AI is either a magic wand or a massive distraction. At Stripe, they’ve decided it’s the former and they have the data to prove it.

In this episode of The Emblazers Show, host Tim Riesterer sits down with Kevin Bognar, Head of Commercial & SMB Sales - Americas at Stripe. Kevin reveals how his team moved past the AI hype to build "AI Agents" that find ICP twins, successfully slashing their SMB sales cycle from 76 days down to just 13.

But high-velocity sales isn't just about the tech. Kevin shares his approachable yet data-driven philosophy on leadership, including the five core principles every aspiring CRO needs to know and the story of his 'Time to Shine' initiative, which is a masterclass in building an authentic culture in a high-pressure world.

Tune in to learn:

How Stripe uses AI for prospecting "twins" of their best customers
Why the best sales cultures sit exactly between high accountability and high fun
Kevin’s personal roadmap for navigating VC, PE, and Public leadership structures
Why meaningful, in-person connection still outperforms a "boiler room" mentality

Episode Highlights
(00:00) Introduction

(00:32) Meet Kevin Bognar, CRO at Stripe

(02:15) Kevin’s path from consulting to leading global revenue teams

(06:48) What younger sellers need from leaders today

(08:22) How Stripe powers internet commerce and digital payments

(10:47) Why AI is reshaping the CRO role

(12:09) Real examples of AI improving sales execution

(13:50) How Stripe reduced SMB sales cycles from 76 days to 13

(16:46) Why AI creates capacity, not just efficiency

(18:00) The five leadership principles Kevin uses to lead teams

(22:53) Why culture matters as much as accountability

(26:21) The “Time to Shine” leadership idea that built team connection

(29:25) Why in-person collaboration still matters in sales

(31:24) Building competitive teams without creating burnout

Links and Resources:

Connect with Abby Kerr: https://www.linkedin.com/in/abbycathkerr/
Connect with Tim Riesterer: https://www.linkedin.com/in/tim-riesterer/
Connect with Kevin Bognar: https://www.linkedin.com/in/kevinjbognar/

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Learn about Kevin Bognar

As the Head of Commercial & SMB Sales - Americas at Stripe, Kevin Bognar leads a high-growth sales organization at the heart of the internet’s financial infrastructure. His leadership journey spans over 20 years of experience in the technology sector, including an 18-year tenure at Microsoft where he navigated various leadership roles across public and private sectors. Kevin is a vocal advocate for the strategic integration of AI to expand sales capacity, but he remains deeply committed to "human-first" leadership—proving that even in high-velocity environments, authenticity and community are the primary drivers of sustainable growth.

Learn about Tim Riesterer

As Chief Strategy Officer at Corporate Visions and Chief Research Officer at Emblaze revenue leaders’ community, Tim Riesterer is a pioneering force in developing customer conversations that break through the status quo and drive measurable business results. His innovative approach helps companies craft differentiated messages and deploy them through powerful self-service and sales-directed tools that consistently outperform traditional content strategies. A recognized expert in value creation and capture, Tim enables organizations to transform their customer conversations through proven methodologies that elevate their market position and drive sustainable growth.

Learn about Abby Kerr

As Director of Content & Community at Emblaze, Abby Kerr designs content experiences that spark conversations and strengthen the connective tissue between B2B revenue leaders. With a background spanning brand voice strategy, enterprise B2B content, and education, she brings a sharp eye for nuance and a deep understanding of how people learn and grow. A champion of insight-driven storytelling and peer-to-peer learning, Abby helps make Emblaze a place where leaders don’t just consume content—they contribute to it. She’s also a warm, un-shy introvert who reads fiction, asks big questions, and drinks her coffee black.