Building AI-Powered Sales Teams with Finally's CRO Kevin "KD" Dorsey
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 Overview01:22 Guest Introduction: Kevin Dorsey02:00 Diving into AI and GTM02:51 AI in Sales: Practical Applications06:36 Building AI Tools Internally14:21 Call Scoring and AI Coaching20:44 Issue Diagnosis with AI33:08 Leveraging AI for Documentation and Training35:36 Choosing Between Building and Buying AI Solutions40:28 The Decision to Step Away from Founding41:01 Challenges in Building AI Companies42:08 The Future of SaaS Companies43:29 Leveraging AI for Business Success46:02 Learning and Adapting with AI46:50 Exploring AI Tools and Resources58:04 Evaluating AI Vendors01:03:04 Personal Productivity with AI01:13:42 Final Thoughts and Advice
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1:18:50
Mastering Sales Commission Plans with QuotaPath's Ryan Milligan
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
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1:19:17
Interns to Enterprise: How Cresta’s CRO Built a Category Leader
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.
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1:18:17
How Matt Braley Built a Multi-Million Dollar Alliance Ecosystem at InvoiceCloud
Matt Braley joined InvoiceCloud as the third AE, rose to CRO, and led the company from early growth through a successful IPO, and ultimately a $4B acquisition by Vista Equity Partners. In this episode, Matt reveals how he grew their alliance ecosystem from 15 to 50 partners—ultimately generating over half of the company's revenue. You'll discover the VECTOR framework he developed for qualifying partnerships, avoiding "paper partnerships," and creating true strategic alignment.Whether you're considering technical alliances or wondering if partnerships are right for your business model, Matt provides actionable insights on when, why, and how to build alliances that deliver real revenue impact.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.
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1:19:28
Signals That Separate Great Companies from Risky Bets with Neal Patel, CRO of Crunchbase
What should CROs really be looking for when evaluating their next move? In this episode, Kyle sits down with Neal Patel, CRO at Crunchbase, to unpack how revenue leaders can vet companies like investors—by looking past vanity metrics and digging into signals that actually matter. They cover how to evaluate long-term viability, the importance of alignment with executive peers, and why being asked to "just run your old playbook" is a red flag.The conversation also dives deep into how AI is disrupting traditional go-to-market models, how Crunchbase is using predictive data to reshape its strategy, and why the GTM stack of the future might be smaller—and smarter.Thanks for tuning in! Want more content from Pavilion?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 chapters:(00:00) - Introduction to Neal Patel and Crunchbase(02:28) - State of the Market and AI's Impact(11:01) - Navigating Macro Conditions as a CRO(14:26) - Crunchbase's Shift Towards Predictive Analytics(23:27) - AI's Transformative Role in Go-to-Market Strategies(30:12) - Future of GTM: Embracing AI and Relationship Building(36:18) - The Importance of Team Innovation(41:55) - Navigating Company Selection as a CRO(46:05) - Building Relationships in Leadership(52:15) - Evaluating Market Potential and Company Goals(57:05) - Understanding AI's Impact on Business Strategy(01:01:00) - Red Flags in Company Selection(01:03:51) - Key Traits of Successful CROs
About The Revenue Leadership Podcast with Kyle Norton
The Revenue Leadership Podcast with Kyle Norton is a new show from Topline that dives deep into how to succeed as a revenue leader. Kyle Norton, CRO of Owner.com, will host real revenue operators and share framework and tactics you can apply today. No fluff, no sales pitches, and no platitudes.
This podcast is built for Founders, CRO’s, Directors and VP’s of Sales (and people who aspire for those roles) who want to level up their craft and grow revenue faster.
Listen to The Revenue Leadership Podcast with Kyle Norton, The Happy Heat Pump Podcast and many other podcasts from around the world with the radio.net app
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