Topline

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

Sam Slevin, Global SVP of Customer Success at AlphaSense, joins Sam Jacobs, AJ Bruno, and Asad Zaman on the AI-era customer success playbook. Topics include why service is the differentiator over the next 2 to 3 years, the case for customer success owning a revenue number from day one, the gap between finance's productivity targets and real-life capacity. Plus, the origins of customer success, why consumption-based pricing can quickly become a trap, and a bull-versus-bear debate on whether HubSpot can get back to a $20 billion market cap. In short... big episode!
Key Takeaways:
- After 17 years building customer success teams, Sam Slevin doesn't entertain the "should CS own a number" debate. As Sam Slevin, Global SVP of Customer Success at AlphaSense, put it: "in my 17 years of, of customer success and leadership within customer success, that has never actually been a debate for, for me. I, I would never take a role that doesn't have revenue focused and like impact owning a number, calling your forecast from day one." His standing practice when he joins a new company: build a top-down and bottoms-up forecast on day one and validate it the same way sales does.
- Slevin's central thesis is that AI raises the floor on automation while service becomes the upside lever for the next 2 to 3 years. As Slevin put it: "I don't think there could be a more exciting time to be in customer success where service feels like it could be the major differentiator over the next 2 to 3 years." The CS team that listens carefully, builds deep relationships, and meets customers where they are wins the renewal and the expansion.
- The hardest tension in CS productivity is the gap between what finance models demand and what individual accounts actually support. As Slevin put it on his approach: "I definitely want to increase productivity in ARR per AM. What's interesting is I feel like there's a finance model and then there's a real life model… finance will say we need $15 million per AM." The leader's job, Slevin argues, is to find the 10% operational drag (AM-to-AE handoffs, billing friction, segmentation gaps) and remove it to close the gap.
- On HubSpot's path back to $20 billion, AJ Bruno takes the bullish side based on customer behavior signals. As AJ Bruno, CEO at QuotaPath, put it: "And the fact that they've gone horizontal, um, now I know that there are like 70% of their customers are still looking for answers for HubSpot of what AI needs to look like, and they haven't let the opportunity yet pass them by, but it's getting shaky right now." Sam Jacobs took the bearish side, citing structural challenges and faster-moving AI-first competitors.
 
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: Sam Slevin, Global SVP Customer Success at AlphaSense - https://www.linkedin.com/in/sam-slevin-9b2ba21b/
 
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 Sam Slevin
03:13 Customer Success in the AI Era
04:28 Should CS Own a Number?
07:43 Gross Retention vs. Growth
11:02 The Number-Owner Premium
14:37 Service as the AI-Era Moat
22:19 Productivity Per Person
26:34 Vendor Spend and AI Voice Modes
35:12 Reimagining GTM Roles
38:51 Quiz Pro Quo
45:38 Seat to Usage-Based Pricing
50:12 Pricing AI Like a Meter
55:43 CSM vs Salesperson Comp Gap
58:43 Bulls and Bears

Ryan Burke, VP of Worldwide Sales at Crogl, joins Sam Jacobs, AJ Bruno, and Asad Zaman on the new economics of enterprise cyber risk. Topics include Anthropic's Mythos model, AI for the security operations center, why vibe-coded apps are far more likely to have security issues, why Claude Design tanked Figma's stock, and what the Elon Musk versus OpenAI lawsuit signals for AI governance.
Key takeaways:
AI has crashed the cost of running sophisticated attacks, putting nation-state-grade tooling in the hands of low-skill operators. As Ryan Burke, VP of Worldwide Sales at Crogl, put it on Anthropic's Mythos model: "Mythos has lowered the cost to like the dollar menu equivalent of...running an attack...so more people can do it." Enterprises are staring down a multi-year patching backlog that runs from now until the end of time.
Non-technical teams in finance, ops, and HR are shipping internal tools using Replit and Claude, and almost none of them are securing what they build. Ryan Burke flagged the research: "vibe-coded software is almost 3 times as likely to have security issues." When the employee who built the agent quits, the agent stays behind with no owner, no documentation, and quiet access to systems it never should have had in the first place.
For founders eyeing an exit, security has joined revenue, IP, and hitting your numbers as a non-negotiable diligence pillar. As Ryan Burke explained: "lack of security can kill an acquisition...a fourth pillar now is you're secure." Acquirers like JPMorgan Chase will not buy a fintech startup that turns into a vector for attackers to walk straight into their environment.
The market case for NRR-fortress legacy SaaS may be weaker than the last decade made it look. As Asad Zaman, CEO of Sales Talent Agency, argued: "there was a generation of software companies that had signs that they had really good customer relationships...but their customers felt more like prisoners." If AI makes switching cheap and a new generation of software actually delights users, the moats around system-of-record incumbents start to compress fast.
Connect with the hosts and guest: 
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: Ryan Burke, VP Worldwide Sales at Crogl - https://www.linkedin.com/in/ryan-burke-bos/
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 Ryan Burke
03:14 Anthropic Mythos and Cyber Risk
04:20 How Attackers Use AI at Scale 
07:00 Dollar Menu Attacks Explained 
10:41 AI for the Security Ops Center 
14:53 Why Claude Tanks Figma's Stock 
18:30 Sam's Advice on Falling Stocks 
20:50 Are Legacy SaaS Companies Back? 
24:04 The Vibe-Coding Risk Surface 
27:56 Quiz Pro: Cybersecurity Edition 
33:46 Replit Apps Inside Enterprises 
40:18 Security as the M&A Fourth Pillar 
44:17 Personal Data and Digital Legacy 
47:24 Bulls vs Bears: Elon vs OpenAI 
52:03 Will ServiceNow Hit $32B?

Stage 2 Capital General Partner Liz Christo joins the show to discuss the disconnect between venture expectations and reality in the software market. The conversation covers the hidden costs of the new build versus buy debate, the structural changes happening within modern sales organizations, and whether traditional B2B SaaS go-to-market strategies and moats still matter when AI coding tools make software replication cheaper than ever.
Key Takeaways:
-The shift toward building internal AI tools instead of buying SaaS products overlooks long-term technical debt, as Liz Christo points out that "there's like a huge amount of cost buried behind the scenes that we're not really talking about today because it's still like sexy and fun."
-Founders are artificially inflating their Total Addressable Market to meet new venture capital baseline expectations, with Liz Christo noting that "pitch decks read like really ridiculous right now where everybody wants to tell the story of like a $10 billion outcome because that's the new milestone that got set."
-Revenue Operations is becoming the most direct path to the Chief Revenue Officer seat in AI-first organizations, which Sam Jacobs explains is "because as we use fewer humans and more agents, the sort of the half technical, the semi-technical capabilities of most RevOps people will translate into orchestrating armies of agents."
-Delegating analysis and writing to AI risks destroying strategic judgment across go-to-market teams, a trend Liz Christo summarizes by stating, "I think we are producing an incredible amount of content that's not getting consumed... I just think we're like losing the ability to think and we're not teaching junior employees how to do it."
Connect with the Hosts & Guests:
Host: Sam Jacobs - https://www.linkedin.com/in/samfjacobs/ 
Host: AJ Bruno - https://www.linkedin.com/in/ajbruno3/ 
Host: Asad Zaman - https://www.linkedin.com/in/azaman1/ 
Guest: Liz Christo - https://www.linkedin.com/in/lizchristo/
 
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 Intro and Cold Open
02:41 The New Build vs Buy Debate
06:10 Engineers in Every Department
10:48 Pitch Decks and 10B Dollar TAMs
17:53 Venture Capital Funding Quiz
23:43 AI Memos and Critical Thinking
42:41 Software Moats and Switching Costs
47:46 Bulls vs Bears Segment
48:23 RevOps as a Path to CRO
51:25 The Future of SDR Managers
55:14 Is Clay Actually Undervalued
59:12 Odds of Hitting 50M ARR