In the Trenches: Startups Edition

Our biggest takeaway after 10 episodes of In The Trenches? GTM isn’t a playbook. It’s messy, non-linear, and full of failures. This episode is a compilation of the most tactical lessons across sales, customer success, product marketing, partnerships, and revops from our first 10 episodes of In The Trenches. Key Chapters 00:23 - How to Nail Inbound (n8n’s Playbook) 03:05 - How to Do Cold Outreach W...

Most GTM advice sounds great…until you try to execute it. This episode is a compilation of the spiciest, most controversial takes from our first 10 episodes of In The Trenches. These are the kind of opinions that don’t make it into LinkedIn posts or VC decks.🎧 In this clip show, we break down the ideas that challenge how most people think about building revenue: Why VCs, founders, and operators l...

What does RevOps actually mean when the company is still figuring out how to sell? And why do most early startups introduce tooling long before they understand the motion? This is an honest look at what RevOps really looks like in early-stage startups and why the job is less about dashboards and more about judgment, behavior, and fixing broken GTM fundamentals. Alexia Charbonnier (RevOps leader at...

What happens when your buyers don’t trust marketing? And every message gets questioned by default? This is an honest look at what GTM actually looks like in cybersecurity, where you're not selling to curious buyers, but to professional skeptics. Daniel Rotaru (12 years in cybersecurity, building GTM engines from 0 to 1 and scaling to multi-million ARR) shares how marketing works in an industry...

What happens when product marketing is the only role that touches every team? Even before the company even knows who its real buyer is? This is an honest look at what product marketing actually looks like in early-stage startups and why the role becomes far more operational, strategic, and political than most people expect. Hande (Product Marketing leader, ex-DataSnipper) joined DataSnipper as the...

What happens when a product-led company tries to scale enterprise before truly understanding its buyers? This is an honest look at why outbound often fails in early-stage startups — and why timing matters more than tactics. Emilio Turco (founding sales hire at n8n) helped build the company’s enterprise motion as it scaled from ~40 people to hundreds, growing revenue 50x in the process. In this con...

Most founders waste their first 60 days chasing growth. Arnon Shimoni argues that’s a mistake. Before scale, before outbound, before paid ads — you need brutal clarity on the problem. And that only comes from customer discovery. In this episode, Arnon breaks down: Why your first 2 months should be 100% customer discovery How to dig into problems instead of pitching features Why falling in love wit...

What happens when your cost per lead stops falling and your growth engine quietly stalls? In this episode of In the Trenches , Yannick Marlot (Aircall, Mooncard) breaks down why relying on demand capture alone eventually hits a ceiling and what operators miss when they confuse inbound efficiency with real growth. This isn’t a conversation about surface-level growth hacks. It’s about the uncomforta...

What is it actually like to build Customer Success when nothing is clearly defined? This is an honest look at why the Customer Success role often breaks down in early-stage companies. Sam Brown (ex-Deel, ex-DataSnipper) has built and led Customer Success teams through rapid growth, messy data, unrealistic expectations, and constant pressure to scale before things are ready. In this conversation, w...

What is it actually like to be the first sales hire before anything works? This is an honest look at early sales before metrics and dashboards exist. Jay Mirpuri joined Light at the seed stage with no pipeline, no outbound motion, and no real proof that sales would scale. In this conversation, we unpack what it really takes to build early sales from zero, before playbooks exist and before results...

In this episode of In the Trenches, Stefan Ross (early operator at Pigment and Celonis) joins Navin to unpack what actually happens when you’re an operator building revenue without a playbook. Stefan has been on the ground at Celonis and Pigment, navigating first GTM hires, early ICP bets, partnerships, and the messy reality between founder ambition and operator execution. We talk about what opera...

In this inaugural episode of IN THE TRENCHES, Jaap Boven, Enterprise Sales Executive @ charles, shares how enterprise deals are really shaped, reflects on joining tech scaleups DocuSign & Freshworks in their early days, and how GTM operators can influence outcomes before sales conversations even begin. A grounded, operator-led conversation for founders and early GTM hires navigating complex B2...