Host Callan Harrington sits down with Chris Kessler, Chief Product and Platform Officer at Bold Penguin, for an in-depth look at enterprise solution selling. Chris brings a unique background in strategy consulting that has directly shaped how Bold Penguin consistently lands household names as enterprise clients in the insurance space.

The conversation centers on Chris's detailed solutioning process, which goes far beyond typical sales approaches. He walks through his methodology of engaging with the right stakeholders, conducting strategic whiteboard sessions, and building comprehensive roadmaps that blend core product with custom services.

He covers everything from identifying P&L owners with long-term mandates to navigating brutal procurement processes in the insurance industry.

Key topics covered:

[00:00] Intro
[01:49] Solution in Enterprise Sales
[03:42] How Chris Fell Into Insurance
[08:15] Strategy Consulting to Corporate Strategy
[13:38] Solution Process Deep Dive
[16:00] Finding the Right Decision Makers
[18:48] In-Person Strategy Sessions Matter
[20:00] Whiteboarding Current State Process
[24:28] Charging for Discovery Work
[27:17] Building the Future State Roadmap
[32:48] Procurement Doesn't Get Easier
[36:15] Implementing Consulting Skills at Bold Penguin
[39:07] Recognizing a Real Opportunity
[42:24] Career Advice for Your Younger Self

Connect with Chris Kessler on LinkedIn: https://www.linkedin.com/in/kesslerchris/
Learn more about Bold Penguin: https://www.boldpenguin.com/

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How Chris Kessler Built Multi-Million Dollar Insurance Partnerships

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