Jun 27, 2025 · 1h 17m · 20sales
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
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of 20 Sales, host Harry Stebbings interviews Kim Graves, GTM leader at Notion, on scaling enterprise sales within product-led growth companies, building and managing high-performing sales teams, and strategically navigating AI adoption in enterprise software.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 33.1% of the talking time here. How this is scored →
Harry as informed peer 3.5 Guest teaching 6.3 Guest disagreement 1.6 Harry pushing back 2.0
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 1:00:09 Explicit rejection of sales gimmicks
Kim firmly rejects Harry's suggestion of using creative gimmicks or physical gifts to close deals, making it clear that she relies entirely on strategic multi-threading rather than stunts.
Hardest push from Harry ▶ 45:31 Refusal of cold calling validityHarry strongly rejects Kim's defense of cold calling, arguing that invading someone's phone directly creates hostility rather than sales opportunity.
Biggest teaching moment ▶ 14:31 Debunking raw PLG signal trapsKim educates Harry on why following raw PLG user numbers leads founders astray, using early Slack data to show how large community workspaces lacked budget and corrupted product roadmaps.
Harry holds his own ▶ 19:40 Citing HBR sales learning frameworksHarry demonstrates deep knowledge of sales organizational theory by citing Harvard Business Review's Sales Learning Curve framework to challenge Kim on early sales hiring sequence.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Kim Graves' First Sales Role and Advice to Her Younger Self | 2 | 5 | 1 | 1 | Kim details her early career journey from a beauty salon to becoming Slack's first account manager, explaining how the role encompassed AE, SE, and CSM functions. Harry agrees with her advice on confidence and draws a brief parallel to fundraising mindsets. | |
| Navigating Price Discounts and Sales Stage Mindsets | 4 | 6 | 1 | 1 | Kim advises treating discount requests like discovery questions rather than tense negotiations, introducing Notion's approach of defining deal stages by seller mindsets rather than exit criteria. Harry validates this approach by connecting it to how venture investors create psychological safety during founder interviews. | |
| Avoiding PLG Sales Traps and Defining Ideal Customer Profiles | 3 | 7 | 2 | 2 | Kim warns against premature pitching and reframes PLG data signals, explaining how targeting Slack's largest user groups like communities was a trap due to lack of budget and misaligned product requirements. Harry asks targeted questions on sales playbooks and call recording workflows. | |
| Layering Enterprise Sales on PLG and Hiring Renaissance Reps | 4 | 7 | 2 | 2 | Kim firmly insists that founders must personally conduct customer discovery rather than delegating it to early sales hires. Harry demonstrates industry familiarity by citing the Harvard Business Review Sales Learning Curve model while questioning how founders should scale GTM. | |
| Evaluating Sales Candidates Through Behavioral Screening and Mock Demos | 3 | 6 | 1 | 1 | Kim outlines behavioral interview strategies to assess candidate accountability and problem-solving, along with mock call scenarios to test composure under pressure. Harry reinforces her point about identifying candidates who deflect responsibility. | |
| Compensation Negotiation, Onboarding Milestones, and Portfolio Management | 3 | 6 | 1 | 2 | Kim advises sales hires at scale-ups to prioritize equity over OTE and advocates for portfolio management that balances big-bet strategic accounts with high-velocity deals. Harry pushes back on whether managing mixed portfolios contradicts traditional enterprise rep segmentation. | |
| Account Executive Pipeline Ownership and Performance Management | 4 | 7 | 1 | 2 | Kim asserts that account executives must own pipeline generation and breaks down the REKS framework for diagnosing underperformance, introducing the term churn bombs for misaligned sales wins. Harry presents edge cases on talent skill mismatches and pressure-driven hiring mistakes. | |
| Outbound Strategy, Cold Calling, and In-Person Sales Collaboration | 3 | 7 | 3 | 4 | Kim advocates cold calling as the most underrated outbound channel and explains Notion's in-office outbound call blitzes, highlighting in-person sales collaboration. Harry forcefully pushes back with comedic exasperation, declaring he would tell any rep who cold-called him on a Friday to fuck off. | |
| AI Adoption in Sales Workflows and Debunking Fully Autonomous AI Reps | 4 | 6 | 2 | 2 | Harry directly challenges the current wave of AI sales reps, stating that none of them work in practice. Kim agrees with his assessment for complex multi-stakeholder deals, explaining that AI automates transactional tasks but cannot build human executive consensus. | |
| Enterprise AI Adoption Realities and Overcoming Competitive Comparison | 4 | 6 | 2 | 2 | Harry cites a quote from Duolingo's founder regarding public market sentiment toward AI adoption. Kim discusses enterprise adoption realities, distinguishing temporary vibe revenue from long-term value driving renewals, and details customer-obsessed competitive positioning. | |
| Strategic Deal Execution, Multi-Threading, and Beating the Status Quo | 5 | 7 | 2 | 4 | Kim dismisses gimmicky closing tactics in favor of multi-threading executive relationships and overcomes deal inertia. Harry challenges Notion's why now urgency, arguing that productivity software lacks the existential deadline of a cybersecurity breach or system outage. | |
| Sales Leadership Mentorship, Career Trajectory, and Long-Term Vision | 3 | 5 | 1 | 1 | Kim reflects on mentorship from Danny Herzberg, navigating executive turnover at Slack, and advocating for women in tech sales. Harry offers additional guidance on self-advocacy and female candidate confidence. |
Statements from this episode (23)
Early Slack Account Managers handled AE, SE, and CSM duties combined
“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.”
Graves: Reps facing price pushback should ask questions, not defend price
“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 conver…”
Graves: Notion structures sales pipeline stages around seller mindsets
“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 negotiatio…”
Stebbings: Top venture investors benefit from having prior interviewing experience
“I actually think that the best investors started life 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 guests feel very comfortable.”
Notion uses Gong and Notion AI internally for sales call transcription
“We have both Gong, which records the calls and the video, but we also use Notion AI internally to transcribe those calls.”
Slack deliberately avoided sales outreach to community workspaces despite high user counts
“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…”
Graves: PLG founders must personally establish their ideal customer profile
“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.”
Graves: First sales hires should focus on learning, not quota execution
“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.”
Graves: Startup Equity Outweighs High OTE for Early Sales Hires
“If you're at a fast growing company that is doing really well, your equity is going to be way more meaningful than your OTE.”
Graves: Sales Reps Should Manage Pipeline Like an Investment Portfolio
“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. Portfolio. I bring that mentality into sales to think about, okay, in …”
Graves: Account executives must own their own pipeline generation
“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.”
Kim Graves: Fortune 100 executives cannot be reached via PLG motions
“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 moti…”
Kim Graves: Establishing successful outbound sales messaging takes a full year
“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?”
Kim Graves: Cold calling is the most underrated outbound sales channel
“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 i…”
Kim Graves: High-performing sales teams cannot be built fully remote
“I don't think you can build the same type of collaborative, dedicated sales team where everyone's just working from home.”
Graves: Top sales reps are consultative and curious, not extroverts
“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.”
Graves: AI will automate down-market, transactional selling motions
“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.”
Graves: AI sellers remain far from replacing enterprise sales reps
“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 y…”
Kim Graves: Enterprise AI adoption remains slow as companies wait and see
“I've been very impressed with the pace of AI innovation, but in terms of AI adoption is actually been very slow. And the average enterprise company is still waiting and seeing what happens.”
Kim Graves predicts enterprise SaaS sprawl will worsen before consolidating long term
“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.”
Kim Graves: A prospect refusing internal introductions is not a real champion
“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.”
Kim Graves: Status quo, not competition, is Notion's top reason for lost deals
“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.”
Kim Graves: Pitching cost savings closes enterprise sales faster than pitching innovation
“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 exac…”