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Jonathan Moss

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A mix of an entrepreneur and scaled operator skilled at crafting go-to-market strategies, implementing AI across businesses, developing high-performing teams, and optimizing the GTM systems to drive durable growth. The majority of my career has been spent digitizing the physical world by reimagining legacy industries that are heavy on atoms (e.g. physical presence) and transforming them into bits (e.g digitizing the way they operate). My superpower is architecting revenue (traffic to churn) across the go-to-market operating system (e.g. data/insights, processes, and technology) and helping people be a culture catalyst for organizational success. My journey has given me diverse experiences across many different industries, business models, products, and functions at different scales. ➡️ Experience across multiple industries including Software, Healthcare, Retail, Real Estate, Hospitality, Transportation/Logistics, Telecommunications. 🚀 Company Stages: Venture Capital, Private Equity, and Bootstrapped at Pre-Revenue, Seed, Series A, Series C, Series D, Publicly traded 💵 Investment Partners: Sequoia, Lightspeed, Madrona, GTCR, Warburg Pincus, Mubadala Capital, AirBnB, Microsoft, JP Morgan, UBS Asset Management, Softbank and JC2 Ventures 💰Company Revenue: $0-$15B (87% median growth rate; over $1B of capital raised) 👉 $0-$6M+ 👉 $0-$7M+ 👉 $17M-$200M+ 👉 $30M-$100M+ 👉 $80M-$150M+ 👉 $165M-$260M+ 👉 $190M-$2XX (Current role) 👉 $13B-$15B+ 📍Geographies: North America, LATAM, EMEA, and APAC ✅ Team Size: 1-200 🤓 Experience 👉 AI: 5+ years 👉 GTM: 21+ years 👉 Sales: 12 years (B2B); 10 years (B2C) 👉 Revenue Operations: 13 years 👉 Customer Success / Account Management: 9 years 👉 Product: 9 years 👉 Revenue / Sales Enablement: 5 years 👉 Marketing / Demand Generation: 3 years 👉 Business Development/Partnerships: 3 years

Check out Jonathan Moss's verified LinkedIn stats (last 30 days)

Followers
11,366
Posts
4
Engagements
102
Likes
73

What is Jonathan talking about?

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Jonathan Moss's Best Posts (last 30 days)

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AI isn't just changing how we work. It's redefining why we work. Today’s GTM AI Podcast was 🔥. I sat down with Jacco van der Kooij (Founder of Winning by Design) to break down the real impact of AI on modern go-to-market teams. We’re not just automating tasks. We’re redesigning the business blueprint. For years, GTM meant brute-force: hire more reps, blast more emails, pray for pipeline. But that model? It’s broken. We’ve shifted from “growth at all costs” to “profitable, scalable, AI-led growth.” Here’s how Jacco breaks it down: ✅ Product-Led Growth (PLG) gets users in the door. ✅ Human-Led Growth (HLG) builds trust. ✅ AI-Led Growth (AILG) makes it sustainable. When your business starts running like a factory, with AI optimizing every process, you get scale without doubling headcount. And in today’s economy, that’s a superpower. But let’s be clear: humans still matter. A lot. In high-value deals, trust wins. Brand wins. Relationships always win. The magic is using AI to reduce friction, so your people can do what they do best: connect, inspire, and close. If you’re still trying to scale with the same old outbound motion and a bloated sales team, you're not just behind. You're bleeding cash. This episode was a masterclass in the new era of GTM. Listen now, take notes and maybe rethink your 2025 plan. Because the renaissance of business? It’s already here.


16

🔥 “Our leads are down!” 💥 “Conversion rates are tanking!” 🚨 “GTM costs are through the roof!” Everyone’s shouting about the symptoms. But barely anyone’s treating the real disease. Here’s what most exec teams 𝘵𝘩𝘪𝘯𝘬 is happening: ↳ Leads are drying up ↳ Conversion rates are falling ↳ GTM costs are rising So they spin in circles: New vendors. More headcount. AI tools to “optimize.” But here’s the twist: 𝗧𝗵𝗼𝘀𝗲 𝗮𝗿𝗲𝗻'𝘁 𝗰𝗮𝘂𝘀𝗲𝘀…𝘁𝗵𝗲𝘆’𝗿𝗲 𝗲𝗳𝗳𝗲𝗰𝘁𝘀. The 𝘳𝘦𝘢𝘭 cause? We're still running 2020 playbooks in a 2025 world. Layering AI on outdated processes just means… 💩 Same crappy results, now automated. Want change? Start with the system, not the symptoms: ↳ Audit your GTM motions, brutally. ↳ Kill the sacred cows (yes, even that SDR workflow). ↳ Use AI to 𝗿𝗲𝘁𝗵𝗶𝗻𝗸, not just 𝗿𝗲𝗽𝗹𝗶𝗰𝗮𝘁𝗲. You’re not just competing on cost anymore. You’re competing on creativity, agility, and speed. Let’s stop blaming the thermometer when we’re the ones standing in the fire. 🔥 Time to rewrite the playbook. Images and Inspo: Jacco van der Kooij


30

Are AI SDRs a scam? All depends on how you define and use them. But either way they can be a shortcut to terrible results and damage to your brand. Leslie Venetz posted that AI SDRs are a scam. Is she right? Depends. For the longest time people have given an untrained, junior employee the power of a sales engagement tool, a list of contacts, a generic sequence and goal quantity based goal. If you use AI and automation on top of this already broken process you will only 1000x a bad process and you will get bad results. If you are calling that an AI SDR, then she is right.   If you have defined what outcome you want AI to own, have the right foundational (e.g. strategy, ICP/Persona, personalization, data and process) elements in place,  treat AI like your digital teammate through training (e.g. brand, culture, value proposition, etc.), and you have properly trained the person using AI. If you are calling that an AI SDR, then she is not right.   The challenge isn't if AI SDRs are a scam.. it is how you are defining and using them. Neil Weitzman completely agree with you on not worrying about labels and focusing on problems. We all have a lot of them. There is a lot of noise in the market today about the definition of an AI SDR, AI agent, Copilot, and more... which is only confusing people. I see all the time people talking about building AI agents, but when you pull the hood back it is really just an automated workflow with an AI agent like a webscrapper. I have seen great AI agents and swarms of agents working together, advising a few of these companies. They are truly making a difference in fixing GTM which is extremely broken as people are still running old, inefficient playbooks. And yes static playbooks are still a thing. Crazy I know. These companies and their products are focused on the problem of helping sellers sell better/faster/smarter and eliminating the friction that we have put into the buying process. Because we have added a ton of it over time. Focus should always be about what problem you are trying to solve.  But here’s the truth: ↳ If your ICP is vague ↳ your data is trash ↳ and your process is duct-taped together... AI just helps you scale garbage faster. Here are the differences ↳ 𝗔𝘂𝘁𝗼𝗺𝗮𝘁𝗶𝗼𝗻: Sequences, scraping, surface-level personalization. Saves time, but that’s it. ↳ 𝗔𝘂𝗴𝗺𝗲𝗻𝘁𝗮𝘁𝗶𝗼𝗻: AI copilots that help humans run smarter plays with better data. ↳ 𝗔𝗴𝗲𝗻𝘁𝘀: AI that can take action on its own—with a human in the loop for oversight and context. Each has a place. But none are magic wands. If your go-to-market motion is broken, AI won’t fix it. It’ll expose it. And then amplify it. And that is what you will see if you use AI the wrong way, regardless of if you call them AI SDRs or something else.


14

There are core GTM models today, but a new one is emerging fast. Jacco van der Kooij and I unpack this and much more on the GTM AI Pod launching tomorrow. Make sure you tune in. Core GTM Models today: ↳ 𝗣𝗿𝗼𝗱𝘂𝗰𝘁-𝗟𝗲𝗱 𝗚𝗿𝗼𝘄𝘁𝗵 – the self-serve, try-before-you-buy era. ↳ 𝗛𝘂𝗺𝗮𝗻-𝗟𝗲𝗱 𝗚𝗿𝗼𝘄𝘁𝗵 – the classic sales-led motion with reps driving deals. But there’s a new kid on the block: ↳ 𝗔𝗜-𝗟𝗲𝗱 𝗚𝗿𝗼𝘄𝘁𝗵 – and no, it’s 𝘯𝘰𝘵 just automation. AI-led growth is about more than faster emails or automated workflows. It’s about AI actually driving pipeline. → Building your TAM. → Prioritizing accounts. → Personalizing at scale. → And even kicking off conversations. It's not replacing sales. It's reshaping 𝘸𝘩𝘰 does what—and 𝘩𝘰𝘸 𝘧𝘢𝘴𝘵 you can scale. The deeper transformation? AI-led growth makes product-led and human-led growth both more efficient. It’s the glue that connects data to action, and teams to outcomes. We’re not just watching a shift. We’re in the middle of a go-to-market revolution.


13

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