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 Chapters00:23 - How to Nail Inbound (n8n’s Playbook)03:05 - How to Do Cold Outreach When Nobody Knows You05:56 - How to Sell to Enterprises Like Meta (Navigating Complex Stakeholders)12:15 - When & How to Build Enterprise Partnerships (Pigment & Celonis Framework)17:07 - How to Structure Customer Success Teams for Growth19:26 - How Product Marketers Should Experiment21:00 - How to Launch a Brand (and Create Real Demand)24:10 - How to Onboard Sales Teams for Success👥 Featuring insights from:Stefan Ross (ex-Celonis, Pigment | Co-founder, CG Partners)Yannick Marlot (Mooncard, ex-Aircall)Jaap Boven (Smartly, ex-charles)Arnon Shimoni (ex-Paid, now Solvimom)Emilio Turco (n8n, ex-Algolia)Jay Mirpuri (Light)Daniel Rotaru (Qevlar)Alexia Charbonnier (Pivot, ex-Pennylane)Hande Kahraman (DataSnipper)Sam Brown (ex-Deel, ex-DataSnipper)If you’re:A founder building your first GTM motionAn operator trying to make sense of early-stage chaosOr someone tired of polished “playbooks”This episode is for you.🔔 Subscribe for new episodes every Wednesday, 8:30AM CET

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 live in completely different realitiesWhy ABM without signals is just spamWhy RevOps ≠ tooling...and so much more[Key Chapters]00:28 - How VC's and GTM operators actually work together04:19 - Product hot takes from the GTM perspective10:13 - How to get started on talking about GTM on LinkedIn10:45 - Hot takes on sales tactics (outbound, ABM)12:14 - Advice for some of the hottest growth and marketing functions (RevOps and PMM)👥 Featuring insights from:Stefan Ross (ex-Celonis, Pigment | Co-founder, CG Partners)Yannick Marlot (Mooncard, ex-Aircall)Jaap Boven (Smartly, ex-charles)Arnon Shimoni (ex-Paid, now Solvimon)Emilio Turco (n8n, ex-Algolia)Jay Mirpuri (Light)Daniel Rotaru (Qevlar)Alexia Charbonnier (Pivot, ex-Pennylane)Hande Kahraman (ex-DataSnipper)If you’re a:Founder hiring your first GTM teamEarly operator trying to make sense of chaosOr someone tired of polished “playbooks”This episode is for you.🔔 Subscribe for new episodes every Wednesday, 8:30AM CET

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 Pivot, previously at Pennylane) built revenue operations from the ground up in high-growth environments where sales processes, ICP, and reporting were still evolving at the same time.In this conversation, we unpack what RevOps actually means before scale exists and why early operators often have to design systems while the company is still learning how to sell.We talk about:Why RevOps is not a tooling jobHow to design onboarding that actually builds real sales skillsWhat goes wrong when you assume reps already know the basicsHow Pennylane structured early GTM operationsWhy clean data is hard when the motion isn’t stable yetThis episode is for RevOps, Sales Ops, and GTM operators working in early-stage startups, as well as founders hiring their first revenue team and trying to make sense of pipeline, forecasting, and CRM chaos.In the Trenches is a podcast about how revenue actually gets built before playbooks exist.🎧 Follow the show for more operator-led GTM stories🔔 New episodes every Wednesday, 8:30AM CET

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 where buyers are highly technical, risk-aware, and resistant to traditional tactics.In this conversation, we unpack why most “standard” marketing approaches fail in cybersecurity and what actually drives pipeline instead.We talk about:• Why cybersecurity buyers are “professional skeptics”• How real customer language (not marketing language) drives pipeline• How listening to sales calls led to better positioning• Why trust matters more than volume in technical markets• What early-stage teams get wrong when building pipeline• What relevant AI use-cases actually work in cybersecurity marketingThis episode is for GTM operators, marketers, and founders building in technical or enterprise markets where trust is everything and hype doesn’t convert.In the Trenches is a podcast about how revenue actually gets built before playbooks exist.🎧 Follow the show for more operator-led GTM stories🔔 New episodes every Wednesday, 8:30AM CET

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 their first marketing hire when the company was still bootstrapped and around 20 people. Over the next few years, she helped build the product marketing function from the ground up while the company scaled globally and the role itself kept changing.In this conversation, we unpack what PMM really means before specialization exists and why early product marketers often end up owning much more than messaging.We talk about:Why early product marketers always become generalistsWhy PMMs need to “market themselves” internally to have influenceHow the role evolves when the company starts to scaleWhat changes when you go from IC to team leadHow to decide which channels actually deserve focusThis episode is for product marketers, GTM operators, and early startup hires trying to figure out what the role really looks like before the org chart makes sense.In the Trenches is a podcast about how revenue actually gets built before playbooks exist.🎧 Follow the show for more operator-led GTM stories🔔 New episodes every Wednesday, 8:30AM CET

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 conversation, we unpack what it actually takes to move from PLG to enterprise — and the mistakes most startups make along the way.We talk about:Why startups rush into outbound before understanding inboundHow PLG creates real enterprise championsWhat qualification actually looks like in a technical productWhy some deals should be killed earlierHow implementation risk affects sales cyclesThe reality of hypergrowth — and why 8-hour workdays don’t exist in itThis episode is for founders, GTM leaders, and sales operators trying to build repeatable enterprise revenue on top of a PLG foundation.In the Trenches is a podcast about how revenue actually gets built before playbooks exist.🎧 Follow the show for more operator-led GTM stories🔔 Subscribe for new episodes every Wednesday, 8:30AM CET

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 discoveryHow to dig into problems instead of pitching featuresWhy falling in love with your solution kills early-stage momentumWhy early pivots are easier than founders thinkWhy intent beats lead scoring when booking meetingsThe real difference between traction and signalThis is a tactical conversation about building ARR when nothing is repeatable yet.No playbooks. No growth hacks. Just judgment in motion.If you’re a first commercial hire, a founder building your first GTM motion, or navigating unclear message-market fit — this episode is for you.In the Trenches is a podcast about how revenue actually gets built before playbooks exist.

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 uncomfortable shift from harvesting existing demand to creating it.We talk about:Why cost per lead improvements are often a short-term illusionThe difference between demand capture and demand creationWhat actually happens when performance marketing “works” too wellWhy narrowing ICP too early can distort your growth engineThe tension between brand investment and short-term pipeline targetsHow growth teams accidentally optimize themselves into stagnationWhat founders and VCs misunderstand about sustainable GTM expansionIf you’re a growth leader, founding marketer, or operator trying to scale beyond early traction, this episode will challenge how you think about pipeline.In the Trenches is a podcast about how revenue actually gets built before playbooks exist from the operators on the ground, not the boardroom slides.🎧 Follow the show for more operator-led GTM stories🔔 New episodes every Wednesday, 8:30AM CET

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, we unpack what actually causes Customer Success to fail and what operators can do differently.We talk about:Why Customer Success is often set up to fail by mandate, ownership, and incentivesHow automating onboarding too early created more problems instead of leverageWhy dashboards and health scores often hide real GTM issuesThe danger of building CRM processes before understanding what actually worksWhy customers needing Customer Success is often a product or GTM failure, not a winThis episode is for CS leaders and operators and founders who are trying to build user-first foundations.In the Trenches is a podcast about how revenue actually gets built before playbooks exist.🎧 Follow the show for more operator-led GTM stories🔔 Subscribe for new episodes every Wednesday, 8:30AM CET

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 look impressive.We talk about:Why Jay’s first outbound attempts failed and what finally unlocked tractionThe shift from product-pushing to curiosity-led conversationsHow AI is used day-to-day by founding GTM teams (and where it doesn’t help)Why events became one of Light’s most effective pipeline enginesThis episode is for early-stage GTM operators and founders who are building before there’s clarity, structure, or repeatability.In the Trenches is a podcast about how revenue actually gets built before playbooks exist.🎧 Follow the show for more operator-led GTM stories🔔 Subscribe for new episodes every Wednesday, 8:30AM CET

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 operators see that board decks miss, why comparison to outliers breaks decision-making, how partnerships actually work (and when they don’t), and what GTM teams should push back on harder.Chapters00:33 – The disconnect between VC's and operators07:49 – First principles for early startup hires13:58 – The most common mistakes founders make22:59 – How to crack the partnerships motion in a startup (Pigment & Celonis case studies)34:25 – Must-have operational habits for sales37:41 – Leveraging AI in business operations48:22 – Advice for sales🎧 Subscribe to the show for more operator-led GTM stories🔔 Subscribe for new episodes every Wednesday, 8:30AM CET

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 B2B sales.Chapters01:11 – Anatomy of a big-tech enterprise deal (and how to win it)11:04 – Scaling sales from day one at early-stage scaleups23:57 – How outbound sales has evolved26:05 – Lessons learned from M&A28:27 – Using AI in sales today36:35 – Common hiring mistakes in sales38:56 – Advice for GTM operators👉 Follow the podcast for weekly episodes on building GTM from the ground up