Keith Rabkin, the Chief Revenue Officer at PandaDoc, brings an unconventional yet compelling perspective to sales leadership. A veteran of companies like Google and Adobe, Keith’s ascent to sales leadership without “carrying the bag” emphasizes intellect, curiosity, and a relentless focus on team development over mere quota attainment. Here are the key takeaways from his recent conversation on the Coach to Scale podcast.
1. Breaking the Myth: Salespeople Are More Than Coin-Operated
One of the enduring myths in sales leadership is that reps are solely motivated by money. Keith challenged this assumption, emphasizing that while financial incentives matter, personal growth, recognition, and craftsmanship are equally significant.
CoachEm Insight: Leaders should identify individual motivators—be it personal bests, skill mastery, or long-term career goals—and align these with organizational needs.
2. The Two-by-Three Coaching Framework: A Structured Path to Growth
Keith shared his go-to coaching framework: a two-column, three-row matrix.
- Columns: One focuses on rep-driven goals (e.g., promotion, skill improvement), and the other on leadership-driven needs (e.g., pipeline generation, cross-functional collaboration).
- Rows: Tied to short-term (next quarter), medium-term (1-2 years), and long-term (5+ years) outcomes.
This structure provides clarity, tying individual aspirations to business priorities.
CoachEm Insight: Use AI-powered insights, prompts, and coaching frameworks to foster alignment and accountability in coaching sessions.
3. Customer-Centric Selling: No Room for Lone Wolves
Keith championed team selling over the lone wolf mentality. He argued that prioritizing short-term wins over customer outcomes damages long-term relationships and organizational health.
- Evidence: Reps who embrace team dynamics—looping in customer success, solutions engineers, or executives—achieve higher close rates and larger deal sizes.
- Practical Application: Create a culture where collaboration is celebrated, and lone ranger behaviors are coached out.
4. Tough Conversations: The Cornerstone of Leadership
Keith didn’t mince words about the necessity of difficult conversations. His philosophy? Have them early, base them on data, and approach with compassion.
CoachEm Insight: Frame feedback factually (“Your close rate is X; the expectation is Y”) to depersonalize criticism, making it easier for reps to act on.
5. Urgency and Change Management: Lessons from Transitioning to Value Selling
Transitioning PandaDoc to a value-selling model was a humbling experience for Keith. Despite a talented team, the behavioral shift took longer than expected.
CoachEm Insight: Change takes time. Success requires repetition, alignment between enablement and frontline managers, and a relentless focus on the “why” behind new initiatives.
6. AI in Sales: Experimentation Over Perfection
Keith sees AI as an untapped frontier for sales, urging leaders to experiment with emerging tools to discover what works for their teams.
CoachEm Insight: Encourage reps to test technologies and share insights. Focus on measurable outcomes—like pipeline quality or deal velocity—rather than superficial efficiencies.
7. From Operations to Revenue Leadership: A Lesson in Hard Work
Keith’s journey from operational roles to CRO exemplifies the power of being a “student of the game.” His relentless focus on data, coaching frameworks, and authentic customer interactions has earned him respect despite his non-traditional background.
“Hard work and curiosity are the great equalizers in sales leadership.”
Building a Culture of Coaching
Keith Rabkin’s leadership playbook highlights the profound impact of structured coaching, team-oriented selling, and relentless focus on personal and organizational growth. Sales leaders should take a page out of Keith’s book: invest in understanding individual motivators, lean into difficult conversations, and prioritize long-term value over short-term gains. As we always say, “Coach them if you want to keep them.”
For sales leaders looking to embed these principles into their teams, platforms like CoachEm offer a structured approach to scaling coaching culture and aligning rep performance with organizational goals. For more information, talk to a human at CoachEm.
