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

Unknown Source June 27, 2025 77 min

artificial-intelligence startup generative-ai ai-infrastructure investment anthropic microsoft google

🎧 Listen to Original

71 Companies

162 Key Quotes

5 Topics

3 Insights

🎯 Summary

Technology Professional’s Summary: Scaling Go-to-Market and Building High-Performance Sales Teams

This episode of 20 Sales features Kim Graves, Head of Sales, Pre-Sales, Customer Success, and Renewals at Notion, detailing her experience scaling go-to-market (GTM) functions, particularly in Product-Led Growth (PLG) environments like Notion and Slack, and offering tactical advice on building foundational sales teams.

1. Main Narrative Arc and Key Discussion Points

The conversation traces Kim Graves’ career trajectory from an accidental first sales role at Slack (which combined AE, SE, and CSM duties) to leading GTM at Notion. The core narrative shifts from personal sales confidence to establishing structured, mindset-driven sales processes, and finally, advising technical founders on transitioning from a pure PLG motion to an enterprise sales motion.

2. Major Topics and Subject Areas Covered

Sales Confidence & Negotiation: Handling customer pressure, specifically discount requests, by maintaining composure and pivoting back to discovery.
Sales Process Frameworks: Moving beyond traditional stage checklists to defining mindsets for each stage of the sales cycle.
PLG to Enterprise Transition: The strategic challenges and necessary steps for founders to layer an enterprise sales motion onto an existing PLG base.
Ideal Customer Profile (ICP) Definition: The critical importance of founder-led discovery to define the B2B ICP, rather than relying solely on product usage signals.
Early Sales Team Hiring: Identifying the core competencies for “Renaissance reps” needed during the initial learning phase of sales team buildout.

3. Technical Concepts, Methodologies, or Frameworks Discussed

Mindset-Driven Sales Stages: Notion structures its sales process not by exit criteria, but by the required seller mindset:
- Stage 2: Curious Investigator: Deep research and genuine curiosity, avoiding premature pitching.
- Stage 5: Value Articulator: Focusing on clearly connecting product value to articulated customer problems during negotiation.
PLG Signal Trap: The danger of using product usage data (e.g., large community workspaces) to define the enterprise ICP, which may lead to investing in low-budget segments.
Firmographic Analysis: Using non-product data (industry, company size, location) to define the target ICP for enterprise sales.
Sales Learning Curve (HBR): The concept that the first few sales hires (3-4 “Renaissance reps”) are expensive learning investments, not immediate playbook executors.

4. Business Implications and Strategic Insights

Strategic Finance Integration (Sponsor Content): The necessity for finance operations (Payhawk) to shift from a cost center to a strategic growth driver using AI orchestration.
Startup Financial Stack (Sponsor Content): The importance of scalable financial infrastructure (Brex) that maximizes runway and cash yield for venture-backed startups.
PLG Focus Deliberation: Successful PLG companies must make deliberate choices about which user segments to monetize via sales. Slack/Notion chose B2B over high-volume, low-budget communities, guiding product roadmap away from community-specific features.
Founder Involvement in GTM: The founder must lead the initial ICP discovery to ensure the GTM strategy aligns with the product roadmap and core business mission.

5. Key Personalities and Thought Leaders Mentioned

Kim Graves (Notion): Guest expert on GTM scaling, formerly at Slack and Salesforce.
Stewart Butterfield (Slack Founder): Mentioned as the catalyst for Kim’s entry into tech sales.
Montrebege (HBR Author): Referenced for the “sales learning curve” article.

6. Predictions, Trends, or Future-Looking Statements

The discussion heavily implies a trend toward process formalization through mindset definition in sales, suggesting that how a seller feels and approaches a stage is as critical as what they execute.

7. Practical Applications and Actionable Advice

Handling Discount Pushback: When a customer calls the price expensive, pause, do not immediately defend or offer concessions. Instead, pivot back to discovery: “Tell me more. Why do you think it’s expensive? What do you think is the right price?”
Hiring Early Sellers: Founders should hire 3-4 adaptable “Renaissance reps” who are motivated by learning and building over immediate high commission.
Key Competencies for Early Hires: Focus interviews on assessing High Motivation, Effective Problem-Solving, and Continuous Learning. Use behavioral questions (“Tell me about a time you weren’t set up for success”) to gauge accountability and perseverance.

8. Controversies, Challenges, or Problems Highlighted

Premature Pitching Syndrome: Sellers who love their product too much often jump into feature discussions before fully understanding customer needs (failing the “Curious Investigator” stage).
Founder Reluctance: Technical founders often resist the necessary deep-dive interviews required to define the enterprise ICP, preferring to rely on surface-level PLG data.
Victim Mentality in Sales: A key red flag in hiring is candidates who attribute past failures solely to external factors (e.g., poor management, lack of inbound leads) rather than taking accountability.

9. Context: Why This Conversation Matters

This episode is crucial for technology professionals, especially those in scaling SaaS companies, because it provides a blueprint for operationalizing sales maturity. It bridges the gap between product-centric PL

🏢 Companies Mentioned

(Speaker's Company) ✅ Tech/SaaS

Microsoft Teams ✅ tech

Google Drive ✅ tech

Mark Benioff ✅ tech/business

Sales Navigator ✅ unknown

Do I ✅ unknown

Google Drive ✅ unknown

Microsoft Teams ✅ unknown

Wall Street ✅ unknown

Hugh Grant ✅ unknown

Because I ✅ unknown

What I ✅ unknown

Mark Benioff ✅ unknown

LinkedIn Sales Navigator ✅ unknown

Like I ✅ unknown

💬 Key Insights

"Like you need to get multi-threaded with different lines of business and who actually holds the budget."

Impact Score: 10

"And then they'll even give 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."

Impact Score: 10

"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."

Impact Score: 10

"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."

Impact Score: 10

"making sure that every important person in the deal is aligned to someone at my company, whether that's a subject matter expertise that 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."

Impact Score: 10

"It's figuring out how do we align to stakeholders at all levels and make sure that we bring them value."

Impact Score: 10

📊 Topics

#artificialintelligence 88 #startup 27 #generativeai 5 #aiinfrastructure 3 #investment 1

🧠 Key Takeaways

💡 be focusing on

💡 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

💡 start trying? And honestly, it's actually really helpful selling an AI product because with Notion AI, we can do all of that