The Exchanges

Q see the incredible sales playbook that you have there at Slack, the incredible enterprise division that you built out, but they're a lot earlier, and they go, do I need to be the first person to create this playbook, or can I bring in a head of sales, seasoned head of sales, to create the playbook for me in the early days? How do you advise founders in those situations?

A Such a good question. So the founder needs to sell the product before anyone else can. So day one, founder equals head of sales. And I'm less concerned about a playbook per se, but he or she needs to find a way to get in front of customers, understand what makes them light up, understand what hurts without their product, understand the objections that come up, and feel that experience of asking for money and managing a timeline. And after selling the first 10, 20 customers, the founder will, number one, have a really good sense of Empathy for the first official salespeople that he or she brings on. And number two, we'll learn that selling is one of the most important input mechanisms for product direction too. So I just think it's a really, really healthy first step for the founder to wear that hat before hiring someone else to professionally wear that hat going.

AI assessment note: “the founder needs to sell the product before anyone else can.”

Q What questions do you like to ask in the references? Because I think this is where a lot of people go wrong. And so I'm just intrigued How do you uncover what it was like and the questions to get there?

A Well, I think giving a reference is a tricky thing. You never want to inhibit someone's career. So first I give someone a chance to brag about the candidate or say good things about the candidate so that they can feel good about themselves. So I'll probably start by saying, tell me about some of the highlights about working with this person. I wouldn't be calling you if we didn't have some good conversations already. And I let them do that. And then I say on a scale of one to 10, how likely would you be? Or, you know, how strongly would you recommend Hiring this person or a VP of sales role. And if they say anything under 10, I say why. And sometimes I add the word blindly in there. So I'd say on a scale of one to 10, would you blindly recommend this person into a VP of sales role or even into a sales rep role? Usually someone pauses when you say blindly and they go, hmm, and I go, tell me about that pause. And if they tell you about the pause, it's kind of their way of giving you the nuance for what Context. They do or don't thrive within, and I think that helps you understand where to take the rest of the reference call.

AI assessment note: “on a scale of one to 10, would you blindly recommend this person”

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

A In a product-led growth company, a rep and a leader have to be Very well versed in the product because prospects come to you very well versed in the product. They may have been using it for free for months or years before you talk to them. So signal number one is actually in the interview process. A good candidate will use the product and perhaps deliver some of the interview unprompted by utilizing the product itself, just to show that they know how to geek out in there and that they've taken the time to understand the user journey. Once you're on the other side of red or yellow flags, when you're onboarding a new rep or a new leader, It's kind of biased toward action, so I did talk about the listening tour for a leader, and on the leader side, I would look to see whether they've developed a point of view about what are the one to two things that are most important to deliver on over the course of this year, and what's their action plan for doing that, and that comes from a combination of learning from the founder during the interview process and hearing from customers directly. If a leader had not gotten in front of a customer, if he or she was sitting in virtual or physical conference rooms for their first two months, And wasn't talking to one new customer at minimum every single week. That is a major flag for me about customer orientation and the health of the org that they…

AI assessment note: “If a leader had not gotten in front of a customer... That is a major flag”

Q What questions do you like to ask in the references? Because I think this is where a lot of people go wrong. And so I'm just intrigued How do you uncover what it was like and the questions to get there?

A Well, I think giving a reference is a tricky thing. You never want to inhibit someone's career. So first I give someone a chance to brag about the candidate or say good things about the candidate so that they can feel good about themselves. So I'll probably start by saying, tell me about some of the highlights about working with this person. I wouldn't be calling you if we didn't have some good conversations already. And I let them do that. And then I say on a scale of one to 10, how likely would you be? Or, you know, how strongly would you recommend Hiring this person or a VP of sales role. And if they say anything under 10, I say why. And sometimes I add the word blindly in there. So I'd say on a scale of one to 10, would you blindly recommend this person into a VP of sales role or even into a sales rep role? Usually someone pauses when you say blindly and they go, hmm, and I go, tell me about that pause. And if they tell you about the pause, it's kind of their way of giving you the nuance for what Context. They do or don't thrive within, and I think that helps you understand where to take the rest of the reference call.

AI assessment note: “tell me about some of the highlights about working with this person.”

Q people brilliant, if we go back to that sales rep slash head of sales, when trying to uncover non-obvious characteristics or signals that they're great, what are some signs for you that the person's not only good, but really a game changer for the potential company? Advise me, imagine I'm a CEO and you're like me, what would you say is like non-obvious traits that make the best the best?

A Okay, I have non-obvious traits for head of sales, and I have non-obvious traits for hiring a sales rep. So for head of sales, number one is that they love to sell. And you may say, Danny, that's a very obvious trait, but there are just some ways that you should vet that out and test it. Like, is this the kind of person that when you text them, they pick up the phone and call you, and they are just a natural connector. When they have the opportunity to meet up in person, do they take that opportunity? That's why I look for people who genuinely love to sell. I ask someone who would follow you if you were to take this role. If they don't have Three or four people off the top of their head that would follow them. To me, that's a yellow flag, maybe a red flag about who they are as a leader. So they may be humble about it, but every good leader knows a handful of lieutenants who will immediately and basically blindly follow them to whatever they do. And I actually ask for names just to see if it's at the tip of their tongue. And then number three, I want someone who breaks glass. So you're not bringing on a sales leader to stroke your ego, to agree with you, take the easy path or the path of Of least resistance. You're are hiring someone to come with opinions at times to have healthy debate into the company and not be afraid to shatter glass as long as they're comfortable cleaning i…

AI assessment note: “So for head of sales, number one is that they love to sell.”

Q Would you hire someone if you don't like them? I know that sounds strange, but someone can be incredibly talented and gifted if you don't like them.

A Yeah, Harry, I would hire someone if I didn't. Like them. And I would hire someone so long as I respect them and they can earn the respect of other people around them. I have plenty of friends. I have a loving family. I have lots of people I like. And in a dream world, I'm getting joy out of everyone I work with. But that joy doesn't have to be from connecting with the person through a sense of like, if that makes any sense. And frankly, it's something I've worked on a lot in my career, especially in the early days. Like my number one priority when I started in sales and started at HubSpot was to be liked above all. I thought being everyone's best friend was the The key to success and the only way to live life. And what I realized is if you're striving for people to like you, you don't have the courage to say hard things, to challenge your peers, to challenge someone you work for. So for that reason, I'm totally okay hiring someone who I don't like per se, so long as I respect the way that they think, and I think that they are a high integrity human being.

AI assessment note: “Yeah, Harry, I would hire someone if I didn't. Like them.”

Q What the questions are to uncover it, because the attributes, I guess, will differ dependent on enterprise sales led versus PLG led. What are the questions that uncover the characteristics? Is it, what's your price point? Who is the Customer segment. What do they look?

A So the questions that uncover whether someone has an attribute give you a sense of how that person thinks in an unscripted way. So let's say that our attribute is business acumen. Let's say we're selling a really complex product to a very intellectual buyer and someone needs to understand how the business works rather than just, you know, going through a simple ban qualification. If I'm testing for business acumen, I might ask the person, what's a company that interests you deeply or what's a company you've been following? What is it about their business model that interests you? What do you think might hurt? What would it take for them to 10 X in terms of their own growth? And I go deep to see, are they reading? Are they thinking? Are they curious? You know, you do that for each of the attributes that you're looking for.

AI assessment note: “If I'm testing for business acumen, I might ask the person, what's a company”

Q Danny, I did not listen to anything post meeting husband through English. Can we just understand, what was this first message?

A Okay, it's the opposite advice that I would give to any sales rep, where you say, be thoughtful, customize it, do your research. I thought, Danny, you have a really good intuition. You know your type. So I went on Toki Cupid, and I looked for who met that criteria. Witty didn't hurt that Jake was holding a guitar in his opening photo. Kept it simple. It was something like a, hey, how's your weekend? Broke the ice, and you know, one marriage, two kids later, it's going very, very well. So I would say, know yourself and go for it. Like, worst thing, if someone doesn't respond, they probably just didn't get the message, right? It's not like they're rejecting me personally. So I had literally nothing to lose.

AI assessment note: “It was something like a, hey, how's your weekend?”

Q I had someone on the show the other day and they said, you're never going to get that pedigreed head of sales from that Decacorn company. They won't join your startup as a head of sales or a VP of sales. You always have to internally promote. Do you agree with that? And how do you think about that? You know, it Hailed, you know, Salesforce branched versus internal promotion.

A I do, and I don't agree with that. There's two elements of what you're describing. One is what company they built their career in, or what companies they built their career in, and number two is at what level did, did they end up at that company? So do you need the CRO of publicly traded, high growth, hot, hot, hot company to be the head of sales at your very early stage startup? Probably not, or that might not be the right spec for the first head of sales hire. Do you want someone who has seen what good looks And seeing what really high caliber talent looks like, seeing rate of rapid change, seeing really good processes in action, yes. So you may just go one to two clicks under that CRO, and that's a perfectly acceptable hire. That said, you said another part of it, which was, do I need to promote from within in order to have successful head of sales, or perhaps to emphasize a positive culture? For me, for this key role, the answer is not necessarily no. It's too important of a role. You need someone who can see around the corner, anticipate what's coming, bring in a second layer of senior leadership who's going to help run the engine. And it's just hard to do that from within. So should you create a culture of promoting within? Yes. Should you always be aware as the company grows of how many hires are coming externally versus internally? Yes. But for first senior leadership h…

AI assessment note: “I do, and I don't agree with that. There's two elements”

Q What do you find more productive or efficient in terms of uncovering quality? Is it putting them on the phone with customers and having sales loft and recording? Or is it selling to you and selling internally? How do you think about that one?

A Oh, no. I want to see what it looks like when they are in their absolute Comfort zone. And I want to see them rock it in their comfort zone. So I would say, pitch me your product, or let's do a discovery call, because I think that's more telling than a pitch. And help me understand who am I as the buyer? What are the most common objections you hear? And you only need like, 30 seconds of prep on it. And then ask them to run you through a discovery call. And what you're listening for is, do they ask open-ended questions when you give them the objections that they just told you they hear all the time? Can they handle those with thoughtful questions? Can they dig in? Can they avoid going straight to discount? Accounting or any sort of transactional interaction. So I would put them in their comfort zone and let them do their thing, and hopefully they can shine there. And perhaps if it's light prep, you can have them try pitching your product to them. But when you're evaluating them on that criteria, just be reasonable with the bar. Because you're the expert in your product, they're not. What you want to look for there is craftsmanship. Are they putting together one or two slides that don't have any typos? Are they getting the gist of who your customers are? Have they done their homework? Have they watched YouTube videos, podcasts, et cetera?

AI assessment note: “So I would say, pitch me your product, or let's do a discovery call”

Q I mean, this has gone off piece, but I'm enjoying this so much. My biggest weakness, Danny, I've done well early, but my biggest weakness, I just desperately want to be liked. And it means that I am not as strong as I could be sometimes on certain things. My question is, how do you think I get over that? Sorry, it's not an easy question.

A What we didn't talk about, Harry, is that I broke into tech, but what I really wanted to be was a therapist. I just needed to be able to pay off my college loans pretty quickly, so I really appreciate this question. I think if you make it a priority to be respected versus liked, it will inch you in that direction, and especially if you have an accountability partner. So this is silly, but When I was age 24 at HubSpot, I had taken the sales assessment that said, you want people to like you too badly, and my boss at the time, Pete Caputo, was the one who saw the results of that assessment, and he put a sticky note on my cubicle, which was next to his, that said, need for approval, and every time he could hear me gratuitously complimenting someone or avoiding asking a hard question, he would point to the sticky note, and it was so nice to have an accountability partner where it almost tapped into my desire for him to like me, probably, but I would want To prove that I could be respected over liked for the sake of working on this core skill. I guess, Harry, a better way to answer the question is think about someone who loves you unconditionally. I'm sure you have many of those people in your life. Those are the people who we need and want to like us. And when I want to ask a really courageous question, and I'm worried that it's going to ruffle some feathers or piss someone off, I t…

AI assessment note: “if you make it a priority to be respected versus liked, it will inch you”

Q Not at all. As I said, I've been excited for this one. So let's start with a little bit of context. So how did you make your way into the world of tech, and how did you come to lead some of the most powerful sales orgs, and the entry into sales for you?

A Combination, like all good things, of personal priorities, A little bit of serendipity, and I would say professional ambition in terms of what got me into tech in the first place. So the personal story is my parents moved here in the early eighties as refugees from the Soviet Union, landed in Pittsburgh, Jewish family services, welcomed them, gave them English classes, money, furniture, and eventually helped my dad land a job at Motorola. He was an engineer, as was my mom. And so family landed in Boston, settled down, laid roots there. Essentially, my parents took this big, bold risk To move themselves and their three-year-old daughter at the time to give us all the opportunities in the world. And so I go to college kind of understanding that that's in the back of my mind. Senior year of college, I unfortunately find out that my mom is sick. Immediately make the decision to move home after graduating Penn. So when everyone else is moving to New York, I moved to Boston to be a caretaker of my mom, along with my dad. And because I'm in Boston and because essentially I'm in the right place at the right time, I'm there just as this Little company called HubSpot is getting started in Cambridge, Massachusetts. I land on the HubSpot website at some point during job exploration. I immediately fall in love with the company. Like it's a complete culture magnet before the word culture was…

AI assessment note: “I'm there just as this Little company called HubSpot is getting started in Cambridge”

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

A In a product-led growth company, a rep and a leader have to be very well versed in the product because prospects come to you very well versed in the product. They may have been using it for free for months or years before you talk to them. So signal number one is actually in the interview process. A good candidate will use the product And perhaps deliver some of the interview unprompted by utilizing the product itself, just to show that they know how to geek out in there and that they've taken the time to understand the user journey. Once you're on the other side of red or yellow flags, when you're onboarding a new rep or a new leader, it's kind of biased toward action. So I did talk about the listening tour for a leader and on the leader side, I would look to see whether they've developed a point of view about what are the one to two things that are most important to deliver on over the course of this year and what's their action plan. For doing that. And that comes from a combination of learning from the founder during the interview process and hearing from customers directly. If a leader had not gotten in front of a customer, if he or she was sitting in virtual or physical conference rooms for their first two months and wasn't talking to one new customer at minimum every single week, that is a major flag for me about customer orientation and the health of the org that they w…

AI assessment note: “if he or she was sitting in virtual or physical conference rooms for their first two months”

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

A In a product-led growth company, a rep and a leader have to be Very well versed in the product because prospects come to you very well versed in the product. They may have been using it for free for months or years before you talk to them. So signal number one is actually in the interview process. A good candidate will use the product and perhaps deliver some of the interview unprompted by utilizing the product itself, just to show that they know how to geek out in there and that they've taken the time to understand the user journey. Once you're on the other side of red or yellow flags, when you're onboarding a new rep or a new leader, It's kind of biased toward action, so I did talk about the listening tour for a leader, and on the leader side, I would look to see whether they've developed a point of view about what are the one to two things that are most important to deliver on over the course of this year, and what's their action plan for doing that, and that comes from a combination of learning from the founder during the interview process and hearing from customers directly. If a leader had not gotten in front of a customer, if he or she was sitting in virtual or physical conference rooms for their first two months, And wasn't talking to one new customer at minimum every single week. That is a major flag for me about customer orientation and the health of the org that they…

AI assessment note: “That is a major flag for me about customer orientation”

Q see the incredible sales playbook that you have there at Slack, the incredible enterprise division that you built out, but they're a lot earlier, and they go, do I need to be the first person to create this playbook, or can I bring in a head of sales, seasoned head of sales, to create the playbook for me in the early days? How do you advise founders in those situations?

A Such a good question. So the founder needs to sell the product before anyone else can. So day one, founder equals head of sales. And I'm less concerned about a playbook per se, but he or she needs to find a way to get in front of customers, understand what makes them light up, understand what hurts without their product, understand the objections that come up, and feel that experience of asking for money and managing a timeline. And after selling the first 10, 20 customers, the founder will, number one, have a really good sense of Empathy for the first official salespeople that he or she brings on. And number two, we'll learn that selling is one of the most important input mechanisms for product direction too. So I just think it's a really, really healthy first step for the founder to wear that hat before hiring someone else to professionally wear that hat going.

AI assessment note: “the founder needs to sell the product before anyone else can”

Q missed a company like a five million pre that's now a six billion dollar company because I listened to the reference on the founder, and they said he was a shit employee, and he was, you know, Opinionated and rude and all these things. And it was wrong. He was a great founder and a terrible employee. How do you think about the things to not take from reference schools?

A Let's go back to earlier in the conversation. We talked about what makes someone a 10 X sales hire, a 10 X sales hire, in my opinion, breaks glass. So if I got a reference from someone, for example, that said this person was not a joy to work with a hundred percent of the time. In fact, sometimes he or she was a bull in a China shop, but let me tell you, this person was very effective. And once you broke into their inner circle, they are extremely loyal. You know, something like that, like that's okay. That's not an unequivocally positive reference on all dimensions, but it fits the spec of my criteria. I also, I want to hear holistic references, and not every spiky individual gets glowing references from every single person. So if I hear 10 glowing references, and I hear one negative reference, I decide whether the red flags I heard are absolute deal breakers. Maybe I'll do even more references vetting into that, and I'm comfortable ignoring it at times. So there's another thing, Harry, which is like, your intuition matters. References are critical, but they aren't everything. And if your intuition is saying, I had a good connection with this person, I've heard plenty of good things around them, and sure, they may have frustrated one person or been a really bad employee in that stage of their career. Who knows what was going on in their personal life? Fine. Trust the intuition…

AI assessment note: “I decide whether the red flags I heard are absolute deal breakers”

Q I agree totally in terms of them understanding the messaging, what works, what doesn't, seeing that pain point for the customers. The question is when they do suddenly need that hire, How do they determine between young, hungry, jack-of-all-trade sales reps or a seasoned sales leader who can bring in and form their own team? What's the thinking there?

A A yes end, a little bit sequential. Say the first head of sales is the founder, like we said. The next one could be a player coach who can roll up his or her sleeves, do the selling while simultaneously taking the lead on hiring the next four account executives. And often we see that. We look for someone who has led a team before, so they are Thinking company first, not just individual first or quota first, but they're not so, so senior that they're not ready to go do the work. And we look for that person to carry the bag, hire a few others. And then at that point, it's probably time to bring on a more official head of sales. If this person isn't really ready to stretch and step into that role and by ready to stretch and step into that role, it's a two way conversation. That's not just, they feel ready, but it also means CEO and founder believes that that's what gives them the best chance of success.

AI assessment note: “A yes end, a little bit sequential. Say the first head of sales is the founder”

Q I think confidence is such an important part of sales, especially on the wrap side when they're maybe a little bit younger. Is there anything that can be done to maybe create a little bit of artificial confidence for them, maybe super low-hanging fruit on the customer basis? Is there anything that you think works In terms of giving that early confidence boost for reps in their first few months?

A Part of it is the culture that the founder sets and that the CRO sets within the company. So if there is a culture where experimentation is welcome and failure is okay, someone doesn't have to feel perfect when they hop on that first Zoom call with a customer. If you can give a new rep some really small business leads to go after. So folks that don't have a jaded, you know, head of IT who's going to be really strict In negotiations and really tough and guarded, that could be a really good place to start. Set them up for success in some of their first conversations. As soon as they run their first call, bring them into a Zoom room or bring them into a conference room, recap and celebrate what went well. I'm personally like much more of a positive reinforcement versus motivate through fear kind of person. So I think genuinely celebrating anything that they rocked in that interview process is Even if it was building non-transactional rapport, like going deeper than just asking about the weather, I would celebrate that and let the person own it as part of their personal brand so that they keep letting their guard down and having more and more swagger on these conversations.

AI assessment note: “give a new rep some really small business leads to go after”

Q to do outbound. They don't want to pavements really getting prospects through the door and just into the funnel in the first place. Everyone wants to do the cool and the sell when they're educated and they've reached a certain qualification level. Do you find that in terms of this unwillingness to do outbound now in this rather luxurious world of product-led growth and educated customers that we live in?

A Remember what we talked about is the number one trait of a 10 X seller. They love to sell. Loving to sell does not mean sitting back in your chair and waiting for product qualified inbounds to fall into your lap. Yes. The beauty of being a sales professional at a PLG company is that you get to talk to customers who are already warmed up and teed up and hopefully effusive about the product, but you have to be really proactive. So a good seller within a PLG company is kind of like an extroverted user researcher. So they may have talked to 10 different users on the front lines who are effusive about the product, and then they're synthesizing those user interviews, putting those into some sort of an email that they're going to send up to the CIO saying, here's what I've learned about how your company operates, and here's a unique insight that you would have never gotten on your own that I'm serving to you as kind of a carrot for a live conversation together.

AI assessment note: “Loving to sell does not mean sitting back in your chair and waiting for product qualified inbounds”

Q We're going to move into the characteristics that make those 10 X heads of sales 10 X. I do just want to touch on timing again, though, but for the role of CRO, because there is a transition moment for when the CRO is needed. How do you think about that turning point for when not only you need a head of sales, but you need to add that CRO?

A Yeah, you need a CRO when you're past the zero to one phase. So the sales formula is working. It's time to scale it to the next level. And personally, I like to leave room for someone to grow. So if you're an earlier stage company, let's say in the low two Tens of millions. I would hire a VP or an SVP so that they have something to grow into. We with sales DNA are very internally competitive, so it's always good if there's something to work toward. And if you're at a later stage company, you can hire a CRO who's seen the movie for the next stage of growth. And the one thing that I would say is the CRO is going to significantly influence the DNA of your sales work. Good folks see people follow them into a new gig. So you want to be really, really thoughtful about which company's culture and DNA you want super infused into your own when you are making Making that higher. It's a very important decision.

AI assessment note: “you need a CRO when you're past the zero to one phase.”

Q missed a company like a five million pre that's now a six billion dollar company because I listened to the reference on the founder, and they said he was a shit employee, and he was, you know, Opinionated and rude and all these things. And it was wrong. He was a great founder and a terrible employee. How do you think about the things to not take from reference schools?

A Let's go back to earlier in the conversation. We talked about what makes someone a 10 X sales hire, a 10 X sales hire, in my opinion, breaks glass. So if I got a reference from someone, for example, that said this person was not a joy to work with a hundred percent of the time. In fact, sometimes he or she was a bull in a China shop, but let me tell you, this person was very effective. And once you broke into their inner circle, they are extremely loyal. You know, something like that, like that's okay. That's not an unequivocally positive reference on all dimensions, but it fits the spec of my criteria. I also, I want to hear holistic references, and not every spiky individual gets glowing references from every single person. So if I hear 10 glowing references, and I hear one negative reference, I decide whether the red flags I heard are absolute deal breakers. Maybe I'll do even more references vetting into that, and I'm comfortable ignoring it at times. So there's another thing, Harry, which is like, your intuition matters. References are critical, but they aren't everything. And if your intuition is saying, I had a good connection with this person, I've heard plenty of good things around them, and sure, they may have frustrated one person or been a really bad employee in that stage of their career. Who knows what was going on in their personal life? Fine. Trust the intuition…

AI assessment note: “I decide whether the red flags I heard are absolute deal breakers.”

Q relationship points between sales and Other parts of the org before we do a quick fire. One is sales and product. You said about at the beginning, the feedback loop between sales and the founder being close to sales and the benefits it has in terms of his feedback and communication with products. How do you think about creating really tight communication channels between sales and product within your org?

A Number one, incentives should be aligned. If it's a product-led growth company, then product essentially owns the pipeline number. And you may have a CML, but I would want the chief Product officer to have a constant sense of what the self-serve funnel looks like, levers we can pull and feel serious accountability, and I want them to have a hire who is exclusively focused on growth and setting up product momentum for the specific ICP that you're going after. So it's not enough, for example, to have product momentum in the SMB if you're a company that wants to march up to the enterprise. And then alignment-wise, I mean, it's just human engagement, one-on-one, meet regularly, create an opportunity to have Yeah. Personal relationships there.

AI assessment note: “Number one, incentives should be aligned... it's just human engagement, one-on-one, meet regularly”

Q If you bring in an External talent. How do you do that in a way that doesn't disincentivize or demotivate younger people in the team who were hoping that they might have their shot at that role? How do you bring in without demotivating?

A Well, I talked about this concept earlier of giving away your Legos. I said it was a hallmark trade of the hyper growth phase at Slack where I was there. I think you need to make that a part of each employee's personal brand. And if you're not familiar with the concept, this amazing woman named Molly Graham wrote an article talking about giving away Legos, which basically At a hyper growth startup, the company is changing so quickly that you need to take pride in being the person who stands something up, allows it to run pretty well, and then hands it off for someone else to scale it. And so I would imbue that into the culture. So there are no surprises when you make senior leadership hires from the outside. And also I would interview the prospective sales leader to figure out what worked for you. Let's use Salesforce as an example. What worked for you at Salesforce that fundamentally will not work For you when you join us here at, insert name of the company, Linear, Loom, Figma, whatever. And if that person cannot name what won't fit a new culture as opposed to what worked in their old one, they're not showing any flexibility. And my hunch is they're going to be a playbook person, takes a carbon copy and brings it from one place to the other. They need to be thoughtful about what's not going to match the new culture they're stepping into.

AI assessment note: “I would imbue that into the culture. So there are no surprises”

Q Not at all. As I said, I've been excited for this one. So let's start with a little bit of context. So how did you make your way into the world of tech, and how did you come to lead some of the most powerful sales orgs, and the entry into sales for you?

A Combination, like all good things, of personal priorities, A little bit of serendipity, and I would say professional ambition in terms of what got me into tech in the first place. So the personal story is my parents moved here in the early eighties as refugees from the Soviet Union, landed in Pittsburgh, Jewish family services, welcomed them, gave them English classes, money, furniture, and eventually helped my dad land a job at Motorola. He was an engineer, as was my mom. And so family landed in Boston, settled down, laid roots there. Essentially, my parents took this big, bold risk To move themselves and their three-year-old daughter at the time to give us all the opportunities in the world. And so I go to college kind of understanding that that's in the back of my mind. Senior year of college, I unfortunately find out that my mom is sick. Immediately make the decision to move home after graduating Penn. So when everyone else is moving to New York, I moved to Boston to be a caretaker of my mom, along with my dad. And because I'm in Boston and because essentially I'm in the right place at the right time, I'm there just as this Little company called HubSpot is getting started in Cambridge, Massachusetts. I land on the HubSpot website at some point during job exploration. I immediately fall in love with the company. Like it's a complete culture magnet before the word culture was…

AI assessment note: “Combination, like all good things, of personal priorities, A little bit of serendipity”

Q How do you test for that in the companies that you meet? Because everyone says they have great culture, and everyone says they prioritize it, but how do you test for it when you meet founders?

A It's a great question. So let's take Notion as an example. Notion is the first company that I've partnered with since joining Sequoia, and I've known Ivan and Akshay for almost four years. If you go on YouTube and you type in the word Notion, you will find creators with millions of views just explaining how to geek out on Notion and use it for personal or professional or educational purposes. If you go to Twitter and you type in the word Notion, you don't go to Notion's handle, but you just type the word into search, you will find 1000, Of people who just like HubSpot have bet their career on Notion so much so that they put it in their Twitter handle as a part of their professional or personal identity. So like that is a phenomenal way to vet out community engagement. The third thing was, I remember when I went to their office a few years ago, they had a printed manual of how to use Notion. I think it was Korean manual that the community, no one who worked at the company, just people who were enthusiasts had written out and printed and bound to help I totally agree with you in terms of that community content creation.

AI assessment note: “that is a phenomenal way to vet out community engagement.”

Q that flexibility within their mindset. So totally agree with you there. Can I ask, in terms of the process, I think founders lack a little bit of awareness as to the right structure in terms of hiring these sales reps or heads of sales. How do you literally structure it? Like meeting one, intro, meeting two, case study, meeting three, offer? What does structure look like in an ideal world?

A Most founders, as you know, have a background in product or eng, so they've nailed these tech interviews. They have no idea where to begin from. For evaluating salespeople or sales leaders. And on top of that, you know, what's really tricky about interviewing sales folks? Well, they are very good at selling. So if you ask hypothetical and behavioral questions, like what's your 30, 60, 90 plan, you are going to get really articulate, well-scripted answers that do not help you vet the candidate in earnest. So when I work with founders on creating a sales interview process, we start by creating a scorecard. That scorecard has no more than five must-have Attributes and skills, and we figure out what those are, and then we start structuring the questions around them.

AI assessment note: “we start by creating a scorecard. That scorecard has no more than five must-have Attributes”

Q If you bring in an External talent. How do you do that in a way that doesn't disincentivize or demotivate younger people in the team who were hoping that they might have their shot at that role? How do you bring in without demotivating?

A Well, I talked about this concept earlier of giving away your Legos. I said it was a hallmark trade of the hyper growth phase at Slack where I was there. I think you need to make that a part of each employee's personal brand. And if you're not familiar with the concept, this amazing woman named Molly Graham wrote an article talking about giving away Legos, which basically At a hyper growth startup, the company is changing so quickly that you need to take pride in being the person who stands something up, allows it to run pretty well, and then hands it off for someone else to scale it. And so I would imbue that into the culture. So there are no surprises when you make senior leadership hires from the outside. And also I would interview the prospective sales leader to figure out what worked for you. Let's use Salesforce as an example. What worked for you at Salesforce that fundamentally will not work For you when you join us here at, insert name of the company, Linear, Loom, Figma, whatever. And if that person cannot name what won't fit a new culture as opposed to what worked in their old one, they're not showing any flexibility. And my hunch is they're going to be a playbook person, takes a carbon copy and brings it from one place to the other. They need to be thoughtful about what's not going to match the new culture they're stepping into.

AI assessment note: “imbue that into the culture. So there are no surprises when you make senior leadership hires”

Q that flexibility within their mindset. So totally agree with you there. Can I ask, in terms of the process, I think founders lack a little bit of awareness as to the right structure in terms of hiring these sales reps or heads of sales. How do you literally structure it? Like meeting one, intro, meeting two, case study, meeting three, offer? What does structure look like in an ideal world?

A Most founders, as you know, have a background in product or eng, so they've nailed these tech interviews. They have no idea where to begin from. For evaluating salespeople or sales leaders. And on top of that, you know, what's really tricky about interviewing sales folks? Well, they are very good at selling. So if you ask hypothetical and behavioral questions, like what's your 30, 60, 90 plan, you are going to get really articulate, well-scripted answers that do not help you vet the candidate in earnest. So when I work with founders on creating a sales interview process, we start by creating a scorecard. That scorecard has no more than five must-have Attributes and skills, and we figure out what those are, and then we start structuring the questions around them.

AI assessment note: “we start by creating a scorecard. That scorecard has no more than five must-have”

Q How do you test for that in the companies that you meet? Because everyone says they have great culture, and everyone says they prioritize it, but how do you test for it when you meet founders?

A It's a great question. So let's take Notion as an example. Notion is the first company that I've partnered with since joining Sequoia, and I've known Ivan and Akshay for almost four years. If you go on YouTube and you type in the word Notion, you will find creators with millions of views just explaining how to geek out on Notion and use it for personal or professional or educational purposes. If you go to Twitter and you type in the word Notion, you don't go to Notion's handle, but you just type the word into search, you will find 1000, Of people who just like HubSpot have bet their career on Notion so much so that they put it in their Twitter handle as a part of their professional or personal identity. So like that is a phenomenal way to vet out community engagement. The third thing was, I remember when I went to their office a few years ago, they had a printed manual of how to use Notion. I think it was Korean manual that the community, no one who worked at the company, just people who were enthusiasts had written out and printed and bound to help I totally agree with you in terms of that community content creation.

AI assessment note: “that is a phenomenal way to vet out community engagement”

Q relationship points between sales and Other parts of the org before we do a quick fire. One is sales and product. You said about at the beginning, the feedback loop between sales and the founder being close to sales and the benefits it has in terms of his feedback and communication with products. How do you think about creating really tight communication channels between sales and product within your org?

A Number one, incentives should be aligned. If it's a product-led growth company, then product essentially owns the pipeline number. And you may have a CML, but I would want the chief Product officer to have a constant sense of what the self-serve funnel looks like, levers we can pull and feel serious accountability, and I want them to have a hire who is exclusively focused on growth and setting up product momentum for the specific ICP that you're going after. So it's not enough, for example, to have product momentum in the SMB if you're a company that wants to march up to the enterprise. And then alignment-wise, I mean, it's just human engagement, one-on-one, meet regularly, create an opportunity to have Yeah. Personal relationships there.

AI assessment note: “alignment-wise, I mean, it's just human engagement, one-on-one, meet regularly”