StepOne is a shortform podcast for tech founders who don't have time for hour-long interviews.
We interview the world's most successful founders, builders, and investors. Every episode is 10-15 minutes and covers one thing: the critical first move they made that actually moved the needle. Not their entire playbook — the foundational thing they did early (or wish they'd done) that unlocked everything else. Maybe it's how they found the right problem to solve, or the first cultural decision that set the tone, or the early board practice that built trust.
How Top Executives Land Their Next Role | Gia Scinto, ex-A16Z, YC Talent Leader
Gia Scinto (https://www.linkedin.com/in/giascinto), ex-A16Z, YC Talent Leader and Partner at The Cole Group (https://www.colegroup.com), flips the table to the candidate's side. In her second conversation with Ashish, she lays out how a senior leader should run their own search, from working the three channels that reveal the market and picking the right filters, to de-risking a company before joining, standing out at the hottest companies, and negotiating the offer.
Topics discussed:
The three channels every executive should work when thinking about their next move
Why most candidate filters are wrong, and the only reliable way to de-risk a company
The build, grow, scale framework for finding the right stage
How to stand out at the hottest companies by doing the work
Showing up as a genuinely AI-forward candidate
Negotiating the offer, reading comp data, and thinking clearly about equity
How to Hire Your First Executive Team (How to Hire Your First Executive Team)
2 Sept 2026
How to Hire Your First Executive Team | Gia Scinto, ex-A16Z, YC Talent Leader
Gia Scinto (https://www.linkedin.com/in/giascinto), ex-A16Z, YC Talent Leader and Partner at The Cole Group (https://www.colegroup.com), has placed sales and marketing leaders at companies like OpenAI, Stripe, and Figma. In her first conversation with Ashish, she breaks down how founders should build an executive team from the very first hire, from how to pick a search firm and what a top-tier firm's fee actually buys, to why you should define the role around the three problems it needs to solve rather than chase the big-name CRO.
Topics discussed:
Choosing a search firm, and why specialization and chemistry beat the brand name
What the 33% fee actually buys you at a top-tier firm
Stage-appropriate hiring, and why the big-name CRO is the wrong first hire
What "AI-first" talent really means
How long a search should take and how many candidates to see
Back channels, and how to judge whether one is credible
10 Aug 2026
Cross functional and organizational dynamics for a CRO (AJ Tennant)
AJ Tennant (https://www.linkedin.com/in/alexandertennant/), Founder of Tenacity Capital (https://www.tenacity-cap.com/) and ex-CRO at Glean, spent three years scaling the company to $100M+ ARR. The hardest problems were rarely in the sales org. They lived in the CEO relationship, the board room, and the R&D roadmap.
He shares how he and CEO Arvind settled their AE to SE fight, why GTM strategy is entirely the CEO's remit, and the board-meeting lesson that changed how he brings decisions forward.
Topics discussed:
Reforming QBRs into future-focused problem solving
Extending recognition beyond sales to engineers
Resolving the CEO and CRO fight over solution engineers
Why GTM strategy is entirely the CEO's remit
Giving the board pipeline generation accountability
The board-meeting lesson on strong points of view
Building CEO and CRO trust through time and meals
Aligning R&D when moving upmarket into security-heavy deals
10 Aug 2026
Selling AI vs. SaaS products (AJ Tennant)
AJ Tennant (https://www.linkedin.com/in/alexandertennant/), Founder of Tenacity Capital (https://www.tenacity-cap.com/) and ex-CRO at Glean, pioneered enterprise AI selling as the leader who scaled the company to $100M+ ARR. Selling an AI transformation is closer to selling business consulting than shipping a feature list. The reps who win can walk into a CIO's office, run discovery, and build a seven or eight figure business case on the spot.
He explains why generalist AEs beat vertical specialists, why free pilots have to die, and how regional partners open doors before Deloitte.
Topics discussed:
Hiring sellers who build business cases, not demo features
Why transformation selling beats point-solution selling
Finding the executive who owns AI transformation
Running top-down and bottoms-up motions together
Why generalist AEs beat vertical specialists early
Killing free pilots for paid, structured proofs
Winning through regional partners before Deloitte and PwC
How hyperscaler incentives drove Glean's enterprise deals
10 Aug 2026
What it takes to build $2 to $100M ARR engine (AJ Tennant)
AJ Tennant (https://www.linkedin.com/in/alexandertennant/), Founder of Tenacity Capital (https://www.tenacity-cap.com/) and ex-CRO at Glean, scaled the company to $100M+ ARR. The engine was a repeatable hiring system. Pair an experienced AE with an up and comer, add one aggressively vetted SE, then give frontline leaders hiring quotas with no relief until seats fill.
He explains why AEs own pipeline generation and how counting ARR only when seats went active, shaped expansion at Slack and Glean.
Topics discussed:
Hiring the founder-stage trio of AE, up-and-comer, SE
Why solution engineers need aggressive vetting by R&D
Giving frontline leaders hiring quotas tied to number
Splitting pipeline 50% marketing, 50% AEs and SDRs
Making AEs the true owners of pipeline generation
Counting ARR only when seats go active
AEs owning upsells in partnership with CSMs
Value selling and command of the message for large deals
21 Apr 2026
Why Your API Is Your Moat (Mohit Aron)
Mohit Aron has spent nearly 20 years watching technology shifts play out, and his read on AI moats is blunt: the fundamentals of competitive advantage haven't changed, the tools just have. Most founders are asking the wrong question entirely.
With AI agents increasingly acting as the primary interface between users and software, Mohit breaks down exactly where durable value lives, why the "SaaS is dead" crowd is conflating two very different things, and why most AI-native ERP and CRM startups are walking into a market positioning trap they don't see coming.
Topics discussed:
API depth as the primary moat for AI agents, not data or model fine-tuning
Why "SaaS is dead" confuses the UI layer with the underlying service value
Ecosystem interoperability as a moat that wipe-coded clones cannot replicate
Why early-stage startups should use vanilla LLMs before touching fine-tuning
The SMB gravity trap pulling AI-native enterprise challengers permanently down-market
Working backwards from go-to-market motion before designing the product
The insertion point strategy for breaking into enterprise without trying to replace incumbents directly
21 Apr 2026
The Role of CTO in AI Companies (Mohit Aron)
Most CTOs talk about AI productivity gains in the abstract. Mohit Aron, Founder of Cohesity and Nutanix, has a concrete system — one he built by taking his pre-AI coding methodology and mapping AI directly onto every phase of it. He still writes unit tests, runs two coding agents in parallel for different tasks, and has a firm view on why hiring for AI fluency before engineering fundamentals is a trap that will cost you.
In this conversation with Ashish, Mohit shares his full AI-assisted development methodology — natural language spec first, then API boundaries, intermediate state, skeleton functions, implementation, and only then unit tests — and why skipping that order is exactly how teams end up owning code they don't understand. He also pushes back on blanket productivity claims: 20x gains are real for unit tests and pattern-heavy work, but design-heavy work with humans in the loop will see far less. And on the prediction that 90% of engineering jobs disappear in 18 months, he's not buying it — his company is still actively hiring, and good engineers remain hard to find.
Topics discussed:
Early-stage CTO as player-coach: when to build alongside the team vs. step back
The 5-step AI coding methodology: spec, API, intermediate state, skeleton functions, implementation
Why open-ended AI prompting produces bad output and who is accountable when it does
Applying a looser review standard to AI-written unit tests vs. production code and why
Interviewing engineers without AI to test fundamentals — fluency is a bonus, not a baseline
Why high token usage means nothing if the output quality is poor
Running multiple coding agents in parallel and switching between them by task type
Why AI as a pattern matcher still requires strong engineers to catch what it gets wrong
21 Apr 2026
Your First Sales Hire Is Wrong (Mohit Aron)
Mohit Aron has built two companies past $10B+ valuations and is now on his third. In this episode, he walks through the exact go-to-market playbook he has run each time, starting with why the founder has to be the primary seller early on, a practical necessity before messaging has been proven in the field.
He also shares the three-scorecard hiring framework he uses across every go-to-market role, and a blind reference technique where you use a candidate's own provided references to find people they never intended to give you access to.
Topics discussed:
Founder as primary seller until messaging is proven in the field
Product-market fit defined as: average rep sells to average customer without pulling in HQ
Why giving a CRO title early attracts mediocre candidates and sets them up to fail
Building geography-based pods first, then creating internal competition before hiring a leader
Three-scorecard hiring system: pre-interview resume screen, structured interview, and reference check
Using a candidate's own references to surface second-order contacts they never meant to share
Why pattern-matching leaders plateau and what first-principles thinking actually looks like in a sales org
Reassessing every leader at the two-year mark as the company's growth rate changes the job entirely
25 Feb 2026
Culture as Competitive Advantage (Marcus Ryu)
Most founders delay culture work until later. Marcus Ryu made it foundational at Guidewire when they had no customers—because no one would talk to them about a non-existent product. That decision became their survival mechanism through a product failure, an existential lawsuit, and multiple breaking points. In this episode, Marcus distinguishes between moral values that matter under pressure and operational preferences that don't, explains why adversity binds teams more powerfully than success, and shares the specific practices—from value-citing in decisions to the quarterly "granite award"—that made culture a competitive advantage worth billions.
What founders will learn:
Defining moral vs. operational values
The integrity, rationality, collegiality framework
Leading through product failures and lawsuits
Why shared sacrifice binds more than shared success
Creating reciprocal accountability with leadership
Making values dispositive, not debatable
Ritualizing difficult, unglamorous work
Why radical transparency is non-negotiable for startups
12 Feb 2026
The Power of Agenda: Managing Your Board (Marcus Ryu)
Most founders approach board meetings like performance reviews: exhausting themselves trying to look good while board members gradually encroach into operational decisions. Marcus Ryu reveals this is a failure mode. In this episode, he reframes the board relationship from governance to advisory, explains why you have more power than you realize through "the power of agenda," and shares the specific practices that kept his board focused on cadence and accountability rather than marketing software decisions. From choosing who's in the room (worth far more than valuation points) to knowing when to escalate to a "code red" discussion, Marcus provides the framework for maintaining founder authority while leveraging board wisdom.
What founders will learn:
Reframing boards as advisory, not governance
Using "the power of agenda" to control discussions
Why boards add little thrust but tons of drag
Selecting investors beyond valuation optimization
Keeping boards at 5-6 people maximum
Candor vs. radical candor with your board
When directors cross sacred CEO lines (team selection, culture)
Managing forecasting failures without losing authority
The 80% templated deck approach
Why two weeks of board prep is a failure mode
28 Jan 2026
How to Choose the Right Problem to Work On (Marcus Ryu)
Marcus Ryu built a $20 billion insurance software company by answering a question most founders never ask: why has this problem persisted unsolved? In this episode, Markus walks through his framework for strategic coherence — defining your market attack with enough precision to build an excellent product while capturing enough market to fuel your next round. From writing testable propositions about market dynamics to determining the right level of generalization for your product scope, Marcus shares the specific practices that helped him frame a market others had over-focused or under-focused.
What founders will learn:
Choosing the right problem
Testing ideas before building
Framing markets for scale
Developing strategic coherence
Validating through customers
Navigating early competition
Reach and audience
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