
Hosted by Finn Thormeier · EN

Jack Newton is the founder and CEO of Clio. He started the company in 2008 in Canada, and has since grown it to over 400,000 customers, 2,000 employees, and $400M+ in ARR. They raised a $500M Series G in 2025.In this episode, we talk about applying lessons from having navigated the Cloud Era to the AI Era, why the best SaaS companies are moving from selling software to selling work, what 17 years of building in legal tech teaches you about selling technology to skeptical buyers, and much more.---We discuss:* Jacks learnings from cloud adoption in 2008 and how they translate to AI adoption today* The Slack message Jack sent his CTO the day ChatGPT launched* Why “cool technology is less than half the battle” - and why education and movement-building are the rest* The Steve Jobs approach to product launches* How Clio went from a system of record to a system of action, and why every vertical SaaS founder should be thinking about this* The “Sell Work, Not Software” thesis and how it expanded Clio’s TAM from $20B to $1T* Why your MAUs dropping might actually be a good sign in the AI era* Jack’s advice for first-time SaaS / AI founders* Bonus - How he never missed a single day of running in over 20 years (that’s over 7,000 days in a row)---Connect with Jack:LinkedIn: https://www.linkedin.com/in/jackbnewton/Clio: https://www.clio.com/The Client-Centered Law Firm by Jack Newton: https://a.co/d/0hrcAvfAThe Hard Thing About Hard Things, Ben Horowitz: https://www.amazon.com/Hard-Thing-About-Things-Building/dp/0062273205The Four Steps to the Epiphany, Steve Blank: https://www.amazon.com/Four-Steps-Epiphany-Steve-Blank/dp/0989200507Sell Work, Not Software by Sarah Tavel: https://www.sarahtavel.com/p/ai-startups-sell-work-not-software---Connect with Finn:LinkedIn: https://www.linkedin.com/in/finnthormeier/Project 33 - LinkedIn Agency for CEOs: https://www.project33.io/---My personal takeaways:* AI is compressing a decade into a year: What took cloud adoption 10 years to achieve in legal is happening in 12 months with AI. And the impact is at least an order of magnitude bigger.* “Sell work, not software” is the new SaaS playbook: Clio’s TAM went from $20B (software + payments) to $1T (global legal services spend) by shifting from helping manage work to actually doing the work. Every vertical SaaS founder should be asking: what does my “sell work” version look like?* Education was Clio’s real moat, not the technology. When no one else in legal tech was publishing research or running events, Jack invested in white papers, a conference (ClioCon), keynotes - basically a full-blown education movement to get lawyers comfortable with change. The AI chapter is following the same playbook. He’s touring the country doing live demos of AI features in front of lawyer audiences and showing them what’s possible* Only talk about what’s shipping today: Jack’s approach (inspired by Steve Jobs) is to never announce future products, only demo what customers can use starting today. Very different to most AI startups who overpromise and underdeliver. He believes, long-term, his approach builds lasting trust when everyone else leans on hype* Five of Clio’s six acquisitions started as integrations in their app ecosystem. It’s a brilliant acquisition pipeline because you get to see real usage data, real product-market fit, and how well the team integrates before you ever write a check. Hadn’t thought about an app marketplace as a sourcing strategy for M&A, but it makes a lot of sense* Lower engagement can be a feature, not a bug. If your AI agents are automating work for customers, they might spend LESS time in your app. That breaks every SaaS engagement metric we’ve been taught to optimize for. Jack is actively rethinking what “good” usage looks like when the product’s job is to make itself invisible This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.executivebrand.org

Tony Scott is the CEO of Intrusion, a publicly traded cybersecurity company. Before joining Intrusion in 2021, he served as the Federal CIO of the United States under President Obama, as CIO at VMWare, CIO at Microsoft, CIO at Disney, and as CTO at General Motors. Yes, let that sink in.In this episode, we talk about what Tony learned from working with Bill Gates, Obama, and other world leaders, what it actually takes to land a C-level role at a Fortune 5 company, and why he predicts a major AI disaster is coming in 2026.---We discuss:* The three most stressful weeks of his career (and there were many)* Why he chose to become CEO of a struggling cybersecurity company after serving as the Federal CIO* What Bill Gates really meant when he said “that’s the dumbest thing I’ve ever heard” in meetings* How to actually get a C-level role at a Fortune 5 company* Tips for founders trying to sell into the enterprise or government and the phrases that immediately kill deals* Why he predicts a major AI disaster in 2026* What flying taught him about business* Why someone who’s already “made it” still invests in LinkedIn---Connect with Tony:LinkedIn: https://www.linkedin.com/in/tony-scott-intrusion/Intrusion: https://www.intrusion.com/---Connect with Finn:LinkedIn: https://www.linkedin.com/in/finnthormeier/Project 33: https://www.project33.io/---My personal takeaways:* What gets you a meeting with a CIO at a Fortune 100 company is doing your homework & finding a top 3 organizational problem they're trying to solve. If you come to pitch on innovative tech, you won't get far. And if you start the conversation with "what keeps you up at night?" you've already lost. It shows you did zero research. Tony had a secret signal with his assistants to get rescued from bed vendor meetings. That question was usually the trigger.* Tony's prediction for 2026: there's going to be a very big disaster as a result of the abuse, misuse, or accidental use of AI. Something attention-grabbing. And people are going to go "oh my god, we didn't know that could happen." We're building so much on top of AI without understanding all the points of failure, so when that failure occurs, it'll bring on a bunch of governance and regulatory inspections. It happened with every big invention we've ever had.* What impressed Tony most about interacting with Obama: his questions. He’d ask surprisingly deep questions about technical topics. When Tony’s team would send in a draft white paper (about something cybersecurity related), they’d often overnight get back a markup from the president with all kinds of notes & questions in his handwriting in the margins.* At Microsoft, Tony interfaced with Bill Gates, who would often say "that's the dumbest thing I've ever heard” in meetings. Tony saw it as a test to see if the person had done their homework on their idea/proposal/opinion, and were able to stand their ground. Problems happened when other executives tried to copy that style without context and without being Bill (Tony decided not to emulate it)* None of the things Tony did in his career were direct predictors of the thing he was gonna do next. He went from Sun Microsystems to startups to being the CIO at Microsoft, Disney, VMware, then Federal CIO under President Obama, and finally, CEO of a public cybersecurity company navigating headwinds. Recruiters kept finding him because he had an unusual combination of tech experience + a law degree. That made him stand out. His advice if you want unique opportunities: build a unique skill stack. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.executivebrand.org

Kacie Jenkins is the new Head of Marketing for Claude Code (she joined a couple weeks after this recording). Before joining Anthropic, she was SVP Marketing at Sendoso, VP Marketing at Sourcegraph, and VP Marketing at Fastly, where she helped take the company from Series A to $200M ARR and an IPO.In this episode, we talk about how she built executive brand programs before it was a thing, what actually drives pipeline from LinkedIn, and why anything that sounds corporate is dead on arrival.We discuss:- Why she felt like she had to perform a “TV version” of an executive when she first got promoted- How Fastly built their brand around their CEO’s personality and why they let him swear in F1000 meetings- How to turn LinkedIn DMs into pipeline- Where ghostwriting works & where it breaks- Anything that sounds corporate is dead on arrival- The organic content playbook that made her paid ads perform 50% better- Why developer marketing starts with credibility---Connect with Kacie:LinkedIn: https://www.linkedin.com/in/kaciejenkins/Claude Code (Anthropic): https://www.anthropic.com/---Connect with me:LinkedIn: https://www.linkedin.com/in/finnthormeier/Project 33: https://www.project33.io/---My personal takeaways:1. Corporate is dead upon arrival. Anything that sounds or feels corporate, developers will write off immediately2. The worst thing you can do with a CEO who doesn’t naturally want to do founder brand: try to make them sound more formal or executive-y. Everyone will know because that’s not how they show up in person. At Fastly, their CEO swore all the time. He’d roll into Fortune 1000 meetings and drop an F-bomb when he really meant something. People found it endearing because he was exactly the same in every room. 3. She spent way too long performing a version of herself she thought should be at the table without emotion, very serious, and didn’t ask for help. People told her no one wanted to be around her anymore. What got her there was that she was different than everyone else. She was a writer, a singer, understood how to build communities and scale human connection. 4. Building trust is now more important than it even was 10 years ago. No one will listen to you if they don’t think you’re credible and trustworthy, and they can learn from you. You start with great documentation, technical writing, your subject matter experts sharing in public, and building in public5. Kacie tracks how many connections each exec has with their ICP in target accounts. She puts it on a dashboard. Most CEOs are competitive and they don’t want to be the lowest on the board in front of the whole company. It had a rising tide effect on all other channels.6. Her two tools for mining content ideas: Granola to record & transcribe every meeting, then use AI to surface patterns across calls. And a weekly brain dump call: “What pissed you off this week? What do you think needs to change? What are we hearing in customer calls that shouldn’t be happening to them?”7. Asking for help brings people closer to you. It doesn’t make them think you’re incompetent. Lean into what got you there. You don’t have to have all the answers. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.executivebrand.org

Sydney Sloan was previously the CMO at G2, Drata, and Salesloft, prior to which she spent 16 years at Adobe in a variety of marketing leadership roles. She is currently an advisor at G2 and Executive in Residence at Scale Venture Partners, working with early-stage founders on go-to-market strategy.In this episode, we talk about her biggest lessons, how buyer behavior has fundamentally changed, why brand matters more than ever, and what the 2026 marketing playbook actually looks like.---We discuss:* Why this is the biggest transformation in 30 years of B2B marketing* Buyer research shifted from 29% to 50% on AI chatbots in 4 months, and what that means for you AEO strategy* Why you probably don't need marketing automation the way you used to* “Human in the loop” vs “human in the lead”* How to build brand in 2026 - and why it matters more than ever* The Show-Up-Bigger-Than-You-Are playbook* Reorganizing GTM teams around outcomes, not functions* The advice Sydney would give herself before her first CMO role---Connect with Sydney:* LinkedIn: https://www.linkedin.com/in/sydsloan/* G2: https://www.g2.com/* Scale Venture Partners: https://www.scalevp.com/---Connect with Finn:* LinkedIn: https://www.linkedin.com/in/finnthormeier/* Project 33: https://www.project33.io/---My personal takeaways:1. The shift to AI search is happening faster than we think. Internal G2 data showed that in April 2025, 29% of buyers said they started their research in of of the AI chatbots. By August that number hit 50%, just four months later. In 2026, every company needs to focus on their AEO strategy making sure their brand is the citation source LLMs use.2. Marketing automation as we know it is dead. Companies need to capture high-intent signals using tools like Clay or Common Room, and immediately deploy AI agents to act on them. Speed is the new currency.3. Show up bigger than you are. Sydney got this advice from the CMOs of Okta and Snyk, and used it to scale Drata and Salesloft. You don’t need a massive budget, you need one anchor event or one bold move. At Drata, they bought out every ad space for two blocks around Moscone Center for RSA Conference so attendees couldn’t miss them. At Salesloft, they bought a billboard on Highway 101, but the ROI didn’t come from the traffic driving by, it came from leveraging photos of it online. Big one-off events, if properly leveraged, signal momentum to investors, customers and potential employees.4. We’re entering the “Rick Rubin Economy”, because AI lowers the barrier to entry for content and code, so the only differentiator is taste. You can’t prompt your way to good taste. We need to hire for context and judgment, or leverage advisory boards of influencers who actually understand the market. AI provides the speed, but humans provide the creative direction that determines if anyone actually cares.5. Do we need GTM Architects? Everyone is rushing to hire GTM Engineers and build AI workflows, but in software development, you need engineers and architects. They work at different levels of abstraction. Software Engineers build and maintain software, Software Architects design the system as a whole. We need this for GTM. You need someone to map the strategy, choose the agentic platforms, and decide *what* to automate before you build it. Sydney said she sees this as a separate role, likely sitting in RevOps, not something for the CMO.6. The biggest mistake new CMOs make is obsessing over their domain of the marketing department. Sydney’s advice for someone stepping into a C-level role for the first time: Spend your first 90 days building deep relationships with your peers - the CFO, CRO, CEO. If you don’t understand the business context and have alignment with your peers, the best marketing strategy in the world won’t save you. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.executivebrand.org

Jessica Gilmartin was previously the CMO and CRO at Calendly, Head of Revenue Marketing at Asana, and Head of Product Marketing for Wildfire at Google. Today, she works closely with founders and first-time CMOs from pre-revenue through $100M ARR, advising them on everything from hiring, org design to GTM focus and executive communication.In this episode, we talk about how AI is changing the CMO role and marketing org, where it’s wildly overhyped vs working, and many other topics.Listen on: YouTube, Spotify or Apple PodcastWe discuss:* Why CMO + CRO combo roles usually fail* Why companies now hire CMOs from smaller, scrappier startups* Where AI is truly useful vs pure hype* Why random acts of marketing kill momentum* How Calendly moved from viral PLG to focused enterprise ABM* The real reason CMOs only last 18 months* Why taste, courage, and focus still matter more than toolsConnect with Jessica:* LinkedIn: https://www.linkedin.com/in/jessicagilmartin/Connect with Finn:* LinkedIn: https://www.linkedin.com/in/finnthormeier/* Project 33: https://www.project33.io/My personal takeaways:* We’re overvaluing AI right now: Jessica believes we’ll replace most of our day-to-day work with AI in 5-10 years. But right now board members are mandating AI adoption without specific use cases. The reality is AI is making teams 10-20% more efficient and that it works as an enabler, but not as a replacement. The best use cases she’s seeing are data enrichment for lead prioritization, competitive research for product marketing, and using LLMs as synthetic customer panels.* There are three paths to CMO and CEOs keep hiring wrong. 50% of B2B CMOs come from product marketing, 50% from demand gen, brand CMOs are rare in B2B. CEOs want a unicorn who’s great at both strategic messaging and technical growth. Jessica’s advice: “It’s like asking a backend engineer why they can’t code mobile apps.” Hire for your actual problem right now, not the one you’ll have at $100M.* The only mistake with bad hires is keeping them. Jessica repeats this constantly to clients, that you will always make bad hires. Or you hire people who were good then but aren’t right now. The mistake afterwards is keeping them too long. When you bring the right person on board, your life gets 10-100x easier.* Attribution is broken and that’s okay. You’re getting 70-80% accuracy at best. Jessica’s approach is to use the 80-20 rule. Get directionally correct data so teams understand where they can make impact and then work from there. The bigger issue is that companies wait too long to implement basic data and reporting infrastructure.* Random acts of marketing kill focus. At Calendly, Jessica pivoted the entire team to one thing: repositioning for enterprise customers. Because their CAC was zero for casual users due to viral growth. Marketers hate focus and they want to sprinkle seeds everywhere. But the winning strategy is making big bets, being explicit about trade-offs, and ensuring no one does random acts of marketing. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.executivebrand.org

Ashley Faus is the Head of Lifecycle Marketing at Atlassian and author of Human-Centered Marketing. Besides helping build Atlassian’s thought leadership playbook, over the last year, she built her own executive presence on LinkedIn with now over 22,000 followers.In this podcast, we cover her thought leadership framework.We discuss:1. Ashley’s approach to LinkedIn2. The 4 pillars of thought leadership3. SMEs vs. influencers vs. thought leaders4. The “Internal Influencer” strategy5. How to operationalize employee advocacy6. Understanding trust intent vs buying intent7. And much moreConnect with Ashley:LinkedIn: https://www.linkedin.com/in/ashleyfaus/Human-Centered Marketing book: https://a.co/d/bbd8nV2Atlassian: https://atlassian.com/Connect with Finn:LinkedIn: https://www.linkedin.com/in/finnthormeier/Project 33: https://www.project33.io/Some key takeaways:1. Ashley’s content idea generation prompts: Write about “One question I asked today” and “One question I answered today”. It anchors your content in real experiences rather than generic advice.2. The 4 Pillars Framework: Thought leadership requires credibility (being the source), profile (audience size), prolificness (showing up often), and depth of ideas (saying new things)3. SME vs. thought leader: Subject-matter experts solve gnarly internal problems but lack profile. Thought leaders are disruptive and forward-looking4. A CEO’s job is often to show the market they are steady and predictable. Thought leadership is naturally disruptive, so it can actually be better to have non-C-suite experts as your primary visionaries.5. Build up your internal influencers. Laura Erdem at Dreamdata is a good example. She built an audience of now 50k+ LinkedIn followers by talking about how she actually uses the product in her own deals.6. Don’t fear employees leaving with their audience. Careers are long and the Valley is small. Investing in them creates lifelong partners, customers, and advocates.7. The first thing to NOT do is buy an advocacy platform and force people to register. Focus on the small handful of people who are “willing and able” and pair them with a marketer to help slice and dice their ideas.8. Revenue vs. thought leadership: Revenue belongs with “buy intent”. Thought leadership is about “trust intent” and “learn intent”. If you force it to drive short-term sales, you end up with a thinly veiled sales pitch that breaks trust.9. What “human-centered” marketing means: Most marketers talk about “capturing” leads and “converting” an MQL. Human-centered marketing means solving a problem for an actual person behind the screen, even if it doesn’t fit perfectly into a dashboard. Which is a fundamental mindset shift for most marketers. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.executivebrand.org

Peter Kang runs social at Clay, the GTM Engineering Platform valued at $3.1B. Peter turned LinkedIn into one of Clay’s strongest growth channels, without paid ads, without corporate content, and with a team of one. In 69 weeks, he posted 961 times and grew the Clay company page from ~14K to 120K+ followers.This episode is a deep, tactical breakdown of what actually works on LinkedIn in 2025, and why most B2B advice completely misses the point.What we cover: - Why company pages still matter and what they’re actually good for- How Peter posted 961 times in a year as a team of one (and what broke)- Why video works even when it breaks every rule- Why “taste” is the real moat in modern marketing & how to hire for it- How Clay is activating their founders on LinkedIn and the playbook they’re following- Why LinkedIn runs on ACV, not CPM- How Clay connects social engagement to pipeline- Why optimization advice creates noise, not signal- The authenticity test most content failsConnect with Peter:LinkedIn: https://www.linkedin.com/in/peterhoilkang/Clay: https://www.clay.com/Connect with Finn: LinkedIn: https://www.linkedin.com/in/finnthormeier/Project 33: https://www.project33.io/Chapters:00:00 — Posting 961 times in 69 weeks02:00 — Why company pages still matter04:15 — Founder profiles vs company pages06:00 — Why long-form video works on LinkedIn08:45 — Followers are a vanity metric10:25 — Running social as a team of one13:00 — Clay’s real content portfolio15:00 — How Clay films executive videos18:45 — When to activate founders (and when not to)20:05 — What “taste” actually means23:00 — Hiring creatives with taste26:45 — Why product success drives social success29:00 — Why most LinkedIn copy fails31:00 — LinkedIn vs TikTok vs YouTube35:00 — LinkedIn as scaled ABM36:00 — How to test for authenticity38:30 — Why optimization advice is noise39:00 — Designed-by-committee content40:20 — Clay’s internal prompts and style guides42:00 — Claude vs ChatGPT42:30 — Closing This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.executivebrand.org

Jacco van der Kooij is the founder of Winning by Design. Winning By Design helps customer to design, build and scale their sales efforts. We talk about how GTM strategies have changed over the years, the impact of AI on revenue and many other topics like: - The Future of Go-to-Market Strategies - AI's Role in Revenue Generation - The Importance of Brand Trust - The Evolution of Marketing Skills for Founders - Intuition vs. Data in Marketing - Common Pitfalls in Go-to-Market Strategies Perfect for: CEOs and founders of B2B SaaS companies focused on creating awareness, building trust, and driving pipeline by implementing a proven content process. Don't forget to subscribe to the podcast for more conversations with industry leaders who are reshaping B2B GTM and growth. Connect withJ acco: Jacco’s Linkedin: https://www.linkedin.com/in/jaccovanderkooij/ Winning by Design: https://winningbydesign.com/ Connect with me: LinkedIn: https://www.linkedin.com/in/finnthormeier/ Website: https://www.project33.io/ Chapters Introduction to Winning by Design (00:00:00) The Future of Go-to-Market Strategies (00:03:07) AI's Role in Revenue Generation (00:06:00) Understanding AI's Capabilities (00:08:52) The Importance of Brand Trust (00:12:06) Founder-Led Marketing: A Double-Edged Sword (00:14:54) The Evolution of Marketing Skills for Founders (00:18:08) Data-Driven Decision Making in Sales (00:21:00) Intuition vs. Data in Marketing (00:24:13) Common Pitfalls in Go-to-Market Strategies (00:26:57) Building Relationships in a Digital Age (00:29:46) The Future of Events and Conferences (00:33:01) #linkedin #founderledmarketing #linkedinads #linkedinagency #founderbranding #saas #b2bmarketing #demandgeneration #demandgen #content #b2b #revenue #contentmarketing #performancemarketing #videomarketing #personalbranding

Emir Atli is the CRO of HockeyStack. HockeyStack helps marketing and sales teams prioritize the right campaigns, channels, and accounts at the right time to accelerate revenue. We discuss Hockey Stack's evolution, how Emir uses LinkedIn as a growth channel, and the nuances of marketing strategies like Account-Based Marketing (ABM) and influencer marketing. He also shares practical insights on building a following, handling criticism, and celebrating small wins while staying focused on long-term goals and many other topics like: - His Content Strategy and LinkedIn Engagement - Building a Personal Brand and Effective Outreach - Influencer Marketing: Approaches and Best Practices - Navigating Hate and Building Resilience in Marketing - How to Find Your Voice on LinkedIn Don’t forget to subscribe to the podcast for more deep-dive conversations with industry leaders. If you enjoyed this episode, leave a review and share it with your network. Connect with Emir: Emir on LinkedIn: https://www.linkedin.com/in/emircatli/ Learn more about Hockey Stack: https://hockeystack.com/ Podcast: https://open.spotify.com/show/03CXzsZp7wdqIRVDcqPTFH LinkedIn: https://www.linkedin.com/in/finnthormeier/ Website: https://www.project33.io/ #linkedin #founderledmarketing #linkedinads #linkedinagency #founderbranding #saas #b2bmarketing #demandgeneration #demandgen #content #b2b #revenue #contentmarketing #performancemarketing #videomarketing #personalbranding

In this episode, I chat with Nico Ferreyra, founder and CEO of Default, about the practical side of founder-led marketing and why it’s such a game-changer for startups. Default is helping companies scale faster with an integrated GTM orchestration suite. Nico shares his experience building Default, the challenges of positioning a product, and why founders need to be hands-on when it comes to connecting with their audience. We cover why building an audience early on platforms like LinkedIn can make a huge difference, how sharing insights can drive real engagement, and what Default’s content strategy looks like moving forward. We also talk about: - The Journey of Founder-Led Marketing - Benefits and Challenges of Founder-Led Marketing - The Importance of Building an Audience on LinkedIn Nico's Linkedin: https://www.linkedin.com/in/nicoaferr/ Default: https://www.default.com/ Podcast: https://open.spotify.com/show/03CXzsZp7wdqIRVDcqPTFH LinkedIn: https://www.linkedin.com/in/finnthormeier/ Website: https://www.project33.io/ #linkedin #founderledmarketing #linkedinads #linkedinagency #founderbranding #saas #b2bmarketing #demandgeneration #demandgen #content #b2b #revenue #contentmarketing #performancemarketing #videomarketing #personalbranding