Podcast Summary: The Twenty Minute VC (20VC) Episode with Kim Graves
Title: 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
Release Date: June 27, 2025
Host: Harry Stebbings
Guest: Kim Graves, Head of Sales, Pre-Sales, Customer Success, and Renewals at Notion
1. Introduction to Kim Graves
Harry Stebbings welcomes Kim Graves, an accomplished sales leader who has significantly contributed to Notion's record-breaking 2024 growth and the expansion of its AI-powered go-to-market strategy across North America. With a robust background at Slack and as a co-founder of 20 Sales, Kim brings a wealth of experience in scaling sales teams and investing in top go-to-market technologies.
Notable Quote:
"At the first day with Slack, I realized that the account manager role was an account executive, a solutions engineer, and a customer success manager all in one." (04:43)
2. Kim's Early Sales Journey and Advice to Her Younger Self
Kim shares her unexpected entry into sales, beginning at her mother's beauty salon and transitioning into a marketing role at a tech startup. Her passion for Slack led her to secure a role as an account manager, which broadened her understanding of sales roles.
Notable Quote:
"I would tell myself, be confident. You've got this role for a reason." (06:19)
3. Building Confidence in Sales
Emphasizing the importance of confidence, Kim advises new sales reps to maintain a positive demeanor during customer interactions, especially when facing objections or negotiating discounts.
Notable Quote:
"Treat negotiation as any other conversation. Your customer will feel your energy." (07:01)
4. Handling Discount Negotiations
Kim provides strategies for managing discount requests without feeling awkward. She encourages reps to transition the conversation back to understanding customer needs and seeking mutual value.
Notable Quote:
"Instead of defending your price, ask, 'Why do you think it's expensive? What is the right price to pay?'" (07:30)
5. Structuring the Sales Process with a Mindset Approach
At Notion, the sales process is redefined by focusing on the mindset at each stage rather than traditional stage names. This approach fosters adaptability and emphasizes the importance of embodying specific roles such as "Curious Investigator" and "Value Articulator."
Notable Quote:
"We think about the mindset in each stage because it makes for a much more adaptable approach." (09:05)
6. Transitioning from Product-Led Growth (PLG) to Enterprise Sales
Kim discusses the challenges PLG companies face when layering enterprise sales on top of existing product-led strategies. She highlights the common misconception that the product alone can drive enterprise sales and underscores the necessity of a dedicated sales team to engage with larger, high-value customers.
Notable Quote:
"Building sales is vital to continue accelerating your company forward." (44:15)
7. Identifying the Ideal Customer Profile (ICP) Beyond Usage Signals
Kim advises founders to go beyond product usage metrics when identifying their ICP. Instead, she emphasizes the importance of firmographic details such as industry, company size, and geographic location, alongside understanding key personas within target organizations.
Notable Quote:
"Look at the firmographic details and the personas in those companies that are getting the most value." (17:04)
8. Hiring Strategies for Scaling Sales Teams
Kim outlines essential competencies for hiring early-stage sales reps, including high motivation, effective problem-solving skills, and a propensity for continuous learning. She advocates for a diverse team comprising both early-career individuals and those making career transitions.
Notable Quote:
"The first few sales reps are going to be very costly because you're hiring generalists who are adaptable and highly skilled in communication." (20:59)
9. Effective Onboarding of New Reps
Emphasizing the importance of clear objectives, Kim describes Notion's onboarding program centered around key outcomes such as prioritizing accounts and mastering mock sales scenarios. This structured approach ensures reps are well-prepared for customer interactions.
Notable Quote:
"One of the first key outcomes is learning how to prioritize their book of business." (30:36)
10. Diversifying the Sales Pipeline: Balancing Big Deals and Velocity
Kim recommends a diversified portfolio approach where sales reps manage both strategic, high-value deals and smaller, more predictable "velocity" deals. This balance ensures a steady revenue stream while pursuing significant growth opportunities.
Notable Quote:
"You should have a few big bet accounts that are going to get you the hundred thousand or million-dollar deals and also the tried and true accounts." (30:48)
11. Outbound Strategies and the Underrated Role of Cold Calling
Highlighting cold calling as an undervalued outbound strategy, Kim shares insights on its effectiveness despite being challenging. She details how Notion fosters a supportive environment to encourage reps to embrace cold calling through collaborative initiatives like global outbound days.
Notable Quote:
"Cold calling is hard, but if you put yourself out there, it can be incredibly effective." (46:41)
12. Leveraging AI in Sales Workflows
Kim discusses the integration of AI tools to enhance sales processes, such as using Notion AI for research and generating briefing documents. She emphasizes celebrating innovative use of AI within the team to drive adoption and efficiency.
Notable Quote:
"We use Notion Research mode to aggregate information and create polished briefing docs within seconds." (51:58)
13. Challenges with AI Sales Reps and the Future of Sales
Addressing the limitations of AI in sales, Kim believes that while AI can handle transactional activities, human sales reps are essential for complex, strategic sales requiring relationship-building and technical expertise. She anticipates an increase in enterprise sales roles as product complexity grows.
Notable Quote:
"AI can handle transactional selling, but strategic sales require human intuition and relationship-building." (50:26)
14. Handling Mis-hires and Performance Management
Kim outlines a framework to identify and address mis-hires based on results, effort, knowledge, and skills. She advocates for swift action and adjusting hiring processes to mitigate the costs associated with bad hires.
Notable Quote:
"It's more costly to have a bad hire, so instead of lowering hiring standards, increase the hiring funnel to find the right people." (42:13)
15. Insights on Sales Leadership and Personal Growth
Reflecting on her career, Kim shares the influence of her mentor, Danny Herzberg, who taught her the value of data-driven sales and the consultative approach. She also emphasizes the importance of seeking role models and advocating for oneself, especially for women in sales.
Notable Quote:
"Sales is almost like being a therapist, asking the right questions to uncover pain points." (69:21)
16. Advice for Women in Sales
Kim encourages young women in sales to actively seek out role models and advocate for themselves. She highlights the necessity of confidence and self-belief to overcome challenges and advance in their careers.
Notable Quote:
"Actively seek out role models and don't check yourself too much. Believe in your intuition." (72:52)
17. Future Outlook and Personal Aspirations
Looking ahead, Kim envisions building a world-class enterprise team at Notion and possibly transitioning into academia as an adjunct professor. Her focus remains on driving revenue, fostering team growth, and integrating innovative sales strategies.
Notable Quote:
"I hope to help accelerate the careers of those around me and possibly teach the lessons I've learned in sales." (76:03)
Conclusion
Harry Stebbings wraps up the episode by expressing gratitude for Kim Graves' insights and highlighting the significance of her contributions to sales leadership. The episode provides a comprehensive exploration of layering enterprise sales onto product-led growth, effective hiring and onboarding strategies, leveraging AI in sales, and the evolving landscape of sales roles.
Final Notable Quote:
"The best sales teams see celebration and collaboration as a competitive advantage." (49:54)
Additional Information: For more episodes and resources from The Twenty Minute VC (20VC), visit www.20vc.com.