In this exciting Leadership Lessons episode, Tash sits down with Sam Killip, VP of Customer Success at Attest, to explore the critical role of executive engagement in customer success. Together, they dive into how structuring CS teams around business objectives drives impact, and why clear, concise communication with executives is essential.


The discussion unpacks strategies for creating value-driven interactions — from setting engagement targets to involving senior leaders — while highlighting how OKRs and proactive communication can help customer success teams stay aligned, credible, and renewal-ready.


Key Takeaways

  • Executive engagement is a game-changer — it drives stronger alignment and deeper customer relationships.

  • Value delivery is central — customer success thrives when teams consistently connect actions to business impact.

  • Know the business, not just the account — understanding customer objectives is key for effective conversations.

  • Less is more — short, clear communication resonates most with executives.

  • Set engagement goals — tracking and targeting executive touchpoints ensures accountability.

  • Bring in senior leaders — involving higher-level executives can strengthen customer trust.

  • Learn together — sharing experiences across the team builds growth and resilience.

  • OKRs provide focus — aligning objectives sharpens priorities and unites the team.

  • Tie back to outcomes — connecting daily work to strategic goals builds credibility.

  • Be proactive — staying visible prevents being a “stranger” at renewal time.