The Exchanges

Q a PLG motion as efficient as Slack or Notion, do you choose the verticals that are the biggest in the PLG side of the business and go after them? And so what I mean by that is you look at Notion or Slack and you go, okay, financial services is a big component of our PLG users that also has budget. Let's go after them. Is that how it works?

A Not quite. And this is the common trap that PLG companies fall into, because they'll typically look at their data and look at product usage signals, and they'll use that product signal to figure out where should they focus. And so at Slack, we saw that our biggest workspaces were actually communities. They were professional networks that were using Slack to trade best practices. There were student groups that were using Slack to work on projects. And the sales team was tempted to sell them because our sales team was using product-led growth signals and seeing what are the biggest workspaces because lots of active members translate translated to lots of licenses. And it was very important that we actually remained focused on the biggest customers that had the most value from the product. And so that wasn't necessarily communities because when you think of communities, It's a very different post sales motion. The values that you're seeking are different than if you were selling to a company. It would have led your product roadmap in a very different direction because you would have had to invest in features like inappropriate message flagging within a community. Those groups also don't have a lot of money. And so while they might have had a lot of licenses, there's not a lot of budget to unlock there. And so we made a very deliberate decision to not focus on communities.

AI assessment note: “Not quite. And this is the common trap that PLG companies fall into”

Q a PLG motion as efficient as Slack or Notion, do you choose the verticals that are the biggest in the PLG side of the business and go after them? And so what I mean by that is you look at Notion or Slack and you go, okay, financial services is a big component of our PLG users that also has budget. Let's go after them. Is that how it works?

A Not quite. And this is the common trap that PLG companies fall into, because they'll typically look at their data and look at product usage signals, and they'll use that product signal to figure out where should they focus. And so at Slack, we saw that our biggest workspaces were actually communities. They were professional networks that were using Slack to trade best practices. There were student groups that were using Slack to work on projects. And the sales team was tempted to sell them because our sales team was using product-led growth signals and seeing what are the biggest workspaces because lots of active members translate translated to lots of licenses. And it was very important that we actually remained focused on the biggest customers that had the most value from the product. And so that wasn't necessarily communities because when you think of communities, It's a very different post sales motion. The values that you're seeking are different than if you were selling to a company. It would have led your product roadmap in a very different direction because you would have had to invest in features like inappropriate message flagging within a community. Those groups also don't have a lot of money. And so while they might have had a lot of licenses, there's not a lot of budget to unlock there. And so we made a very deliberate decision to not focus on communities.

AI assessment note: “Not quite. And this is the common trap that PLG companies fall into”

Q How do you know if someone's a good problem solver? Without being direct to me like, Kim, are you a good problem solver? Yes, I'm very good. Very good at problems.

A This is where past behavior is the best predictor of future behavior. So asking for stories and examples of how they've solved problems in the past. Questions that I really like are, tell me about a time you weren't set up for success. Because then you can also start to hear, not only did they solve that problem, But did they take accountability, or were they a victim in that scenario? Another line of question that I really like is, tell me about a really big challenge that you had to overcome. Great. Tell me another challenge that was really hard, that you had to figure out the right path forward. And you'll start to see, like, is there a pattern of them taking an ambiguous problem and just finding a way to persevere and get to a great outcome?

AI assessment note: “asking for stories and examples of how they've solved problems in the past.”

Q But it's, but what do you do in that case? Okay, so go back to this founder scenario. I've got pressure from my VCs. They're telling me I need to hire salespeople. I need to hire salespeople. I need to hit revenue numbers. Sarah's great, but she's not the best. Should I just hire good, not great?

A No, because that is a very costly mistake, and it's way more costly to have a bad hire. What I would do in that scenario is I would say like, okay, instead of lowering my hiring bar, we need to change something else within our hiring process and And usually that's, we need to increase our hiring funnel and people coming in at the top of our funnel. And so I'd say if we're seeing five candidates a week and none of them are working out, we need to see 10 candidates next week to make sure that we're finding the right people. And there's a few ways to do that. I've seen us do hiring jams, where even though you ask people in your company who are the best referrals, make sure to refer them, we actually make it fun. We all say we're going to do a hiring jam. At 12 o'clock today, we're gonna order in donuts. Everyone opens their laptop, and on LinkedIn, here is the query that we want you to search. Everyone go through everyone in their network to figure out who meets that query, and let's start to strike a conversation with them. It's also tapping into your friendlies, tapping into your network to say, like, can you please post this on LinkedIn? We're looking for an amazing seller to widen that pipeline. And try to get more candidates into your pipeline so you have more of a selection.

AI assessment note: “No, because that is a very costly mistake, and it's way more costly”

Q where AI can be really exciting, in terms of, like, being that AI coach mock interview, do it on your phone, and even in chat, so to speak. Like, Really interesting ways you can see that happen. When you are a young rep, should you be responsible, and this is a bigger question, should you be responsible for your own demand gen and pipe gen when you are an AE?

A Hundred percent. Every sales team I've led or account executives are responsible for their pipeline, and they're responsible for their pipeline because they're also responsible for their number. While they may have resources, Like a business development rep to help them build their pipeline. They are at the end of the day, the ones that have to figure out what does that motion look like? How do I want to coach my BDR to be really effective in my book of business? Where do I see the accounts that we should prioritize? Who are the key stakeholders that we need to map in order to build consensus? And what is the messaging that is Tailored to that customer that we're going after, especially for the big deals, like personalization to the nth degree is really important. Otherwise you're not going to get a meeting.

AI assessment note: “Hundred percent. Every sales team I've led or account executives are responsible for their pipeline”

Q I do in that case? I get a hand slap. I get a bit of an icky vibe that maybe they don't, and they're pontificating, uh, postulating about having power that they maybe don't have. Do I keep going down the single threaded road with the threat that it might not land because they may not have the power, or do I force the multi-thread even when they hand slap?

A My take here is that you start to use other people in your company to help doing the multi-threading for you, and you make it easy for them. And so instead of that message coming from you directly, you ghostwrite messages for your manager or another person in the company that you see has a connection on Sales Navigator, and you start to build inroads with your team. I found that is the best way to start testing. Do you have a real deal here? I've often sent a message to who we think is the executive sponsor to understand like, hey, we hear that you're evaluating. Is this on your radar? And oftentimes I'll be like, oh, never heard of it. Or like, yes, this actually is on my radar. And then you'll start to see like, do you have a real deal here? And is your champion actually selling internally? I would argue it's not a real champion if they're not willing to introduce you to more people. Because a real champion is putting you in front of the right people to get the deal done.

AI assessment note: “you start to use other people in your company to help doing the multi-threading”

Q don't focus on equity very much at all. I mean, even less so than the US, and you really see that in building out, especially like sales and marketing teams. So if we fast forward then, and we think about the onboarding process for a new rep, what are your biggest lessons in how to onboard reps effectively? Because it's a really hard thing to do for a new founder.

A So my biggest advice is to think about the key outcomes that you're looking for. For the seller to achieve in the early days. And oftentimes it's not like they make their first huge sale. It's actually looking at the leading indicators before that. And we're actually redesigning our onboarding program at notion. And what I really like about it is we're thinking about the key outcomes that we expect our sellers to learn in the first few weeks. As an example, one of the first key outcomes is learning how to prioritize their book of business. What are the accounts that they're going to focus on that deserves the time and the attention to ensure that we're focusing on the right accounts?

AI assessment note: “my biggest advice is to think about the key outcomes that you're looking for”

Q At what point do you do outbound? When you have PLG, you have a huge amount of leads existing that are, you know, consumer users that you can try and convert into enterprise users. At what point do you go, okay, we're also going to continue to convert them, but also proactively hunt net new enterprises?

A I would say it's always earlier than you think, because you think your sales team needs inbound leads. Whereas there is going to be a point where as you go up market, those customers do not buy without talking to a human. And you need to figure out without a product led growth motion, because executives of fortune, 100 companies aren't typically tinkering with the latest technology. They're focusing on their business priorities. They're focusing on How to drive the business forward. And you don't get in front of those people with a product led motion. And so it's earlier than you think. I would say it's typically after your three or four Renaissance reps that you're bringing in just to learn about the business, then start building outbound because it takes a while. It's going to take longer than you think. And when I think back on my experience, like it typically takes like a year to figure out, Who are the accounts that we're outbounding? Who within those accounts care about what we're selling? What is the messaging that is going to compel them to book a meeting with us?

AI assessment note: “typically after your three or four Renaissance reps that you're bringing in”

Q What do I do now? Do we just start randomly outbounding people in our PLG motion? What do I actually do, Kim?

A So if I was a founder, and I had a PLG motion, so I saw that customers are already using my product, I would start doing a lot of interviews. And I would interview all of those customers. And I would understand what motivated them to try the product. How are they using it today? How do they see it fitting into their business priorities and what they're ultimately trying to drive as a business or if it's a consumer as a consumer? I would start to put in the pieces of what are those customers look at, and instead of looking at the product-led growth signals, which is the common trap, I would actually look at the firmographic details.

AI assessment note: “I would start doing a lot of interviews. And I would interview all of those customers.”

Q Final one. When we look forward 10 years, where are you in 10 years? If everything pans out, what does that look like, Kim Graves, in 20, 35?

A In my job today, when I look ahead, it would be we built a world-class enterprise, strategic team. All of the companies around me, when I look at their laptops, they're all working in Notion. I've been able to help and accelerate a lot of the people around me in their careers. We would have already rung the bell and made life-changing money for our team. I think personally that that might be me moving from San Francisco to my hometown, Vancouver, and figuring out what a new career path could look like in Vancouver. I've always had an aspiration for teaching, and so a part of me has always contemplated going back and being an adjunct professor and teaching about the lessons I've learned in sales from Slack, Salesforce, Notion, and the other great companies.

AI assessment note: “I think personally that that might be me moving from San Francisco to my hometown”

Q How do you know if someone's a good problem solver? Without being direct to me like, Kim, are you a good problem solver? Yes, I'm very good. Very good at problems.

A This is where past behavior is the best predictor of future behavior. So asking for stories and examples of how they've solved problems in the past. Questions that I really like are, tell me about a time you weren't set up for success. Because then you can also start to hear, not only did they solve that problem, But did they take accountability, or were they a victim in that scenario? Another line of question that I really like is, tell me about a really big challenge that you had to overcome. Great. Tell me another challenge that was really hard, that you had to figure out the right path forward. And you'll start to see, like, is there a pattern of them taking an ambiguous problem and just finding a way to persevere and get to a great outcome?

AI assessment note: “asking for stories and examples of how they've solved problems in the past”

Q where AI can be really exciting, in terms of, like, being that AI coach mock interview, do it on your phone, and even in chat, so to speak. Like, Really interesting ways you can see that happen. When you are a young rep, should you be responsible, and this is a bigger question, should you be responsible for your own demand gen and pipe gen when you are an AE?

A Hundred percent. Every sales team I've led or account executives are responsible for their pipeline, and they're responsible for their pipeline because they're also responsible for their number. While they may have resources, Like a business development rep to help them build their pipeline. They are at the end of the day, the ones that have to figure out what does that motion look like? How do I want to coach my BDR to be really effective in my book of business? Where do I see the accounts that we should prioritize? Who are the key stakeholders that we need to map in order to build consensus? And what is the messaging that is Tailored to that customer that we're going after, especially for the big deals, like personalization to the nth degree is really important. Otherwise you're not going to get a meeting.

AI assessment note: “Hundred percent. Every sales team I've led or account executives are responsible for their pipeline”

Q like Hugh Grant, not because I'm suave and charismatic, because I'm a grumpy old man. I'll be like, Kim, Kim, you cold called me on a Friday? Where are you from? Notion? Yeah. I would say, fuck you. I'm so, I'm so moody. You invade my phone? I'm pissed off now. Uh, that's so, I'm in awe that cold calling is it. Wow. Do you train people on cold calling?

A Of course we have to. And we actually did just did something at notion where we hosted a global outbound day. And because cold calling is hard, no one wakes up and is like, I want a cold call. And I think it's even harder if you're sitting at home. So at notion, we support a hybrid policy where we have our team coming in at least three days a week. And so we use one of those in office days to say, we're going to make this fun. We're going to call a call. And every single person on this team, including your sales leaders are going to get on these calls. And we're going to start practicing what that sounds like. And we're going to listen to the people who are actually able to book meetings. And it's way easier to be around your colleagues in person and get rejected. Cause then you're like, and like people will console you. But then when you actually get a win and you book a meeting, you are a hero. People are celebrating you. They're like asking, how did you do it? We actually brought out prizes to make it even more fun. And so that's a way for us to, like, start building the momentum, because you can't do this from scratch. Like, you really need to create that celebratory, collaborative environment to actually start seeing what works and what doesn't work. And you know what? It may not work, but you have to try it.

AI assessment note: “Of course we have to. And we actually did just did something at notion”

Q You're gonna kill me. The why now on Notion versus like a cybersecurity company where it's like, you've just had a hack, you just lost three million customer details, you're fucked if this happens again. Okay, I get it. Fair enough. Or you just had massive downtime. You need our crash analytics software. For Notion, how do you do that?

A That's looking at why companies do anything. They either do it to make more money, to save costs, or in your example, to mitigate risk. So what's stopping them from making more money? Oftentimes, it's the innovation and the pace of innovation, especially In this AI world. And so it's trying to figure out how are they staying ahead and how can they look at a product like notion to help them do that? The other is saving costs. As we spoke about SAS sprawl is real and they're paying for a lot of different solutions that is adding up. And so oftentimes it's looking at a compelling event. Like when is that renewal and let's work backwards from that renewal to figure out how we can save you some money.

AI assessment note: “oftentimes it's looking at a compelling event. Like when is that renewal”

Q At what point do you do outbound? When you have PLG, you have a huge amount of leads existing that are, you know, consumer users that you can try and convert into enterprise users. At what point do you go, okay, we're also going to continue to convert them, but also proactively hunt net new enterprises?

A I would say it's always earlier than you think, because you think your sales team needs inbound leads. Whereas there is going to be a point where as you go up market, those customers do not buy without talking to a human. And you need to figure out without a product led growth motion, because executives of fortune, 100 companies aren't typically tinkering with the latest technology. They're focusing on their business priorities. They're focusing on How to drive the business forward. And you don't get in front of those people with a product led motion. And so it's earlier than you think. I would say it's typically after your three or four Renaissance reps that you're bringing in just to learn about the business, then start building outbound because it takes a while. It's going to take longer than you think. And when I think back on my experience, like it typically takes like a year to figure out, Who are the accounts that we're outbounding? Who within those accounts care about what we're selling? What is the messaging that is going to compel them to book a meeting with us?

AI assessment note: “it's typically after your three or four Renaissance reps that you're bringing in”

Q Listen, you're doing an incredible job with enterprise. We often hear that enterprises are still dipping their toes in AI waters in terms of experimental budgets. Do you agree with that, or do you think we've made a full-scale transition to full budgets?

A I agree with that. I've been very impressed with the pace of AI innovation, but in terms of AI adoption is actually been very slow. And the average enterprise company is still waiting and seeing what happens. And we actually just ran a survey and we see that the biggest thing that's top of mind for executives is how do they integrate AI into their existing workflows? And that makes sense to me, because when you think of the average enterprise company, they have a lot of process. They've already built what that looks like internally. There's a lot of priorities across many individuals, so getting them aligned on what AI can look like for them can take a while, and so it's our job to figure out how do we make that easier for them.

AI assessment note: “I agree with that... in terms of AI adoption is actually been very slow.”

Q Ah, but I have granola, and so I like granola. What do you do when competitive comparison comes up? It's another awkward one in calls. How do you advise reps to deal with the competitive comparison without shitting on your competitors?

A I agree. I think it's bad form for you to shit on your competitors. I like the phrase, customer-obsessed, competitor-aware. So you should know what your competitors are doing, and I think it's much better to have a factual perspective and have a conversation around it, and I'd probably go back to Discovery if this was a real conversation. I'd say, great, what do you like about Granola? Okay, what does that help you do? And what we're seeing in the market is there is a lot of SaaS sprawl. And I think I actually heard this on your podcast recently where you're like the average company uses over a 170 different software solutions. And that's real. And my prediction is it's going to get a bit worse in the short term, but long term, we are going to consolidation because there's no way an employee can learn 200 different tools and be effective in their day to day. It's also extremely costly because all of those come with a price tag. So how much are you paying for software?

AI assessment note: “I'd probably go back to Discovery... I'd say, great, what do you like about Granola?”

Q What do I do now? Do we just start randomly outbounding people in our PLG motion? What do I actually do, Kim?

A So if I was a founder, and I had a PLG motion, so I saw that customers are already using my product, I would start doing a lot of interviews. And I would interview all of those customers. And I would understand what motivated them to try the product. How are they using it today? How do they see it fitting into their business priorities and what they're ultimately trying to drive as a business or if it's a consumer as a consumer? I would start to put in the pieces of what are those customers look at, and instead of looking at the product-led growth signals, which is the common trap, I would actually look at the firmographic details.

AI assessment note: “I would start doing a lot of interviews. And I would interview all of those”

Q don't focus on equity very much at all. I mean, even less so than the US, and you really see that in building out, especially like sales and marketing teams. So if we fast forward then, and we think about the onboarding process for a new rep, what are your biggest lessons in how to onboard reps effectively? Because it's a really hard thing to do for a new founder.

A So my biggest advice is to think about the key outcomes that you're looking for. For the seller to achieve in the early days. And oftentimes it's not like they make their first huge sale. It's actually looking at the leading indicators before that. And we're actually redesigning our onboarding program at notion. And what I really like about it is we're thinking about the key outcomes that we expect our sellers to learn in the first few weeks. As an example, one of the first key outcomes is learning how to prioritize their book of business. What are the accounts that they're going to focus on that deserves the time and the attention to ensure that we're focusing on the right accounts?

AI assessment note: “my biggest advice is to think about the key outcomes that you're looking for”

Q Can I ask, is it difficult when you have a PLG motion and then you layer on top an enterprise motion? Because the sales team almost feels like second class citizens.

A It is difficult because when you have a product led growth motion, there's often the perception of the product sells itself. We don't need salespeople. It's going to be way more efficient for us to just focus on product led distribution. And this is the biggest mistake that PLG companies make. They are afraid to hire salespeople because they want to do it differently. And so if I think back to all of those founders, They eventually come around and realize that building sales is going to be vital to continue accelerating your company forward. You shouldn't try and reinvent the wheel when it comes to sales. And so it does require the first few sales leaders coming into the business to really educate the founders, the business around why sales is so important and how we can work together to make sure it's not product-led growth For sales, the best companies I've seen layer sales on top of product-led growth.

AI assessment note: “It is difficult because when you have a product led growth motion, there's often the perception”

Q What was the hardest phase of growth from six million to two billion for you in sales?

A For me, it's very personal. I actually think back to, like, the point where I didn't know if I was going to stick it out, and it was when my boss left, my boss's boss left, and it felt like everything was crumbling around me, and I was working with a coach, which I highly encourage if you have the resources or the learning and development funds to work with a professional coach, because she helped me reflect on what was actually happening. And she asked me questions like, okay, well, what's the worst thing that can happen? And when you actually put words to it, it's never that bad. And she was like, okay, well, what, what's actually true? Because what I had said is like, oh, I don't have my advocates, my leaders in my corner to really push me and my career forward. And she's like, that's not true. Like, you have a lot of advocates in this company. Like, who else can you look to? And you need to believe in yourself. And then she asked me, What's the best thing that can happen? Oftentimes, change leads to opportunity, and so the best thing is actually stepping up, and for me, it was like, how could I actually do my boss's job and, like, use this as an opportunity versus a point of crumbling, and so that's ultimately what I did. It felt at the time like I was at, like, a huge crossroads, but now looking back, I'm so happy I persevered and stayed.

AI assessment note: “it was when my boss left, my boss's boss left”

Q When you're selling AI and enterprise, are you using AI and AI and AI to make them feel like they're frontier technology adopters, or are you kind of shielding it to make them feel less scared of some buzzwords that they often hear in media?

A It's funny because, yeah, I go to events and I'm like, this can't be an event if we don't say AI. But the, the hype is real. I actually will say like the hype is real and executives genuinely want to see and hear How other companies are leveraging AI. And so what I found to be most impactful is using customer stories. And so we'll say here, like the fastest growing companies like OpenAI, Vercel, Perplexity, they're all relying on Notion. Their product and engineering teams are collaborating on everything from meeting notes to how they do their product planning to ensure that they're staying ahead of innovation. And it's those stories that start to showcase like, okay, There's real advantage here. Tell me, how do they do that?

AI assessment note: “executives genuinely want to see and hear How other companies are leveraging AI”

Q comp negotiation, switch sides of the table. If you were to advise an AE or a rep on how to handle comp negotiation, maybe I'm British, and so we're just awkward talking about money, but it's a bit of an awkward one, but I do want the most money, obviously. How should I approach that in the right way, which doesn't come across as money grabbing, but is also authoritative?

A The expectations are set up front, especially in the U S you can see what the comp ranges are for all of our jobs. And so it's important to also see as like a seller. Okay. Does that range meet what I'm looking for? And then what I would say at a company that's a startup or scale up, if you're just looking to maximize your OTE, that's probably not the best place. Like go to one of the large giants, cause that's where you're going to maximize your OTE. You also want to think about the equity and the full package. It depends on where you are in your career. Like early days, I actually think it's a big miss to just focus on comp and to not focus on the bigger picture. Because if you're at a fast growing company that is doing really well, your equity is going to be way more meaningful than your OTE.

AI assessment note: “You also want to think about the equity and the full package.”

Q closed, um, effort, they work really hard, uh, knowledge, they're super smart, but the skills They're an enterprise seller, and you're doing a more SMB, high-velocity motion. They're not as charismatic, maybe. They're more strategic. They're more academic and intellectual, and they're not that high-velocity seller. They've got everything except the actual human skills to do a high-velocity sales. Can you be off so badly in one that it's irredeemable?

A Yeah, well, I'd try and figure out, like, what is the negative consequence then? Is the negative consequence then that they are selling deals, but they're not selling a high volume of deals? Because then I would argue that is a problem, and you need to look for a different skill set. Or it could be they're selling a lot of deals, but they're actually churn bombs. So they're bringing in bad deals, they're overselling, and when it gets to our customer success team, we're realizing that Those are not the right customers that are going to get long-term value from our product. And we need to figure out how we can implement better qualification. And so like, those are a few of the nuances that we would also want to look out for.

AI assessment note: “then I would argue that is a problem, and you need to look for”

Q I'll pay you later. That's incredibly kind of you to say. Um, listen, I want to start with your first sales role. What was your first sales role? And if you could go back to the Kim who took that job on the first day, what would you tell yourself knowing all that you know now?

A Well, the interesting thing about my first sales role is I didn't realize it was a sales role until I accepted the job and was in the role. I would say my first customer facing role was at my mom's beauty salon, where I was picking up the phone, talking to customers, answering their questions, and booking appointments. And I went to university for marketing. I landed my first job outside of school at a tech startup in a marketing role. And it was there that I started hearing whispers about a local founder in Vancouver who was starting his next gig. And that was Stuart Butterfield, and he was starting Slack. And I became obsessed. I read everything about Slack. I read all of their customer tweets. I read all of their blog posts. I saw on their website that they were hiring their first account manager. Now, I didn't know what an account manager was, but I saw they were looking for someone with great communication skills. And I figured I've got that, so I threw my application in cold on their careers page. I went through a few interviews, and I got the job. And it was in the job that I realized that the account manager role was an account executive, a solutions engineer, and a customer success manager, all in one, helping our customers. From that point forward, I've been in sales ever since. Now I lead our go-to-market team across the Americas at Notion.

AI assessment note: “it was in the job that I realized that the account manager role was”

Q I'll pay you later. That's incredibly kind of you to say. Um, listen, I want to start with your first sales role. What was your first sales role? And if you could go back to the Kim who took that job on the first day, what would you tell yourself knowing all that you know now?

A Well, the interesting thing about my first sales role is I didn't realize it was a sales role until I accepted the job and was in the role. I would say my first customer facing role was at my mom's beauty salon, where I was picking up the phone, talking to customers, answering their questions, and booking appointments. And I went to university for marketing. I landed my first job outside of school at a tech startup in a marketing role. And it was there that I started hearing whispers about a local founder in Vancouver who was starting his next gig. And that was Stuart Butterfield, and he was starting Slack. And I became obsessed. I read everything about Slack. I read all of their customer tweets. I read all of their blog posts. I saw on their website that they were hiring their first account manager. Now, I didn't know what an account manager was, but I saw they were looking for someone with great communication skills. And I figured I've got that, so I threw my application in cold on their careers page. I went through a few interviews, and I got the job. And it was in the job that I realized that the account manager role was an account executive, a solutions engineer, and a customer success manager, all in one, helping our customers. From that point forward, I've been in sales ever since. Now I lead our go-to-market team across the Americas at Notion.

AI assessment note: “I saw on their website that they were hiring their first account manager.”

Q Ah, but I have granola, and so I like granola. What do you do when competitive comparison comes up? It's another awkward one in calls. How do you advise reps to deal with the competitive comparison without shitting on your competitors?

A I agree. I think it's bad form for you to shit on your competitors. I like the phrase, customer-obsessed, competitor-aware. So you should know what your competitors are doing, and I think it's much better to have a factual perspective and have a conversation around it, and I'd probably go back to Discovery if this was a real conversation. I'd say, great, what do you like about Granola? Okay, what does that help you do? And what we're seeing in the market is there is a lot of SaaS sprawl. And I think I actually heard this on your podcast recently where you're like the average company uses over a 170 different software solutions. And that's real. And my prediction is it's going to get a bit worse in the short term, but long term, we are going to consolidation because there's no way an employee can learn 200 different tools and be effective in their day to day. It's also extremely costly because all of those come with a price tag. So how much are you paying for software?

AI assessment note: “I'd probably go back to Discovery... I'd say, great, what do you like about Granola?”

Q comp negotiation, switch sides of the table. If you were to advise an AE or a rep on how to handle comp negotiation, maybe I'm British, and so we're just awkward talking about money, but it's a bit of an awkward one, but I do want the most money, obviously. How should I approach that in the right way, which doesn't come across as money grabbing, but is also authoritative?

A The expectations are set up front, especially in the U S you can see what the comp ranges are for all of our jobs. And so it's important to also see as like a seller. Okay. Does that range meet what I'm looking for? And then what I would say at a company that's a startup or scale up, if you're just looking to maximize your OTE, that's probably not the best place. Like go to one of the large giants, cause that's where you're going to maximize your OTE. You also want to think about the equity and the full package. It depends on where you are in your career. Like early days, I actually think it's a big miss to just focus on comp and to not focus on the bigger picture. Because if you're at a fast growing company that is doing really well, your equity is going to be way more meaningful than your OTE.

AI assessment note: “I actually think it's a big miss to just focus on comp”

Q Can you talk to me about the most creative you've ever had to get to win a deal? I was literally talking about winning a deal this morning, and I said, We never leave anything on the field. How many hockey sticks are we sending to their kids? And I use it as a joke, but when have you got creative and what did you do?

A I will say, Harry, I'm not a gimmicky person. So I'm not the seller or sales leader who's like, let's send them a cake. And on the cake, we're going to say, will you sign our order form? That's just not how I sell. Sometimes it works. I'm much more like, how do we think Strategically about this and get really creative in our strategic approach. So it's figuring out how do we align to stakeholders at all levels and make sure that we bring them value. And so the creativity that I would bring is like, okay, making sure that every important person in the deal is aligned to someone at my company, whether that's a subject matter expertise where they can get value from learning how say another product manager is using Our software, what they're seeing within their field and comparing notes so that we have that relationship, or it's a CFO to CFO relationship to ensure that they're looking at the financials in the right way, and they have that relationship. And then it's using different touch points like workshops. How can we bring in a workshop where we're just jamming on what are the ideas that we can hack away at and implement in the next week? It's also showing teachable moments in every part of the deal. So I wouldn't say like there's one Really big moment where I'm like, this was it. I think it's continuing to look at how are you getting in front of the right people and like surro…

AI assessment note: “I wouldn't say like there's one Really big moment where I'm like, this was it.”

Q the public markets puts a label on you. You're an AI winner or you're an AI loser. And the way that you build your company will determine which one you are. And so there is a moment when Wall Street will penalize you for not embracing AI. And at that moment, you think that they will then change because market cap is impacted. But when do you think that is?

A It's like picking up. And I see enterprises going from experimental AI budgets to looking at what are the outcomes that they're trying to drive. With AI, because that's where AI is going to be very sticky. Another thing I've heard recently is vibe revenue, where there's a lot of experimental budget with AI, and companies are just trying things out. But the real winners will be the companies that have those renewals a year or two later, because they've, they've figured out how to drive business priorities with AI. And I was actually thinking about this in my reflection. Of my performance review. So I had my performance review on Tuesday. My performance isn't based on like, how well am I using AI? How savvy am I? My performance review continues to be, how do I drive revenue? How do I drive pipeline? How do I drive my people? So there I think through like, okay, how can I use AI to do that more effectively? So I drive those results even further. And I think the companies that really figure out how to drive the ultimate bottom line Are going to be the ones that win. The other thing I will say is from selling AI, I think it's also the companies making it easier for them to get started. And one solution would be how can you really easily integrate with their existing solution? So if they're already using Salesforce, they're already using Microsoft Teams, or Slack, or Google Drive, ho…

AI assessment note: “I see enterprises going from experimental AI budgets to looking at what are the outcomes”