20 Sales: Notion's CRO Olivia Nottebohm on How To Build Great Operations at Your Company, How To Use The Trust Equation in Hiring, How To Do Referencing Most Effectively and Whether To Fill Seats or Wait for the Perfect Hire?

Olivia Nottebohm is the Chief Revenue Officer @ Notion where she leads the Sales, Marketing, Customer Success and Customer Experience teams. Prior to Notion, Olivia was the COO @ Dropbox where she achieved the first 4 quarters of profitable growth. Before Dropbox Olivia spent over 5 years at Google including as VP Cloud GTM Operations and Global SMB Sales. Finally, before Google, Olivia spent a whopping 15 years at McKinsey & Company. In Today’s Episode with Olivia Nottebohm You Will Learn: 1.) Origins: How Olivia made her way into the world of startups and tech? What are 1-2 big takeaways Olivia has from her 5+ years at Google? How have they shaped her operating mindset today? How does Olivia balance her love for analysis and data with speed and agility of decisions? 2.) Good vs Great Operations (Ops): What does great ops really mean to Olivia? What are the 1-2 things founders can implement today to improve their ops immediately? What are the core mistakes founders make when instilling ops for the first time? How does Olivia coordinate the global Notion team to be as effective as possible? What has worked? What has not worked? 3.) The Hiring Process: Why does Olivia believe all leaders will have to accept they will not have all the talent they need over the coming years? With that in mind, is it best to hire B players or always keep the bar high? If and when can the bar be lowered? How does Olivia construct the hiring process? What are the core questions she will always ask? What is the secret to great referencing? How does Olivia enable the other side to feel safe telling her everything they know about the candidate? 4.) Cross-Functional Communication: How does Olivia advise founders on the best way to get different functions working together? What works? What does not? What are some big mistakes Olivia sees over and over? At what point in company scaling does this comms begin to breakdown? Item’s Mentioned In Today’s Episode with Olivia Nottebohm Grow Fast or Die Slow: The role of profitability in sustainable growth

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

• 0:00Harry Stebbings?

  This is 20 Sales with me, Harry Stebbings. Now, 20 Sales is the monthly show that takes you inside the mind of the best sales leaders in the world to unpack their tips, tactics and strategies to scaling truly world-class sales organizations. Today, we're joined by a great. I'd heard so many incredible things from many different people. And so I was so thrilled to welcome Olivia Nottebohm, Chief Revenue Officer at Notion, where she leads the sales, marketing, customer success and customer experience teams. Prior to Notion, Olivia was the COO at Dropbox, where she achieved the first four quarters of profitable growth. Before Dropbox, Olivia spent over five years at Google, including as VP of Cloud Go-to-Market Operations and Global SMB Sales. And finally, before Google, Olivia spent a whopping 15 years at McKinsey & Company.

• 0:43Harry Stebbings?

  And I also want to say a huge thank you to Danny at Sequoia for the kind intro, and then Akshay and Camille at Notion for some amazing question suggestions today. But before we dive into the show today, Sales Loft is the leading sales engagement platform, helping sales teams drive more revenue with the modern revenue workspace. It's the one place sales teams can go to prospect, manage active deals, and get the insights they need to coach seller performance, forecast with accuracy, and find out what steps to take to close more deals. Some of the world's leading companies like IBM, Shopify and Stripe all love a new Sales Loft, and so can you. It's the new way to sell, and find out more today at salesloft.com. And founders, if you've got recurring revenue like so many of you have, there is a smarter way to grow your business. As a VC, this pains me to say.

• 1:26Harry Stebbings?

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• 2:10Harry Stebbings?

  Twenty sales to start trading today. And finally, to scale your business, you need customers. But this CRM software model is thirty five years old and it's never evolved to properly support modern businesses. Most legacy platforms were built for a single rigid, repeatable sales process. But guess what? Copper is a dramatically different kind of CRM. Built for Google Workspace businesses, Copper works right alongside you in your inbox. And it's so flexible and versatile that you'll love it regardless of how you run your business. Plus, it requires virtually no training because it works just like all your other Google apps. Get set up in less than a day and easily customize your CRM to fit your needs. I promise you, this will be the first time that your team love you as a leader for choosing a CRM solution. That is a personal experience of mine.

• 2:52Harry Stebbings?

  And so see why more than thirty thousand businesses love Copper, a flexible CRM that grows with you. Get a twenty percent discount on any annual plan. Just go to copper.com/20vc. But that's enough from me. So now I'm so excited to hand over to the one and only Olivia Notterbaum, Chief Revenue Officer at Notion.

• 3:14Speaker 01

  You have now arrived at your destination.

• 3:17Harry Stebbings?

  Olivia, I have been so excited about this one. I've heard so many great things from so many different mutual friends. So thank you so much for joining me today.

• 3:24Speaker 02

  Well, it's lovely to be here, Harry. Thank you for having me.

• 3:27Harry Stebbings?

  Not at all, but I want to start with a little bit on you. So when we look, we've got Google, we've got Dropbox, we have now Notion. Tell me, how did you make your way into the world of tech? And how did you come now to be where you are in terms of CRM, Notion?

• 3:39Speaker 02

  Tech has always been something that for me was this fast moving pace that I adored. So early on, I was an analyst at McKinsey and I found myself really being drawn into tech because you're always having to push yourself. The innovation was always happening. Something like Moore's Law just fascinated me in terms of the pace of innovation. And so, yeah, it feels like a place where you have to keep on your toes and you have to keep on thinking. And it's nice to push yourself. And so I just adore being in tech.

• 4:09Harry Stebbings?

  Can I ask, how did Notion come about?

• 4:11Speaker 02

  Yes, well, it's one of those classic stories of you happen to be talking to someone who happens to talk to someone here in Silicon Valley. I was Talking to David Schneider, he was over at ServiceNow and he's now at Co2. He had been chatting with Ivan and Akshay over at Notion and they were thinking through some things and he connected us. And so we were just chatting about the business. I had led the SMB sales business and broad SMB business over at Google Cloud and had a number of tremendous leaders over there. But we had learned a lot in the world of SaaS. It was, you know, an interesting space where you're not only acquiring SMBs, but you're trying to be very thoughtful about acquiring digital natives because they will be your future enterprise players.

• 4:56Speaker 02

  And how to navigate that and how to keep up the pace of growth in a space that's very competitive. And so we were problem solving on that topic. And at one point Ivan and Akshay said, hey, do you want to come join the team?

• 5:09Speaker 02

  So that's how it happened.

• 5:10Harry Stebbings?

  I love that and I love the kind of casual nature of conversations in the valley that come to such great things. I do want to ask, you mentioned there about kind of learnings from Google, didn't you? You were six years at Google almost and then obviously your time at Dropbox. I'm really intrigued, both such iconic institutions. When you think about like a core takeaway that's really impacted your mindset from each, is there one or two things that really comes to mind from Google and Dropbox?

• 5:31Speaker 02

  From Google, there were two things that I took away. One is that outside in, it looks like this beautiful business model and it is. The auction model that Hal Varian introduced into the ads world was truly genius. As an economics major, by training, something that I have deep respect for. What really wowed me at Google was the operating rigor. It is not an accident that they perform as well as they perform. And it's a high bar that's held. And then the second takeaway, I would say after two years, I went over and joined Diane Green over at Google Cloud. And she was just this amazing, amazing person that always put the customer in the center of it all. And when you're building a business where you have to convince the world

• 6:14Speaker 02

  that Google is ready to serve enterprises because, you know, it's perceived as an ads business. And here we are wanting to provide infrastructure as a service and platform as a service and software as a service. By putting customers in the middle really was just this unifying force that gave us the Escape velocity that we needed. Diane Green ran her staff meetings that way. Every Monday, we were problem solving how we could help a certain customer and a certain type of customer and what we needed to do to get them truly just loving the product. And that was very special.

• 6:44Harry Stebbings?

  You spoke about rigor of ops there. Before we dive in a little bit more into the granular, I spoke to Ashleigh before the discussion today at Notion, who's obviously with you on your team. And he said about your unique world-class talent at implementing process, but also on the importance of ops and what great ops is. Respectfully, I kind of looked at the email from him and I was like, that sounds great. But what is great ops? So can you just help me understand Ashleigh a little bit? What is great ops? And how do you think about coming in and great implementation?

• 7:13Speaker 02

  Ops is really about connecting end to end, how functions work together. I mean that very respectfully. You can have amazing functions in a company, but if they're not working in lockstep with each other, you can have tremendous amount of friction, rethinking of decision-making, behavior where you feel like you're taking three steps forwards just to take two or four steps back, right? So it's kind of this constant thinking of, okay, what is the chess game I'm playing? And I need to have played three, four steps ahead to anticipate what the blocker is going to be so that I can do my part in unblocking my teams to make sure that when they get to that point, they're able to go through with no friction.

• 7:56Speaker 02

  No, I don't try to lead the functions myself, right? As a CRO, I have amazing leaders in marketing, there are amazing leaders in sales, support, customer success, revenue and operations. These are all functional luminaries in their own right, and I deeply respect what they do. And I see my job very much as making sure they're all connected and talking and making sure that as I look out across the things that we're trying to get done as a company, that those functions are unblocked for what they need to do to deliver the targets that we set for them.

• 8:28Harry Stebbings?

  So is it a challenge then? Because you know, you've got revenue optimization, but then you've got a lot of other things that you have to be very aware of. How do you balance?

• 8:35Speaker 02

  You never want to make decisions as you're building to optimize for revenue. You really, really have to be careful not to do that. In fact, I would almost recommend that you take away things that pull you in the direction of something that would make you optimize for revenue decisions. So let me give you an example. Some businesses have portions of them that, you know, were there at the origin and were an early entry, but over time it's clear that there's just not enough TAM there. There's not enough opportunity there to actually sustain that being the business driver for the company. And especially in a world where you're trying to double and then double and then double, right?

• 9:16Speaker 02

  Because growth is paramount, because really what we're trying to do is reach as many users as possible, right? You want to make sure that you don't have these distractions. So I much prefer to actually sunset that and not have it be a distraction with people having to spend parts of their time thinking about, well, how do I get this piece of the business from 10% growth up to, you know, 110% growth, which is what the rest of our business is pacing at? It's almost better to just cut off the branch and say, you know, that was a great entry. That gives us a great halo. We'll actually just offer that for free now, but we're not going to try to resuscitate this piece of the business back up to 110% growth when it really just doesn't have the ability to do that. And frankly, we spent a lot of time doing it.

• 9:57Speaker 02

  So I also think you have to make very important decisions like that so you don't get distracted.

• 10:02Harry Stebbings?

  Tam and Shadi, going back to the conversation we had on the revenue meeting and bringing the different people who own different parts of the funnel. The thing I find challenging today, Olivia, is like, you know, customer success leads to new signups. And then, you know, marketing leads to sales. And there's such an overlap and convergence now of the different parts of the funnel, where traditionally, you know, sales and marketing were quite split. But as we both know, buyers are so much more educated and actually marketing's eaten so much into the sales funnel. So I guess it's like, how does one think about attribution today in a world where it's so intermingled?

• 10:34Speaker 02

  Well, I mean, this part is like what I love, so.

• 10:38Speaker 02

  For me, it's really fun to, you operate as a cohesive engine, but actually you do isolate out who is driving what outcome. The brand team, the top of the funnel team is owning net new visitors. They are obviously working in concert with product to drive signup flow, right? And we have to make sure that the quality of those visitors stays consistent. And they offer a counterforce with each other, right? So yes, you are monitoring that net new visitor traffic, and that can come from many, many areas, right? And then you are monitoring that signup. And what you want to be able to do is over time, obviously, improve that signup. And you are seeing, and you're doing tests about what is it that's

• 11:22Speaker 02

  improving that signup rate, right? Is it you're sending different quality of traffic, and nothing has changed in terms of the interaction on the website itself and the product, and you get better signup, then, okay, we attribute that to marketing, they're driving better quality. If in fact, they've just been driving the same quality, but the product team and the web team have just been doing great work in terms of getting those conversions and signups, well, then we attribute it to them. And each of those teams have targets. But we also talk about it openly, right? So, okay, we see that web traffic coming in, we've been able to hold our signup even though we spiked on web traffic. That's great, right? So we're not diluting the quality. And we talk through all of that. That's what the forecast call is for, so that we are truly understanding what's happening in our business. It's not just like a set of traffic lights that are red or green and we move on.

• 12:07Harry Stebbings?

  When you look at your direct reports in particular, and how you think about managing them, what does that look like for you today? And what do you think is too much? I often see too much, and people don't quite see it. So I'm intrigued, like, what does that look like for you today? And what does the communication with those direct reports look like?

• 12:24Speaker 02

  I do believe in more of a flat structure. So a span of control of eight, I feel is very comfortable, especially in my role where I'm really not trying to do the job of any one of the functional leaders on my team, right? Like, you never want to be a micromanager, right? You always want to be bridging across those roles. And sometimes you do see structures where people have kind of four reports, or whatever it may be. But it's usually because then they're taking on a work stream themselves as if it were just professionally, the way that I evolved, at a certain point, you're never owning a piece of work yourself, because that then takes away from your ability to coordinate and look forward and think strategically.

• 13:03Harry Stebbings?

  So if we think about those eight, what does the communication cadence and channels look like between you and them? Is it a week? Sorry, I do go quite randomly, but is it

• 13:12Speaker 02

  Yeah.

• 13:13Harry Stebbings?

  Is it a weekly phone call? Is it like just messages throughout the week on Slack and on WhatsApp? What does that communication pathway look like?

• 13:21Speaker 02

  So what it looks like today is that we have a weekly go-to-market leadership meeting. We call it the business leadership meeting. I really love that meeting. It's held early in the morning so that Europe can join. The only downside is that our J-PAC leader is not available to make it, so he listens to the recordings. And we do try to alternate. So once a month, we try to have it at a time that's friendly to J-PAC, but not so friendly to Europe. And so trying to be thoughtful about that, that's just the reality of operating in a global environment. And then we also have a shared Slack channel, which we use a lot. And it's just us, right? So it's just that leadership team. So we're able to talk about sensitive things. We're able to throw out whatever issues, concerns we have. We're just trying to tag team things. And then I also have one-on-ones with each

• 14:06Speaker 02

  of the leaders every week. Often, that's just grabbing a coffee, going on a walk, but really try to make sure that we have that time. We have standing one-on-one documents in Notion. They're amazing. Everyone should try it. It's very structured. You can pull in whatever content you want. And I always start with whatever they want to talk about. Then I can be a sounding board. I can be a clearinghouse. I can be there to note action items that I need to take to unblock things. Inevitably, I have one or two things that I've been thinking about that I want to make sure that we chat through as well.

• 14:34Harry Stebbings?

  How do you communicate a concern with a functional lead, a direct report, without really kind of ruining their confidence even more if they probably already know that they're struggling? How do you do it?

• 14:43Speaker 02

  The very, very tough conversation kind of of, hey, you've kind of really hit a wall, comes from me in the form of checking in on them and seeing how they think they're doing. Like, how are you feeling right now? Where do you feel the most challenged? Most part, people are self-aware and they actually welcome the time to openly just be able to talk. And frankly, positioning yourself is there to help to say, okay, where are the areas that you feel like you need some coaching on? Or perhaps you need to hire someone on your team who can supplement that skill set? Because maybe you yourself don't have it and that's okay, coming in it from a helping perspective. And that's also frankly, how I handle the even like glitches, right? Like, how can I help get this person hired?

• 15:28Speaker 02

  It seems to be a struggle. This is a key part of your team. You need this leverage. How can I help? Of course, people understand that I'm not offering to help for no reason. But it is important that they know that I truly am spirit-wise there to help and there to make them successful.

• 15:45Harry Stebbings?

  Can I ask another really tough one? I'm really, really making this one easy. But when you have like a role, say, an exact function available and you have people within the team thinking that this is their chance. They are ready for this promotion. Yes, I can do this. But you're actually like, no, we need someone from X business and I know this person and they're fantastic. How do you bring in external talent without demotivating, disincentivizing internal talent who thought that they had it?

• 16:10Speaker 02

  There has to be a very high bar for bringing in external talent if you have a high caliber team. Especially when you're growing a business and especially when you're trying to be innovative. You do want to give people a chance to shine and try things that maybe they haven't tried before. Often people join these smaller hyperscale companies so that they can expand their scope, right? And you don't want to just come in and assume that de facto every time position opens that, you know, you need to go to the external market for it. Because I do think that's disillusioning. I do think that removes people's belief that they too can continue to advance in their careers at this company.

• 16:54Speaker 02

  Really being thoughtful about that decision. Picking the one or two spots where you feel like, okay, this is the time where I really do need to do this. And then to answer your question about having that conversation, it's Still about how do you make that person successful? One thing I think about in these hyperscale companies is by definition, you're almost getting promoted once a year anyway. If you just continue to keep the scope you have because, you know, you continue to double your function, you're responsible for double the output, all of these things, right? So the job doesn't get easier. It actually gets harder. It's not like it's maintaining status quo. You're actually continuing to get pushed over in a really awesome way, I would say. And so also reminding people of that, right?

• 17:36Speaker 02

  Which is the bar keeps on going up in terms of what each function needs to deliver. And I'm confident that you can continue to deliver more and more and more.

• 17:44Harry Stebbings?

  Can I ask, when you think about making these cool decisions? I always struggle with the head versus heart. Being, you know, a romantic European, I tend to go with my heart most of the time. Sometimes it's right, sometimes it's not. How do you think about a head versus heart in decision making? And where you most often go?

• 17:59Speaker 02

  So we have a value at Notion that I feel very, very resonant with. And it's be kind and direct. If you pair the two, you are better off. So you understand person, you deeply care about the person. You have empathy for the journey that they are on. Because you yourself have, I myself have had many times where I thought I should get a role. I didn't get a role. I wanted to be promoted. I didn't get promoted, you know, whatever it may be, right? So in the sense of like, gosh, I've been there too. It's not what you expected. So let's talk about the human element of this. And then let's talk about the right answer for the business. And let's just openly have that conversation.

• 18:42Harry Stebbings?

  Can I ask you, Olivia, a bit of a weird one before we do a quick fire? But you seem incredibly calm, serene, thoughtful, unflappable. Do you feel pressure? And when you do feel pressure, how does that show?

• 18:54Speaker 02

  Honestly, I think you just understand the pressure over time. I would say early in my career, I would feel the pressure and I would transfer the pressure. And I think part of as you decide that you want to try to help a company grow and be in a leadership position, part of what you're signing up to is absorbing the pressure. That is part of your. Function if you just take the pressure and pass down the anxiety that doesn't provide your team with the space they need to operate and a leader who is constantly questioning what their leadership, their own leadership thinks of them is operating at half speed, right? Like you really need your leaders to know that the wind is behind their back and

• 19:39Speaker 02

  they have open waters ahead of them. The seas are rough, but you're there supporting them. So I would say that I go on runs every day. I've been told that it helps me then I'm in my zen state. Like before we chatted, I went on a run.

• 19:53Harry Stebbings?

  I loved the pressure absorber versus pressure transfer. What are the signs when adding to the team, probably most importantly to the C-suite, what are the signs that an individual is a pressure absorber versus a pressure transfer? Are there ways where it can show you, do you think?

• 20:09Speaker 02

  You know, here's the thing I will say, as someone who's done a lot of interviews over time and a lot of learnings, like I've mis-hired a number of times and done all these postmortems of hiring and all of this, I view interviews as highly, highly likely to get a false positive, less likely to get a false negative. Once you have the set that you're like, oh, this person seems capable, wonderful, all of these things, then I just really lean into references. And I reference people, not the ones they've provided to me. Yes, I talk to those as well, but you know, if anyone's smart, they've provided you with someone who's gonna speak well of them. And then I tell them, look, I'm gonna reference you. And I reach out into their network and I find people who've worked with them and I find peers and I find managers and

• 20:54Speaker 02

  I have those conversations because it does really matter. And at the end of the day, if it's still a positive, I've learned a ton and I can coach that person better. And in some cases, it ends up being then a negative and then I'm really glad I put all the work into the reference check.

• 21:09Harry Stebbings?

  I find references useless and it's because I'm probably crap at taking references. How do you get to weaknesses without the person feeling like they've betrayed the person? Even if they don't like them, they're worried that it will get back. How do you make them feel safe? Like, what questions do you ask and how do you bring the truth out?

• 21:26Speaker 02

  I know that I will be more effective in my reference checking if I can actually talk to someone who feels like, actually, if I hire this person and they're a bad egg, they will feel like their own brand is tarnished because they told me that they were stellar. True, by the way, right? Like when someone I know calls me about a reference. We know each other enough, or we run in the same circles enough that, you know, if I give a false reference, my brand value has gone down with that person, right? So, yeah, you have to be very thoughtful in who you reach out to as the reference.

• 21:59Harry Stebbings?

  Are you as direct as saying, hey, where does Olivia suck? Or where is she really weak? We had this fun chat before this interview. But like, you know, do you literally say, hey, where are their biggest weaknesses? Or is there a more graceful, specific, actionable way?

• 22:12Speaker 02

  We're asking you to give away all my secrets, Harry. Next time I'm gonna run a reference, people are gonna say, oh, wait, I know this question. No, I'm happy to answer the question. I start with really getting to know the context in which the person. First of all, it's a good half hour, right? Like, it's a real time investment to do these. It's not like five minutes, like, hey, what's their weaknesses, right? And I know you know that, but just to state the obvious. You know, what's the context in which you know this person? What are their strengths? Where have you seen them really shine? And then diving in deeper on, okay, well, no one's perfect. I myself am not perfect. What would be the one thing that exhibits as something that you're like, no one's perfect? This is the thing I just need to navigate around with this person. People know that all of the good things they said about the person aren't credible

• 22:56Speaker 02

  if they really can't note a weakness.

• 22:58Harry Stebbings?

  Final one before we do a quick fiver, I'm just too intrigued. But my question too is, you mentioned like, you know, the very rare miss hire that you make. When you think about that very rare miss hire, what were some of the lessons for you from the miss hire or the miss hires that you've made in the past?

• 23:12Speaker 02

  That's a great question. I would say that you realize that you did the reference and you heard a flag and you were just so eager to get that role filled that you noted it as, oh, I'm sure it's coachable, and you moved on. And that, I think, is where I've had the most learning, where I was frankly too believing in myself that I could coach that person through it because we just needed to serve this role. And I would say 2022 will be a very challenging year globally in the world of talent, right? Because you saw this kind of great resignation that occurred. Then you saw a great shift in talent across different roles in 2021. Like, actually, a lot of people took new jobs. And so, as you

• 23:56Speaker 02

  Look out into 2022 as operators, I think we all need to be comfortable that we are going to be not playing with a full deck of cards. Like you will not have the perfect person in each of the roles that you need to get the job done. I really have been thinking about that learning. Do not make that hire out of deep necessity and think that you're just gonna solve it. It's actually better to go a little longer and wait for the right talent, even though it's hard to operate in that environment. But in the long run, it's the right decision. So I actually am constantly telling myself that at the back of my head because at Notion, we have a very high bar for hiring. We also have an intense talent need.

• 24:36Harry Stebbings?

  Recognizing that talent winter, how does that impact your mindset around talent acquisition today? Because I thought it would be the opposite almost. I thought you'd be going get talent in the door as fast as possible. It's gonna get even worse tomorrow and it's gonna be even worse later after. But instead you said take longer. Help me understand, how does the talent winter recognition impact your hiring decisions?

• 24:56Speaker 02

  What you realize is that everyone has to be hiring. Hiring managers have to be out there making lists of people who they think are fantastic talent. Their own leadership team has to be sourcing great people. And a lot of it will be done through relationships. People you have worked with who over time want to come work with you again. The recruiting team is an amazing, amazing team, but they can only take it so far if they have to drum up all the pipeline themselves. Making sure that A, it's truly a team effort. You know, one of the values that we have at Notion is that the referrals and who we bring into the company are the responsibilities across the company.

• 25:34Speaker 02

  And we have this referral tournament and we have a lot of great refers from functions who have nothing to do with functions that are being hired for, right? And you see it like, oh, I worked with this great engineer over at so and so, even though I'm in sales, let me send them over, right? And we celebrate those refers because it's so, so important. And then we just keep the bar at the end of the day. Don't let everyone through, even though the final recommendation is a yes. Ivan still interviews everyone, which I deeply, deeply respect. And so we're really trying to be cognizant of keeping an amazing. Culture and I do think at the end of the day, people decide to join teams that they want to be part of. And I think that's true more than ever.

• 26:13Harry Stebbings?

  I'm amazed. I did not know Ivan still interviews everyone. That is.

• 26:17Speaker 02

  He has such incredible high EQ. It's just a gift, honestly, to have a CEO with such incredible EQ. And I've been learning just tag teaming with him on that and calibrating. And I think over time that will transition, but it's been really wonderful.

• 26:32Harry Stebbings?

  Olivia, I could chant you all day, but I do want to move into a quick fire round. So I want to start with what makes a great relationship between CRO and CEO?

• 26:41Speaker 02

  Trust.

• 26:41Harry Stebbings?

  How do you approach trust? Do you start a relationship with full trust and it's yours to be lost? Or do you start with none and it's yours to be built over time?

• 26:48Speaker 02

  I actually believe in the trust equation. The trust equation, again, it's algorithmic, so not surprising based on my analytical background. But so at the top, the numerator is credibility. So do you know what you're talking about when you are talking about something? Accessibility. So if I need to reach you because it's really important, am I able to reach you? And dependability. So if you say you're going to do something, do you do it? And then the numerator, which is the element that takes away trust, is level of self-interest. If someone engages with you and they're highly credible, they're highly accessible, and they do what they say they're going to do, but it's very clear that they're always in it for themselves and only themselves. You do tend to have a lower trust of that individual.

• 27:31Speaker 02

  They're not a team player. They're not aligned with kind of the greater good and the greater goal. And so I really do believe in that. Like, it's very important that people, if they say they're going to do something, that they do it. That if they're claiming to be an expert on a topic, that, you know, when you poke once or twice, they actually know what they're talking about. And if you need to reach them because you're working together and it's urgent, you need to be able to call them, you do that, right? It's not to say everyone needs to be, you know, on call nights and weekends, but there is a level there of, hey, when I need you, you're there. It's not a senior, less senior. That is just two people working together.

• 28:06Harry Stebbings?

  Olivia, what's the most challenging aspect of your role with Notion today? We know all the fantastic. What's just the challenging aspect?

• 28:13Speaker 02

  Well, fun challenging. I mean, the reason I joined Notion is.

• 28:16Harry Stebbings?

  It's growing too fast.

• 28:20Speaker 02

  But it's not a guarantee, right? I think, you know, history doesn't necessarily always predict the future. And, you know, one of the things that we looked at early on, when I was looking at, you know, a long time ago, actually, in 2004, I wrote an article called "Live Fast or Die Slow." And then subsequently, there was a Silicon Valley episode named the same thing. When you look at it, at the numbers, there's this concept of hyper growers, and that is companies growing over 60%. And companies who are growing over 60% are, you know, five times as likely to make it to a billion dollars, six times as likely, right? But only 15% of those companies who are growing at over 60% as they reach 100 million ARR are able to maintain that growth.

• 29:05Speaker 02

  That's a very low percentage, right? So there's no guarantee that as you hit 100 million ARR and you're, you know, celebrating that you're pacing at over 100% growth. Actually, only 15% of companies who hit that, which is pretty magical, by the way, you know, the fact that you're able to hit 100 million ARR and, and over 60% growth, you're already in refined air at that point. Only 15% of companies continue to maintain that pace. Now, if you do maintain that pace and you're able to maintain that pace, you're far, far more likely to hit a billion dollars in revenue over time. And, you know, as we know, there's only frankly, less than 10 companies who are over billions and billions of dollars in revenue who are public, right? So actually, then the numbers are very, very small in terms of success rate. When I say it's a challenge, it's because I take it very seriously.

• 29:49Speaker 02

  Like, I take the responsibility of continuing to double our user reach, and of course, again, lagging indicator being revenue, very seriously. It is real work. It's not just gonna happen.

• 29:59Harry Stebbings?

  I had no idea about that stat. That is a great stat. You should put that on Twitter. Yeah, this is a very tweetable thing. Tell me, I spoke to many mutual friends, as you know, none of them provided me with one single weakness, not one. So I'm intrigued, self-reflectively, what do you think you're world-class at? And what do you think you really are quite weak at?

• 30:20Speaker 02

  I do think I'm a world-class operator. I do love bringing teams together and making sure that we are just knocking it out of the park. In terms of my weakness... Weakness, the part where I want to make sure that I'm always cognizant of is as you're scaling and as you're in hyperscale, you don't try to be overly analytical. And again, I have worked on this a lot, so I wouldn't say this is a, you know, something that, that I'm, I just want to be careful of, right? Because the tendency is always like, okay, let's have it, there's got to be a data answer to this. And sometimes you just have to go with your gut. And that's something that I've grown into, I feel like, as an operator. Especially when you're operating in hyperscale, you only have so much longitudinal analysis to go on.

• 31:04Speaker 02

  And so you just have to start also making some decisions on your gut.

• 31:08Harry Stebbings?

  What have you changed your mind on recently? What did you believe that you no longer believe or disbelieve or think differently about? What one thing have you changed your mind about recently?

• 31:18Speaker 02

  Well, for the longest time, thought that both of my kids should learn how to play ice hockey.

• 31:25Harry Stebbings?

  And then you realize not.

• 31:26Speaker 02

  And I relaxed that constraint, yes, yes. Just because I grew up playing pond hockey does not mean, you know, in the East Coast and upstate New York, does not mean that my California kids need to do the same. They will have their own journey that does not need to mimic things that I loved when I was growing up.

• 31:43Harry Stebbings?

  What do you think from a professional?

• 31:44Speaker 02

  Well, I have a corollary to that. It's not that I've changed my mind on it, but I do have a corollary to that, which is, when you make decisions, you always have to have a rationale that you can stand up in front of an entire company and explain. The reason I feel really strongly about that is, no matter what decision you make, someone's going to be unhappy. So if you find yourself trying to play the popularity game of guessing, like, what do these constituents think? Then you start making decisions that you can't defend. That is really, really problematic in hyperscale, because what you realize is that every six months, you've added 100 people, truly, at least, right? And you need to be able to explain why the business is run the way it's run to those 50 people.

• 32:25Speaker 02

  And the second you start having scenarios where as people join, they think it's a total Frankenstein.

• 32:33Speaker 02

  Or even worse, they don't join because they look at it and they just don't understand why things are run the way they're run. And it's really hard to explain. Then I think you start running into problems. And actually, this has been the downfall of a number of startups who early on were doing really well. And then they started kind of making decisions based on people or piece parting things in a way that made sense to if you're in the inside inside. But frankly, to talent that they're trying to recruit or the broader team that they're trying to motivate does not make a ton of sense. And so I hold that very dear as an operating principle.

• 33:07Harry Stebbings?

  Olivia, I told you beforehand that I didn't send the schedule deliberately. I'm so glad I didn't send the schedule because I didn't really ask anything on it. The conversation was just so natural and brilliant, but thank you so much for giving the time today. I so enjoyed doing this and it really means a lot to me.

• 33:21Speaker 02

  Thank you, Harry. It was wonderful to spend the time with you as well.

• 33:26Harry Stebbings?

  I just love that discussion with Olivia. Just such exciting times ahead for Notion and for her. So huge thanks to her for giving her the time to stay to be on the show. Such a special one. If you'd like to see more from us behind the scenes, of course you can on Twitter at Harry Stebbings or on the site at twenty vc dot com. But before we leave you today. Sales Loft is a leading sales engagement platform, helping sales teams drive more revenue with the modern revenue workspace. It's the one place sales teams can go to prospect, manage active deals and get the insights they need to coach seller performance, forecast with accuracy and find out what steps to take to close more deals. Some of the world's leading companies like IBM, Shopify and Stripe all love a new Sales Loft and so can you. It's the new way to sell and find out more today at salesloft dot com.

• 34:09Harry Stebbings?

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• 34:53Harry Stebbings?

  you tens of thousands of dollars depending on the size of your business. Sign up today at pipe.com/20sales to start trading today. And finally, to scale your business, you need customers. But this CRM software model is 35 years old and has never evolved to properly support modern businesses. Most legacy platforms were built for a single, rigid, repeatable sales process. But guess what? Copper is a dramatically different kind of CRM, built for Google Workspace businesses. Copper works right alongside you in your inbox, and it's so flexible and versatile that you'll love it regardless of how you run your business. Plus, it requires virtually no training because it works just like all your other Google apps. Get set up in less than a day and easily customize your CRM to fit your needs.

• 35:35Harry Stebbings?

  I promise you, this will be the first time that your team love you as a leader for choosing a CRM solution. That is a personal experience of mine, and so see why more than 30,000 businesses love Copper. A flexible CRM that grows with you. Get a 20% discount on any annual plan. Just go to copper.com/20vc. As always, I so appreciate all your support, and I cannot wait to bring you a fantastic episode this coming Friday.