20Sales: How to Layer Enterprise Sales on PLG | How to Sell AI...

Full 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

Summary

This episode features Kim Graves, a sales leader at Notion, discussing strategies for building and scaling sales teams, particularly when layering enterprise sales onto a product-led growth (PLG) motion. The discussion focuses on effective sales processes, hiring practices for early-stage sales, and adapting to the evolving landscape with AI.

Key Points

• Sales confidence is paramount, especially during difficult conversations like price negotiations or objections, where maintaining a calm, discovery-oriented approach is more effective than defensive pitching.
• Structuring a sales process around seller mindsets, such as "curious investigator" or "value articulator," fosters adaptability and deeper customer engagement beyond mere checklist completion.
• Product-led growth (PLG) companies should identify their ideal customer profile (ICP) based on firmographic data, not solely on product usage signals, to avoid targeting non-monetizable segments.
• Founders should personally lead initial sales discovery to build intuition and guide both go-to-market strategy and product roadmap before delegating to hired sales leaders.
• Early sales hires should be "renaissance reps" who are generalists, adaptable, collaborative, highly motivated, effective problem-solvers, and continuous learners, prioritizing building over immediate high earnings.
• Effective onboarding for new sales representatives should focus on achieving key outcomes and leading indicators, such as account prioritization and mock call scenarios, before live customer interactions.
• Account executives should be responsible for their own pipeline generation, engaging in multi-channel outbound efforts like cold calling and personalized outreach, as it fosters crucial ownership and perseverance.
• Mis-hires can be quickly identified by assessing results, effort, knowledge, and skills (REKS), with issues often stemming from a misaligned skill set or a lack of accountability rather than just low volume.
• AI is expected to automate transactional sales activities, shifting the human sales role towards complex, strategic enterprise deals that require deep relationship building, consensus, and technical aptitude.
• Enterprise adoption of AI is slow due to significant concerns regarding security, legal implications, and integration challenges with existing workflows, but will be driven by market pressure and demonstrated business outcomes.
• Deals often fail due to the customer maintaining the status quo, indicating the sales team did not sufficiently identify or articulate a compelling pain point or engage the ultimate decision-makers.

Conclusion

Sales leaders should strategically define sales processes by focusing on seller mindsets to foster adaptability and deeper customer understanding.

Companies layering enterprise sales onto PLG motions must prioritize firmographic data and hands-on founder involvement in early sales discovery to identify valuable customer profiles.

The future of sales involves leveraging AI for transactional tasks while concentrating human effort on complex enterprise deals that require strategic thinking, deep relationship building, and technical expertise.

Discussion Topics

• How can founders effectively transition from a product-led growth model to incorporating a successful enterprise sales motion without losing focus?
• What are the most underrated sales channels or strategies that companies should be leveraging more in today's digital-first environment?
• How should sales teams balance the adoption of AI tools for efficiency with the enduring need for human relationship-building in complex sales cycles?

Key Terms

PLG

Product-Led Growth; a business strategy where product usage drives customer acquisition, conversion, and expansion.

ICP

Ideal Customer Profile; a description of the type of company that would gain the most value from your product or service and is also valuable to your business.

OTE

On-Target Earnings; the total expected compensation for a sales role, including base salary and commission, assuming sales targets are met.

REKS

Results, Effort, Knowledge, Skills; a framework used to assess sales representative performance and diagnose areas for improvement.

SaaS sprawl

Software as a Service sprawl; the proliferation of multiple SaaS applications within an organization, leading to inefficiencies and increased costs.

Sales Learning Curve

A concept suggesting that early sales efforts in a new product or market are costly but crucial for learning and defining a scalable sales process.

Firmographic details

Descriptive attributes of companies or organizations, such as industry, company size, revenue, and location.

Renaissance reps

Generalist sales representatives hired in the early stages of building a sales team, valued for their adaptability, problem-solving, and collaboration skills rather than just quota attainment.

Churn bombs

Customers or deals acquired that are likely to churn quickly or generate low long-term value, often due to misqualification or overselling.

PIP

Performance Improvement Plan; a formal document outlining specific areas where an employee needs to improve, along with a plan and timeline for achieving those improvements.

Timeline