In this episode of Sales Is King, host Dan Sixsmith sits down with Jon Addison, Chief Revenue Officer at Okta, to unpack how identity is becoming mission-critical in a world of AI agents, distributed work, and rising security expectations. Jon shares how Okta is evolving from product to platform, why identity is central to securing AI, and what it really takes to lead large, global go-to-market organizations today. The conversation ranges from AI ROI and agent security to sales leadership, relationship selling in a post‑pandemic world, and Jon’s unconventional path from door‑to‑door sales and technical roles into the CRO seat.
Key Topics
- Okta’s mission and why identity sits at the center of security and AI.
- The early, messy phase of AI and agents and why standardization and consolidation are coming.
- How Okta thinks about securing AI agents for 20,000+ customers through policy, platform, and design.
- Moving from “product company” to “platform company” and what that means for GTM, partners, and customers.
- Jon’s view of the CRO role: being a change agent, driving parallel transformations, and balancing data with instinct.
- The “Formula to Win” (Focus, Compete, Lead) and the decision to specialize across Okta and Auth0 buying personas.
- Why enterprise selling is going “back to relationships” in an era of hyper‑informed, AI‑enabled buyers.
- Skill vs. art in sales: practice, rehearsal, and the X‑factor of human connection and courage.
- Methodologies, MEDDIC, and how frameworks and creativity can and should coexist.
- Jon’s career path: door‑to‑door sales, technical consulting, product management, Oracle, LinkedIn, and now Okta.
- How to think about talent, instincts, and building high‑performing, international sales teams.
- Jon’s definition of success: growth, unlocking potential in reps, and meaningful customer outcomes.
Highlights
- AI and agent deployments are still in early, fragmented stages, and most enterprises are experimenting without yet seeing consistent ROI—creating a big opening for vendors who can standardize and secure these environments.
- Okta sees AI agents much like cloud apps in the early days: scattered pilots that will eventually need centralized identity, policy, and governance—an area where its platforms are already embedded.
- The CRO role is fundamentally about being an empowered change agent: driving multiple transformation streams at once, building trust across functions, and having the courage to move fast without creating “one‑way doors.”
- Specialization across platforms (Okta vs. Auth0) and buying personas is unlocking deeper expertise, better customer conversations, and sharper competitive positioning.
- Enterprise sellers will increasingly face highly educated buyers who have already self‑researched with AI, which shifts the seller’s value from information transfer to relationship, insight, orchestration, and outcome design.
- World‑class sellers treat sales like a craft: they rehearse, review call recordings, seek coaching, and study both customers and industries the way elite athletes study film.
- Strong sales cultures blend a clear methodology and shared language with individual creativity, ambition, and “brave” outreach that truly differentiates the experience for customers.
Guest Bio – Jon Addison
Jon Addison is the Chief Revenue Officer at Okta, where he leads the global field organization and is responsible for driving worldwide growth. He brings over 20 years of sales leadership experience from roles at LinkedIn, Oracle, and other global technology firms, and is focused on building high‑performing teams, scaling platform‑led go‑to‑market motions, and helping customers modernize and secure identity in the age of AI.
Connect with Jon and Okta
- Jon on Okta’s leadership page: https://www.okta.com/company/leadership/jon-addison/
- Okta newsroom and updates: https://www.okta.com/newsroom/
Connect with Dan Sixsmith & Sales Is King
- Dan Sixsmith on LinkedIn: https://www.linkedin.com/in/dansixsmith/