SPOTLIGHT: Solving SaaS Pricing Challenges with Pricing I/O Founder Marcos Rivera | Marcos Rivera, Founder and CEO @ Pricing I/O

More marketing spend doesn't always mean more growth. And having the right people doesn't necessarily mean you have the right structure. As customer acquisition costs rise and traditional B2B channels become increasingly competitive, companies need to rethink how they approach performance marketing, demand generation, and team structure. John Short, CEO of Compound Growth Marketing, spent more than a decade building performance marketing teams at companies like Workable, Monster.com, and LogMeIn before launching his own agency eight years ago. Today, he helps high-growth B2B companies build more predictable and efficient growth engines. In this episode of Topline Spotlight, Sam Jacobs sits down with John to discuss the changing B2B marketing landscape, the opportunities beyond LinkedIn and Google, and the operational lessons he's learned while scaling his own business. What we get into: - Why B2B companies need to diversify beyond LinkedIn and Google - The growing opportunity in CTV, Meta, Reddit, and other channels - How to find more efficient customer acquisition opportunities - Why specialization gives marketing agencies a competitive advantage - Why roles and responsibilities matter more than traditional org charts - How marketing teams can connect individual KPIs to company-wide growth Chapters: 00:45 Intro to John Short and Compound Growth Marketing 03:10 The Power of Specialization in B2B Marketing 04:27 Why B2B Companies Need to Look Beyond LinkedIn 06:19 The Opportunity in Connected TV Advertising 08:15 Customer Acquisition Costs and Finding Efficiency 09:20 Lessons From Building a Marketing Agency 10:57 Why Roles and Responsibilities Beat Traditional Org Charts 15:06 Connecting Marketing KPIs to Business Growth 20:02 The Books and Ideas That Influenced John 21:00 Where to Find John Short Try Compound Growth Marketing: compoundgrowthmarketing.com

Before today's conversation, Sam, AJ and Asad share a few words in memory of Adam Robinson. Rajeev Dham, Managing Director at Sapphire Ventures (a $10 billion venture firm), joins Sam Jacobs, AJ Bruno, and Asad Zaman to make sense of the recent tech selloff and what it means for AI investing. Topics include why Rajeev sees a "duration mismatch" as a core challenge, how the funding bar has changed after months of $50 to $100 million decisions made in days, and why AI application companies are growing from $15 to $100 million in revenue even as steady-state gross margins may settle closer to 30%. Plus, advice for pre-AI SaaS companies, why private equity is still frozen, a data company that went from zero to a $900 million run rate, whether the models will eat the harness, what the Anthropic IPO means for everyone else, and whether go-to-market AI can ever be more than a spam cannon. Key Takeaways: - The selloff is about timing, not the technology. The AI buildout is expensive, and Wall Street now wants to see it in S&P 500 earnings, not just in Anthropic's run rate. "I'm a believer. I think there's just a duration mismatch," said Rajeev, who compares it to Amazon's AWS buildout rather than the dot-com crash: "I think it could be a 6-month, 9-month period… when this mismatch needs to be reconciled." - AI margins may never look like SaaS, and that can be fine. "I don't know if we're going to have the 78% margin businesses. It could very well be you have a 30% gross margin business," said Rajeev. What matters is gross profit dollars: "if you could charge 30 to 40% of $10,000 per person per year versus $1,000 versus 80% of $1,000, your gross profit dollars are a lot bigger." His bet: "I think ASPs will grow by 10x." - When everything grows fast, growth stops being the signal. "I don't even look at growth rates," said Rajeev. The founder used to be maybe a 30 to 50% weight in a growth-stage decision; "Now it's an 80, 90% weight, even at sometimes a billion of run rate." He looks for founders who rebuilt their product "after the Opus 4.5 moment in December" to keep winning share. - For pre-AI SaaS companies, the advice is to burn the boats. Rajeev told one founder running a cash flow breakeven $300 million business that "whether you grow 24% or 18%, it doesn't matter," and to "hire a COO, a private equity-like COO just to run that business" while the founder builds the AI products and eventually merges the two. Connect with the Hosts & Guests: Host: Sam Jacobs, CEO at Pavilion - https://www.linkedin.com/in/samfjacobs/ Host: AJ Bruno, CEO at QuotaPath - https://www.linkedin.com/in/ajbruno3/ Host: Asad Zaman, CEO at STA - https://www.linkedin.com/in/azaman1/ Guest: Rajeev Dham, Managing Director at Sapphire Ventures - https://www.linkedin.com/in/rajeev-dham-79332812/ Topline is more than a podcast: Subscribe to Topline Newsletter: https://toplinemedia.substack.com/ Check us out on YouTube for the #1 video podcast for founders, operators, and investors in B2B tech: https://www.youtube.com/@TOPLINE-Media Join the free Topline Slack channel to connect with 600+ revenue leaders to keep the conversation going beyond the podcast: https://www.joinpavilion.com/topline-slack Chapters: 00:00 Introducing Rajeev Dham 01:04 In memory of Adam Robinson 05:51 The Great Tech Selloff 10:35 How the Funding Bar Has Changed 12:46 Why AI Apps Grow So Fast 15:47 The 30% Gross Margin Future 21:28 When Does the AI Land Grab End? 24:38 Advice for Pre-AI SaaS Companies 26:53 Why Private Equity Is Still Frozen 35:11 What Gets a VC Excited Now 39:12 The Unfundable $9M to $38M Company 45:17 Founders Who Pivot at Warp Speed 49:43 Will the Models Eat the Harness? 57:50 Anthropic and the New IPO Bar 59:44 Is Go-to-Market AI a Spam Cannon? Sources & Attribution: Clip: https://youtu.be/TNq79c8QNlg Clip: https://youtu.be/lgMTA5GU7TE Article: https://www.axios.com/2026/10/26/anthropic-ipo

AI has transformed software engineering. It's changing nearly every knowledge-based profession. So why hasn't sales changed at the same pace? Dan Lee, Co-Founder and CEO of Nooks, is building what he believes will power the next generation of go-to-market teams: AI agents and revenue infrastructure that execute across the entire revenue lifecycle. In this episode of Topline Spotlight, Sam Jacobs sits down with Dan to unpack how Nooks evolved from a virtual collaboration platform into an AI-powered revenue platform and why the future of sales will look fundamentally different. What we get into: - Why sales is the next profession to be transformed by AI - How AI is changing software development and product velocity - Why sales reps need to become revenue AI consultants - Serving demand vs. generating demand - What AI agents can automate—and where humans still matter - Why the future belongs to highly consultative, 10X sales reps Chapters: 00:36 Intro to Dan Lee and Nooks 01:23 Why Sales Is the Next Job AI Will Transform 03:01 The Evolution of Nooks 05:55 The Future of Software: The Barbell Effect 08:01 Why Customer Outcomes Matter 10:22 How AI Is Changing Software Engineering 12:08 Retraining Sales Teams for the AI Era 13:22 Serving Demand vs. Generating Demand 14:36 The Future of Human Salespeople vs. AI Agents 17:01 How to Be the Right CEO for the Moment 19:06 Building Proactive AI Agents for Sales 19:46 Where to Find Nooks Try Nooks: nooks.ai

Geoffrey Moore, author of Crossing the Chasm (over 1 million copies sold) and Zone to Win, and an advisor to the CEOs of Microsoft, Salesforce, and Cisco, joins Sam Jacobs, AJ Bruno, and Asad Zaman for a first appearance on Topline. Topics include whether agentic AI has crossed the chasm, why there's "zero chance" the AI bubble doesn't pop (and who will make it out the other side!), how startups win in a downturn, and how the Zone to Win framework is useful to help move AI pilots out of incubation and into the core business. Plus, a closer look at the SaaS-pocalypse and Salesforce's platform play, trapped value as the only durable moat, the hierarchy of powers behind today's valuations, whether AI has to eat the labor budget to pay off, and whether Geoffrey would buy the Anthropic IPO at a $2 trillion valuation. Key Takeaways: - The AI bubble will pop, but the category leaders will be fine. "There is zero chance that this bubble doesn't pop. We're so far over our skis in terms of valuations, it's crazy," said Geoffrey, pointing to circular financing that echoes the dot-com era. The survivors are the number 1 and number 2 players: "The winners are actually gonna win… But 3, 4, 5, 6, 7, 8, 9, 10? No." - Most AI initiatives are stuck in the incubation zone. "People were piloting like crazy and having great success" said of the last two years of enterprise AI pilots... but then they got stuck. The Zone to Win fix is to make the productivity zone customer zero, re-engineering internal shared services first, then bring the new technology to the sales team use case by use case rather than all at once. - Where are moats today? Geoffrey points to trapped value as one type of moat. Trapped value analysis is a method to continually discover the new ways you can be irreplaceable to your customers, and stay ahead of the market. - The ROI from AI won't come mainly from cutting headcount. "I think they're coming from quality improvement and latency reduction, not from labor reduction," said Geoffrey. For the next decade, probabilistic agents will sit in front of deterministic systems of record with a human checking in between, because "AI can be accountable, but it cannot be responsible." Connect with the Hosts & Guests: Host: Sam Jacobs, CEO at Pavilion - https://www.linkedin.com/in/samfjacobs/ Host: AJ Bruno, CEO at QuotaPath - https://www.linkedin.com/in/ajbruno3/ Host: Asad Zaman, CEO at STA - https://www.linkedin.com/in/azaman1/ Guest: Geoffrey Moore, Board Member, Venture Partner, Author - https://www.linkedin.com/in/geoffreyamoore/ Topline is more than a podcast: Subscribe to Topline Newsletter: https://toplinemedia.substack.com/ Check us out on YouTube for the #1 video podcast for founders, operators, and investors in B2B tech: https://www.youtube.com/@TOPLINE-Media Join the free Topline Slack channel to connect with 600+ revenue leaders to keep the conversation going beyond the podcast: https://www.joinpavilion.com/topline-slack Chapters: 00:00 Introducing Geoffrey Moore 02:01 Has Agentic AI Crossed the Chasm? 03:59 Will the AI Bubble Pop? 08:59 Startups That Win in a Downturn 12:00 The Zone to Win Framework 17:51 Getting AI Pilots Out of Incubation 19:21 Is Every SaaS Company Under Threat? 21:35 Zone Offense vs. Zone Defense 25:12 Salesforce, Headless and Platforms 33:34 Trapped Value Is the Real Moat 43:00 The Hierarchy of Powers 49:14 Can OpenAI and Anthropic Stay on Top? 53:13 Will AI Eat the Labor Budget? 01:02:07 Speed of Adoption vs. Innovation 01:04:57 Bulls and Bears

Marcos Rivera, Founder and CEO of Pricing I/O, has grown his solo consultancy into a team of pricing experts serving B2B SaaS companies. But building a specialized business came with a major challenge: finding people who could do more than understand pricing—they needed to connect customer value, business strategy, and software. In this episode of Topline Spotlight, Marcos joins Sam Jacobs and Asad Zaman to explain how he rethought his hiring process, from defining what success looks like to using practical case studies and structured onboarding. He also shares his perspective on pricing strategy, customer retention, and why companies need to ensure their pricing keeps pace with the value they deliver. Marcos talks about: - Why pricing should be revisited as your product and customer experience evolve - How underpricing can influence customers' perceptions of quality - Why giving customers more features won't necessarily solve churn - How to evaluate candidates' problem-solving skills through structured case studies - Why a thoughtful onboarding plan can help new hires reach productivity faster - How trust shapes the way you serve clients and build a business Chapters 00:00 Topline Introduction 01:26 Introduction to Topline Spotlight 01:53 Meet Marcos Rivera, Founder and CEO of Pricing I/O 04:45 Common Misconceptions About Pricing 14:11 Solving a Critical Business Problem: Hiring the Right Talent 23:01 Reflections and Recommendations 25:02 Where to Find Marcos Rivera 25:39 Closing Remarks Try Pricing I/O: pricingio.com

John McMahon, a five-time public company CRO whose team at PTC created MEDDIC, joins Sam Jacobs, AJ Bruno, and Asad Zaman on building enterprise sales teams that last. Topics include the PTC lineage that has produced over 100 CROs, including OpenAI's Dali Rajic, why he hires on characteristics over resumes, whether a CRO who never carried a bag can lead, and how first-time CROs should work with their CEO. Plus, capped commissions at Anthropic, why AI makes lazy reps lazier, what conversational intelligence tools miss in deal qualification, and quick takes on Dali, Carlos at Harness, Dev Ittycheria, and Chris at Cognition. Key Takeaways: - Hire on characteristics, not resumes. John sorts candidates by skills, knowledge, experience and characteristics, and the last one is the hardest to teach: "I've always hired on characteristics. So I'll take someone with less experience but great characteristics." He looks for intelligence, drive, coachability, adaptability and integrity, because when a hire fails, "it's always a character flaw." - Don't take the CRO seat before you're ready. John once refused a promotion Dali pushed him for: "I told him, I'm not gonna do that to you because you're not ready… you're gonna fail. Your ego's not gonna be able to take it." For John, readiness comes down to whether you can recruit, coach, and lead people who actually want to follow you. - Talk to the CEO as a partner. Plenty of first-time CROs hold the C-level title without acting like the CEO's peer, and John coaches them to speak up: "You're the CRO. You have a fiduciary responsibility. Tell the CEO specifically what you think is wrong with the business." Blaming revenue problems on the product "is a non-starter," so come with a solution and talk like a business owner. - AI hasn't changed the methodology. John sees AI mostly as a research tool, and "it makes the really good sales reps better, and it makes the lazy sales reps lazier." He is just as blunt about conversational intelligence: "All they're doing is verifying that something was said, but there's no true qualification." Qualifying still means knowing whether you're talking to a champion, a coach, or the enemy. Connect with the Hosts & Guests: Host: Sam Jacobs, CEO at Pavilion - https://www.linkedin.com/in/samfjacobs/ Host: AJ Bruno, CEO at QuotaPath - https://www.linkedin.com/in/ajbruno3/ Host: Asad Zaman, CEO at STA - https://www.linkedin.com/in/azaman1/ Guest: John McMahon, 5x Public Company CRO - https://www.linkedin.com/in/johnmcmahon1/ Topline is more than a podcast: Subscribe to Topline Newsletter: https://toplinemedia.substack.com/ Check us out on YouTube for the #1 video podcast for founders, operators, and investors in B2B tech: https://www.youtube.com/@TOPLINE-Media Join the free Topline Slack channel to connect with 600+ revenue leaders to keep the conversation going beyond the podcast: https://www.joinpavilion.com/topline-slack Chapters: 00:00 Introducing John McMahon 02:18 The PTC Sales Leadership Tree 07:20 Hiring on Characteristics, Not Resumes 12:10 Should a CRO Have Carried a Bag? 16:50 Capped Commissions vs. Equity Upside 19:05 When Are You Ready to Be CRO? 22:56 How CROs Should Evaluate the CEO 34:52 AI and Sales Methodology 38:10 AI Call Tools Don't Qualify Deals 40:52 MEDDIC and Bigger Buying Groups 42:51 The Art and Science of Selling 48:47 Coaching Mark Roberge at HubSpot 59:31 Managing Heads Like a Bond Portfolio 01:03:42 Hiring Batting Average and Ramp Time 01:09:40 Rapid Fire: Dali, Carlos, Dev, Chris

Russ Mikowski, CEO of SurePeople and longtime revenue leader in tech, never planned to become a CEO. Recruited to lead a 10-year-old company into its next stage of growth, he faced technical debt, an unfocused ideal customer profile (ICP), and the challenge of turning the company's potential into a scalable business. In this episode of Topline Spotlight, Russ joins Sam Jacobs and AJ Bruno to discuss the decisions behind SurePeople's transformation, including rebuilding parts of its product, narrowing its target market, and resisting custom requests that could pull the business off course. Russ talks about: - How to identify and focus on the customers your product serves best - When rebuilding is a better option than refactoring - Why saying no to the wrong opportunities can protect long-term growth - How to keep a team aligned through organizational change - Why great leaders attract and retain talent by removing obstacles Chapters 00:00 Introduction to Topline Spotlight 01:54 Meet Russ Mikowski, CEO of SurePeople 03:00 SurePeople and the PRISM Assessment 05:51 Russ's Journey to CEO 08:55 Tackling Technical Debt and Rebuilding the Product 12:01 Narrowing the ICP and Finding Market Focus 14:50 Communicating Change and Aligning the Team 17:53 Leadership Lessons from a Mentor 24:00 Where to Find Russ Mikowski and SurePeople Try SurePeople: surepeople.com

Michael Walrath, CEO of Yext, is back on Topline to explain how Yext went from breakeven to 31% EBITDA margins on an 80% gross margin business, after halving its headcount and using its balance sheet to buy back roughly 35% of every share it ever issued. He joins Sam Jacobs, AJ Bruno, and Asad Zaman to argue that the old rules of business still apply: why VC math and founder math are different games, why employees lose the most when an overvalued startup like Airtable lands far below its peak valuation, and why this market feels like 2004. Plus, why Yext stopped doing earnings calls and replaced most stock comp with cash, why cutting the bottom half of a sales team can raise bookings, and how Yext is blurring the lines between AEs, account managers, CSMs and sales engineers. Key Takeaways: - Real profitability turns any growth into fuel. As Michael put it, "when you're actually profitable, like really profitable, then any growth becomes hugely accretive." With 80% gross margins and 31% EBITDA margins, "Every incremental dollar, I can spend 45 cents of it and not affect my margins in any way," so a left-for-dead software company can fund its own growth whatever the market says it's worth. - Chase growth only where it actually exists. "Nothing's more powerful than growth at creating value. Nothing is more destructive to value than chasing growth when the growth isn't there," said Michael. Airtable avoided the trap by leaving its cash on the balance sheet, while Yext once spent 74% of revenue on sales and marketing into a declining growth rate. - Cutting your weakest sellers can grow bookings. When 20% of reps make quota and the bottom half brings in 20% of bookings, the spreadsheet says cutting them costs you that 20%. "It's not even close to true. It's the opposite," said Michael (his numbers were illustrative). Yext now has fewer, better sellers, and is "effectively eliminating all distinction between go-to-market roles" in favor of teams that own books of customers. - Stock comp can turn your own employees into sellers of your stock. Most people sold their RSUs the day they vested, and every quarterly issuance meant the company sold shares to cover taxes too. "The last thing you need are more sellers of your stock every quarter," said Michael, so Yext now pays most employees more cash and points long-term believers to its employee stock purchase plan. Connect with the Hosts & Guests: Host: Sam Jacobs, CEO at Pavilion - https://www.linkedin.com/in/samfjacobs/ Host: AJ Bruno, CEO at QuotaPath - https://www.linkedin.com/in/ajbruno3/ Host: Asad Zaman, CEO at STA - https://www.linkedin.com/in/azaman1/ Guest: Michael Walrath, CEO at Yext - https://www.linkedin.com/in/michael-walrath-b63166/ Topline is more than a podcast: Subscribe to Topline Newsletter: https://toplinemedia.substack.com/ Check us out on YouTube for the #1 video podcast for founders, operators, and investors in B2B tech: https://www.youtube.com/@TOPLINE-Media Join the free Topline Slack channel to connect with 600+ revenue leaders to keep the conversation going beyond the podcast: https://www.joinpavilion.com/topline-slack Chapters: 00:00 Introducing Mike Walrath 03:13 VC Math vs Founder Math 04:46 Why Employees Lose the Most 09:05 Why This Market Feels Like 2004 12:04 31% EBITDA Makes Growth Accretive 16:12 Why Mike Is a Jobs Bull 19:48 What Airtable Got Right 28:19 Hot Startup Equity Is a Lottery 41:37 Yes, You Can Attract Talent 44:16 The Road to 30% EBITDA Margins 47:45 No Earnings Calls, No IR Team 51:52 Replacing Stock Comp With Cash 54:41 Cut the Bottom 50% of Sellers 57:19 Collapsing Go-to-Market Roles 01:01:22 From PE Guy Back to Growth

When Rick Smolen stepped into the CRO role at ShipHero, he took on responsibility for the entire customer lifecycle, from marketing and partnerships to customer success and support.  With a background primarily in sales, he had to learn how to lead functions outside his expertise without needing to have all the answers. In this episode, Rick joins Sam Jacobs to discuss the leadership lessons that came with that transition, from asking better questions to building trust with his team. He also explains how to learn from failure, navigate setbacks, and focus on what you can control as a leader. Rick talks about: - Why curiosity makes you a stronger cross-functional leader - How to challenge your team without micromanaging - Why experimentation requires accepting failure - What leaders should focus on when business results fall short - How to prioritize important work that rarely feels urgent Chapters 00:00 Introduction to Rick Smolen and ShipHero 01:10 What ShipHero Does 05:14 Rick's Career Journey 07:50 From Sales Leader to CRO: The Biggest Shift 10:49 Why Curiosity Makes You a Better Leader 16:23 Building a Leadership Team That Learns and Experiments 17:54 Evaluating Leadership Beyond Revenue 22:50 Rick's Book Recommendation: The 7 Habits of Highly Effective People 24:53 Where to Find Rick Smolen Try ShipHero: shiphero.com

Amy Konary, Founder & Chair of The Subscribed Institute at Zuora, coined the term SaaS as an IDC analyst around 2000, when her first forecast sized the whole market at $40 million. She joins Sam Jacobs, AJ Bruno, and Asad Zaman for the first in-person Topline to ask whether AI company economics are a house of cards, and whether circular financing and double counting are real problems. Plus, why POCs have stopped being a pipeline signal, experimental revenue versus true ARR, a new leverage index for sticky revenue, tokens versus credits, and how close outcome pricing can really get. Key Takeaways: - Treat POCs as a weak pipeline signal. As Amy put it, "it used to be that hands-on product was a really good signal from a pipeline perspective, but everyone's doing POCs just to kick the tires, but actually has no mandate to buy." Many are free, production-ready builds, and very few convert. - Usage alone won't tell you which revenue will last. Amy scores customers on scope and workflows, trust in the system's outputs, and how much of their own context they upload, because "you can have 2 customers with the exact same usage, but very different leverage." Low leverage means "That revenue is less durable." - Pure usage pricing can leave you as exposed as seats did. "If you're just tracking usage, and usage is highly experimental, and usage decreases over time as people optimize the tools, you're in the same vulnerable position you were in with seats," said Amy, who expects hybrid models with a smaller, trackable outcome piece. - Build for durability without rigidity. "So I think there's a difference between durability and rigidity," Amy said, and her metaphor is bamboo: one of the strongest construction materials, yet flexible, anchored by a clear focus on the customer's progress. Connect with the Hosts & Guests: Host: Sam Jacobs, CEO at Pavilion - https://www.linkedin.com/in/samfjacobs/ Host: AJ Bruno, CEO at QuotaPath - https://www.linkedin.com/in/ajbruno3/ Host: Asad Zaman, CEO at STA - https://www.linkedin.com/in/azaman1/ Guest: Amy Konary, Founder & Chair, The Subscribed Institute at Zuora - https://www.linkedin.com/in/amykonary/ Topline is more than a podcast: Subscribe to Topline Newsletter: https://toplinemedia.substack.com/ Check us out on YouTube for the #1 video podcast for founders, operators, and investors in B2B tech: https://www.youtube.com/@TOPLINE-Media Join the free Topline Slack channel to connect with 600+ revenue leaders to keep the conversation going beyond the podcast: https://www.joinpavilion.com/topline-slack Chapters: 00:00 Introducing Amy Konary 01:43 From ERP Sales to Industry Analyst 03:33 How Amy Konary Named SaaS 08:03 How Salesforce Taught the Street SaaS 10:31 Building Durable Companies for AI 11:52 Does Gross Margin Still Matter? 15:10 Who Is Checking AI Company Math? 17:03 Circular Financing and Double Counting 18:30 Is AI a House of Cards? 21:49 Durability Versus Rigidity 29:19 Be Careful About Your POCs 33:40 The Leverage Index for Sticky Revenue 39:12 SaaS Companies Moving Into Services 41:59 Tokens, Credits and Outcome Pricing 48:32 P(doom) and Raising Kids With AI