
Hosted by Pavilion · EN

Crescendo went from zero to $100M ARR in under two years. And today's guest, CRO Michelle Donnelly, is leading the revenue team. In a market where every AI competitor claims the exact same capabilities, Michelle argues that "trust me" sales tactics don't work anymore, and what her team is doing instead. She explains why she banned traditional sales demos in favor of building functional prototypes using prospect data (sometimes within 24 hours). Michelle also breaks down the transition to outcome-based pricing and how she she's working to compress new rep ramp time. All this, and a ton more! Thanks for tuning in. Catch new episodes every Wednesday. Subscribe to Topline Newsletter. Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech. Join the free Topline Slack channel to connect with 600+ revenue leaders to keep the conversation going beyond the podcast! Chapters: 01:39 Introduction to Michelle Donnelly and Crescendo 04:54 Leaving Salesforce for a risky hardware startup 11:25 Leveraging your network to spot market trends 16:18 Navigating pivots and finding product-market fit 19:44 Selling amidst the noise of the AI market 25:50 The challenge of simplifying complex messaging 30:45 Strategic priorities for scaling revenue teams 33:18 Replacing standard demos with "show me" solutions 35:50 Building trust by becoming your customer's customer 40:21 Balancing high-level strategy with frontline realities 43:02 Maintaining focus with the rule of three 45:09 Using internal AI to accelerate rep onboarding 48:23 Rapid fire: Traits of great revenue leade

In this episode of the Revenue Leadership Podcast, host Kyle Norton converses with Jordan Crawford, a GTM Data Scientist, to examine the transformative impact of AI in business. They delve into the DeepSeek AI model and its potential to revolutionize the industry while critiquing traditional sales models and emphasizing the importance of data-driven strategies. The discussion highlights how revenue leaders can integrate AI into their daily operations, utilizing tools like ChatGPT and Claude to boost productivity and learning. Jordan offers insights on crafting a strategic approach to AI implementation, underscoring the need for specialized roles and external expertise to guide organizational transformation. If you like what you heard from Kyle today, make sure to follow The Revenue Leadership Podcast by Pavilion for new episodes every Wednesday. Want more content from the Topline media family? Listen to Topline Podcast with Sam Jacobs, AJ Bruno, and Asad Zaman. Join the Topline Slack channel to engage with hosts, guests, and other listeners. Subscribe to Topline Newsletter written by Asad Zaman.

In this episode of The Revenue Leadership Podcast, host Kyle Norton sits down with Nate Follen, head of business systems operations at Ramp, to explore the company's rapid growth and the strategies behind building scalable systems. They discuss Ramp's use of AI tools like Momentum to boost sales and operations, as well as their strategy for building versus buying software solutions. The conversation also explores AI's transformative overall impact on sales, shifting reps toward more strategic, relationship-driven roles. If you like what you heard from Kyle today, make sure to follow The Revenue Leadership Podcast by Pavilion for new episodes every Wednesday. Want more content from the Topline media family? Listen to Topline Podcast with Sam Jacobs, AJ Bruno, and Asad Zaman. Join the Topline Slack channel to engage with hosts, guests, and other listeners. Subscribe to Topline Newsletter written by Asad Zaman.

In this episode of the Revenue Leadership Podcast, host Kyle Norton connects with Catie Ivey, the CRO at Walnut, to explore her journey as a first-time CRO. Catie shares her experiences in navigating the challenges of establishing foundational processes in a startup environment, emphasizing the importance of aligning teams and refining customer profiles. The discussion also covers competitive strategies in crowded markets, with Catie highlighting the need for clear positioning and transparency in sales methodologies. Together, they explore the qualities that distinguish great CROs and leaders, focusing on the ability to identify and nurture team members' strengths. If you like what you heard from Kyle today, make sure to follow The Revenue Leadership Podcast by Pavilion for new episodes every Wednesday. Want more content from the Topline media family? Listen to Topline Podcast with Sam Jacobs, AJ Bruno, and Asad Zaman. Join the Topline Slack channel to engage with hosts, guests, and other listeners. Subscribe to Topline Newsletter written by Asad Zaman.

In this episode of the Revenue Leadership Podcast, host Kyle Norton chats with Ron Gabrisko, the Chief Revenue Officer of Databricks, to explore the journey from startup to a multi-billion dollar powerhouse. Ron shares his insights on the pivotal strategies that fueled Databricks' growth, emphasizing the need for constant reinvention at every stage of development. The discussion covers the evolution of go-to-market strategies, the intricacies of pricing, and the importance of leadership development in scaling a business. *Please note that Databricks raised $10B in funding in December 2024, not $20B. If you like what you heard from Kyle today, make sure to follow The Revenue Leadership Podcast for new episodes every Wednesday. Want more content from the Topline media family? Listen to Topline Podcast with Sam Jacobs, AJ Bruno, and Asad Zaman. Join the Topline Slack channel to engage with hosts, guests, and other listeners. Subscribe to Topline Newsletter written by Asad Zaman.

In this episode of the Revenue Leadership Podcast, host Kyle Norton chats with JD Miller, a seasoned CRO with over 20 years of experience in private equity-backed software. JD shares his journey from pre-law to B2B tech sales and dives into the unique dynamics of PE, including fast-paced execution, the "rule of 40," and disciplined value creation. He also unveils his CRO Playbook, detailing strategies for building annual plans, aligning teams, and driving growth. Drawing on his time at Motus, JD highlights how to scale revenue teams, enter new markets, and adapt to disruption. Buy a copy of The CRO's Guide to Winning in Private Equity by JD Miller. If you like what you heard from Kyle today, make sure to follow The Revenue Leadership Podcast for new episodes every Wednesday. Calling all CEOs! Are you busy January 22-23? Join Pavilion at CEO Summit in vibrant New Orleans. Want more content from the Topline media family? Listen to Topline Podcast with Sam Jacobs, AJ Bruno, and Asad Zaman. Join the Topline Slack channel to engage with hosts, guests, and other listeners. Subscribe to Topline Newsletter written by Asad Zaman.

In this episode of the Revenue Leadership Podcast, host Kyle Norton sits down with Kyle Lacy, CMO of Jellyfish, to explore the complex relationship between sales and marketing and how to foster better alignment. They dive into the evolution of brand marketing as a key driver of growth, blending creative storytelling with measurable revenue impact. The conversation also touches on the new (old?) world of AI, with Lacy offering insights on leveraging technology while preserving the human touch that fuels authentic creativity. If you like what you heard from Kyle today, make sure to follow The Revenue Leadership Podcast for new episodes every Wednesday. Calling all CEOs! Are you busy January 22-23? Join Pavilion at CEO Summit in vibrant New Orleans. Want more content from the Topline media family? Listen to Topline Podcast with Sam Jacobs, AJ Bruno, and Asad Zaman. Join the Topline Slack channel to engage with hosts, guests, and other listeners. Subscribe to Topline Newsletter written by Asad Zaman.

In this week's episode of the Revenue Leadership Podcast, host Kyle Norton sits down with Scott Leese, a seasoned sales leader and multi-time founder, to unpack the intricate dynamics between VPs of Sales and Founders. Scott shares invaluable insights on aligning strategies, hiring the right talent, and fostering effective communication in high-stakes environments. The conversation delves into the critical importance of vetting opportunities thoroughly, both for VPs of Sales and founders, emphasizing the need for stage-appropriate hires and realistic goal-setting. Scott also offers practical advice on navigating challenging conversations and maintaining alignment throughout the leadership journey. If you like what you heard from Kyle today, make sure to follow The Revenue Leadership Podcast for new episodes every Wednesday. Want more content from the Topline media family? Listen to Topline Podcast with Sam Jacobs, AJ Bruno, and Asad Zaman. Join the Topline Slack channel to engage with hosts, guests, and other listeners. Subscribe to Topline Newsletter written by Asad Zaman.

In this episode of the Revenue Leadership Podcast, host Kyle Norton engages with Eric Gilpin, CRO of G2, to explore the intricacies of strategic planning in revenue leadership. Eric delves into the transition from sales leader to revenue executive, emphasizing the importance of aligning organizational goals with a clear mission. The discussion highlights G2's strategic approach to refining their Ideal Customer Profile, focusing on how to prioritize resources effectively. Eric also shares insights on the annual planning process, underscoring the need for adaptability and contingency strategies to navigate market changes. If you like what you heard from Kyle today, follow The Revenue Leadership Podcast for new episodes every Wednesday. Want more content from the Topline media family? Listen to Topline Podcast with Sam Jacobs, AJ Bruno, and Asad Zaman. Join the Topline Slack channel to engage with hosts, guests, and other listeners. Subscribe to Topline Newsletter written by Asad Zaman.

In this episode of the Revenue Leadership Podcast, host Kyle Norton sits down with Mark Kosoglow, co-founder & CEO of Operator.ai, to unpack the art of building a repeatable sales motion. Mark takes us through his journey—from selling shoes in a mall to leading high-performing sales teams at Outreach and Catalyst. Along the way, he highlights the critical role of process, measurement, and building the right team. The conversation dives into the challenges of creating consistent sales strategies, why proper instrumentation matters, and how enablement can accelerate onboarding for new hires. If you like what you heard from Kyle today, make sure to follow The Revenue Leadership Podcast for new episodes every Wednesday. Want more content from the Topline media family? Listen to Topline Podcast with Sam Jacobs, AJ Bruno, and Asad Zaman. Join the Topline Slack channel to engage with hosts, guests, and other listeners. Subscribe to Topline Newsletter written by Asad Zaman.