Pod Insights The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch 20Sales: How to Layer Enterprise Sales on PLG | How to Sell AI Tools To Enterprises That Are Scared | Should Reps Own Their Own Pipeline | Mistakes All Founders Make When Moving From Founder-Led to Rep-Led Sales with Kim Graves About this episode Kim Graves is GM, Americas at Notion, where she oversees all Sales and Customer Success efforts across the region. She brings extensive experience in building and scaling high-performing sales organizations, most notably at Slack where she helped grow revenue from $6M to over $1.5B. In addition to her operational role, Kim serves as a founding partner at 20SALES, a GTM-focused VC firm, where she advises early-stage companies on scaling revenue and optimizing sales processes. Agenda: 07:00 – The Secret to Winning a Discount Conversation 09:30 – Notion’s Wild New Sales Method: Mindsets Over Stages 12:00 – Why Great Sellers Never Talk Product Too Soon 14:00 – How Slack Avoided the Biggest PLG Trap of All 17:00 – The Fatal Mistake Founders Make Layering Sales on PLG 20:00 – The “Renaissance Reps” That Build Billion-Dollar Motions 23:00 – How to Spot True Grit in a Sales Hire (Without Asking Directly) 26:00 – The Case Study Test That Filters Out Bullshitters 30:00 – The Real Reason Most Reps Fail Onboarding 33:00 – Should Reps Own Their Own Pipeline? Kim’s Take Is Clear 36:00 – Why Cold Calling Works in 2025 (And Nobody Does It) 39:00 – The Sales Team Audit: The REKS Framework That Changes Everything 43:00 – How to Avoid Hiring the Wrong Rep Under Pressure 45:00 – When Sales Feels Second Class: PLG vs Enterprise Tension 47:00 – The One Thing Reps Still Do That AI Will Obliterate 50:00 – AI Sales Tools: Why Every Startup Is Failing to Get It Right 53:00 – Will We Have More or Fewer Reps in 5 Years? 56:00 – Enterprises Are Scared of AI – Here’s How You Break In Anyway 59:00 – Kim’s Secret for Getting Past Gatekeepers and Fake Champions 1:09:00 – Kim’s Hardest Phase at Slack and How She Survived It
Transcript 14,024 words · 2 speakers
Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.
0:00 Harry Stebbings? This is 20 Sales with me, Harry Stebbings. Now, 20 Sales is the monthly show where we sit down with the best sales leaders in the world to discuss how they start and scale sales teams successfully. Today, we have one of the best joining us, Kim Graves. Kim leads sales, pre-sales, customer success and renewals at Notion, where she recently spearheaded record-breaking 2024 growth and led the expansion of Notion's AI-powered go-to-market strategy across North America. She's also held incredible roles at Slack, where she spent an incredible seven years, and Salesforce, and she also co-founded 20 Sales, where she's invested in some of the best go-to-market technologies. But before we dive into the show today, is your finance team a cost center tied up in enforcing policies, bogged down by cumbersome processes,
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4:17 Harry Stebbings? Kim, I am so excited for this. Listen, we've been friends for a few years now and I've wanted to make this happen for a while. So thank you so much for joining me today.
4:25 Speaker 01 I learned so much from your shows, Harry. I'm excited to be here.
4:28 Harry Stebbings? I'll pay you later. It's incredibly kind of you to say. 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?
4:43 Speaker 01 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.
5:25 Speaker 01 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.
6:06 Harry Stebbings? That's quite a big ask for a first role, isn't it?
6:10 Harry Stebbings? So, okay, take me back to that first day. What would you tell yourself, knowing all that you know now, you get your Slack email address day one?
6:19 Speaker 01 I would tell myself, be confident. I would say that especially in getting into the customer calls and when the customer calls got hard.
6:29 Speaker 01 Because it was easy enough to talk to someone who loved using Slack, loved the product, but then as soon as they asked for a discount or they had an objection, like they were evaluating Slack with a competitor, I started to feel a little bit more insecure. I would say to myself, you've got this. Like, it's all in confidence, in like, in how you present yourself. And just be confident, you got this role for a reason. And like, learn as much as you can.
7:01 Harry Stebbings? I totally agree with you on the confidence, having fundraised. Confidence is everything. Also, I also just say like, what is the worst that could happen? Like, you don't actually get the sale. It's fine, there's more clients, Bunnly. It's okay. Can I ask you, you mentioned that, like, discount. My whole desire with this conversation was to have a very natural conversation. It is a really awkward thing, especially when you're earlier in your career, when someone's pushing for a discount.
7:24 Speaker 01 Yes.
7:25 Harry Stebbings? What would you advise a young A rep when that awkward conversation of a discount comes up?
7:30 Speaker 01 My advice is don't treat it as awkward. Treat it as any other conversation that you're having with the customer. Early stages of a deal, you lean into discovery, and that's where you're learning about them, asking questions. And things typically seem very friendly. As soon as you get to the negotiation stage, instead of thinking about it as a tense conversation, think about it as another conversation because your customer is going to feel your energy. So if your energy is, oof, I don't know if they're gonna like this price, or this, this is expensive, I'm scared what they're gonna say, they're gonna feel that energy. Whereas if you just go in and you say, hey,
8:14 Speaker 01 so we've been talking for a while, here's the value that I'm hearing that we can bring to you, and here are the problems that we're solving. This is what it's gonna cost, and pause, and just see what they say. Because they're probably going to say something like, whoa, this is expensive. And instead of going into defending your product and why the price is the price, go back into question asking, go into like, okay, tell me more. Why do you think it's expensive? What do you think is the right price to pay? And then just treat it as that conversation to understand like, how can both parties seek mutual value here?
8:46 Harry Stebbings? Absolutely love the waiting for their response. I think so many people have a little bit of silence and then interject with, but I'm sure there's something we could do. I'm sure there's some way that we could change that or what can I do? And it instantly breeds this desperation if it sounds bluntly too direct.
9:05 Speaker 01 I was going to add, and that's actually something that we've brought into our sales process here at Notion. So when you're building a sales process, it's very typical to think about the stages of the deal. Stage one, qualify the deal. Stage two, do discovery. Stage five is negotiation. Stage seven is closed one. Instead of calling it those stages, we actually think about the mindset in each of those stages. Because that's what we want our sellers to embody. It makes for a much more adaptable mindset than just having the exit criteria or the checkboxes that a seller needs to do at each stage of the deal. So as an example, at stage two, we call that the curious investigator.
9:47 Speaker 01 So we expect our sellers to embody being a curious investigator that researches the heck out of their customers, understands how they make money, asks questions from a place of genuine curiosity. And then just what we were saying about stage five, negotiation. Instead of calling it negotiation, we expect our sellers to embody the mindset of a value articulator. So how are you truly articulating the value of your product? It's a nuance, but I don't know if you think about this even in podcast hosting, where instead of thinking about the content that you're going to ask, it's actually thinking about what's, what's the tone, the body language, the feeling that I want to give off in this conversation? Because people often say they'll remember how you made them feel versus what you actually said.
10:32 Harry Stebbings? I actually think that the best investors started like. In some form of interviewing capacity, because you have this similar dynamic where you have three to five minutes at the beginning of each show, where you have to make the guest feel very comfortable. You have to show some form of vulnerability and really allow them to feel like it's a space of no judgment. Exactly the same like with a founder when you're investing. If you create that no judgment zone, they'll bring their whole self to the meeting. They'll open up about missing Q1 last year and why and what failed. And you have to have that in both interviewing and in investing.
11:05 Speaker 01 I agree. You need to create that psychological safety. If you're creating a fear-based environment or you don't have that safety, people are not going to tell you the real answer. They're going to hold back.
11:16 Harry Stebbings? The best shows found is just scribble scribble notes. And you said about these seven stages and I just, we have a stage one, which is qualify. Stage two, which is curious investigator. How do reps fuck up curious investigator? Like, what's a good versus a bad question?
11:34 Speaker 01 This is what I found when you really love the product that you're selling. This was the same at Slack and at Notion, where we love selling the product and our customers who are using the product love hearing about the product and the features. What mistakes sellers make early on is they'll talk about the product. They'll have premature pitching syndrome. And so it's hard to stay in this zone of let's just ask questions and let's actually not even talk about the product. We're just going to talk about the observations we've seen of what makes the company great, what makes that person great? What are their new challenges that they're coming up against? What are the biggest risks that might prevent them from getting there? And just like really leaning into that conversation without talking about your product at all.
12:19 Harry Stebbings? And we record all of these calls?
12:21 Speaker 01 Yes, we record all of these calls. We have both Gong, which records the calls and the video. But we also use Notion AI internally to transcribe those calls.
12:32 Harry Stebbings? Okay, so we have that with this curious investigator. We ask loads of questions. What's stage three?
12:37 Speaker 01 Stage three is solution design. This is when you start to talk about your solution and start to think through where can your solution Help them based on the problems that you've heard. The key here is not taking all of that research and discovery that you've just done and then completely neglecting it and just talking about all of the wonderful problems that your solution solves for. It's actually starting to connect the pieces. Or if you're hearing pieces that they're actually not within your wheelhouse or like that's not what you do best at, it's also being honest and being the the challenging skeptic to say like, is this deal really going to go anywhere? Or should we part ways?
13:19 Harry Stebbings? How uniform or similar is your solution's design between customers? We often hear about a sales playbook, which makes us think that you could bluntly press play. And it's kind of the same pattern in terms of, hey, well, here's our solution. And these are all the problems it solves. How uniform are they versus how custom are they?
13:37 Speaker 01 So I've spent my career at PLG companies Slack and Notion, which have great distribution across a whole host of different customers. You have students, you have communities, you have B2B companies across all industries, across all departments. The uniformity tends to start very general. But the key here is ensuring that your sales team is very focused so that you can build or bring in the most successful customers. And those customers tend to have patterns.
14:08 Harry Stebbings? When you are 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 Slacks 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?
14:31 Speaker 01 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
15:11 Speaker 01 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
15:52 Speaker 01 a very deliberate decision to not focus on communities. That was great if they were using Slack from a product-led growth motion, they were using our freemium product, but from a B2B sales motion, we were very focused on selling to B2B.
16:07 Harry Stebbings? If I'm a PLG founder listening to you today, and I've got a load of great users all through a PLG motion, and I want to layer on top an enterprise sales motion.
16:16 Speaker 01 Yeah.
16:16 Harry Stebbings? What do I do now? Do we just start randomly outbounding people in our PLG motion? What do I actually do, Kim?
16:24 Speaker 01 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 do 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.
17:02 Harry Stebbings? What's a firmographic detail?
17:04 Speaker 01 It's like, what is the industry that they're operating in? How big is their company? Where are they located? Are they located in major cities? Or are they located in a certain geographical area? Basically, everything outside of your product that you could use to describe them. And then going even deeper inside of those companies, if you are B2B, who are the personas in those companies that are getting the most value? And I would use that to work backwards to figure out who is getting the most value that unlocks the most budget that we should be focusing on.
17:39 Harry Stebbings? Does that need to be the founder? Or can it be a head of sales that I bring in? If I'm a brilliant tech product person and I've built this great product like Growth Motion, but I'm like, fuck, that sounds like a lot of interviews and stuff that I don't want to do. Can I hire that in? Or should I be the one who's building out that discovery ICP?
17:59 Speaker 01 Well, I wouldn't even call it dis- well, I guess it is. It's ICP. It's figuring out who is your ideal customer profile. And I strongly believe it's the founder. Because that's not only going to guide your go to market strategy, it's also going to guide your product roadmap. And where do you continue to lean in? So back to my Slack example, like, we actually didn't lean into community roadmap features. We leaned in to B2B specifically for our distribution as we went up market.
18:26 Harry Stebbings? And your messaging. Your messaging is so impacted by it. And I think that's so important.
18:32 Speaker 01 Yes, exactly. Having the founder start to build sales initially, that helps bring intuition into the product. It also helps to figure out who to hire for. Like, if you don't know who your ideal customer profile is, or what kind of sales motion is going to work for your company, how do you know who you're going to hire as a sales leader? Who will actually bring your business to the next level?
18:55 Harry Stebbings? Okay, so we're having a coffee. I mean, this is sadly a virtual coffee, but we're having a coffee in Palo Alto. And you're advising me. Imagine I'm technical, which is quite a stretch, I know. But I'm this technical product founder who's built this great PLG motion. Okay, fine, I'll do the ICP discovery process that we mentioned there. And I'll ask the questions. Now that I have this ICP in mind, can I dip my toe in enterprise and give it a go? Or do I need to invest full scale?
19:24 Speaker 01 What do you mean by full scale?
19:26 Harry Stebbings? Well, like, do I need to hire out reps and a sales leader and put millions of dollars to work? Or can I just bluntly dip my toe in and see if we get many customers?
19:35 Speaker 01 My biggest advice for the early stages of building a sales team is thinking through it as if you were thinking through a manufacturing supply chain. And this idea comes from the HBR article of the sales learning curve. Have you read it?
19:53 Harry Stebbings? This is Mark Roberge.
19:54 Speaker 01 It's a Harvard Business Review, but I highly recommend founders to read this article because it talks about the stages of building a sales team. And the earliest stage of building a sales team is not looking for traditional coin operated reps that are going to come in and just build the sales playbook for you. The earliest stages are actually about learning, similar to how if you were bringing a manufacturing product to market, like you were selling bathing suits. Your first 10 that you make are going to be really expensive, but you're going to learn a lot in making those first 10 bathing suits. That's like when you're hiring sales, your first few sales reps, say three to four sales reps. It's going to be very costly because you're not going to know what they're exactly doing, but we call them the Renaissance reps.
20:38 Speaker 01 Where they're generalists, they're adaptable, they're highly skilled in communicating and collaborating with the internal stakeholders at your company. That being marketing, product, engineering and talking to customers. And that's where you learn the most.
20:54 Harry Stebbings? Are they quite early in their career? Are they a little bit more mature and senior? Just where are they in their career?
20:59 Speaker 01 I've found it's a little bit of both, and it's not as a matter of like where they are in their career. Because I think you want to build a diverse sales team. And so typically you hire three to four reps. Some could be earlier on in their career, but I've shown a high attitude for learning. And then others can be potentially making a career switch or they're really excited about building. And that's the thing, they're not excited. About just making a lot of money because that's not the point in the first year of sales. They're actually really excited about learning and building something and bringing the mission forward.
21:35 Harry Stebbings? Okay. And so we have these three to four.
21:38 Speaker 01 Yeah.
21:39 Harry Stebbings? If we actually just dig into that process, then
21:42 Speaker 01 Yeah.
21:42 Harry Stebbings? I'm a technical product led founder. I don't know how to hire a rep.
21:47 Speaker 01 Yeah.
21:47 Harry Stebbings? What do I do? Where do I source the candidates from first?
21:52 Speaker 01 So if I'm a founder, I would make sure that I have some great go to market advisors on my board or in my arena. And I would talk to them and learn what do they look for in hiring great early sellers? What are the key competencies that are important to look for? And knowing the business and the unique aspects of your business, what's important to that business to double down on? So if it's a certain industry that you're selling into, perhaps it's some industry knowledge. I can't think of another example, but it's like starting to define what that looks like. Because I think a common mistake is not knowing what you're looking for. And then just relying on heuristics that can lead you astray.
22:34 Speaker 01 Heuristics like they come from a big flashy company, so they must be a great seller. Or heuristics like they're a great communicator and presenter. Customers are going to love them. That's surface level. Like you really need to dig into what are the key competencies that you should be looking for? And when I'm talking to early stage founders, there's three competencies that I think are really important. The first is high motivation. The second is effective at problem solving. And the third is a continuous learner. If you start to define what those competencies look like, then you can start figuring out what is your process? What are the questions that you can ask so that you can figure out whether that's a great hire for your business?
23:16 Harry Stebbings? 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.
23:24 Speaker 01 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
24:09 Speaker 01 and get to a great outcome?
24:11 Harry Stebbings? I totally agree. Over time, one of my biggest like turn offs with hires is when everything's just someone else's fault. I get it, it's not always your fault, but there's just also a way to do it. The instant, well, it wasn't me, but, and it's like,
24:26 Speaker 01 Exactly. Because it will be everything from like, I, we didn't have enough inbound, or my manager left and I didn't know what to do. And so those are the places where you're like, okay, so what did you do?
24:39 Harry Stebbings? Quit. I did the responsible thing and I left the job. Okay, you mentioned that, like, they're great storytellers, they're great salespeople, and customers will love them. One way to do that is like demos or case studies. Do you do demos and case studies? And any lessons on what works and what doesn't there?
24:58 Speaker 01 Yes, we do, especially for our sellers in commercial and mid-market. We expect them to be very well-versed in the product. And so we'll ask them to research our product, and let's do a case scenario where we're going to be a customer. You're going to pretend to be the account executive selling our product. And let's go through a first call to see what that sounds like. What we're looking for is what are the questions that they're asking? Can they adapt and learn about what we're selling and the actual problems that we're solving? And then without any training, how far can they get with our product? And that's another example of assessing problem solving.
25:41 Speaker 01 Like, can they be resourceful and do this without a lot of guidance?
25:45 Harry Stebbings? Do you give them much prep time? Is that like a week's notice?
25:49 Speaker 01 Few days. We, because the other thing is like, we need to move fast. We need to get hires and so we can't draw out our hiring process. We want to get hires and fast. We give them a few days because we also want to see how can they be a pace setter? How can they deliver with short time deliverables? Because that's going to be the reality of the environment that they're operating when they're getting here.
26:13 Harry Stebbings? How do people most mess up demos or case studies?
26:18 Speaker 01 I would say there are two ways. The first is a lack of preparation. A lack of preparation, research and actually doing their homework to come up with a polished first meeting. And so I'm looking for, did they look at our customer stories and read through all of our customer stories? Did they watch all of the videos that we've published about what we're trying to solve? Did they actually sign up for the product and start using it themselves to see what it feels like? And so you can see where someone put a lot of time, put a lot of effort in actually learning, or they sort of just winged it or relied on a playbook that they've used before.
27:01 Speaker 01 And then I would say the second place that people mess up is thinking on their fee. That's very important in sales. We say a seller needs to be audible ready. So if we throw them off, what do they do? If we, as an example, give an objection and we say, hey, do you offer discounts?
27:21 Speaker 01 And they just make something up and they're like, yes, we offer a 40% discount and they like cave under pressure, then we're like, ah, or if we ask them a technical question and they just make up an answer versus saying like, hey, let me get back to you. Those are some areas where we're like, okay, there's an integrity piece here and can they really think on their feet and adapt?
27:43 Harry Stebbings? Do you have a hiring panel when it comes to deciding whether to hire or not hire?
27:49 Speaker 01 Yes, we do. Early stages, it's a lot of cross-functional partners. So it's not just sellers on the team, but also looking at the partners that they would be working with most closely. It's similar, but we have a few people on the panel and we ensure that we have laid out what are the competencies that we're looking for so that we all know what we're looking for.
28:09 Harry Stebbings? And so now you've decided you're going to hire me. Okay. Fantastic. Very excited for this potential job. When it comes to the 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.
28:27 Speaker 01 Yeah.
28:28 Harry Stebbings? 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?
28:39 Speaker 01 The expectations are set upfront, especially in the US. 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 in 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 because 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
29:24 Speaker 01 at a fast growing company that is doing really well, your equity is going to be way more meaningful Your O T E.
29:32 Harry Stebbings? Totally agree with you. I think it's one of the big problems actually with Europe, which is we don't focus on equity very much at all. I mean, even lesser than the U. S. And you really see that in building out, especially at 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.
29:54 Speaker 01 So my biggest advice is to think about the key outcomes that you're looking 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?
30:36 Harry Stebbings? When you think about like the right accounts where you can actually do that very customized tailored approach.
30:42 Speaker 01 Yeah.
30:42 Harry Stebbings? How big are those contracts? They have to be big enough. Is that like a hundred K plus? Is it fifty K plus?
30:48 Speaker 01 We say a hundred thousand dollars plus. And that's actually a really good question because I think it's important to have a dual focus as a seller. So you have your strategic deals that are a hundred thousand dollars and above. But you also have your velocity deals that are more tried and true. So those are like your twenty fifty K deals that you know you can win and that are less risky. And I've seen that where if you have a diversified portfolio, similar to financial advising, like you don't want to just focus on the highest risk stock. Like you want to make sure you have a diversified portfolio. I bring that mentality into sales to think about, okay,
31:28 Speaker 01 in your week, in your months, as you're planning your path to target, what are the accounts that you should be focused on? You should have a few big bed accounts that are going to get you the hundred thousand or million dollar deals. And then you should have the tried and true accounts that you know that these are the customers that typically evaluate more quickly. You know you can win them. There are all the right signals here for you and ensure that you're not minimizing focus on those accounts. And so that you build this pipeline that can reliably get you to your number.
31:59 Harry Stebbings? Does that go against the traditional structure of sales teams where there's like real enterprise salespeople who just handle like the mega mega accounts? Does that advice go against that?
32:09 Speaker 01 That's a good question. And no, I would say this is diversified within your portfolio of the segment that you're selling into. So if you're a commercial seller selling to SMB, your big accounts might actually be like the $50,000 accounts and above, while still making sure that you're knocking out the $10,000 to $20,000 deals. If you're an enterprise seller, it's most likely like your big accounts are those million dollar deals and the velocity accounts are like the 50, the 100K deals that you're bringing in.
32:37 Harry Stebbings? How fast do you put reps on with customers in terms of that customer facing interaction? They're not ready the first day. Is it the first month? Is it the first week? What does that look like in terms of like, yep, green light for you to lead a sales deal?
32:51 Speaker 01 So I have different answers depending on the stage of your company.
32:55 Harry Stebbings? Okay.
32:55 Speaker 01 Early days, like as the first account manager at Slack, I was on customer calls on day two. It was just like, get in there, you're adaptable, start talking to customers. Now at Notion, we think about like, what are the checkpoints that we need them to meet before being in front of a customer? And I'm a big fan of mock scenarios. So instead of having your first discovery meeting or your first pitch in front of a real customer, you're doing that with your manager or you're doing that with your onboarding cohort so that you can practice it. And then once your manager says, yes, you are ready, then you can start working with your customers directly.
33:33 Harry Stebbings? Totally agree. I actually think this is 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?
33:56 Speaker 01 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
34:41 Speaker 01 to the nth degree is really important. Otherwise, you're not going to get a meeting.
34:45 Harry Stebbings? Also, just like the little things go a long way, like commenting on several LinkedIn posts. Like, awesome to see. People recognize continuity of commenting. Like, I have it today. We obviously have lots of comments, but the people that consistently comment, I'm like, I almost feel like I know them. And when they then message me after 10 comments, I'm like, I'm much more likely to respond. It's impressive.
35:07 Speaker 01 I agree. You can get very strategic in your outbound playbook, and it's on the seller to really understand that. We're also diversified in our channels. We're not just emailing, we're cold calling, we're using LinkedIn, we're using warm connections from LinkedIn Sales Navigator. And it's on the sales, it's on the account executive to be that quarterback and understand, like, who do we need to get in front of? And then how do I divide and conquer with my BDR if you happen to have a BDR?
35:35 Harry Stebbings? You basically become a professional stalker. I totally get you. No, I agree. I am brilliant actually at sales. So, yeah.
35:42 Speaker 01 I was gonna say, Har, you are brilliant. The fact that on the 53rd email, you got Mark Bennie off to come on your show is so impressive, because that's the other trick with outbound pipelining. You just have to keep going. Just because you don't get a response on your first, your second, your third, your seventh, you gotta keep going.
36:02 Harry Stebbings? But this is why anyone who's done door-to-door sales, I think, is actually getting the best training round ever, because no one opens the door and is like, yeah, you've just come into like my own personal space now on my like front doorstep. Yeah, sell me something. It is the best training ground for rejection.
36:17 Speaker 01 Totally. And you build empathy for the people around. Like, yes, exactly.
36:21 Harry Stebbings? Totally. You mentioned the words account prioritization there. My question on that was like, is it just like, who's the biggest dollar number attached to them? Is there a right way to think about account prioritization, other than just sheer size of contract?
36:34 Speaker 01 Yes, this is where I'd go back to the firmographic data points to figure out what are the firmographic data points that signal the best long-term customers for your business? Those can be industry, company size, location, what their tech stack looks like, everything outside of your product. And then if you are a product-led growth company, what are the other product signals that signal to you that you can accelerate this expansion, this upsell, or this deal, and then using those signals to figure out how, where do you focus your time?
37:08 Harry Stebbings? When you get a hire wrong, how fast do you think you can tell that they're wrong?
37:14 Speaker 01 Pretty fast. And I like this framework that I got from Winning by Design, a sales enablement program where they talk about REKS, R-E-K-S, results, effort, knowledge, and skills. And it's working through that to understand where are we going wrong with this rep? So if they're not hitting the results, they're not hitting the pipeline or revenue results, then we work backwards. Do we see the effort? Are they putting in the emails, the meetings, in order to drive that pipeline? They could be high in volume, and if that's the case, then you look back further. Okay, you look at skills. Are they prioritizing their accounts in the right way? So are they just completely prioritizing the wrong accounts?
37:57 Speaker 01 They're hammering them with emails and meetings, and they're just not going anywhere? Or is it other sales skills, like discovery? They're not asking the right questions to compel the customer to move forward with the evaluation? Or the negotiation calls are falling flat? Or the last place to look is the knowledge? Or are they not coming off as credible in front of their customers because they're not speaking the customer language? Or are they not knowledgeable enough in the product to really understand where to take the conversation? Because when you think about starting to piece together what the actual problem is, that will help you figure out, can you coach this rep on that specific area? Or is this just not going to work out?
38:39 Harry Stebbings? What do you do in the case of, I've got this results, effort, knowledge skills.
38:44 Speaker 01 Yes.
38:44 Harry Stebbings? When you have that, very often I've had the results, which often are there, the effort, which can be there, the knowledge, they're super smart. But the skills, often they're just not, it's a misalignment. So a good example of this in sales would be like, you know what? They can close and they probably have closed.
39:00 Speaker 01 We've moved.
39:01 Harry Stebbings? Effort, they work really hard. 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?
39:29 Speaker 01 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 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.
40:11 Harry Stebbings? I love that churn bombs. I haven't heard that before. And so we learn pretty quickly. When we say pretty quickly, is it like two weeks? Is it like two months? Like, how long do you actually know?
40:22 Speaker 01 It really depends. We keep track in our onboarding program. So like I said, we look at outcomes in the onboarding program, like, okay, first check, did they prioritize their accounts correctly? Second check, how did they do in their mock call scenarios? And then you can tell pretty quickly of, are we on the right path here? Or could this potentially be a mis-hire? And then depending on the ramping period, so for enterprise reps, the ramping is longer than commercial reps. But I would still look at indicators like what we just talked about to figure out, is this going to work?
40:55 Harry Stebbings? When you make a mis-hire, reflect back on a mis-hire, what did you not see that you should have seen?
41:02 Speaker 01 Honestly, I would say I actually saw it and I just felt the pressure of hiring quickly that I felt like I needed to hire the person.
41:13 Harry Stebbings? But it's but what do you do in that case? Okay, so go back to this founder scenario.
41:16 Speaker 01 Yeah.
41:16 Harry Stebbings? 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?
41:27 Speaker 01 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 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
42:09 Speaker 01 going to do a hiring jam at 12 o'clock today. We're going to 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.
42:42 Harry Stebbings? I always find that great people have two to three great friends who they're like, I've worked with them before. They are my ride or die partner. I would definitely work with them again. Great people always have that.
42:53 Speaker 01 I agree, and our most successful hires are referred people.
42:56 Harry Stebbings? 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?
43:05 Speaker 01 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.
43:46 Speaker 01 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 or sales. The best companies I've seen layer sales on top of product-led growth.
44:06 Harry Stebbings? At what point do you do outbound? When you have PLG, you have a huge amount of leads existing that are 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?
44:23 Speaker 01 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 ruts that you're bringing in just to learn about
45:08 Speaker 01 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?
45:27 Harry Stebbings? What outbound channel do you think is most underrated right now?
45:31 Speaker 01 Cold calling.
45:31 Harry Stebbings? Well, like, like hello, Kim, it's Harry.
45:34 Speaker 01 Yes.
45:35 Harry Stebbings? Are you serious?
45:36 Speaker 01 I agree. Yes.
45:37 Harry Stebbings? Wh- what makes you say that?
45:39 Speaker 01 Because I see it working and people don't do it. Cold calling is hard. It's way easier to send an email and get a rejection. That's easy. When you cold call someone and you get a rejection, that hurts. And so when you think about the other sellers around you in this landscape, they are not cold calling. So if you are putting yourself out there and cold calling, and oftentimes it's actually just leaving a message because a lot of people don't answer their phone and it's just leaving a message. So that audio memo also gets you top of mind for the people that you want to get in front of.
46:15 Harry Stebbings? I think I'm so British. People call me 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 invaded my phone? I'm pissed off now. Uh, that's so far. I'm in awe that cold calling is it. Wow. Do you train people on cold calling?
46:41 Speaker 01 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 used one of those in-office days to say, we're going to make this fun. We're going to cold call and every single person on this team, including our 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
47:23 Speaker 01 Get rejected because then you're like, ah, and like people will console you. But then when you actually get a win and you book a meeting, you're 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.
47:54 Harry Stebbings? I totally agree. You know what you also have there? You actually have lessons and knowledge transfer when you hear that Kim's repeatedly done that same messaging three times and it's worked. And it seems really well. I'm going to try the same. And then it's why I just hate remote those stories. Cause like, you know, when you sit near customer support and you hear that everyone is complaining about the X being there or Y being there. And you're like, oh, great. I can get ahead of that. I think it's so important.
48:20 Speaker 01 I think it's so important too. And that's why I'm so happy that we have a hybrid work environment here. I don't think you can build the same type of collaborative, dedicated sales team where everyone's just working from home. I think there's really something to that in-person collaboration. And I will say the best sales teams see celebration and collaboration as a competitive advantage.
48:44 Harry Stebbings? What did you believe about sales that you now no longer believe?
48:49 Speaker 01 The best sellers are extroverts. They're great at messaging and pitching. Now I don't believe that. I think the best sellers are consultative, curious and ask the best questions.
49:01 Harry Stebbings? Do we move into a world where sales reps, leaders need to be far more technical than they've ever been before? To bluntly walk people through solutions that are more technical, especially in a world of AI? Or do we need much more relationship focus or both?
49:16 Speaker 01 I would say both, and here's why. I see AI taking on a lot of the transactional selling activities. And if you have a point solution, or if it's a small deal, I can see AI taking a lot of that down-market selling motion. So sellers really have to focus on the complex strategic sales that require multiple stakeholders, building consensus across the company, finding who the right people are that have influence, and then to your point, like the technical aptitude to map their solution back to them.
49:55 Harry Stebbings? What do we do in sales today that we will not do in five years' time?
50:00 Speaker 01 Oh, okay. The area that I really hope that is completely fixed is data enrichment. And so what sellers dislike the most is when there is bad data within their Salesforce or their CRM. Bad data, meaning the account has the wrong employee count, so they're not able to prioritize them correctly, or the territory is inequitable. I hate manual data entry, and I'm really excited to get more and more enriched data that doesn't require that manual entry.
50:34 Harry Stebbings? I love that. I totally agree. I also think like customer research. When you think about what you used to do, like it took maybe an hour to do great customer research on a prospect. Now it's like ChatGPT, pretty much deep research does a lot for you now.
50:48 Speaker 01 Well, internally, we use Notion AI that's powered by the best models like ChatGPT, Claude, and it is incredible. Like just this week, we had our executives meet in front of customers, and they always ask for an executive briefing doc. And so before, the seller would have to aggregate all of this information from Slack and the customer's website and Salesforce. Now we use Notion Research Mode that aggregates information from all of those different sources and then creates a polished briefing doc within seconds.
51:20 Harry Stebbings? How do you make sure that your sales team is embracing every aspect of AI? For me, as like the leader of a media company, I'm always wanting to push them. I'm like, should we instill a thirty minutes a week where they have playtime with AI? How do you think about enforcing your team to bluntly get out of a mold and behavior set and embrace new tools?
51:39 Speaker 01 I think it's figuring out what are the most impactful workflows that they would benefit from using AI. So start with like, what is the challenge that they're trying to solve? If it is preparing research documents, like let's start there. I found that celebrating the people who are doing it best internally is the best way to actually get that behavior spread across your entire team. And that's why I really like a culture of celebration, because I think that's the best way to lead. Instead of being like, you're not using AI, bad, saying like, wow, these are the best sellers. They're using AI. Here's how they're using it. Like, how can we incorporate this more into our process? And I also think it's involving them into this exploration.
52:22 Speaker 01 So asking questions in our team meetings, like, how might we use AI with the bottleneck activities that we have today? What are some ideas that you've had? What are some things that you've looked out into the market and used recently that we should start trying? And honestly, it's actually really helpful selling an AI product, because with Notion AI, we can do all of that. I like saying, we're constantly drinking our own champagne versus we're dog fooding our own product. We're constantly drinking our own champagne and trying to figure out what are the best use cases for Notion AI? So that we can also speak intelligently about it when we're going out to market and talking to our customers.
52:57 Harry Stebbings? So I think we've both, you know, you obviously invest with 20 sales, obviously invest with 20 VC. We've both seen a ton of AI sales reps. I mean, a ton, and none of them actually work, is the honest truth. Why?
53:12 Speaker 01 Because selling in today's environment is very complex. You have to figure out who are the stakeholders and you have to build relationships. It's a complex product that you're selling. I will say, I believe it would work if it's a very transactional product. Like, if you're like, hey, we're a conference and we are selling conference booths. This is the price. I think like an AI seller can actually probably sell that quite well. But when you're selling solutions like Notion and Slack, like, we're a long, long ways away to ever being able to take those sales roles.
53:47 Harry Stebbings? 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?
54:02 Speaker 01 I agree with that. I've been very impressed with the pace of AI innovation, but in terms of AI adoption, it's 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.
54:46 Speaker 01 And so it's our job to figure out how do we make that easier for them.
54:49 Harry Stebbings? Totally get you. Are there commonalities in their concerns about adopting AI? Be it security, be it accuracy, be it change of behaviors? What are their biggest concerns?
54:59 Speaker 01 For enterprise, it's security, legal. And some enterprises have policies where they just have a no AI policy right now because they're worried about the legal aspects of AI. And so it's trying to figure out how do we get around that?
55:15 Harry Stebbings? Fuck. Europe is even worse, by the way. How like long do you think that transition is between experimental to full scale? Because there is a moment when Wall Street will start penalizing you for not embracing AI. And, you know, I had the founder of Duolingo on the show the other day and they said bluntly that the public market 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?
55:53 Speaker 01 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?
56:38 Speaker 01 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, how can you start to integrate into those systems?
57:21 Speaker 01 So you're starting to change that AI behavior in processes that they're already used to.
57:27 Harry Stebbings? When you're selling AI in 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?
57:44 Speaker 01 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 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've found to be most impactful is using customer stories. And so we'll say here, like the fastest growing companies like OpenAI, Versal, 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?
58:28 Harry Stebbings? 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?
58:45 Speaker 01 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 sass sprawl. And I think I actually heard this on your podcast recently where you're like, the average company uses over 170 different software solutions. And that's real. And my prediction is it's going to get a bit worse in the short term.
59:29 Speaker 01 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?
59:45 Harry Stebbings? Totally. I mean, the bet on notion is that we're going to move into a bundled software world for enterprise is really where it goes.
59:52 Speaker 01 Exactly.
59:52 Harry Stebbings? Can you talk to me about the most creative you've ever had to get to win a deal? I was actually 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?
1:00:08 Speaker 01 I will say, Harry, I'm not a gimmicky person. So I'm not the seller or a 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
1:00:49 Speaker 01 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 touchpoints, 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 surrounding them with your solution.
1:01:34 Harry Stebbings? I think you learn a lot from losses. When you go back to your biggest loss in a deal, what was the biggest loss and what did you learn?
1:01:42 Speaker 01 The one that I'm thinking of right now is we were just in front of the wrong stakeholders and the people that we were in front of didn't have the influence to get the deal done.
1:01:50 Harry Stebbings? Did they say they did or did you misjudge it?
1:01:52 Speaker 01 No, they said they did. And that's what you'll hear. And the common mistake is that you're single threaded, you're with the wrong people and you're not multi-threaded enough in the company in order to actually change the way that they're doing something and bringing them your new solution. No matter how much this happens, it's still common in losing deals where your champion will say like, I can get this done. Don't worry, we've got this. And then you build this relationship where you trust them. And then they also say things like, we don't need to bring anyone else into the deal. Just trust me. And then they'll even give
1:02:32 Speaker 01 you a hand slap if you talk to anyone else in the company. And that's a really big sign that you don't have a real deal here. Like you need to get multi-threaded with different lines of business and who actually holds the budget.
1:02:46 Harry Stebbings? So what do 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, 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?
1:03:08 Speaker 01 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
1:03:53 Speaker 01 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.
1:04:05 Harry Stebbings? What is the number one reason why deals don't convert today for you?
1:04:10 Speaker 01 Status quo. We use a framework. Why change? Why your product? Why now? And it's not a competitor. It's the company isn't stuck in their ways. They don't see a big enough problem and they don't do anything. And so what that signals to us is we didn't truly identify the real pain point or priority that we could tie to, or we weren't in front of the right person who could actually give us what those priorities are.
1:04:40 Harry Stebbings? 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?
1:05:02 Speaker 01 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, SaaS 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?
1:05:45 Speaker 01 And let's work backwards from that renewal to figure out how we can save you some money.
1:05:49 Harry Stebbings? Honestly, which one converts better? Is it like the hey, improve efficiency innovation? Or is it, hey, you're spending a fuck ton of money on a load of tools that you don't need? Just bundle it into one and amazing product called Notion.
1:06:01 Speaker 01 The easier one, I would say, is saving money because that is cut and dry. But the long-term one and where we want our customer success to really help them see the value, because otherwise the risk is another competitor is going to come along and do the exact same sell. And so it's you can get them in the door, but ensure that they are seeing that value in their workflows.
1:06:25 Harry Stebbings? Okay, so who's the best sales leader that you've ever worked with? And what did you take from that?
1:06:31 Speaker 01 I've been fortunate to work with a lot of great sales leaders. I would say the early mentor that stands out to me is Danny Hersberg. And here's why. Before meeting Danny Hersberg, I always thought that sales was a stepping stone for me and I didn't know if it was going to be a long-term career path. And what she taught me was, one, the parts of my job that bring me the most joy all points back to sales. I love achieving wins. I love working collaboratively with a team. I love figuring out go-to-market across sales, marketing, product. And the other piece of it was also seeing how sales could be done differently.
1:07:14 Speaker 01 One, she was a very, she's a very successful female sales leader. And she taught me that sales can be very data-driven. And sales is almost like being a therapist. Like, you're asking a lot of questions and you're truly trying to figure out where is the pain? And so those two things made me realize, like, oh, I could do sales in a different way. And that's, that's a big part of why I continue to be in sales.
1:07:41 Harry Stebbings? Should people worry about title? We see different people focus on a lot, others who say, hey, it doesn't matter, doesn't matter. Does title matter?
1:07:50 Speaker 01 No, title does not matter. The company matters way more than the title. Case in point, I was at Slack. I didn't even know what an account manager was, but I was like, sure, I, I really like this company and I see where this is going. And I got to help Slack grow from six million to nearly two billion in revenue by the time I left. And if I cared about title, I don't know if I would have joined, but I am sure as hell lucky and excited and fortunate that I did.
1:08:22 Harry Stebbings? What was the hardest phase of growth from six million to two billion for you in sales?
1:08:28 Speaker 01 For me, it's very personal. I actually think back to like the point where I didn't know if I was gonna 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. But 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?
1:09:09 Speaker 01 Because what I had said is like, oh, I don't have my advocates, my leaders in my corner to really push me in 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.
1:09:46 Speaker 01 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.
1:09:55 Harry Stebbings? What advice would you give to a young woman in sales? That you don't think is applicable to a young man in sales?
1:10:02 Speaker 01 When you're looking for jobs, even if you meet eighty percent, go for it. Because the man beside you is going for it. And I would also say something I've learned in my career is just because you do hard work. Doesn't mean it's going to get noticed. That may work when you're very junior, but as you go on in your career. You need to learn how to advocate for yourself and ask for it. Ask for the for the promotion.
1:10:29 Harry Stebbings? Also, don't check yourself so much. I work with many amazing women now and they just continuously like check themselves and ask me like to check them. And I'm like, no, no, your intuition was right. Like you should have totally gone with that and you're you're so right. You don't need to check with with anyone. It's right.
1:10:47 Speaker 01 Totally. That goes back full circle to the beginning of this podcast. Like confidence and belief in yourself is going to go so far. I like that advice better. Just go for it. And the worst that can happen is you fail or they say no.
1:11:01 Harry Stebbings? I think it's a good book title. Eighty percent is enough. It could be like a spiritual self-development, eat, pray, love type thing. I'm just offering ideas. It's fine. Don't shoot me down. Okay. Question for you. Where do you need to improve most as a sales leader?
1:11:16 Speaker 01 Focus less on doing and more on reflecting and zooming out. It is in my DNA to just do it, to build, to showcase that I can do it. And I think it's being okay with not always having doing as the outcome, like writing the next Slack message, creating the next Notion document, ensuring that I'm doing all of the things and actually zooming out as a sales leader and reflecting, because that's going to be what's most impactful in seeing around corners and understanding what is the road need to look like ahead.
1:11:51 Harry Stebbings? What's the hardest role to hire for in sales today?
1:11:54 Speaker 01 Enterprise sales.
1:11:55 Harry Stebbings? Why?
1:11:56 Speaker 01 Specifically at a scale up like Notion, you need to hire someone who is familiar with doing the big deals, but also scrappy enough that they're willing to be resourceful and build from scratch.
1:12:10 Harry Stebbings? 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's in 2035.
1:12:19 Speaker 01 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.
1:13:01 Speaker 01 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.
1:13:14 Harry Stebbings? Listen, I've so loved doing this. As I said, we've been friends for years. I so appreciate you being so open. This has been fantastic for me and you are the best.
1:13:23 Speaker 01 Thank you, Harry.
1:13:25 Harry Stebbings? That was such a special show to do with Kim. We've been friends for a long time. We worked together on 20 sales, so really special one for me to do there. If you want to see the episode, you can find it on Spotify. It'd make a huge difference if you want to leave a comment or leave a review. That does make such a difference. But before we leave you today, is your finance team a cost center tied up in enforcing policies, bogged down by cumbersome processes and drowning in operational busy work? Well, what if you could unlock seamless strategic finance that actually fuels your business growth? This is why leading global growth companies use Payhawk, the finance orchestration platform that unifies global spend management with conversational AI to deliver best user experience for everybody dealing with company spending.
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1:16:09 Harry Stebbings? It's no surprise that one in three venture backed startups in the US with companies like Anthropic, Coinbase and Robinhood. I mean, my God, these companies are incredible. Trust Brex to help them grow. If you want to join the smartest startups on the planet, head over to brex.com/startups and see what they can do for you. AppSumo started with one simple idea. The tools you need to grow your business shouldn't put you out of business. That's why they work directly with developers to get exclusive discounts of 80 to 90%. 80 to 90% off software, saving entrepreneurs over half a billion dollars since 2010. Some of the biggest names in tech like Mailchimp, Zapier and Dropbox got their start on AppSumo. Rotating selection of hundreds of tools, you'll find all the software you need to make
1:16:54 Harry Stebbings? your life easier in 2025. Plus with a 60 day money back guarantee, you can try any tool risk free. Start the year off with savings. Get 10% off your first order with the code 20 lowercase vc and a free tool exclusively for 20 vc listeners. That's code 20 lowercase vc for 10% off plus a free tool at appsumo.com. As always, I so appreciate all your support and stay tuned for an incredible episode coming on Monday with the head of private equity at KKR.
Previous 20VC: Nat Friedman and Daniel Gross Bought with Zuck's $100BN AI Budget | Navan Files to Go Public and Canva Pulls the Brakes: Why and What Happens | Why Larry Ellison is the Smartest Man in Tech | Substance or Sizzle: What is Real and What is BS in AI Next 20VC: Inside KKR's Monster $8BN European Fund | The $500M Turkey Gamble That Went Wrong | Do Andreessen & General Catalyst Scare KKR? | Will AI Kill the PE Model? | Can The PE Model Survive without IPOs and Where is the Liquidity with Philip Freise Page updated October 26, 2026 · transcript and summary are machine-generated
