Pavilion

In this episode, Kyle sits down with Mark Roberge, Co-founder of Stage 2 Capital and former CRO of HubSpot, for a deep dive into the evolving role of AI in shaping technology strategy. Mark reflects on his journey from operator to investor, sharing hard-earned lessons and offering a candid perspective on leadership — including why great leaders don't need to be the best at everything.  If you like what you heard from Kyle today, make sure to <a href= "https://www.joinpavilion.com/the-revenue-leadership-podcast">follow The Revenue Leadership Podcast</a> for new episodes every Wednesday. Want more content from the Topline media family? <a href= "https://www.joinpavilion.com/topline-podcast">Listen to Topline Podcast</a> with Sam Jacobs, AJ Bruno, and Asad Zaman. <a href= "https://www.joinpavilion.com/topline-slack">Join the Topline Slack channel</a> to engage with hosts, guests, and other listeners. <a href="https://www.joinpavilion.com/topline-newsletter">S</a><a href="https://www.joinpavilion.com/topline-newsletter">ubs</a><a href="https://www.joinpavilion.com/topline-newsletter">cribe to Topline Newsletter</a> written by Asad Zaman.

Mark Roberge on Redefining Sales Leadership in the AI Era

What does it take to go from zero to your first enterprise customer? For Cresta, it meant their CEO and CTO becoming&nbsp;interns&nbsp;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? <a href="https://www.joinpavilion.com/topline-podcast" rel="noopener noreferrer" target="_blank">Tune into the Topline Podcast</a>, 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 <a href="https://www.joinpavilion.com/topline-slack" rel="noopener noreferrer" target="_blank">join the free Topline Slack channel</a> to connect with 600+ revenue leaders, share insights, and keep the conversation going beyond the podcast! <a href="https://www.joinpavilion.com/topline-newsletter" rel="noopener noreferrer" target="_blank">Subscribe to the Topline Newsletter</a> to get the latest industry developments and emerging go-to-market trends delivered to your inbox every Thursday.

Sales executive for high growth technology companies 

Alex Cramer

CRO | Cresta

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.

Interns to Enterprise: How Cresta’s CRO Built a Category Leader

<a href="https://www.linkedin.com/in/matt-braley-3aa3301b/" rel="noopener noreferrer" target="_blank">Matt Braley</a> 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? <a href="https://www.joinpavilion.com/topline-podcast" rel="noopener noreferrer" target="_blank">Tune into the Topline Podcast</a>, 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 <a href="https://www.joinpavilion.com/topline-slack" rel="noopener noreferrer" target="_blank">join the free Topline Slack channel</a> to connect with 600+ revenue leaders, share insights, and keep the conversation going beyond the podcast! <a href="https://www.joinpavilion.com/topline-newsletter" rel="noopener noreferrer" target="_blank">Subscribe to the Topline Newsletter</a> to get the latest industry developments and emerging go-to-market trends delivered to your inbox every Thursday.

Rep to CRO, through IPO - Vista acquisition for $4B in 2024.

People, process, and innovation-focused leader with expertise in complex, B2B GTM environments. 

Experienced in establishing/growing/leading high-performing teams, co-creating with business partners, and working across all areas of a business. 

Strong belief in servant leadership and investing in talent development: great businesses are built with great people.

Held direct responsibility for sales, strategic alliances, sales engineering, SDRs, sales ops, sales enablement, GTM strategy / messaging, and new market expansion. Additional expertise in product marketing, M&A, pricing strategy, product and customer success.

Matt Braley

Enterprise SaaS Executive | Advisor

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.

How Matt Braley Built a Multi-Million Dollar Alliance Ecosystem at InvoiceCloud

How do you transition from product-led growth to sales-led growth without losing momentum? In this episode, Kyle Norton talks with Andrew Johnston, Head of Sales at Superhuman, about how the company is evolving its go-to-market strategy to win larger B2B deals. They discuss the key challenges of moving upmarket, the differences between PLG and SLG sales motions, and how Superhuman is leveraging data and AI to scale. Andrew also shares insights on building the right sales team, adapting the product for enterprise buyers, and what revenue leaders need to consider when layering in a sales motion. &nbsp; Thanks for tuning in! Want more content from Pavilion? &nbsp; New episodes of The Revenue Leadership Podcast with Kyle Norton drop every Wednesday. &nbsp; Stay ahead with the latest industry developments, emerging go-to-market trends, and valuable benchmarking data. <a href="https://www.joinpavilion.com/topline-newsletter" rel="noopener noreferrer" target="_blank">Subscribe to Topline Newsletter</a> for expert insights from Asad Zaman every Thursday. &nbsp; <a href="https://www.joinpavilion.com/topline-podcast" rel="noopener noreferrer" target="_blank">Tune into Topline Podcast</a>, 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. &nbsp; You're invited! <a href="https://www.joinpavilion.com/topline-slack" rel="noopener noreferrer" target="_blank">Join the free Topline Slack channel</a> to connect with 600+ revenue leaders, share insights, and keep the conversation going beyond the podcast! &nbsp; Key chapters: (00:00) - The Email Problem: A Universal Challenge (09:49) - Superhuman: Revolutionizing Email Productivity (19:47) - Transitioning from PLG to SLG: A New Sales Approach (30:04) - Building Blocks for Sales Success: Data and Team Dynamics (30:32) - Personalization in Sales Outreach (31:31) - Core Pillars of Sales Strategy (32:27) - Common Pitfalls in Sales-Led Growth (33:25) - Building a Sales Culture at Superhuman (37:17) - Leveraging AI in Sales Processes (42:43) - Skills for Sales Reps in the Age of AI (49:58) - Navigating AI-Generated Communication (56:39) - Lessons in Sales Leadership &nbsp;

Transitioning from Product-led to Sales-led Growth with Andrew Johnston of Superhuman

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. <a href="https://www.joinpavilion.com/topline-newsletter" rel="noopener noreferrer" target="_blank">Subscribe to Topline Newsletter</a> for expert insights from Asad Zaman every Thursday. <a href="https://www.joinpavilion.com/topline-podcast" rel="noopener noreferrer" target="_blank">Tune into Topline Podcast</a>, 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! <a href="https://www.joinpavilion.com/topline-slack" rel="noopener noreferrer" target="_blank">Join the free Topline Slack channel</a> 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

Neal Patel is the Chief Revenue Officer at Crunchbase, the leading platform for discovering business information and opportunities. With more than 25 years of experience in the tech industry, Neal has consistently driven progressive growth strategies, forged impactful partnerships, developed new revenue streams, and built high-performing teams.

Beyond his work at Crunchbase, Neal serves as an active board member, advisor, and investor in a number of high-growth startups, where he brings his deep expertise and extensive network to help emerging companies scale and succeed. Prior to joining Crunchbase, Neal held several key roles at Google. He played a pivotal role in building out Google Maps, led global strategic partnerships for Google Search, and helped bring Google Fiber to market in several of its early launch cities.

Neal Patel

CRO, 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.

Signals That Separate Great Companies from Risky Bets with Neal Patel, CRO of Crunchbase

What does it take to lead revenue in a private equity-backed company? In this episode, Kyle Norton talks with Vanessa Brangwyn, CRO at Motus, about the key differences between VC and PE environments, how PE firms drive efficiency and profitability, and what revenue leaders need to succeed. She also shares insights on integrating go-to-market strategies post-acquisition and managing a PE-backed board.   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. <a href="https://www.joinpavilion.com/topline-newsletter">Subscribe to Topline Newsletter</a> for expert insights from Asad Zaman every Thursday.   <a href= "https://www.joinpavilion.com/topline-podcast">Tune into Topline Podcast</a>, 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! <a href= "https://www.joinpavilion.com/topline-slack">Join the free Topline Slack channel</a> to connect with 600+ revenue leaders, share insights, and keep the conversation going beyond the podcast!   Key chapters: (00:00) - Introduction to Vanessa Brangwyn and Achievers' Journey (03:13) - Transitioning from VC to PE: The Achievers Experience (06:03) - Navigating Public Company Dynamics (08:56) - The Spin-Out: Achievers' New Chapter (12:06) - Exploring the Private Equity Landscape (14:56) - CRO Insights: PE vs. VC Dynamics (18:10) - Shared Learnings in Private Equity (20:46) - The Role of Structure in Team Dynamics (24:05) - Profitability vs. Growth: Understanding PE Goals (26:48) - Strategic Decision-Making in PE (29:55) - Efficiency Metrics in Private Equity (37:59) - Tactical Metrics for Sales Efficiency (40:52) - Understanding Board Engagement in PE vs VC (44:42) - Navigating Incentives and Decision-Making in Boards (47:06) - Leveraging Data for Effective Board Management (49:46) - Lessons from Private Equity for Venture-Backed CROs (51:10) - Strategic Rationale Behind Acquisitions (56:38) - Integrating Go-To-Market Strategies Post-Acquisition (01:01:11) - Customer Success Insights for CROs (01:05:42) - The Role of Authenticity in Leadership (01:10:21) - Advice for Emerging Leaders (01:12:20) - Lessons Learned from Leadership Experiences

What PE-Backed CROs Do Differently with Vanessa Brangwyn, CRO of Motus

Great revenue leaders aren’t just sales experts—they’re world-class problem solvers. But how do you separate signal from noise, diagnose the right issues, and make decisions that drive long-term success?    In this episode of The Revenue Leadership Podcast, Ashley Grech, CRO at Xero, joins Kyle to break down her framework for identifying, prioritizing, and solving complex revenue challenges. She shares how revenue leaders can balance instinct with data, avoid limiting beliefs that stall innovation, and use the driver tree framework to diagnose revenue bottlenecks. Ashley also explains why prioritization is the key to unlocking scale, how decision-making frameworks can accelerate growth, and what she’s learned from scaling global go-to-market strategies at Xero and Square.   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. <a href="https://www.joinpavilion.com/topline-newsletter">Subscribe to Topline Newsletter</a> for expert insights from Asad Zaman every Thursday.   <a href= "https://www.joinpavilion.com/topline-podcast">Tune into Topline Podcast</a>, 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! <a href= "https://www.joinpavilion.com/topline-slack">Join the free Topline Slack channel</a> to connect with 600+ revenue leaders, share insights, and keep the conversation going beyond the podcast!   Key chapters: (00:00) - Introduction to Problem Solving in Revenue Leadership (03:11) - The Importance of Problem Solving (06:03) - Frameworks for Problem Identification (08:56) - Utilizing Driver Trees for Diagnostics (11:55) - Data-Driven Decision Making (15:10) - Prioritization of Problems (17:57) - Balancing Urgency and Importance (20:54) - Sourcing Information from the Team (23:49) - Navigating Customer Feedback (27:08) - The Role of Data in Solutioning (30:06) - Finding the Best Solution (32:50) - Conclusion and Key Takeaways (44:18) - Principled Problem Solving (51:38) - Organizing Principles for Success (56:03) - Teaching and Scaling Principles (57:31) - Market Expansion Strategies (01:06:30) - Timing for International Expansion (01:09:17) - Channel Diversification Insights (01:12:43) - Overcoming Limiting Beliefs (01:17:14) - Qualities of a Great CRO

A Guide to High Stakes Decisions with Ashley Grech, CRO of Xero

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.

Pavilion

Mark Roberge on Redefining Sales Leadership in the AI Era

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