13 Jobs - The Chief Revenue Podcast (Formerly Rev-Up Sales)

Drew Leahy has seen sales from every angle - dorm-room founder, venture capitalist, and now operator. He's Head of Sales at Klear, which finances aerospace and defense suppliers, he teaches Startup Sales at the University of Michigan's Center for Entrepreneurship, and he previously co-founded Hawke Ventures. His mantra: ideas are cheap, execution is gold.

Marcos Rivera is the founder and CEO of Pricing I/O and one of SaaS's most sought-after pricing minds - he's helped price over 400 SaaS products and coached more than 100 CEOs across a 20-year career. Before founding Pricing I/O, he was a best practice leader at Vista Equity Partners, and he's the author of Street Pricing: A Pricing Playlist for Hip Leaders in B2B SaaS as well as host of the Street Pricing podcast. In this episode, we dig into how to price your product - how to stop guessing, capture the value you actually create, and build a pricing model that fuels growth instead of fighting it.

Jeremey Donovan is the Executive Vice President of Sales + Customer Success at Insight Partners, one of the world's leading growth equity firms, where he partners with portfolio company leaders to scale commercial teams and build repeatable, data-driven revenue engines.

His career spans over 25 years and cuts across semiconductor engineering, product development, and sales and marketing leadership - giving him a genuinely rare vantage point on how to apply rigorous systems thinking to the messy, human world of sales. 

He's held senior roles at SalesLoft, CB Insights, GLG, Gartner, and the American Management Association, and brings both the operator's instinct and the engineer's precision to everything he touches. Jeremey is the author of five books, including the international bestseller How to Deliver a TED Talk and Predictable Prospecting - a title that tells you everything about how he thinks about go-to-market.

He's also an Adjunct Professor at NYU School of Professional Studies and the host of the Hey Salespeople podcast. He holds an MS in Data Science from the University of Virginia, an MBA from Chicago Booth, and a BS and MS in Electrical Engineering from Cornell.

In this episode, we dig into how revenue leaders should think about AI not as a collection of point solutions, but as a systems-level opportunity to redesign how selling actually works.

Jaimie Buss is a seasoned SaaS revenue leader with 20+ years of experience scaling go-to-market teams. She currently serves as Chief Commercial Officer at Deputy, where she leads Global Sales, Marketing, Partnerships, Support, and Customer Success. Before Deputy, she was CRO at Articulate and held senior sales leadership roles at Zendesk and Cisco Meraki, as well as serving as a Partner at Andreessen Horowitz. At Zendesk, she played an instrumental role in the company's growth from $300M to $1.3B in ARR and doubled the sales team to over 250 people. She's known for her authentic leadership style, talent development, and building collaborative environments that drive revenue growth

Lori Richardson is a longtime B2B sales strategist, author, and speaker, best known for helping companies build stronger sales teams and for championing women in sales leadership. She spent over two decades in tech sales before founding Score More Sales, a consultancy that works with leaders in SaaS, tech, telecom, manufacturing, distribution, financial services and professional services to solve sales problems and grow revenue. Lori Richardson She is also the founder and president of Women Sales Pros, a network and advisory group focused on increasing the number of women in B2B sales and sales leadership roles. WOMEN Sales Pros Beyond consulting, Lori coaches at Harvard Business School, runs the popular podcast “Conversations with Women in Sales,” and is recognized widely as a top sales influencer and #womeninsales advocate.

Jeff Perry is the Chief Revenue Officer at Carta, where he has dramatically scaled the revenue team. Responsible for all Carta core software revenue, Jeff is also accountable for creating synergy across all go-to-market functions and working with Carta’s Product and Engineering teams to deliver a great customer experience. Prior to joining Carta, Jeff grew the SMB sales organization, including New Business and Upsell motions at DocuSign, along with several vertical teams.Before that, Jeff spent 13 years at Oracle where he ultimately served as Vice President of Sales. Jeff holds a Bachelor of Science in Political Science from Santa Clara University.

Adam O’Connor is the Chief Commercial Officer at Gear Inc, where he leads global sales strategy, drives revenue growth, and builds strategic partnerships across North America, Europe, and Asia-Pacific. With over a decade of experience in international business development and offshoring, Adam has scaled operations and optimized customer engagement across sectors like tech, finance, social media, and healthcare. Previously CRO and Chief Sales & Marketing Officer at Cloudstaff, Adam brings deep expertise in BPO, content moderation, and trust & safety. A regular voice in the outsourcing community, he’s been featured on the Outsourcing Fit podcast, sharing insights on leveraging global talent and navigating the complexities of digital operations.

Casey Jacox is a nationally respected sales and leadership coach who helps individuals and companies unlock the power of humility, vulnerability, and curiosity to build stronger relationships and drive sustainable growth. With over 25 years of business experience—including an extraordinary run as the #1 sales producer at a publicly traded company for ten consecutive years—Casey now coaches sales teams and leaders on how to lead with authenticity and exceed revenue goals without ego. He’s the author of the acclaimed book "Win The Relationship, Not The Deal", a practical guide for sales and business professionals focused on long-term success. Casey is also the host of The QB Dad Cast, a podcast that blends leadership and fatherhood, helping men show up better at home and in life. A former college quarterback at Central Washington University, Casey brings his competitive drive, humor, and heart to everything he does—whether it’s coaching, speaking, podcasting, or parenting. He’s a passionate advocate of the TED-based question framework (Tell me, Explain, Describe), and an unapologetic fan of Ted Lasso and Hoosiers. When he’s not coaching or podcasting, you’ll likely find Casey golfing, quoting 80s movies, or spending quality time with his family. Learn more at caseyjacox.com.

​Elliott Boll is a seasoned sales professional currently contributing to Closers.io, a company renowned for delivering world-class sales results and scaling strategies. He holds a degree from Imperial College London and is based in the United Kingdom. ​

Throughout his career, Elliott has demonstrated a deep understanding of sales dynamics and leadership. His insights into generational differences in sales leadership and the impact of fear on potential have been well-received within the professional community.

Elliott's commitment to continuous improvement and his ability to adapt to evolving sales landscapes make him a valuable asset to any organization. His recent transition to Closers.io underscores his dedication to empowering revenue leaders and maximizing value in the sales domain

Brent is a seasoned sales leader and advisor with a proven track record of driving revenue growth and scaling high-performing teams in the SaaS industry. With over 26 years of experience in enterprise software sales and management, Brent specializes in implementing data-driven strategies to enhance sales productivity at both individual and organizational levels. In FY23, Brent spearheaded a 96% year-over-year increase in productivity per Account Executive, showcasing his ability to optimize sales performance. He successfully scaled international SMB and Commercial sales teams from 5 to 52 Account Executives, demonstrating his expertise in team expansion and operational efficiency. His leadership played a critical role in growing ARR from $2M to $70M between 2015 and 2021, ultimately contributing to a successful IPO in 2016. Beyond his leadership roles, Brent is also a thought leader in sales innovation. He co-authored Sales 2.0: Improve Business Results Using Innovative Sales Practices and Technology with industry authority Anneke Seley. Published by John Wiley & Sons, the book reflects his commitment to advancing the sales profession through technology-driven methodologies and best practices. Brent continues to help high-growth SaaS companies scale effectively, leveraging his deep expertise in sales strategy, process optimization, and team development.