Topline

The Unwritten Rules of CRO Survival | Rick Smolen, CRO @ ShipHero
Rick Smolen, CRO of ShipHero and sales advisor to Riverwood Capital's portfolio of more than 2 dozen enterprise software companies, joins Sam Jacobs, AJ Bruno, and Asad Zaman to argue that AI is leverage rather than a shortcut. Topics include why AI note-takers quietly degrade seller performance, why ShipHero has not raised a single quota despite real AI investment, and why the leading AI companies keep hiring classic enterprise CROs. Plus Rick's scorecard for judging revenue leadership beyond the number, an honest conversation about getting fired, and a bull case for HubSpot. In short... big episode!
Key Takeaways:
- AI widens the gap between the best and worst sellers instead of lifting everyone, and Rick Smolen, CRO at ShipHero, frames it in financial terms: "It's like debt... debt is leverage. It can make performance exceptionally good, or it can bankrupt you." His prediction is that the strongest performers get 10x better while the weakest become "unmistakable and hard to hide."
- Outsourcing note-taking to an AI tool costs sellers the exact signal that closes enterprise deals. As Rick put it: "the computer can't capture the tone, can't capture the nuance, can't capture the content." His warning to any rep who treats it as time saved: "when a seller is going to say, oh cool, I don't have to do note-taking anymore, like their performance is going to go backwards."
- The 3-to-5x rep productivity story does not survive contact with an enterprise sales cycle. Despite meaningful AI investment and measurable conversion-rate gains, Rick reports that at ShipHero "we have not raised quotas on anybody on the team," adding that "I don't believe that if I was to double somebody's quota that I give them any chance to be successful."
- The AI-native companies scaling fastest are staffing go-to-market with the most traditional enterprise leaders available. Asad Zaman, CEO at STA, walks through the CRO hires at OpenAI, Cursor, Factory, and Anthropic and lands on the pattern: "we're back to like, let's just hire John McMahon's disciples and let them run at the market."
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: Rick Smolen, CRO at ShipHero - https://www.linkedin.com/in/ricksmolen/
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 Rick Smolen
02:37 AI Is Not Good Or Bad
05:19 The AI Slop Email Mystery
08:25 AI Note-Takers And Lost Nuance
12:01 The Best Get Better, The Rest Worse
15:24 The Soft Part Of Enterprise Sales
18:24 Can Reps Be 5x More Productive?
23:09 Have Quotas Gone Up At ShipHero?
26:48 Why AI Firms Hire Classic CROs
30:48 What Is Driving Pipeline Now
49:37 Leadership In A Confused World
56:44 Should A CRO Jump Ship?
59:35 Have A Plan, Not Excuses
1:06:08 Bulls And Bears: HubSpot
1:09:32 Vibe-Coded Demos And FDE Teams

Mike Carpenter — CEO of Xfactor.io, former President of Global Sales at CrowdStrike — didn't win VP of the Year seven out of eight times by outworking everyone. He did it by finding cheat codes in the data everyone else was ignoring.
In this episode, he walks through the X-Factor methodology: how he staffed ops teams that were abnormally large by industry standards, how he cut rep ramp time from 18 months to 90 days by warming territories before a new hire ever showed up, and why he thinks most companies running AI on their CRM are getting confident, wrong answers and won't know it until the numbers drop.
Mike also shared:
- Why working harder isn't the same as finding an X-Factor
- How he used data to uncover the hidden patterns that drive revenue
- Why static operating plans break down as businesses scale
- How he cut sales ramp time by warming territories before reps entered them
- Why causal AI matters more than simply putting an LLM on your data
- What it takes to build AI that leaders can actually trust
Chapters
00:00 Intro
00:33 Meet Mike Carpenter and Xfactor
04:11 The "X-Factor" mindset that drove 25 years of sales success
08:18 Why working harder isn't a sustainable competitive advantage
10:56 The planning problem that inspired Xfactor
14:57 How AI uncovers hidden revenue opportunities
18:20 Why MQLs are the wrong metric to optimize
23:12 The biggest mistake companies make with AI today
25:52 Where to find Mike and Xfactor
Try Xfactor: xfactor.io/

Enterprise account executives are now signing for $200,000 salaries, $200,000 variable comp plans, and up to half a million dollars in equity at sign-on. Meanwhile, offer acceptance at the top AI companies sits at 45% and half of the 38,000 startup sales reps in San Francisco and New York have taken a new job in the last two years. In this episode, Sam Jacobs, AJ Bruno, and Asad Zaman go hosts-only on why the sales talent market broke, what QuotaPath's compensation data across more than 1,400 companies says about quota attainment splitting into a barbell, and why Paul Graham calling go-to-market bogus says more about Silicon Valley's blind spot than it does about sales. Plus, where young sellers still get their start, whether a CRO can be great without ever carrying a bag, why go-to-market cannot rescue a company that has lost product-market fit, and what HubSpot's 20% stock drop signals for every SaaS business trying to make the AI transition.
Key Takeaways:
- The AI buildout has drained the two talent pools it depends on, and compensation is repricing in real time. As Asad Zaman, CEO of STA, described the enterprise AE market: "Enterprise account executives now get paid $200,000 salaries, $200,000 variable comp plans, up to half a million dollars in equity at sign-on. That used to be $150,000 to $175,000 at the top end, just like a year and a bit ago." With 38,000 startup software sellers in San Francisco and New York and a quarter of them changing jobs in the last twelve months, the constraint on AI companies hitting escape velocity is no longer capital, it is people.
- The jobs data cuts against the automation narrative. Sam Jacobs, CEO of Pavilion, pointed to the Philippines outsourcing sector, 8% of that country's GDP, where employment in IT and business outsourcing is up 20% to 1.9 million workers and industry revenue is up 30% to $42 billion since the launch of ChatGPT: "I just think, you know, it's Jevons' paradox. It is what happens with every new piece of technology. Everybody thinks the technology is going to wipe everybody out, and instead the economy adapts." Companies are leaner per dollar of revenue and still cannot hire fast enough.
- Quota attainment is no longer distributed the way comp plans assume. QuotaPath's first-half numbers put 58% of AEs on track against annual quota versus 55% a year ago, but as AJ Bruno, CEO of QuotaPath, explained, the shape underneath moved: "the standard deviation is way higher this year. Meaning that the winners are going to be winning more … So it's more like a barbell than it is a bell curve." At some AI companies two reps out of ten are closing half the entire number, which breaks the capacity math most sales leaders use to set targets.
- For individual sellers, the window matters more than the title. Asad Zaman's advice to reps weighing a step up into leadership: "this is the moment where you can make millions of dollars right now … So don't make silly choices … Become a leader later. Go make money right now." He now benchmarks offers on whether 300% of plan clears a million dollars, and warns that private equity portfolio companies that never gave equity to individual contributors are losing these candidates outright.
Connect with the Hosts:
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/
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 Three Hosts, Three Topics
02:19 The Talent Market Has Gone Crazy
05:42 $200K Base, $200K Variable
09:00 AI Was Supposed To Kill Sales
15:16 Go Make A Million Right Now
16:53 Where Young Sellers Get Their Start
23:20 Build A University Inside The Company
31:58 Paul Graham Versus Go-To-Market
36:22 Why YC Misses Enterprise Software
40:55 Can A Non-Seller Be A Great CRO?
44:42 GTM Cannot Fix Product-Market Fit
49:30 One To Ten To A Hundred
53:38 Quota Attainment Is A Barbell
1:02:41 The HubSpot Nightmare
1:06:05 Falling Back In Love With The Business

In this episode of Topline Spotlight, Sam Jacobs sits down with Snehal Nimje, co-founder and CEO of Outdoo, to talk about one of the hardest calls an early-stage founder can make: narrowing focus when leads are coming in.
Snehal breaks down how Outdoo went from trying to serve every mid-market and enterprise buyer to getting much more specific about where the product was truly essential. They get into why usage dropped, what customer conversations revealed, how the team handled the internal shift, and what changed once they focused on insurance and finance use cases where compliance and ramp speed mattered most.
They also talk about:

- Why enterprise readiness starts with architecture, compliance, and security
- How to tell the difference between interest and real traction
- What founders miss when they chase every lead
- Where defensibility really comes from in AI
Chapters:
00:00 Intro
00:46 Meet Snehal Nimje and Outdoo
04:55 Why selling to everyone nearly derailed the business
06:51 Finding the customers who truly need your product
08:54 The hard decision to narrow their ICP
11:00 How focus accelerated enterprise growth
13:09 Advice for founders struggling to find product-market fit
15:36 What creates a moat in the AI era?
17:13 Why workflow—not AI models—is the real competitive advantage
18:51 Snehal's biggest business inspiration
19:38 Where to find Snehal and Outdoo
Try Outdoo: outdoo.ai
If you're building an early-stage company and trying to find traction without turning your product into a Frankenstein, this one's worth your time.
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Jaleh Rezaei, Co-founder and CEO of Mutiny, joins Sam Jacobs, AJ Bruno, and Asad Zaman to explain how she deprecated a thriving 8-figure SaaS business in November 2025, shipped a private preview in February, and GA'd an AI-native product in April that is now used by more than 3,500 organizations including Snowflake, Rippling, Uber, and GitLab. Topics include why running a scaled SaaS business and a zero-to-one AI bet at the same time proved impossible, how to price and defend AI credit consumption when a $5,000 design project now costs 50 credits, and the shift from sales-led outbound to product-led growth for enterprise go-to-market. Plus, why brand is one of the few remaining moats in B2B, an AI raccoon launch video that fooled (some of) the panel, and a bulls-versus-bears debate on quota attainment, AI note-takers, and whether salespeople will ever spend 85% of their time selling.
Key Takeaways:
- Make the hard decisions FAST. As Jaleh Rezaei, CEO and Co-founder of Mutiny, put it: "I definitely would've said the job of the CEO is you have to make the hard calls. But what I learned in that experience is that it's actually about making the hard calls really fast, which means that you're getting there before everybody else on your team is there." Her test for founders weighing a similar bet is a single question: "is there one really hard decision, maybe one that scares the hell out of you that you don't want to do, that you can make that would make 50 subsequent downstream decisions a lot easier for your company?"
- AI budgets get cut because vendors let buyers anchor on the credit bill. Instead, they need to help buyers see the value of the work the credits replace. Jaleh Rezaei, CEO and Co-founder of Mutiny, reframed it with her own before-and-after: "I used to have a designer that I paid $5,000 to, and it would take 2 weeks of back and forth, and I paid $5,000 to get to something that I was pretty happy with. But end to end took a month. Now in 6, 7 hours, I can build that in Mutiny, and maybe that does cost me 50 credits. That's really freaking cheap relative to what I used to pay that designer." She argues the vendor has to build the ROI case for the customer, per rep, or budget conversations default to minimizing every AI bill.
- Brand is a durable moat in B2B mostly because so few companies are willing to pay for it in risk. According to Jaleh Rezaei, CEO and Co-founder of Mutiny: "great brand comes when you marry deep customer knowledge and a willingness to take risk … a lot of times people that own brand they don't necessarily either have the deep customer knowledge or they don't have the ability to take that kind of risk inside of the company." Her internal standard is blunt: "anything we do on marketing, like, if it's not different, just stop doing it. It's just not going to matter."
- Quota attainment is snapping back hard, and the data has not caught up to the narrative. AJ Bruno, CEO of QuotaPath, brought Q2 numbers to the bulls-versus-bears round: "I just looked at Q2 numbers and they're trending wildly back up. We're actually, the average quota attainment for a QuotaPath customer was 76% in Q2." Asad Zaman pushed back that a jump from roughly 40% to 76% in a single quarter reads more like a bubble signal than a sudden improvement in selling, and AJ offered to run a comp study with Pavilion on the data.
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: Jaleh Rezaei, CEO & Co-founder at Mutiny - https://www.linkedin.com/in/jalehr/
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 Jaleh Rezaei
04:00 Can SaaS Era Companies Go AI Native?
05:01 From Gusto To Founding Mutiny
07:00 When AI Became A Reasoning Engine
11:28 Why Running Two Products Was Impossible
13:32 Shutting Down An 8-Figure Business
16:18 Winning Formula: Speed, No Backup Plan
20:17 The Hard Months After Deprecation
24:47 Acute Pain Versus Chronic Pain
29:17 CEO Has To Be The Bad Guy (Sometimes)
37:17 AI Margins And Credit-Based Pricing
40:10 A $5,000 Deck Versus 50 Credits
47:03 Sales-Led To PLG For Enterprise
50:37 Brand As The Remaining Moat
1:00:34 Bulls and Bears