Topline

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