YouSaid · the spoken record

Kim Graves

lines on the record: 85
first: 2025-06-27
most recent: 2025-06-27
sittings or episodes: 1
sources: podcast

Every line below is reproduced as it was said and linked to the record it came from. Nothing here is summarised or generated. Directory · Search · Corrections

“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 lab talks, 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 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.”
2025-06-27 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Enterprise sal 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.”
2025-06-27 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2025-06-27 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2025-06-27 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“When you're looking for jobs, even if you meet 80%, 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 promotion.”
2025-06-27 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2025-06-27 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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'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 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?”
2025-06-27 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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 But I was like, sure, I really like this company and I see where this is going. And I got to help Slack grow from 6 million to nearly 2 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”
2025-06-27 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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 a big part of why I continue to be in sales.”
2025-06-27 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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 Herzberg. And here's why. Before meeting Danny Herzberg, 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. 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.”
2025-06-27 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2025-06-27 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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? And let's work backwards from that renewal to figure out how we can save you some money.”
2025-06-27 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Status quo. We use a framework, why change, why your product, why now. And it's not a competitor. It's the company is 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.”
2025-06-27 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2025-06-27 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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 isolation. No matter how much this happens, it's still common in lazing 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 you a handslap 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 a budget.”
2025-06-27 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2025-06-27 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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 surrounding them with your solution.”
2025-06-27 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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 or 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”
2025-06-27 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“I agree. I think it's bad for him 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 SAS 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, 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”
2025-06-27 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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 found to be most impactful is using customer stories. And so we'll say here, like the fastest growing companies like OpenAI, Versel, 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?”
2025-06-27 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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 so you're starting to change that AI behavior in processes that they're already used to?”
2025-06-27 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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 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?”
2025-06-27 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2025-06-27 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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. And so it's our job to figure out how do we make that easier for them.”
2025-06-27 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2025-06-27 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2025-06-27 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“I think it's figuring out what 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. 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?”
2025-06-27 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2025-06-27 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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 sales force or their CRM. Bad data meaning the account has the wrong employee account, 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.”
2025-06-27 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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 downmarket 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.”
2025-06-27 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Bestsellers 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.”
2025-06-27 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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 too that in-person collaboration. And I will say the best sales team see celebration and collaboration as a competitive advantage.”
2025-06-27 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Brought out prizes to make it even more fun. And so that's a way for us to 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.”
2025-06-27 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Of course we have to. And we actually 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 Noshin, 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 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. Because then you're like, 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.”
2025-06-27 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2025-06-27 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Are the accounts that were 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?”
2025-06-27 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2025-06-27 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“It is difficult because when you have a product led growth motion, there's often the perception of the product cells 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.”
2025-06-27 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2025-06-27 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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 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.”
2025-06-27 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2025-06-27 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“It really depends. We keep track of 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 do 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 mishire? 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?”
2025-06-27 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, well, I try and figure out 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 those are a few of the nuances that we would also want to look out for.”
2025-06-27 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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. 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?”
2025-06-27 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Pretty fast, and I like this framework that I got from Winning By Design, a sales enablement program where they talk about Rex 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? They're hammering them with emails and meetings.”
2025-06-27 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Yes, this is where I'd go back to the fermographic data points to figure out what are the fermographic 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 where do you focus your time?”
2025-06-27 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“I was going to say Harry, you were brilliant. The fact that on the 53rd email you got Mark Bennioff to come on your show. 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 got to keep going.”
2025-06-27 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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 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?”
2025-06-27 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“100%. Every sales team I've led are 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.”
2025-06-27 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“So I have different answers depending on the stage of your company. 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.”
2025-06-27 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source