Topline

Evan Huck, CEO and co-founder of UserEvidence, opens up about the hard decision to shift from a tried-and-true outbound sales playbook to a long-term brand-building strategy. After eight straight quarters of flat pipeline growth, Evan had to trust the process, convince his board to stay the course, and rethink how UserEvidence reached its ideal customers. In this conversation, he shares what it takes to stay patient when results don't come fast, how to balance short-term pipeline needs with brand investments, and why the payoff was worth the wait.

Evan also shares:
- Why eight quarters of flat pipeline tested their commitment to brand over quick wins
- How UserEvidence narrowed its ICP to unlock stronger growth
- Why creative, one-to-one outreach can still break through with enterprise buyers
- How Slack communities helped build credibility and generate early enterprise demand
- Why product marketing came before demand generation in building the GTM engine
- How customer advocacy became an increasingly powerful source of growth

Chapters:
00:00 Introduction to Evan Huck and UserEvidence
04:31 From SDR to CEO: Evan's GTM Journey
07:54 Why UserEvidence Bet on Brand
09:31 Eight Quarters of Crickets: Waiting for Brand to Pay Off
12:30 Narrowing the ICP to Unlock Growth
13:51 The CEO Hustle Behind Enterprise Growth
16:00 Building Credibility Through Communities
18:00 Why the Right Team Matters
19:14 Why Product Marketing Came First
20:39 Turning Customers Into a Growth Engine
22:07 The "Chill, Humble" Leadership Philosophy
22:43 Evan's Favorite Book for Founders
Try UserEvidence: userevidence.com

Keenan, founder and CEO of A Sales Growth Company and the bestselling author of Gap Selling, joins Sam Jacobs, AJ Bruno, and Asad Zaman to make the case that two companies with identical revenue can be valued 3 to 4 times apart, depending entirely on how that revenue got made. Topics include the four sales org archetypes (heroic, random, peacock, and compounding), the valuation discount investors quietly apply to revenue produced by heroics, why quota attainment fell from 60% to 23% while enablement spend went up 7x, and the difference between a sales system and sales structure. Plus, what revenue leaders can learn from how Sequoia, Blackstone, and CAA actually run their people, why Keenan is done with the phrase go-to-market, and the story behind the one-name brand.
 
Key Takeaways:
- How you produce revenue changes what the market will pay for it: investors are buying your ability to repeat the number, not the number itself. Keenan puts a figure on it in his paper Not All Revenue Is Created Equal: "the discount could be as much as 15 to 20% discount on the valuation." Heroics hides the cost; nobody opens a CRM and sees "we closed a $2 million deal and nobody saw that that $2 million deal started at $2.6 million."
- Systems are not structure. A system defines the outputs it wants and stays agnostic about how each rep gets there, which is what separates it from a script. "Making people do everything the same is structure," Keenan said. He runs it through golf: "I focus less on what your swing looks like, and I'm asking myself, are you able to hit a draw when you need to hit a draw?"
- Sales teams over-invest in training the behavior (structure) and under-invest in understanding the buyer, which Keenan calls sales physics: "nobody buys anything unless their current state is untenable and intolerable." A good system helps the buyer realize that state, which will allow a deal to close.
- The spending trend is going the wrong way, and Keenan closes the episode with the numbers: "In 2012, depending who you ask, 60% of reps made quota… now 23%… And the spend has gone up 7x… But win rates declined by 29%. Sales cycles extended by 37 days… What we're investing in isn't working." It persists because no CRO gets room to rebuild: "It's the boat's got a hole in it… You got to fix it. But by the way, you cannot dry dock the boat."
And yes: AJ Bruno is buying the book for the first 20 listeners who reach out. Send AJ a direct message on LinkedIn or in the Pavilion Topline Slack and he will buy you a copy of Gap Revenue Performance.

 
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: Keenan, CEO & Founder at A Sales Growth Company - https://www.linkedin.com/in/jimkeenan/
 
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 Keenan And Gap Selling
03:08 A Dollar Of Revenue Is Not A Dollar
03:46 The Four Sales Org Archetypes
06:59 The 15 To 20% Valuation Discount
08:58 The MEDDIC Definition Problem
12:47 The Left Tackle Analogy
18:24 Can Heroics Be Predictable?
23:10 Structure Is Not A System
28:32 What VC Firms Get Right
42:09 The Physics Of Selling
50:16 Awareness First, Then Pipeline
51:55 Tired Of The Word Go-To-Market
1:00:23 AI, Product Velocity And Enablement
1:04:26 Is Sales A Power Law?
1:12:09 The Story Behind One Name

Bryan Murphy, CEO of Smartling, confronts a $40 billion industry stuck in the slow lane—the world of translation. Most companies still handle translations like it's 1999: manual, expensive, and painfully slow. Bryan saw AI as the game changer that could rewrite the rules, but integrating it wasn't a walk in the park.
He shares how Smartling harnessed AI to not just cut costs and speed up translation but to finally boost quality close to human-level precision without losing control over brand voice or nuance. Yet, making this leap meant upheaval: reorganizing teams, hiring AI experts, and establishing ruthless R&D discipline to separate winning ideas from distractions.

Bryan also shares:
- Why a $40 billion translation industry was ripe for disruption
- How AI helped Smartling move from faster and cheaper to dramatically better
- What it took to bring AI into a traditional business without sacrificing quality or brand voice
- Why hiring the right AI talent was critical to making the shift
- How ruthless R&D discipline helps separate breakthrough ideas from distractions
- Why every AI initiative needs a clear connection to customer outcomes

Chapters

00:00 - Introduction to Bryan Murphy and Defining the Translation Challenge
02:30 - The Hidden $40B Translation Market and Its Untapped Potential
06:00 - Early AI in Translation: Faster and Cheaper, But Not Yet Better
09:20 - Human-in-the-Loop AI: Boosting Translator Productivity Tenfold
13:00 - Unlocking Market Expansion Through Improved SEO and Digital Footprint
15:00 - The Moment of Truth: Recognizing GPT's Impact and Rolling Out Rapid Innovation
18:00 - Overcoming Organizational Challenges: From Excitement to Structured Execution
22:00 - The Discipline of "Customer-First" in AI Development and Roadmapping
24:00 - Leadership Lessons: Listening Without Losing Vision Amidst Painful Change
26:00 - Winning Customer Trust: Betting On Proofs of Concept Against Skeptics
28:00 - Personal Insights: Favorite Leadership Books and the Role of Intellectual Curiosity
33:00 - Wrap-up and Invitation to Follow Smartling's AI-Empowered Evolution
Try Smartling: smartling.com

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/