Topline

Gaurav Agarwal, COO of ClickUp, joins Sam Jacobs, AJ Bruno, and Asad Zaman after ClickUp, a company north of $300 million in ARR, parted ways with 22% of its workforce while rolling out pay packages up to $1 million a year for the individual contributors who stay. Gaurav walks through how a central Foundry team builds the tooling while each function's top performers automate their own jobs, why he wants his org to run like a pirate ship before a naval fleet, and how a two-person marketing team now ships 70 to 100 campaigns a week. Topics include which roles get eaten as AI collapses the org chart, why a great seller will never get the AI leverage a great engineer does, the case for working in public so AI has full context, and the mercenary-versus-missionary tension reshaping GTM talent. Plus, a Quiz Pro Quo on the SpaceX IPO and OpenAI's tender offer, and a Bulls and Bears debate on buying applications from foundation model companies versus the pure application layer.
Key Takeaways:
- Gaurav's mental model moved from treating AI as a sidekick to treating AI as the worker itself. As Gaurav Agarwal, COO of ClickUp, framed it: "AI will do the job, you like it or not... Humans will build AI to do the job and AI will do the job better than an 80th percentile human. And then our jobs become managers and trainers of AI."
- ClickUp is rebuilding its compensation bands around the people who create the most leverage with AI. As Gaurav Agarwal put it: "we want our top employees who are using AI to build digital workers... They should be paid higher," and he is blunt that the payoff is uneven by function: "I don't think sales gets the same leverage out of AI the way engineering does."
- Standing up an AI-native org early means choosing chaos before structure. Six months into ClickUp's push, Gaurav Agarwal described it plainly: "what I need right now is I need entropy... let's go be a little bit like a pirate ship... then we will bring in someone who can structure those pirates as a naval fleet."
- As AI collapses engineering, product, and design into overlapping roles, Gaurav Agarwal made the case for the multi-spike specialist over the generalist: "I think it's an E-shaped specialist... specialists who have more than 2 or 3 spikes eat up those spikes." His rule for who wins the consolidation: "the one with the best taste and the drive to work and learn and improve eats up adjacent departments."
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 Sales Talent Agency - https://www.linkedin.com/in/azaman1/
Guest: Gaurav Agarwal, COO at ClickUp - https://www.linkedin.com/in/gauravragarwal/
Topline is more than a YouTube Channel:
Subscribe to Topline Newsletter: https://toplinemedia.substack.com/
Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech: https://www.joinpavilion.com/topline-podcast
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 Gaurav Agarwal
03:55 ClickUp's 22% AI Layoff
05:30 AI Will Do the Job
07:42 Agentic Workflows at ClickUp
10:43 Pirate Ship or Naval Fleet
15:07 AI's Jagged Edges
17:13 Where Do You Start
24:19 AI Amplifies Talent Gaps
25:50 Should You Record Everything
40:28 Quiz Pro Quo
48:56 Paying for AI Leverage
53:27 Mercenary Versus Missionary
1:01:12 Bulls and Bears
1:09:59 Hiring Salesforce GTM Talent
1:12:25 Collapsing Roles and Specialists

Steve Cox, CEO of Clari + Salesloft, joins Sam Jacobs and Asad Zaman to argue that SaaS is far from dead. Steve took the CEO role in December 2025 to merge two of the biggest brands in go-to-market tech into what he calls the world's first predictive revenue system. Topics include the narrative war pushing investors to bet against SaaS-era companies, his one non-negotiable hiring trait, and how to merge two former rivals without one culture eating the other. Plus, a Quiz Pro Quo on go-to-market headcount across US tech and a Bulls and Bears round to close.
Key Takeaways:
- The AI-native startup boom is already hitting a retention wall, and Steve is watching it arrive deal by deal. As Steve Cox, CEO of Clari plus Salesloft, put it: "the amount of AI native companies that come across my desk now that... are up for sale, you know, they've run out of funding... they grew to 2, 3, 4 million of ARR pretty quickly and then struggled with retention." His read is that everyone knows AI exists now, so driving real adoption "has become more important than ever."
- Steve reframes the AI hype cycle as the next layer of infrastructure the industry will absorb, the way it absorbed cloud and big data. As he points out, "how many of us are gonna be talking about AI 3 years from now, 4 years from now?... when was the last time someone mentioned the cloud or Internet of Things or big data?" He expects AI to "layer into everything that we do," which is why he is embedding it into existing revenue workflows rather than fundamentally rebranding the company around it.
- The one non-negotiable trait Steve screens for in every executive hire is low ego, because he believes "high ego kills innovation and kills speed." He pairs that with blunt clarity for a merged workforce, telling his first all-hands "It's okay to not to want to be here," so the people who do not buy into the combined company can find the exit fast instead of dragging it down.
- Sam Jacobs, CEO of Pavilion, argues a profitable SaaS business with strong retention should ignore where the market trades today. "In the short term, markets are voting machines. In the long term, markets are weighing machines," he said, adding that if you are profitable with good retention, "your customers are voting for you on behalf of the market." The job, in his framing, is to be right long enough that you never have to tap the capital markets at the wrong moment.
Connect with the Hosts & Guests:
Host: Sam Jacobs, CEO at Pavilion - https://www.linkedin.com/in/samfjacobs/
Host: Asad Zaman, CEO at Sales Talent Agency - https://www.linkedin.com/in/azaman1/
Guest: Steve Cox, CEO at Clari + Salesloft - https://www.linkedin.com/in/steve-cox-588a2024/
Topline is more than a YouTube Channel:
Subscribe to Topline Newsletter: https://toplinemedia.substack.com/
Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech: https://www.joinpavilion.com/topline-podcast
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 Steve Cox
02:07 From Bananas to Enterprise Tech
03:05 Can SaaS Beat AI Startups?
04:33 AI Hype and the 95% Problem
06:57 The CEO Integration Playbook
10:27 Hiring for Low Ego
15:30 AI Startups Landing on His Desk
21:10 The SaaS vs AI Narrative War
26:23 Is Patience a Moat?
33:43 The Predictive Revenue System
38:21 Quiz Pro Quo
44:10 Merging Two Rivals
49:40 Culture After a Merger
59:03 Founder Mode vs Operators
1:02:48 Bulls and Bears

Michael Walrath, Chairman and CEO of Yext, returns to break down why the market has left a profitable, $400 million mid-cap public software company trading at one times revenue, even with over $100 million in EBITDA. He joins AJ Bruno and Asad Zaman to argue that the so-called SaaS apocalypse has almost no data behind it, that most AI layoffs are really a decade of go-to-market overhiring unwinding, and that boring compounders still out-return the hypergrowth darlings. Topics include how venture capital distorts software valuations, why no one is coming to help the 2021 unicorns stuck in broken cap tables, the great GTM despecialization, and the extend-and-pretend game inside venture funds. Plus, a Quiz Pro Quo on new business creation in the US and a Bulls and Bears debate on the future of mid-cap software and the stickiness of the AI platform.
Read Michael's essay, No One's Coming to Help You: https://x.com/michaelpwalrath/status/2051364181237010778
Key Takeaways:
- The market has left profitable mid-cap software for dead in favor of AI-native growth stories, and Michael Walrath, Chairman and CEO at Yext, leaned into how strange that is for a business that still prints cash. As he put it, "who's writing our obituary? It's the venture capitalists who are funding high-growth ARR companies," even as those same firms can't say what that ARR really means.
- The loudest voices setting software valuations are venture investors, and Michael argued their certainty is out of step with their actual hit rate. He called them "remarkably sure of themselves for guys whose whole business model is being right 5 to 10% of the time," noting that being right much more often than that would mean a VC is playing it too safe.
- Michael's answer to the hypergrowth-or-die mindset is that durable value comes from compounding cash flow, not chasing the next high-growth story. Pointing to a century of market history and operators like Berkshire Hathaway and Liberty Media, he said, "if you compound effectively, you will out-return these super high growth stories, unless those super high growth stories eventually become compounders."
- A lot of the layoffs being blamed on AI may be a decade of go-to-market overhiring finally unwinding. Michael framed the skeptic's question directly: "is it really AI? Or is this a choice that you're making because you overhired for 10 years." Asad Zaman, CEO at Sales Talent Agency, agreed, pointing out that even inside the most AI-native companies he visits, the fundamental way the business runs has not really changed.
Connect with the Hosts & Guests:
Host: AJ Bruno, CEO at QuotaPath - https://www.linkedin.com/in/ajbruno3/
Host: Asad Zaman, CEO at Sales Talent Agency - https://www.linkedin.com/in/azaman1/
Guest: Michael Walrath, Chairman & CEO at Yext - https://www.linkedin.com/in/michael-walrath-b63166/
Topline is more than a YouTube Channel:
Subscribe to Topline Newsletter: https://toplinemedia.substack.com/
Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech: https://www.joinpavilion.com/topline-podcast
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 Cold Open and Intro
02:33 Dead But We Just Don't Know It
08:47 Narrative Violations and Hype
11:00 VCs Right 10% Of The Time
14:22 Whose Case Are You Making?
19:20 Why Boring Compounders Win
24:55 The SaaS Apocalypse Myth
28:47 Are AI Layoffs Really AI?
36:16 The Great GTM Despecialization
39:55 Quiz Pro Quo
48:54 No One Is Coming To Help You
55:11 Extend And Pretend
1:01:41 Doubling Cash Flow In 5 Years
1:04:17 Bulls and Bears
1:07:30 What's The AI Moat?

Craig Rosenberg, Chief Platform Officer at Scale Venture Partners and co-founder of Topo, joins AJ Bruno and Asad Zaman to take on the question every founder is wrestling with: can you still build a world-class sales team when OpenAI and Anthropic are handing individual contributors $10 million equity packages? Craig argues you do not have to compete head-on, then lays out the hiring profile to chase instead, the quota-to-comp discipline that keeps packages sane, and why founder brand has become the most reliable pipeline play left as CAC keeps climbing. Topics include enterprise AE compensation, where private equity is still winning the GTM talent war, the Topo playbook for events and data-as-moat, and a bull-versus-bear debate on whether Gong goes public in the next 36 months. Plus, a Quiz Pro Quo on the real customer counts behind Salesforce, HubSpot, and ZoomInfo.
Key Takeaways:
- Rather than try to outbid OpenAI and Anthropic for talent, build your own farm system and develop people into the role. As Craig Rosenberg, Chief Platform Officer at Scale Venture Partners, put it: "You have to change your hiring profile to a unique profile that's unique to your business, but then you gotta coach 'em up."
- A resume from a hot AI lab is not a guarantee of success at your company. As Craig Rosenberg noted, "The person that is going to do well at Anthropic may not do well at Series B," so hire for the stage and the hunger rather than the logo.
- On compensation, Craig anchors the package to the role's real value: "you pay for what your wedge costs… if you feel like you have to pay $10 million, then you have a huge problem and you gotta go back to the drawing board." If the number runs away from you, the model is broken.
- With CAC climbing and most channels breaking down, founder brand has become the highest-leverage pipeline play. As Craig Rosenberg said, "The value of building a founder brand, when you look at the data, it's amazing," pointing to gains in both pipeline and deal size.
Connect with the Hosts & Guests:
Host: AJ Bruno, CEO at QuotaPath - https://www.linkedin.com/in/ajbruno3/
Host: Asad Zaman, CEO at Sales Talent Agency - https://www.linkedin.com/in/azaman1/
Guest: Craig Rosenberg, Chief Platform Officer at Scale Venture Partners - https://www.linkedin.com/in/craigrosenberg/
Topline is more than a YouTube Channel:
Subscribe to Topline Newsletter: https://toplinemedia.substack.com/
Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech: https://www.joinpavilion.com/topline-podcast
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 Craig Rosenberg
02:34 Can Anyone Out-Hire The AI Labs?
04:33 Why Craig Isn't Worried
06:52 Enterprise AE Comp Is Climbing
08:21 Founders Overpay For Star CROs
10:53 Why AI Reps Struggle At Series B
14:00 Hire The Slighted CRO
14:42 Quota-To-Comp And Attainment
18:45 Can AI Labs Sustain Growth?
22:20 Where PE Still Wins GTM Talent
27:17 Major Runs Reshape GTM
32:36 The Topo GTM Playbook
37:55 Quiz Pro Quo
47:45 Founder Brand And Rising CAC
58:42 Bulls and Bears

Kyle Lacy, CMO at Docebo (previously Lessonly, Seismic, Jellyfish), joins Sam Jacobs, AJ Bruno, and Asad Zaman to push back on AI-era "efficiency" gospel in marketing. Topics include why product marketing under a sales-led organization will die, and the one-page Wall Street Journal manifesto every CMO should make their CEO write. Plus, why OpenAI and Anthropic might be lost when it comes to POV...AND the $300M Windows 95 launch with Jennifer Aniston and a Polish submarine (obviously).
Key Takeaways:
- Build the company manifesto first. As Kyle Lacy, CMO at Docebo, framed it: "I frame it with my CEO as... you have a direction you want to take this company. I need a one-page document that reads like a manifesto that you would publish in the Wall Street Journal tomorrow as a full-page ad. And that's our guiding light." Messaging pillars, ICPs, and personas all flow from that single document; the framework can never be the source.
- Spend 80% on demand, then defend the other 20% for brand. Kyle's decade-long rule: "If you can figure out how to generate the demand you need off of 70 to 80% of your budget, then you can do whatever the hell you want, like golden llamas or hiring Jennifer Aniston to do your software training, whatever." Marketing leaders who haven't earned pipeline credibility lose the brand line item first when budget tightens.
- Don't fold marketing under the CRO. "Product marketing living under a sales-led organization, it will die, will die slowly because you can't get the right people in the role that want to do it," Kyle said. He distinguishes between marketers becoming CROs (good) and marketing being absorbed structurally into the revenue org (fatal) because the executive-level tension between brand and demand is what protects both.
- The Lessonly playbook wouldn't survive 2026. Kyle's honest reading: "Lessonly in this age would get eaten alive. Our software did not have a moat. It was really simple to use. You could probably vibe code it down a weekend." What does survive is the customer-first culture and the storytelling. At Docebo's recent Inspire user conference in Miami, customers organically produced more LinkedIn content about the event than the team had ever seen, with zero solicitation campaigns.
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 Sales Talent Agency - https://www.linkedin.com/in/azaman1/
Guest: Kyle Lacy, CMO at Docebo - https://www.linkedin.com/in/kylelacy/
Topline is more than a YouTube Channel:
Subscribe to Topline Newsletter: https://toplinemedia.substack.com/
Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech: https://www.joinpavilion.com/topline-podcast
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 Kyle Lacy
03:30 Is Brand Building Having Its Moment?
08:33 Word Is Brand: The 60/40 Mix
11:12 Surprise and Delight, Lessonly Lore
16:36 The Manifesto Framework
19:37 OpenAI and Anthropic Have No Manifesto
26:40 Brand at the Application Layer
27:35 Six Figures, No Anthropic Time
32:35 Quiz Pro Quo
39:27 SaaS-Era Marketers Under Attack
43:10 Should Marketing Report to a CRO?
54:42 Authenticity, Jellyfish, and Docebo
57:06 Bulls and Bears