Topline

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...

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...

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, cu...

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...

Russ Mikowski, CEO of SurePeople and longtime revenue leader in tech, never planned to become a CEO. Recruited to lead a 10-year-old company into its next stage of growth, he faced technical debt, an unfocused ideal customer profile (ICP), and the challenge of turning the company's potential into a scalable business.

In this episode of Topline Spotlight, Russ joins Sam Jacobs and AJ Bruno to discuss the decisions behind SurePeople's transformation, including rebuilding parts of its product, narrowing its target market, and resisting custom requests that could pull the business off course.

Russ talks about:<...

Michael Walrath, CEO of Yext, is back on Topline to explain how Yext went from breakeven to 31% EBITDA margins on an 80% gross margin business, after halving its headcount and using its balance sheet to buy back roughly 35% of every share it ever issued. He joins Sam Jacobs, AJ Bruno, and Asad Zaman to argue that the old rules of business still apply: why VC math and founder math are different games, why employees lose the most when an overvalued startup like Airtable lands far below its peak valuation, and why this market feels like 2004. Plus, why Yext stopped doing...

When Rick Smolen stepped into the CRO role at ShipHero, he took on responsibility for the entire customer lifecycle, from marketing and partnerships to customer success and support. 

With a background primarily in sales, he had to learn how to lead functions outside his expertise without needing to have all the answers.

In this episode, Rick joins Sam Jacobs to discuss the leadership lessons that came with that transition, from asking better questions to building trust with his team. He also explains how to learn from failure, navigate setbacks, and focus on what you can c...

Amy Konary, Founder & Chair of The Subscribed Institute at Zuora, coined the term SaaS as an IDC analyst around 2000, when her first forecast sized the whole market at $40 million. She joins Sam Jacobs, AJ Bruno, and Asad Zaman for the first in-person Topline to ask whether AI company economics are a house of cards, and whether circular financing and double counting are real problems. Plus, why POCs have stopped being a pipeline signal, experimental revenue versus true ARR, a new leverage index for sticky revenue, tokens versus credits, and how close outcome pricing can really get.

Key...

When Sam Jacobs founded Pavilion, formerly Revenue Collective, he set out to build a private community for operators in a startup world that traditionally celebrated founders and overlooked the people running the business. But as Pavilion grew to 10,000+ members, the very thing that made the community valuable began to get diluted.

In this special Topline Spotlight episode, Sam joins co-hosts AJ Bruno and Asad Zaman to talk about what happened, why removing the qualification barrier was a mistake, and what it took to bring Pavilion back to its original vision.

Sam talks about:

...

Manny Medina, Co-Founder and CEO of Paid, the monetization platform for AI agents, and the founder who took Outreach from nothing, joins Sam Jacobs, AJ Bruno, and Asad Zaman in person on how to price AI agents once seats stop making sense. Topics include why every SaaS company needs its own agents before someone else's run on its MCP layer, why a token is the wrong unit of value, and the itemized phone bill every agent builder owes its buyers. Plus, why fixed-price deals win logos but stall expansion, the case for 40% to 60% gross margins in the agent era...

You have the CRM. You have the data. You have the sales team. You have the AI tools. So why does everything still feel broken?

Ramin Heydari, CEO & President of XYZies, has spent more than 30 years building businesses across telecom, sales, distribution, and technology.

In this episode of Topline Spotlight, he explains why fragmented systems can become one of the biggest obstacles to growth and why AI requires businesses to rethink how they operate, not simply add another tool.

Sam Jacobs sits down with Ramin to unpack the shift from traditional growth to 10...

Harvey's gross margin fell from roughly positive 50% at the start of 2026 to negative 50% by June, so every $1 of revenue cost $1.50 to deliver. Sam Jacobs, CEO of Pavilion, AJ Bruno, CEO of QuotaPath, and Asad Zaman, CEO of STA, go hosts-only on when AI growth justifies margins like that, why open weight models are no substitute for frontier intelligence, and what happens to the application layer if the exuberant market funding it goes away. Plus, AJ's 100x raise from 2021, a 68% jump in tech M&A and what it means for employee equity, and a Bulls and Bears round on AI...

Keith Peiris, Co-Founder and CEO of Lightfield, joins Sam Jacobs, AJ Bruno, and Asad Zaman to talk about building an agentic CRM that launched in November 2025, has been adopted by more than 5,000 customers, and just raised a $47 million Series A led by Andreessen Horowitz. Topics include why every system of record was really a forecasting tool, how to get reliable output from non-deterministic models, and the two reasons companies actually rip out Salesforce or HubSpot. Plus, a spirited debate on whether the SaaS partner ecosystem is dead, why AI-native deal sizes at 200-person companies can rival enterprise contracts, and how...

What happens when a seasoned GTM leader becomes CEO for the first time and steps into a founder-led company with a global team? 

In this episode, Eric Anderson, CEO of Walnut, shares what it's really like to take over a business built by someone else. He talks with AJ Bruno about building trust across time zones, rebuilding the go-to-market motion, and making bold decisions while honoring legacy culture. 

From listening tours to tough calls on pricing and segmentation, Eric opens up about the challenges and wins of his first six months in the role.

...

Jen Igartua, CEO at Go Nimbly, joins Sam Jacobs, AJ Bruno, and Asad Zaman. Her client roster is wild: Fireworks AI, Perplexity, Exa, and Wispr Flow, plus some of the biggest names in SaaS. Topics in today's episode include how the fastest-growing AI-native companies are growing in spite of their revenue operations (not because of them), the first project she runs when she wants to show ROI fast, and how she makes the case that RevOps is a support function and always was. Plus, whether the GTM engineer is anything more than RevOps with better marketing (and more)!

Matt Allison, CEO and Founder of Handraise, joins us to share why he's skipping the SMB trap and building an AI-powered media intelligence platform for enterprise from day one. Drawing on hard-won lessons from scaling TrendKite, Matt breaks down how Handraise is targeting $30K+ deals with brands like Walgreens and Hershey, the importance of patience in early go-to-market, and how AI is helping them build a more thoughtful, scalable, and enterprise-ready product from the start.

Matt also talks about:
- Why Handraise is skipping the SMB trap and going enterprise from day one
- What...

Forget Growth. Your Valuation Depends On Your AI Story | Tomasz Tunguz, GP @ Theory Ventures

Tomasz Tunguz, General Partner at Theory Ventures, joins Sam Jacobs, AJ Bruno, and Asad Zaman with public software multiples sitting at 4 to 4.5 times forward revenue, down from the 100x ceiling of 2021. Topics include why the market now pays for an AI story rather than growth, the $10 billion AI companies committed in a single year to putting forward-deployed engineers inside customer orgs, and the 41 days a model company gets to commercialize a state-of-the-art release before it is knocked off the perch. Plus, why the...

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...

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...

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...

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...

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 answ...

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...

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...

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...

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...

Amanda Kahlow, Founder & CEO of 1mind, joins Sam Jacobs, AJ Bruno, and Asad Zaman to break down how an AI-powered solutions engineer named Nigel took 33% of the talk time in a two and a half hour enterprise meeting and produced a $278,000 deal. Topics include why AI aimed at efficiency gains misses real revenue impact, Amanda's prediction that marketing, sales, and customer success collapse into one function within 12 months, and why AI adoption has to be top-down instead of bottoms-up. Plus, the 15 agents running behind every superhuman, a 98% accuracy bar measured by live evals, whether agents will negotiate with other...

AI isn't just changing sales. It's completely rewriting how revenue teams operate.

In this episode of Topline Spotlight, Sam Jacobs sits down with Justin Shriber, CEO of Terret AI, to break down how modern revenue organizations are using AI to improve forecasting, shorten sales cycles, ramp reps faster, and operationalize winning sales behavior in real time.

Justin shares:

Why traditional sales enablement is broken
How AI helped reduce rep ramp time by 40%
The "answer-to-action" engine powering modern RevOps
The hidden dangers of decentralized AI adoption
Why companies are struggling...

Tim Rutten, CMO of Backbase, the €2.5 billion Amsterdam tech company whose AI-native Banking OS powers 120+ banks worldwide, joins Sam Jacobs, AJ Bruno, and Asad Zaman with the clearest AI ROI numbers we have heard on the show: double the pipeline on 25% less budget. Topics include the custom go-to-market operating system his team built on the Vercel stack, why real bank deployments are 99% deterministic, the 90% cost reduction banks are finding in customer care, and why most enterprise workloads do not need frontier-model intelligence. Plus, where the AI bubble breaks, what happens to judgment and taste when anyone can generate output, an...

Buyers stopped picking up the phone. They research on their own, ask their peers, and now they ask AI which vendors to consider before a single salesperson ever hears about it. So where does that leave marketers?

Sam Jacobs sits down with Alexander Kesler, founder and CEO of Infuse, to break down the dark funnel and what it means for B2B demand gen right now. They get into why most of the buying journey happens before you're ever contacted, how AI tools are generating "day one" shortlists on the spot, and why the real game is...

A rep says "follow up on that" on a call, then buries it under five more calls and a late-night inbox. Three days later the deal's gone cold, but the CRM still says it's live. The manager forecasts off that. 

The CRO forecasts off the manager. The board asks the CEO if anyone actually has a grip on the number. The whole thing was built on a promise nobody kept. 

Adam Liska worked on the early Gemini models at Google DeepMind before leaving to close that gap. His company, airspeed, just raised a $20M Series A...

Marc Ferrentino, Co-Founder and CEO of Quotient and former chief technical architect at Salesforce, joins Sam Jacobs and Asad Zaman to separate AI-marketing hype from what actually works today. Marc's core claim: the 'AI CMO' is marketing fiction, and the real near-term unlock is clearing the roughly 70% of a marketer's day lost to busywork, so smaller teams can finally operate like big ones. Topics include the collapse of specialized marketing roles into cross-functional generalists, why the apprenticeship model that trained classic marketers is most at risk, where the durable edge moves as performance marketing gets automated... and how taste...

A CEO walks into a board meeting knowing exactly what to say then freezes. A sales rep doomscrolls between calls and shows up to the next one flat. A founder grinds toward the exit, only to sacrifice their relationships and themselves along the way.

The problem isn't always strategy, skill, or effort. Sometimes, it's the nervous system.

Kevin Bailey knows this firsthand. After building a high-growth tech company with around 100 employees, he noticed something strange: some days he was exceptionally creative and productive. Other days, he'd stare at his computer for hours and accomplish almost...

Katie Bullard helped take DiscoverOrg from $30 million to $300 million in revenue, then served as president of A Cloud Guru and Red Canary through exits to Pluralsight and Zscaler. She joins AJ Bruno and Asad Zaman to break down what actually changes for operators in an AI-first world. From why "AI native" is not a growth strategy, to how to align the CRO, CFO, and product team around a single growth plan. Topics include building for customer value before chasing AI ARR, the move from seat-based to consumption pricing, and why 70% of the old playbook for hiring a great executive...

Ghazi Masood, Chief Revenue Officer at Replit, joins Sam Jacobs and Asad Zaman to break down the company scaled from $2 million towards a North Star of $1 billion in revenue in about two years, with roughly 350 employees and a 75-person go-to-market team. Ghazi gets specific on the operational cadence that replaced the quarterly SaaS playbook, why more than 90% of reps overachieved in H1 and why he believes $2 million per rep still isn't the ceiling, and how Replit built its own CPQ, Clari, and Gainsight equivalents on top of Salesforce. Plus, the shift from inbound to outbound pipeline generation, why AI-native...

Mark Roberge, founding CRO at HubSpot and co-founder of Stage 2 Capital, joins Sam Jacobs and AJ Bruno to tackle the question every board is asking in 2026: how do you actually measure AI's impact on a go-to-market team? They get into the revenue velocity formula, why selling time is the one variable AI can realistically double, and the ICONIQ data showing AI lifts top-of-funnel conversion 11% while barely moving active deal cycles. Plus, a Quiz Pro Quo on Palantir's 137% rule of 40 and Twilio's $5.6 million ARR per employee, a debate on whether the AI-era winner is the first mover or the fast...

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...

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...

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...

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...