, I guess, like knowing what your people do is the best recipe and then you learn from them and you continue learning from them and their peers that that you're talking to.
22:20 Harry Stebbings? How do you structure the actual process itself? I often see people have one meeting and offer a role or others who have twenty and still haven't made a decision. How do you think about structuring the right and efficient hiring process for sales and revenue teams?
22:34 Speaker 02 Yeah, I think that a good hiring process is frankly similar at most places. So you have your hiring managers, your interview panel, then you have some final interviews and then you lose the candidate. I will share a few kind of an orthodox design choices that work very well for me. We started with the first one that I may try to make sure always happens, which is if I don't understand what the role that I'm hiring for, I don't open the role until I do. And I will go and research the role before I want to fill it. The second step is as a hiring manager, I try to have very clear must have criterias, three to five must have criterias for the role. And I ruthlessly decline candidates who don't meet at least one of those criterias on the resume stage. I don't talk to them. I look at the resume. There are five criterias I have. If one is not met, it's out. I don't have nice to have.
23:16 Harry Stebbings? Can you give me an example, just so I understand that? So a couple of criterias would be, and then what would show they don't have them?
23:22 Speaker 02 So here on the resume stage, I focus only on the things that I can get and can read from the resume. And I try to have a very short list and I don't have nice to haves, I only have must haves. So for example, let's say that I'm looking for head of Europe for a fifty million dollar A R company. So I'm looking for a person who I may have a criteria, you know, ran a team of at least a hundred people, one. I may have a criteria, was a part of a company that grew from fifty million to hundred million, not necessarily led this company, but was a part of that. I may have a criteria. The company that had a PLG motion, or maybe I don't care about this and I have a criteria worth it. A company that had multiple different, so not only European, purely European company, but an international company that had presence in several different places. So I would focus on those few things.
24:04 Speaker 02 And the fourth thing that I would typically look for, for example, have strong experience in the enterprise. So sold million dollar contracts to the enterprise market. And then those four criteria are fairly simple, but they mean that if I see somebody who has amazing experience and worked at the companies, the amazing companies, but have only sold commercial, I'm not gonna even talk to that person. I'm never gonna say, well, maybe they're great, but my view is I know why I need those must haves. And if one of them is not met, then the candidate is not right. And I'm gonna cycle through until I find people who just qualify everywhere.
24:33 Harry Stebbings? I'm totally with you. And I think in terms of that criteria, I was thinking like ambitious self-starter, but it's actually very tangible and data oriented in terms of what you're looking for.
24:42 Speaker 02 Yeah, at least in this stage. So all the other things I have there as well, but I only will find them when I am talking to them. And then my next step as a hiring manager is that I spend about four or five hours with the candidates in structured one-hour interviews before they go to the interview panel. And I'm striving to be maybe 70% sure that they will actually succeed going through the interview panel. And I also want to be about 90% sure that the candidate will accept the offer if we are to extend an offer to them.
25:09 Harry Stebbings? Let's just pause that because I'm too interested here. So we, how many candidates do you go through this extensive process with? Is it three to five?
25:16 Speaker 02 It really depends on the role I've had roles where I would do three to five, but I also had roles where I would do maybe 20. But it doesn't mean that I spend four or five hours with every candidate. I usually start those interviews with the topics that I think will be the hardest for the candidate to succeed in. And then if under the, after the first interview, the candidate is not succeeding, I will move on to other ones. So the thing for me here is that I don't want them to go to the interview panel until I'm sure that they are actually good and that I am calibrated and like I know what I'm hiring for. They passed my bar. What I find with interview panels is several things, like one is I will lose everybody's time if I pass candidates who I'm like half sure about. And then that's what lead to half a year, a year, 18 months long hiring cycles where all of your exec team have interviewed.
26:00 Speaker 02 Twenty five people and are poured to death from this role. I only want them to talk to maybe three to five people and then say, okay, like all three of them are good. And this one is better than the two others. That's one thing, but also I find that it's only the hiring manager who really, really sets the hiring bar. And your panel doesn't exactly know what you're hiding for. They may have a good feel, right? You're hiring head of sales and your head of marketing interviews and head of engineering interviews them. And they have their own perception of what head of sales should look like. But only you thought about this five times or 10 times as much as they did. And you understand what challenges exactly this person will need to solve in the next year and the next two years. And what do you need them to to be able to do to win? So I think by by investing this much time, you're basically raising the hiring bar for the candidate you're hiring.
26:39 Harry Stebbings? I feel quite naive here, Jenya, but when you say hiring panel, do you have an individual hiring panel for each hire? Is it like a hiring panel across the company? Can you just walk me through this? Because I've never actually heard of like a hiring panel, so to speak.
26:52 Speaker 02 Yeah, I do have a digital hiring panel for each role. So what I'm looking for, I look for maybe three to five people who will talk to the person I'm trying to hire, who will be the most likely to understand well what I'm hiring, what I'm trying to hire, and who will maybe work closely with this person. And if sometimes I don't have those people inside the company, sometimes I may ask my board member to interview. Or I will ask my advisor, who is head of sales at a much larger company, to interview my first head of sales hire to understand what to do with them. But I also will have people from within the company interview the hire as well. So the panel, I think, is tailor made. And I basically, I try to make the panel as hard for the candidate as possible. Because if they pass that, I want them, they're much more likely to succeed when they join the company.
27:32 Harry Stebbings? What makes a panel hard? Is it the people being very experienced and very direct? What makes a panel hard?
27:38 Speaker 02 I think over time, when you interview together with other people, you're on the same interview panels. You over time learn who is a harder and better interviewer and who almost always says yes. At some point at Dropbox, we had this initiative to try to replace our final interviewer. For a very long time, has been the co-founder, Arash, has been the co-founder. He interviewed every single person at the company until we were like 500 plus people. And at some point, it didn't work. And the way that we wanted to find people who could potentially replace Arash, we analyzed who said no more often and who was right in the hiring decisions more often. Like we took the entire data. Base of our interviews for the company and then we found those few people. And what I find in my interviews is that if I did ten interviews, if I had one person on an interview panel
28:18 Speaker 02 for ten different interviews and every single time they said a yes and then half of the time I agreed with them and half of the time I didn't. That's not a very strong signal for me. I'm looking for people who will well disagree with me first of all and second who will be hard to pass, but reasonably hard to pass, not for arbitrary reasons, but they have a good reasoning why this particular candidate may not necessarily be a fit. So that's what I'm looking for.
28:38 Harry Stebbings? I love that and I really like the kind of constructing individualized hiring panels for each role. I think that's awesome. When we think about going back to like the actual candidates themselves, PLG enterprise labs we spend time on. How does what we need in each change when we're thinking about sales leaders? If we're a PLG sales leader versus an enterprise sales leader, how are they different in terms of what we need?
28:58 Speaker 02 Frankly, I think the fundamentals are the same and I think great enterprise seller and enterprise sales leader at a PLG company should be also a great one in a pure play enterprise company. I think to me the only difference is kind of that those people should have the appreciation for the importance of end user experience and appreciation for teams like product or customer experience. So they don't necessarily need to have PLG experience at a PLG company, but I want to see them sort of respect and value perspective of other people and ability to learn new things. And if they can learn new things, then they can easily learn the PLG motion as well. I don't think that there is a special breed of PLG salespeople. I think that a great salesperson is a great salesperson. They just need to be open minded about changing their motion, their sales motion to benefit from the PLG.
29:41 Harry Stebbings? You said about like the many hours you spend with candidates before putting them in front of the hiring panel. Do you use case studies? Do you use data? How do you strategically test them in a more tangible way?
29:52 Speaker 02 Yeah, I probably think that I interviewed maybe like thousands of people at this point. And I think early on in my career, I leaned heavily on case studies and now I barely ever use a case study. I think that what I found is that especially when I'm hiring leaders, I don't want them to solve an artificial puzzle or be a thought partner for me for a given topic. I find that their ability to succeed there very much depends on whether they were exposed to something like this before or not. I really want to talk to them about their own experiences. So if all I do is all about give me a Situation when you did this and that and then I dive into it and ask like 10 follow up questions to understand how they solved the problem. What did they think about? How did they work with other people? Like, why did they make this decision or another decision? I focus primarily on experiences.
30:32 Harry Stebbings? Tough question and not one in the schedule. What are the biggest ways you fucked up in a hiring process? Like, what are the biggest hiring mistakes you've made?
30:38 Speaker 02 Oh, yeah, I made quite a few. Frankly, the biggest ones were when I think that I knew that I'm not doing the right step, but I did the step anyway. I had the criteria for myself at the beginning of the process and either I ignored them or I didn't pay enough attention to them. So example was for a given role, a hired person who had no experience working at similar companies at all. And they worked, they had a third year career in technology, but have never worked at a similar company that would have an international presence. And it was just extremely hard to change the mindset and we had to part ways. And I knew that it would likely be extremely hard. They just, for some reason, I thought that I would be able to. Because of all the other strengths that the person had, that I'd be able to take care of this.
31:17 Speaker 02 The other experience was when I looked at the candidates, I trusted the interview panel too much and I trusted the candidate's resume too much. So I looked, they had like a wonderful, fantastic resume and my interview panel was very fond of them. And I think the problem with this is on your interview panel, everybody has like 40 minutes to an hour to talk to the person. And nearly everybody who has like good experience have about 40 minutes to an hour to attract that they can give you that looks impressive. But I didn't really dig into this candidate's approach to solving problems enough. I didn't do those five hours of interviews. I did like two hours and then mid person joined, I realized, well, I should have found those problems that we are now having in the third hour of interview, but I never did.
31:56 Harry Stebbings? I do wanna take this because now we've been through the process, we've got this amazing candidate. Onboarding is notoriously difficult in every company. And when we think about kind of the right onboarding process, what does that look like for this head of sales that we've just hired? Thank you, by the way, for helping me. What does that onboarding process look like for this first head of sales?
32:14 Speaker 02 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, yet 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 and 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 very hard to do when you're six months into the role.
32:59 Speaker 02 So the first months, I try to give them as much kind of direction to learn broadly about the company and to see them 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. Two, if you're head of 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 go and figure some other thing that people see that you're 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.
33:41 Harry Stebbings? Okay, so just pausing there, I'm the CEO. Do I say, Xianya, 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?
33:58 Speaker 02 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 introduce 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 pay back in the next several years.
34:34 Harry Stebbings? This head of sales hire, what are the biggest signs in the first three months that I've fucked up?
34:40 Speaker 02 If you don't see any results delivered in the first three months, if you see the person sitting and figuring out quote unquote 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. And 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 back week. 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.
35:25 Speaker 02 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, hmm, I didn't know about this new guy. And your job as the CEO is actually to make sure that you go and proactively 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? 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 he 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 resulted and when the person talked to the team, they are now very, very loved, much loved by their team.
36:21 Harry Stebbings? I do want to ask, say they're rejected by the organism or they're not delivering value. How do we communicate that first concern? Do we take them aside and say, hey, we're concerned by X, Y, and Z. You're on warning. Just help me understand the right communication pathways after identifying a concern.
36:37 Speaker 02 Yeah, I think my philosophy here is that anybody in the leadership role, their role is just too important, a lot more important than person's feelings or the process that you need to follow. And I try to lean as direct as. Possible, so radical candor to the extreme. So you care about the person, but you need to deliver that message very clearly. So the moment that you know that there is something to deliver, you take the person aside, you sit down and you're brutally honest in what you're seeing and what consequences follow if those things are not fixed. And I've seen the best reaction when it's super clear, when people also need to feel that you care about them, that you're in their camp, that you need them to succeed in the company and you need the company to succeed together with them, right?
37:18 Speaker 02 But they need to also be clear on what are they doing right or what are they doing wrong and what do they need to fix to be successful?
37:23 Harry Stebbings? This is assessment and monitoring on a kind of person level. I'm intrigued, when we think about on a deal level, do you do postmortems on deals? Do you do deal reviews? And how do you structure them internally? I'm fascinated.
37:35 Speaker 02 We do and we did it both segmented. I think the purpose of the deal reviews is primarily for your sales team to learn what to do well and what not to do well. I think your audience for the deal review is not the person who did the deal, but all the people around. And I think one of the worst way to do a deal review is when one person is listening and nobody else pays attention and only the person who was there in the room like gets any input from your head of sales on how to do the deal better. I think the best deal review is basically a clinic for the entire team on here are the things that we did really well. That was resonated, how do you do it in every deal? Or here's the thing that we didn't do well and how do you do things differently?
38:07 Harry Stebbings? How often do you do them? How long do they last? Who's invited? Who sets the agenda?
38:12 Speaker 02 So I think we had a really good process at segment where we did deal reviews, I think weekly. And we have a couple of deals every week to review on every team. So it's a weekly process.
38:21 Harry Stebbings? How long are they? Sixty minutes, an hour and a half, two hours?
38:24 Speaker 02 Sixty minutes, I think is good for one deal if it's in depth. And we don't necessarily review a deal that is closed. We may review a customer that is mid-flight on a given deal. Or maybe there is a customer where we don't even have a deal, but we are creating opportunities there and we would review that. So it's about one hour. Who sets the agenda? I think the process and the format should be dictated by your senior most salesperson in the room, right? Your head of sales, but then you create the framework. But all the meat and essence that goes into it is delivered by your salesperson who is writing the deal. They should own that meeting.
38:56 Harry Stebbings? Where do you think deal reviews go wrong? How do you see leaders or sales? Sales leaders make mistakes in terms of running deal reviews. I've never run one before.
39:04 Speaker 02 I think the biggest one is when salespeople feel that it's like any adversity in the dealer view. When the dealer view for the salesperson is like a review of their personal success, then it becomes a show. They become defensive, they show you only the things that they want you to see. And you don't really see what's really happening in the field, you see what the salesperson wants you to see. I think the best way to run deal reviews is when salespeople know that it's intended to help. It's intended to help close the deal and it's intended to help create a better motion for the sales organization. And the way that you approach asking questions or giving suggestions, or how do you split the ownership of the dealer view and who's doing what? I think should be targeted at how do I help this particular salesperson win this particular customer best way possible?
39:46 Speaker 02 And how do I help the rest of the sales team who is in the room learn something from this to become better?
39:51 Harry Stebbings? I saved the hardest question till last. You said about kind of structure and process. How do you think about implementing and instilling that process and structure? Without losing the agility and speed that smaller companies have and that Miro once had?
40:04 Speaker 02 Yeah, I think it's a great question. I'm a big fan of agility and giving as much kind of local power and as having as light of a process for the team as possible. I think ideally when we are running a large team, and my team is now what's like 700 people, I want the team not to feel like a huge monolith that needs to move with the speed of the slowest piece of the organization here. But to feel like dozen different villages that have the power to run as fast as they can and have all the opportunity to do it. So for example, when we are setting a new geography like Japan or like France, I want to give as much power and authority to a local leader to be able to run their business as they see fit. So that they can be agile on that scale and that they feel like a small and nimble team as opposed to like a cog in a huge machine.
40:45 Speaker 02 The process is, needs to be as light as possible, but should come from those teams that are actually in front of the customer. And if something helps that team, like for example, there is a very specific sales process and process of discovery, your team and your leaders need to be on board with this process before they adopt it. So I think the biggest problem that I've seen with process is when somebody wants like myself or maybe the CEO wants your team to follow the process that the team doesn't buy into. And if the team doesn't buy into, your job as a leader is to figure out how to either have the buy in or how to change the process so that buy in is there. So that the team has the rules of the game, as light rules of the game as possible, and has the resources to play this game, but also has a lot of flexibility and freedom to do it where they can.
41:24 Harry Stebbings? Jany, I want to move into a quick fly around. So I say a short statement, you give me your immediate thoughts. Does that sound okay?
41:30 Speaker 02 It sounds great.
41:30 Harry Stebbings? Okay, so what sales tactics have not changed over the last five years?
41:34 Speaker 02 Discovery. So understanding the customer problem and how you can solve it.
41:37 Harry Stebbings? What sales tactics have died a painful death over the last five years?
41:41 Speaker 02 I think that the number of deals closed in a golf club is probably much smaller now than ten or twenty years ago. But I did close a deal on a bike ride at one time.
41:49 Harry Stebbings? What are the biggest rate points in scaling to seven hundred people?
41:53 Speaker 02 The biggest one actually is about hundred and fifty, the Dunbar number. When you as a person, as a founder, as a leader, start to not know every single person in your team and start to lose the ability to control every single thing that happens, that happens at about hundred and fifty people. That actually is a real big thing that may take like a couple of years to overcome.
42:11 Harry Stebbings? What were your biggest lessons from international expansion at Segment?
42:15 Speaker 02 I think the biggest one for me was it takes an entire village to win this thing. You need to open local legal entities and have bank accounts and insurance and figure out local contracts and like localize your product to a language and maybe even localize data residency. It takes the entire company to open presence somewhere else, Australia or in Europe or in the US. And you need to be ready for it. And if just to go to market leader, you cannot succeed in it without the support of your CEO and CFO and the operational organization. So that's big. It's a big learning. The second one is that, kind of as big of a journey as it is, it's if you can do it, you should do it rather early and rather fast. I think at Dropbox, we launched the first region outside of the US when we were over hundred million in ER.
42:57 Speaker 02 And I think that frankly was too late. I think you can start doing this when you are at about twenty, thirty million. Because it just takes a very long time to build the reputation in the market, to build strength in the market. And you want to give yourself plenty of time to build strong and ideally cash flow positive business before you go public. Yeah, I think also the biggest learning for me is that is actually in hiring. Is hiring a person who sits across the ocean from you is kind of five times as important as the person who sits in the same office. It's just because it's hard to notice when things go wrong timely and it's very costly to fix mistakes. So I had to replace a few heads of regions before and it's just a very, very painful process because you are not in the same office to support. For the transition and it's very hard to find a replacement and so on. So I think I'm hiring especially cautiously for those head of the region roles now than I used to do before.
43:42 Harry Stebbings? Do you agree when there's doubt, there's no doubt when it comes to teams?
43:46 Speaker 02 Generally, yes. When you are hiring, yes. When I'm in doubt, I try not to hire.
43:51 Harry Stebbings? Tell me, what's the biggest mistake that founders make when hiring sales and revenue teams?
43:55 Speaker 02 I think the biggest one is just not investing the time and not being willing to invest the time to learn this art of sales and kind of learn how those people think and how those people work. So just entirely delegating this and not investing the time to learn how sales works.
44:08 Harry Stebbings? What piece of advice would you give to a sales or a revenue leader starting a new role today?
44:13 Speaker 02 I'd say you have a job to succeed in, but you have to grow with the company as and the company may grow very, very fast. So you need to have a plan for your learning for the next couple of years and you need to stick to it. So kind of figure out how to become better at what you do, what do you need to learn, who do you learn from, how do you get access to those people and treat this plan as a part of your job.
44:32 Harry Stebbings? What would you most like to change about the world of sales?
44:34 Speaker 02 I think that there are not enough people who move from other teams into sales and who move from sales to other teams. So I think that if more salespeople jumped into non-salespeople like product and finance jumped into sales, the world would just be better for everybody. There's just going to be more empathy with the sales team from the rest of the organization, more empathy from sales to the rest of the world as well. And there's just a lot of magic that can happen in areas like product management or operations or finance if some sales DNA is infused there.
44:59 Harry Stebbings? What's the hardest element of your role with Miro today?
45:01 Speaker 02 For the last two years, I think it's been pretty hard to just be away from people not on the same floor with salespeople or engineers and kind of everybody else in the company. So I'm really looking forward to be in the office more often and travel to other offices a lot more often.
45:13 Harry Stebbings? What's the biggest thing that's lost in sales teams when moving to remote? Is it speed? Is it morale? Is it collaboration? What's lost most with the move from in-person to remote?
45:24 Speaker 02 I think biggest one is morale and camaraderie. An experienced salesperson can operate very well in a remote setting and field salespeople do it basically all the time. But having this team together and that they feel like they're a part of something bigger and they are in the same boat. The company is much harder to recreate when you're in a remote setting.
45:42 Harry Stebbings? Final one for you. What one company?
45:44 Harry Stebbings? Sales strategy around you. Have you most been impressed by?
45:47 Speaker 02 So I think that companies that have the most unorthodox approach to building the go to market machine and sales from the beginning, sometimes get the most impressive results. So for me, the one shining example is Atlassian and your example is maybe Coda with their unique monetization model. And I think that companies with exceptionally strong PLG emotions such as Canva or Notion have a great potential to develop new go to market and sales models for the future.
46:09 Harry Stebbings? Jany, this has been such a joy to do. As I said, I heard so many good things. I can't thank you enough for me going all over the place on the schedule here, but you've been fantastic. So thank you so much.
46:18 Speaker 02 Harry, it was a great pleasure and a lot of fun. Thank you.
46:23 Harry Stebbings? I mean, my word, what a load of ground we covered there. I want to say huge thanks to Jany for giving up his time today to reveal so many tips and tricks. If you'd like to see more from us behind the scenes, of course you can on twenty vc.com. I love to see you there. But before we leave you today, walnut.io is the world's first interactive product demo platform. Walnut lets sales leaders easily create, share and analyze insightful sales demos, which are 100% tailor made to their prospect needs. Walnut helps hundreds of customers such as Adobe, Dell, Treasure Data, People AI and many more. Check out walnut.io if you want to generate much more revenue using their codeless demo platform. And what happens next? You need an incredible sales engagement platform. Welcome Sales Loft, helping sales teams drive
47:08 Harry Stebbings? 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 and use Sales Loft and so can you. It's the new way to sell. Find out more at sales loft.com. And finally, only 28% of deals are forecasted accurately. 28%. Why is that? Either you don't have enough reliable data to draw from in Salesforce, or you based your forecast on wishful thinking instead of facts. So how do you get your team to input all the deal data you need without hounding them around every
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48:29 Harry Stebbings? As always, I so appreciate all your support and I cannot wait to bring you an incredible 20 VC on Friday.
Previous 20VC: Gary Vaynerchuk on The Most Painful Lessons Learned but Why it was Good to Learn Them, Why You Have to Change the Timeframe You Have For Success, His Relationship to Money and How it Has Changed Over Time & His First 3 Angel Investments; Twitter, Fa Next 20VC: From Kitchen Table to $134M Fund II; Raising Your First Time Fund: Lessons from 400 LP Meetings, How To Find New LPs, What Materials to Use, How To Get LPs To Commit, The Challenges on Minimum Check Sizes and GP Commits and more with Henri Pierre-Ja Page updated October 26, 2026 · transcript and summary are machine-generated