Kevin "KD" Dorsey is the Chief Revenue Officer at Finally, an all-in-one accounting and finance platform that recently raised $200 million in Series B funding. KD joins the show to discuss real-world examples of how he uses AI in his day-to-day: from developing internal AI agents to evaluating his team's calls.

New episodes of The Revenue Leadership Podcast with Kyle Norton drop every Wednesday.

Stay ahead with the latest industry developments, emerging go-to-market trends, and valuable benchmarking data. Subscribe to Topline Newsletter for expert insights from Asad Zaman every Thursday.

Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech. Catch full-length episodes every Sunday and bite-sized mini-episodes every Thursday, where our hosts sit down with top B2B tech leaders to unpack their biggest challenges—and how they overcame them.

Your’re invited! Join the free Topline Slack channel to connect with 600+ revenue leaders, share insights, and keep the conversation going beyond the podcast!

Key Moments:

00:00 Introduction and Podcast Overview

01:22 Guest Introduction: Kevin Dorsey

02:00 Diving into AI and GTM

02:51 AI in Sales: Practical Applications

06:36 Building AI Tools Internally

14:21 Call Scoring and AI Coaching

20:44 Issue Diagnosis with AI

33:08 Leveraging AI for Documentation and Training

35:36 Choosing Between Building and Buying AI Solutions

40:28 The Decision to Step Away from Founding

41:01 Challenges in Building AI Companies

42:08 The Future of SaaS Companies

43:29 Leveraging AI for Business Success

46:02 Learning and Adapting with AI

46:50 Exploring AI Tools and Resources

58:04 Evaluating AI Vendors

01:03:04 Personal Productivity with AI

01:13:42 Final Thoughts and Advice

Kyle is joined by Ryan Milligan, VP of Sales, Marketing, and RevOps at QuotaPath, to discuss sales commission planning. They dive into the essentials of creating effective comp plans that align with business goals, the importance of incremental incentives, and how to drive desirable sales behavior. Ryan shares insights from his diverse background and how QuotaPath navigates commission planning to ensure high performance and retention. The conversation also touches on key aspects such as measuring incrementally, balancing incentives, diagnosing ineffective plans, and trends in the current market.

New episodes of The Revenue Leadership Podcast with Kyle Norton drop every Wednesday.

Stay ahead with the latest industry developments, emerging go-to-market trends, and valuable benchmarking data. Subscribe to Topline Newsletter for expert insights from Asad Zaman every Thursday.

Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech. Catch full-length episodes every Sunday and bite-sized mini-episodes every Thursday, where our hosts sit down with top B2B tech leaders to unpack their biggest challenges—and how they overcame them.

Your’re invited! Join the free Topline Slack channel to connect with 600+ revenue leaders, share insights, and keep the conversation going beyond the podcast!

Key Moments:

[01:09] — Meet Ryan Milligan: From Data Science to Sales Leadership

[02:58] — The Path from Rev Ops to CRO

[05:40] — Sales Commission Strategy: Ownership and Design

[12:56] — Aligning Comp Plans with Business Metrics

[24:01] — Designing Effective Comp Plans: A Step-by-Step Guide

[33:47] — Testing and Measuring Incrementality in Comp Plans

[41:32] — Building Effective Quotas

[52:34] — Setting Realistic and Motivating Targets

[01:02:30] — Common Pitfalls in Commission Plans

[01:12:18] — Key Traits of Great Revenue Leaders

[01:18:38] — Final Thoughts and Takeaways

What does it take to go from zero to your first enterprise customer? For Cresta, it meant their CEO and CTO becoming interns at Intuit—and their engineering team living in an Airbnb next to the call center they were trying to disrupt.

In this episode, Kyle talks with Alex Cramer, CRO of Cresta, about the unglamorous grind of cold-starting in enterprise, why today’s deals demand more consensus (and skill) than ever, and how to scale a team when every deal feels like a bespoke knife fight.

Plus, Alex’s hardest-won lessons—from equity pitfalls to why endurance separates good CROs from great ones.

New episodes of The Revenue Leadership Podcast with Kyle Norton drop every Wednesday.

Want more from Topline?

Tune into the Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech. Catch full-length episodes every Sunday and bite-sized mini-episodes every Thursday, where our hosts sit down with top B2B tech leaders to unpack their biggest challenges—and how they overcame them. And don't forget to join the free Topline Slack channel to connect with 600+ revenue leaders, share insights, and keep the conversation going beyond the podcast!

Subscribe to the Topline Newsletter to get the latest industry developments and emerging go-to-market trends delivered to your inbox every Thursday.