ProductLed Podcast

In this episode of the ProductLed Podcast, Wes Bush and Esben Friis-Jensen sit down with Roeland Delrue, CEO and co-founder of Aikido Security, to unpack how the company reached $40M+ ARR in just three and a half years in one of the most sales-heavy categories in software.

Roeland shares how his team entered cybersecurity without a traditional security background, simply by living the problem themselves. After juggling eight different security tools and watching a security engineer quit from the sheer pain of triaging endless false positives, they decided to build the product they wished existed.

The conversation digs into why Aikido took a radically product-led path in a market dominated by demos, gated trials, and opaque pricing. Roeland explains how transparent pricing, fast time-to-value, and a no-nonsense buying experience helped Aikido win trust with developers and security teams alike.

They also get into the bigger growth story behind the business: why product-led motions scale so well, how compliance trends like SOC 2 create strong tailwinds, and why Aikido chose to build a multi-product platform from day one instead of another point solution.

Toward the end, Roeland shares his view on AI in cybersecurity, where AI pen testing is already replacing human work, and where humans will still matter for a long time. It is a candid look at building a category-defining security company without following the usual playbook.

Key Highlights:

01:46 - The Pain That Sparked Aikido

How Roeland and his co-founders went from frustrated security-tool buyers to building their own solution.

04:40 - Why Cybersecurity Needed a PLG Rethink

A sharp breakdown of why traditional sales-led security buying feels broken and expensive.

10:11 - Trust in Security Without Heavy Sales

How Aikido built trust through product quality, compliance, transparency, and social proof.

15:24 - What Drove Aikido’s Fast Growth

Why self-serve foundations, fast setup, and faster time-to-value helped the company scale quickly.

18:06 - Compliance and AI Fueling Demand

How SOC 2, ISO requirements, open source risk, and AI-driven software growth are expanding the market.

20:15 - Building a Security Platform Day One

Why Aikido bet on an all-in-one platform instead of a narrow point solution, and how they keep quality high.

27:08 - Brownfield vs Greenfield Growth

Roeland explains why Aikido started by replacing existing tools and is now moving into faster AI-driven markets.

34:16 - A Practical View of AI in Security

Why Roeland believes the future is hybrid, with deterministic scanners and AI working side by side.

36:31 - Can AI Replace Human Pen Testing?

Where AI pen testing already works today, where it still falls short, and what adoption barriers remain.

Resources:

🚀 Aikido Security: https://www.aikido.dev/
💼 Connect with Roeland Delrue on LinkedIn: https://www.linkedin.com/in/roelanddelrue/
💼 Connect with Wes Bush on LinkedIn: https://www.linkedin.com/in/wesbush/
💼 Connect with Esben Friis-Jensen on LinkedIn: https://www.linkedin.com/in/esbenfriisjensen/
🧠 Sign up for the ProductLed Newsletter: https://www.productled.com/newsletter

In this episode of the ProductLed Podcast, Wes Bush and Esben Friis-Jensen sit down with Jaleh Rezaei, co-founder and CEO of Mutiny, to unpack one of the boldest founder moves you’ll hear this year.

After building Mutiny into an eight-figure ARR SaaS company, Jaleh made the rare decision to shut down most of the original business and rebuild around AI agents. She shares why trying to run both a traditional SaaS company and an AI-native company at the same time created constant friction, slowed the team down, and made it impossible to move at the pace the market demanded.

Jaleh walks through how she made the call, what gave her confidence to follow through, and what the first 90 days of the pivot actually looked like. That includes shrinking the team, moving to a smaller in-person setup, carefully migrating customers, and rebuilding company culture around speed, customer obsession, and founder-level context.

The conversation also dives into why Mutiny shifted from sales-led to product-led growth, how self-serve products expose weaknesses faster, and why “showing” value beats explaining it, especially in AI. Jaleh also shares her view on what still counts as defensible in AI, why experience generation and analytics matter more than basic data movement, and how she personally uses AI across recruiting, meeting prep, and writing support.

It’s a candid look at conviction, timing, and what it really takes to rebuild for the next wave.

Key Highlights:

01:41 - Why She Left 8-Figure ARR Behind

Jaleh explains why combining a SaaS business with an AI-native business created roadmap, pricing, and execution conflicts that made a harder pivot inevitable.

05:01 - The Gut Check Behind a High-Stakes Pivot

How she built conviction for a risky decision, what made “moving as fast as possible” the real north star, and the advice she gives founders facing the same choice.

11:13 - Reframing the Pivot as Mission, Not Failure

Why walking away from a successful product did not feel like giving up, and how first-principles thinking helped her reconnect the company to its original vision.

15:05 - The First 90 Days of the Transition

A behind-the-scenes look at shrinking the team, getting back to a small in-person setup, and creating the conditions needed to find product-market fit again.

17:01 - How Mutiny Migrated Customers Gracefully

The detailed playbook for protecting customer trust during the transition, from partner selection and pricing negotiations to white-glove migration support.

23:03 - Building a Team for Startup Intensity Again

How Jaleh thought about team size, in-office culture, and the level of intensity required to compete in the current AI market.

25:58 - What Founders Must Stop Delegating Pre-PMF

Why founders need direct exposure to customer calls, onboarding, pricing conversations, and product friction if they want to move fast and make better decisions.

32:12 - Why the New Mutiny Had to Be Product-Led

Jaleh shares why self-serve makes products better, how AI products benefit from instant hands-on proof, and why PLG also improved the sales-led motion.

40:22 - What a Real AI Moat Looks Like

Her take on defensibility in AI, why simple data workflows will get commoditized, and why Mutiny is focused on experience generation, analytics, and self-improving systems.

45:15 - Jaleh’s Highest-Leverage AI Workflows

The practical ways she uses AI today across recruiting, meeting prep, and writing optimization, plus why she still believes strong writing needs a human point of view.

Resources:

🚀 Mutiny: https://mutinyhq.com
💼 Connect with Jaleh Rezaei on LinkedIn: https://www.linkedin.com/in/jalehr/
💼 Connect with Wes Bush on LinkedIn: https://www.linkedin.com/in/wesbush/
💼 Connect with Esben Friis-Jensen on LinkedIn: https://www.linkedin.com/in/esbenfriisjensen/

🧠 Sign up for the ProductLed Newsletter: https://www.productled.com/newsletter

Most founders hear stories about lean SaaS companies and assume they are the exception.

Jeremy Clarke lived one.

In this episode of the ProductLed Podcast, Wes Bush and Esben Friis-Jensen sit down with Jeremy Clarke, founder of WebMerge and now the builder behind Quin, to unpack what it really took to grow WebMerge into a multi-million dollar business with an incredibly small team.

Jeremy shares how WebMerge started as a simple PDF generation tool, why integrations became the growth engine that unlocked scale, and how a strategic hire helped expand distribution without bloating the company. He also gets honest about what has changed in today’s AI market: thinner margins, tougher distribution, less generous free plans, and far more noise.

The conversation also dives into the founder mindset behind building highly effective companies. Jeremy explains why staying close to support made WebMerge stronger, why he delayed hiring for as long as possible, and what drove his decision to eventually sell. From there, he opens up about building Quin, what it means to compete in a crowded AI category, and why word of mouth and customer trust still matter more than ever.

If you want to build a meaningful software business without defaulting to a big team or venture funding, this episode is packed with practical insight.

Key Highlights:

00:43 - From WebMerge to Quin
Jeremy shares what he’s focused on today, why Quin is a much harder business to build than WebMerge, and how AI margins change the game.
07:36 - The WebMerge growth playbook
How WebMerge evolved from a simple PDF tool into an integration-driven platform, and why partnerships became a major distribution engine.
12:40 - How WebMerge really got off the ground
The early days of the business, the first customer outreach, and how a slow trickle of traction compounded into millions in revenue over time.
16:36 - Why Jeremy bootstrapped from day one
Jeremy talks through his decision to stay self-funded, avoid outside control, and build on his own terms.
19:14 - How to reach $5M with almost no team
A candid discussion on why Jeremy delayed hiring, what work he kept for himself, and when he finally saw the need for a strategic hire.
21:51 - Why founders should stay close to support
Jeremy and Esben discuss support as a product advantage, how it tightens the customer feedback loop, and why speed matters so much.
25:28 - Why he sold a highly profitable business
Jeremy shares the reasoning behind selling WebMerge, including risk, lifestyle, hiring pressure, and the chance to join a larger story.
47:18 - What still wins in a crowded AI market
Jeremy explains what has changed in his new playbook, what has not changed, and why customer trust and word of mouth still matter most.

Resources:

🚀 Quin: AI assistant for busywork and follow-through:
💼 Connect with Jeremy Clarke on LinkedIn
💼 Connect with Wes Bush on LinkedIn
💼 Connect with Esben Friis-Jensen on LinkedIn
🧠 Sign up for the ProductLed Newsletter

When Jeff Wang stepped into the CEO role at Windsurf, it was not part of some long-term succession plan. It happened in the middle of a full-blown crisis.

In this episode of the ProductLed Podcast, Wes Bush and Esben Friis-Jensen sit down with Jeff to unpack the wild chain of events that followed the collapsed OpenAI acquisition, the founders leaving for Google, and the intense 72-hour window Jeff had to help save the company and protect 250 jobs. He shares how Windsurf navigated that moment, how the Cognition deal came together, and what it has been like leading one of the most closely watched teams in AI coding ever since.

Jeff also gets into what made Windsurf so strategically valuable in the first place, from shipping early breakthroughs in autocomplete, chat, context engineering, and agent workflows, to building one of the first generally available coding agents on the market. Beyond the origin story, the conversation goes deep on go-to-market strategy, why free products worked early on, how token economics changed the game, and why enterprise AI adoption takes far more than handing teams a tool.

They also explore Windsurf 2.0, the shift toward managing multiple agents at once, how Jeff uses AI in his own CEO workflows, and why founders need to obsess over painful problems, customer conversations, and product-market fit instead of flashy demos.

Key Highlights:

00:00 - The 72-Hour Crisis That Changed Everything

Jeff shares the short version of the OpenAI, Google, and Cognition saga, and what it was like stepping into the CEO role during a company-defining emergency.

01:40 - Why Big Tech Wanted the Windsurf Team

A look at the execution speed, product breakthroughs, and agent innovations that made Windsurf one of the most valuable teams in AI coding.

04:10 - The Future of Coding Is Multi-Agent

Jeff explains why developers are moving from one-on-one AI assistance to managing many agents at once, and how Windsurf 2.0 is built for that shift.

08:54 - How Free Became Their Growth Wedge

From free autocomplete to on-prem enterprise deals, Jeff walks through Windsurf’s early PLG motion and how it created awareness and pipeline.

13:10 - The Hard Truth About AI Pricing

A candid discussion on token costs, self-serve subsidies, pricing pressure, and why raising prices can reveal whether you truly have product-market fit.

16:13 - Why Enterprise AI Sales Are Top-Down

Jeff shares how Windsurf sells into large companies by focusing on transformation, adoption, security, and measurable outcomes instead of seat counts.

20:51 - What It Takes to Drive Real AI Adoption

Why playbooks, training, and solving a meaningful first use case matter more than just rolling out a shiny new tool to an engineering team.

24:40 - Jeff’s AI Workflows as CEO

Jeff reveals how he uses AI and custom playbooks for go-to-market research, outreach preparation, and spotting product trends before opening dashboards.

32:32 - Jeff’s Advice for Every Product Founder

Build around painful problems, talk to hundreds of prospects, and learn to enjoy rejection because that is often where the real insight comes from.

Resources:

🚀 Windsurf
💼 Connect with Jeff Wang on LinkedIn
💼 Connect with Wes Bush on LinkedIn
💼 Connect with Esben Friis-Jensen on LinkedIn
🧠 Sign up for the ProductLed Newsletter

In this episode of the ProductLed Podcast, Wes Bush and Esben Friis-Jensen sit down with Edith Harbaugh, CEO and co-founder of LaunchDarkly, the feature management platform used by more than 5,000 customers, including 25% of the Fortune 500.

Edith shares how her experience at TripIt led to the insight behind LaunchDarkly, and why feature management became such a critical part of modern software delivery. She explains what it actually took to create a category in the early days, when many companies were still shipping software only a few times a year, and why listening to customer pain mattered more than trying to force a new movement on the market.

The conversation also dives into LaunchDarkly’s unusual balance of product-led and enterprise sales, why the company kept its free tier even as it grew upmarket, and the story behind its first real enterprise deal. Edith also opens up about returning as CEO, how AI is reshaping software delivery, and why she now sees LaunchDarkly as runtime control for the AI era.

One of the biggest themes throughout the episode is Edith’s leadership philosophy: work should be fun. For her, that means helping teams reduce toil, build better software, and stay connected to the real impact they have on customers.

Key Highlights:

01:59 - What Feature Management Actually Does

Edith breaks down feature management in simple terms, from beta rollouts and experimentation to location-based access and safe runtime control.

03:09 - The TripIt Insight Behind LaunchDarkly

How constant mobile and backend releases at TripIt revealed a problem most software teams still had not solved.

04:47 - How to Create a Category People Want

Edith explains why category creation was much harder than it looked, and how meeting customers where they were helped LaunchDarkly gain traction.

07:00 - Why Early Customers Chose Buy Over Build

A look at how teams with homegrown flagging systems became some of LaunchDarkly’s best early customers.

08:50 - Market Pull Matters More Than Pushing

Why category creation only works when buyers already feel the pain, and how Edith looked for real pull instead of forcing the message.

12:23 - The Free Tier That Survived Enterprise Sales

Edith shares why LaunchDarkly kept its free motion, even after realizing the company was becoming an enterprise sales business.

13:57 - The First Enterprise Deal Changed Everything

The story of a customer who refused to buy on a credit card, and how that revealed the buying behavior that shaped the company’s go-to-market.

21:02 - Why Edith Came Back as CEO

Edith talks about stepping away, returning to the role, and why AI created the kind of moment that called for founder-led leadership again.

22:11 - LaunchDarkly as Runtime Control for AI

As AI accelerates code production, Edith explains why launch, measurement, and control are becoming even more important.

27:11 - Why Founders Should Make Work Fun

Edith shares her leadership philosophy on reducing toil, helping teams enjoy the craft, and building in markets you genuinely care about.

Resources:

🚀 LaunchDarkly
💼 Connect with Edith Harbaugh on LinkedIn:
💼 Connect with Wes Bush on LinkedIn
💼 Connect with Esben Friis-Jensen on LinkedIn
🧠 Sign up for the ProductLed Newsletter