Case Study: 4 Enterprise VP Leads ($500K ACV) With 1 LinkedIn Post

Abhay Rajaram is the co-CEO at Sendoso, a Direct Mail and Gifting Platform doing over $100M in annual revenue with 250 employees. They raised a total of $175M, including a $100M Series C led by SoftBank in 2021 during peak ZIRP. Abhay joined in 2023 when the business was struggling, first as Chief Business Officer, then stepping into the co-CEO role to lead a full turnaround.In this episode, we talk about what it looks like to lead a SaaS turnaround after raising at peak valuations, what Abhay made the one single metric he rallied the entire company around, how to build trust with your team, board & founder when the company is walking a tightrope, and much more.---We discuss:* Why Abhay deliberately delayed focusing on new business growth when he first joined* The “trust triangle framework” that allowed Sendoso to improve employee NPS by over 50 points in 2.5 years - and why it matters so much* Managing board & investor expectations after a massive 2021 $100m Series C* The two ways to position your company in an “AI-only” world* Abhay’s 3 keys to working with founders (very important when stepping into a C-level role, especially CEO)* The tension between impatience and patience---Connect with Abhay:Abhay’s Linkedin: https://www.linkedin.com/in/abhayrajaram/Sendoso: https://sendoso.com/---Connect with Finn:LinkedIn: https://www.linkedin.com/in/finnthormeier/Project 33 - LinkedIn Agency for CEOs: https://www.project33.io/---My personal takeaways:* Sendoso had product-market fit and $175M raised, but the business was struggling when Abhay joined. Net retention had been masking gross retention issues during the ZIRP years. He made retention the one metric he rallied the entire company around. That meant deliberately delaying focusing on new business growth, at a company that had raised a massive $100M round by Softbank with very high growth expectations. He talks about how he navigated those conversations with the board and investors. Takes courage + discipline + radical candor to pull it off* The trust triangle (by Frances Frei and Anne Morriss): authenticity (are you the real you?), empathy (do you care about people’s success?), logic (is your judgment actually sound?). Abhay’s point: the first two are relatively easy. The third is the one that earns or breaks trust. You have to prove that your strategy works before people truly buy-in. One of Sendoso’s longest-tenured employees came to him after a few months and said “I didn’t know if we could pull it off, but I’m starting to believe now.” That’s the logic part kicking in. It kinda applies to exec brands too, authenticity and empathy get you attention, but it’s the logic (results, proof, specifics) that converts attention into trust* Abhay’s framework for working with founders:* match their speed, what he calls “scrappy mode” vs “scale mode” (btw scrappy does NOT mean crappy)* understand the why behind the 50 ideas they throw at you* earn credibility by actually being deep in the details - founders sniff out surface-level knowledge instantly* They improved employee NPS by 50+ points in 2.5 years. Not by plastering new “values” on their walls, but through boring, good-old consistency over a long period of time: sharing bad news honestly in All-Hands, Abhay personally following up with employees, reaching out for birthdays, giving people shout-outs, celebrating wins HARD while being honest about the current challenges.* Off topic, but his was Abhay’s first podcast EVER. Luckily only uphill from here for him. But the fact that the CEO of a $100m+ company hasn’t done a single podcast until now tells you how heads-down he’s been 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

Tim Soulo is the CMO at Ahrefs. Over the last 10 years, he helped bootstrap them to now well over $100M ARR - with only 160 employees, no sales team, no outbound, and zero marketing attribution.In this episode, we talk about how Ahrefs got to $100M+ ARR while being super scrappy, why the best marketing is built on common sense rather than quarterly plan, and how Tim personally uses Claude Code and Lovable every day to keep Ahrefs lean & mean.---We discuss:* How Ahrefs got to $100M ARR and the list of things they decided NOT to do to focus* How Tim went from “AI skeptic” to vibe coding a full LinkedIn engagement tracker in a single afternoon + other vibe coded tools* Tim’s advice for CMOs who haven’t worked with Claude Code yet* How to run marketing on intuition instead of quarterly planning and reporting* The “battle webinar” format Tim created with Glenn Allsopp* Why every piece of content should be a sales page for your product - and why that sidesteps the “prove ROI on thought leadership” debate---Connect with Tim:Tim’s Linkedin: https://www.linkedin.com/in/timsoulo/Ahrefs: https://ahrefs.com/Podcast: https://ahrefs.com/podcast---Connect with Finn:LinkedIn: https://www.linkedin.com/in/finnthormeier/Project 33 - LinkedIn Agency for CEOs: https://www.project33.io/---My personal takeaways:* Tim didn’t know you were “supposed to” have a sales team, he just assumed people should find your website, sign up, pay (there’s no free trial), and that’s it. Only now, at quite a bit over $100m ARR, are they starting to build out an enterprise sales motion. I think there’s a pattern where ignorance of the “best practices” can often lead to better outcomes* Ahrefs runs marketing with no Google Analytics installed, no attribution setup, no A/B testing, no retargeting, no discounting, no free trial (!!!), no quarterly plans, and no formal reporting. The fact that they’ve been able to scale to the point that they have should already be a massive wakeup call for many CMOs and marketers. Tim’s answer for how they make decisions instead? Intuition and common sense. They decide what to do based on what talent they have, what formats they’re comfortable with, what makes sense, and what sounds exciting. I’ve done 140+ episodes with founders and marketing leaders, and consistently, the companies that are doing the best marketing all seem to prioritize things that *seem fun to them*. 37signals, PostHog, Clay… Tim is another data point here* Tim’s repurposing framework is the opposite of what everyone teaches. Instead of taking a podcast and chopping it into 15 LinkedIn posts, he starts with a LinkedIn post, tests the hook, reads the comments, then turns it into an article incorporating all the feedback, then combines multiple articles into a conference presentation, then discusses that presentation on a podcast. Small → big, not big → small. The bigger the content piece, the more signal you want, and he builds that signal by layering validated, small ideas. Not sure I agree here, Garyvee and Hormozi seem to be counter examples* Tim built a full LinkedIn engagement tracker with Claude Code in one afternoon. It looks at his post engagements, enriches contacts through Apollo, pulls Ahrefs domain data, and shows him which companies are engaging with his content, sorted by ad spend and organic traffic. This is a CMO at a $100M+ company building his own social selling tool after lunch. We discover other vibe coded tools he built* Tim believes every piece of content you publish should be a sales page for your product. “Thought leadership” is overrated. If you publish an article, and within that article you mention a relevant feature of your product, and it gets 10k visits, if people don’t convert, that’s a product problem, not a marketing problem. As a marketer, you did your job: you got the attention of relevant people and showed them something relevant. It sidesteps the entire attribution/ROI debate 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

I’m trying something new. This week, instead of interviewing a founder or executive, I took my Content Director Tobi and we’re going behind the scenes at Project 33 to talk about what we’re currently building, seeing, and experimenting with - across our own content and 15+ executive clients. Thinking of making this a recurring series.---What we discuss:* The group interview format one customer pitched us that could change how we create content* Tobi’s first LinkedIn post goes live* The Clay + Jungler workflow we’re building to turn organic LinkedIn engagement into pipeline* Why TL ads with a $5k/month budget can do more for pipeline than most companies realize* Using Fibbler to connect LinkedIn ad engagement to influenced revenue* The AI-powered ideation workflow we’re building* How/why we cut our client onboarding from 3 to 1 week* The “gold standard” for executive content interviews---Connect with us:Finn’s LinkedIn: https://www.linkedin.com/in/finnthormeier/Tobi’s LinkedIn: https://www.linkedin.com/in/tobias-moelenkamp/Project 33 - LinkedIn Agency for CEOs: https://www.project33.io/ 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

I was recently a guest on the SteadyRev podcast by Austin Futers. I rarely share my own perspectives on my podcast, and I want to change that.In this episode, I talk about how to grow on LinkedIn, what’s good content, how to get ROI from posting, the role of commenting, how I’d start from zero today, and more.---We I talk about:* Why the people who do well on LinkedIn just do the basics really well - and what “the basics” are* The 1 thing that will guarantee that your posts will tank* What a comment I left under someones posts, that hit 130k impressions & 400 likes, actually proves* Why Adam Robinson spends $20 per month in contractors, freelancers, and equipment on his Linkedin content* The false idea that “good” and “bad” content is subjective* Why most successful Linkedin creators are known for one format, not five, and why that matters to you* How I would grow my LinkedIn from 0 today---Some things I believe about LinkedIn:* Every time I get too busy and stop engaging, answering comments, DMing people, my engagement drops, even when I feel like the content is the same quality. I don’t know if that’s the algorithm or just human reciprocity. I just know it’s true, so I just make it part of my day.* If you approach LinkedIn from an ROI standpoint on day 1 and ask how many leads this is going to generate, you’re going to do it wrong. And you’re going to quit before it works. There are people who turned LinkedIn into a legit lead gen channel. Eg. Adam Robinson - but he also spends over $20,000 a month between employees, contractors, and equipment, as well as 10ish hours of his own time every week. But if that’s not you, you should think about LinkedIn as a brand play.* On the flip side, the companies that stick with us for 2+ years almost always hit a moment in the first 3-6 months where it becomes obvious it’s worth it. They generate one great demo, two VPs at a conference walk up to the CEO and mention their content, a partner forwards your videos to their sales team. Stuff like that shows you that this is working.* There is good and bad content. The false belief that it’s all random, that you just need to find what went viral and make it your own take. That is what makes people produce garbage. Your content is the product. When I write something, I ask: would a real person, like a VP of Marketing at a SaaS company doing 10m ARR, someone whose face I can actually picture, find this valuable enough to forward it? If the answer is no, don’t post it. This kind of content takes real work.* Most people who do well are known for one format, not five. There’s almost no one crushing who does a video on Monday, an infographic on Tuesday, text on Wednesday, selfie on Thursday, AND doing all of it well. They’re usually known for one thing and they just get really good at it. Anthony Pierri from Fletch for inforgraphics. Gal Aga for text-only. Chris Walker for video-only back in the day. Everything works. Video, text, infographics, carousels. Everything. But an infographic doesn’t work because it’s an infographic, it works because it’s a great infographic.* The people who do really well do the basics really well. What are the basics? (1) Add value, (2) actually engage with others, (3) be yourself, and (4) keep showing up. Do that for 12-24 months and there’s a very small chance you’ll not at least have built a decent audience that actually likes & trusts you. It’s when people think they can shortcut it, copy what went viral, say something controversial they don’t actually believe, make up stuff that isn’t true, that’s when it falls apart.---Connect with me:LinkedIn: https://www.linkedin.com/in/finnthormeier/Project 33 - LinkedIn Agency for CEOs: https://www.project33.io/---Thanks for interviewing me Austin:LinkedIn: https://www.linkedin.com/in/austin-futers/Podcast: https://www.youtube.com/@AustinFuters 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

Louis Grenier is the founder of Stand The F*ck Out, and one of my recent favorite new follows on LinkedIn.In this episode, we talk about what a real POV actually is (and why 99% of LinkedIn creators don’t have one), why low likes on a post don’t mean what you think they mean, the one marketing truth most companies are completely ignoring in 2026, and much much more.---We discuss:* The 4-step Stand the F*ck Out framework* Differentiation vs. distinctiveness* What a good POV actually is* How he closed six-figure contracts from Linkedin posts that got almost zero engagement* The “100% intensity” thesis to standing out* Marketing truths too many B2B / SaaS companies are forgetting (again)* Spending over $10k on a YouTube miniseries - for B2B??* Why he stopped his podcast after 2 million downloads, and what he’d do differently if he starting a new one today---Connect with Louis:LinkedIn: https://www.linkedin.com/in/louisgrenier/Stand The F*ck Out: https://www.stfo.io/Stand The F*ck Out Book: https://www.amazon.com/Stand-Out-No-Nonsense-Positioning-Business/dp/B0DVH5C8SPThe Roost Community: https://www.stfo.io/roost---Connect with Finn:LinkedIn: https://www.linkedin.com/in/finnthormeier/Project 33 - LinkedIn Agency for CEOs: https://www.project33.io/---My personal takeaways:* A point of view is not a hot take machine. Louis draws a sharp line between having random opinions and having a point of view, and most people on Linkedin are doing the first and calling it the second. A real POV is a consistent thread baked into everything you put out. His: “What you’ve been taught about marketing is mostly wrong. And it’s not your fault because you’re surrounded by b******t.” He never names names, but he calls out the culture of the category.* Louis has closed six-figure deals from posts with almost no likes. His whole LinkedIn philosophy is that posts are just a signal flare. The real value is the one DM it triggers from the right person, and that DM turns into a real conversation, which turns into a deal. He genuinely doesn’t care about like counts, because he’s watched low-engagement posts lead directly to five- and six-figure contracts.* Differentiation vs. distinctiveness are two completely different games. Differentiation is positioning: we solve a problem others don’t.Distinctiveness is branding: we get noticed through assets that could be completely arbitrary (orange profile pic, a swear word in the name). Louis’s point is that past a certain company size, true differentiation is rare, but distinctiveness is always available. Most large companies are working on a differentiation problem that doesn’t exist for them anymore, when distinctiveness is the actually problem.* Nobody buys because they're in pain. They buy when a trigger event causes them to move. Louis's example: back pain for 10 years doesn't get someone to the physio. Grandkids visiting and wanting to walk to the park does. The marketing version: stop obsessing over the pain your customer has and start obsessing over the specific moments in time that make them go from not moving to moving. He believes that a half-page of trigger events beats a 50-page strategy deck every time.* Louis’s writing advice: start by posting a lot, because the feedback loops on Linkedin are fast and you learn quickly what lands. Then move to quality, but don’t over-optimize to audience response, because chasing engagement too hard turns you into someone who only says what people already want to hear. “If you optimize the website too much, it turns into a porn site.” Once you’ve built taste, then you can think about systems and volume. 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

Pranav Piyush is the CEO of Paramark, a marketing measurement platform. Prior to founding Paramark, he was VP Marketing at BILL, VP Growth at Pilot.com and VP Growth at Magento during its acquisition by Adobe. After 10+ years in marketing and growth, he has strong opinions on why most marketers are getting measurement wrong.In this episode, we talk about why the brand vs performance marketing distinction is a false dichotomy, how to measure channels that don’t produce a click, the exact experiment framework Pranav is running at Paramark right now, and much more.---We discuss:* Why complacency killed brand marketing, and what a book from 1923 about broomstick-selling has to do with it* Pranav’s case for why brand marketing is a false concept* The two metrics every new CMO should align on with their CEO and CFO in month #1* Why he believes that for 90% of companies their win rate wouldn’t change if product marketing, enablement, and customer marketing all stopped tomorrow* Pranav’s “10 experiments in year 1” playbook* How Paramark is geo-testing Google competitor ads in New York only - at a small scale* Pranav’s approach to LinkedIn founder branding* Why Pranav’s posts get “only” 20-50 likes but he’s getting inbound from public companies and AI hyperscalers who never liked a single post* The signal that your organic LinkedIn has hit its ceiling and it’s time to go paid---Connect with PranavLinkedIn: https://www.linkedin.com/in/pranavp/Paramark: https://paramark.com/---MentionsScientific Advertising by Claude Hopkins (1923): https://www.amazon.com/Scientific-Advertising-Claude-C-Hopkins/dp/1453821082---Connect with Finn:LinkedIn: https://www.linkedin.com/in/finnthormeier/Project 33 - LinkedIn Agency for CEOs: https://www.project33.io/---My personal takeaways:* Pranav on why brand is suddenly “back”: it’s not that brand became more important, it’s that digital channels saturated. When Google and Meta were growing from zero to billions of users, you could ride those channels’ growth without great creative. Now user growth is tapped out, CPMs are climbing, and the only differentiator left is - again - creative, storytelling, and emotion.* “Brand marketing” as a category is basically just “stuff that’s hard to measure” and Pranav hates that definition. It’s a self-fulfilling vicious cycle, because your measurement framework defines what counts as brand vs. performance, not anything inherent about the channel. A direct mail campaign in the 1920s selling broomsticks through artistic positioning was simultaneously brand AND performance marketing.* The two metrics a CMO should report on: search volume (Google + LLMs + everywhere else people type your name into a search bar) and hand raisers (demo requests, sign ups etc). Everything else is noise* For a new CMO’s first year: plan 10 real experiments, expect 7-8 to fail, and the 1-2 winners will fuel your growth. But the key detail is what counts as an experiment. It’s not think that could bring a 5% optimization gain, he means bets that could drive 50-100% growth. And where do you get ideas for those bets? Research your audience’s media consumption habits. Literally ask them: what’s on your phone home screen, what’s the last podcast you shared, what TV show are you watching? That tells you where to show up.* Pranav’s geo-testing experiment shows you can do incrementality at small scale. They’re launching competitor Google search ads only in New York, keeping every other state as a control. If New York traffic spikes and Texas stays flat, the only variable was the search ads* Pranav gets around 20-50 likes on his LinkedIn posts. It’s good, but far from viral. Others in his space get 10x that. He doesn’t care. Why? Public companies are booking demos. Heads of Paid Media are DMing him after his podcast episodes. An AI hyperscaler reached out who had never liked a single post. Views and likes are not the measure of success when you’re selling into enterprise. If your ICP is CMOs spending $20M-$100M+ on marketing, those people are not impressed by fluffy “10 cool ChatGPT prompts” content. They’re trying to improve their conversations with their CFO. It’s obvious when you say it, but you need to match your content to the buyer, not the algorithm. Then use thought leadership ads to amplify reach beyond your organic network. 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

Jess Cook and Joshua Perk are the VP of Marketing and CEO of Vector respectively, which is a marketing signal platform. They also host “This Meeting Could Have Been a Podcast”, have a combined 50,000 LinkedIn followers, and actually have fun with their marketing.In this episode, we talk about how they built one of the most entertaining podcasts in B2B marketing, how they’re using LinkedIn holistically as a growth channel, and why the things that work best in marketing are always the hardest to measure.---We discuss:* Why their first podcast concept ”Funnel Cake” flopped, and how Jess pivoted the entire show in 24 hours* The prep that goes into filming an entire season for their podcast in 2 days* Why livestreamers get the most applause, and what that means for your content strategy* How Jess uses Claude projects to turn bi-weekly interviews with her founders into LinkedIn posts + how they outgrew that* 58% of followers came from comments, not posts, and what LinkedIn is signaling us with that* How Vector… uses Vector* The micro-events strategy that closed 100% of attendees (yes, actually)---Connect with Jess and Josh:Jess Cook’s LinkedIn: https://www.linkedin.com/in/jesscook-contentmarketing/Joshua Perk’s LinkedIn: https://www.linkedin.com/in/joshuaperk/Vector: https://www.vector.co/This Meeting Could Have Been a Podcast: https://vector.transistor.fm/---Connect with Finn:LinkedIn: https://www.linkedin.com/in/finnthormeier/Project 33 - LinkedIn Agency for CEOs: https://www.project33.io/---My personal takeaways:* When Jess asked marketer friends what they’d want to hear a VP of Marketing and CEO talk about, every answer was basically what was already on their agendas for their 1-on-1s. That has become the show. Some of the best podcast concepts come from what’s already happening, not what sounds good on paper.* $4,000 for a studio day that produces a podcast 80% of open opportunities listen to vs $6,000 in Clay credits for 10,000 cold emails that get a 0.1% response rate Founders get perceived value wrong constantly.* Attribution is a mechanism of control. As companies grow, they introduce attribution, not because it makes marketing better, but because someone five layers removed from the campaign needs to prove their dollars went somewhere. Actual great marketing takes courage, taste, intuition and, partly, doing the opposite of what everyone else / best practice says is the right approach* Jess’s LinkedIn workflow for her founders: interview them every two weeks, run transcripts through AI trained on their voice, hand them posts. Once Josh understood the mechanics, and got addicted to posts doing well, he started writing more of his own content* Every single prospect from their first dinner event converted to a closed deal. They mixed in existing customers to have advocates present, kept it small, and made the whole thing feel like a fun night out rather than a networking event. Now they’re scaling it into the “Ghost Tour Tour” (see their mascot) - a dinner plus a walking ghost tour in whatever city they’re in, with concert-style merch listing all the tour stops* People should be able to become fans from a single clip (Jess learned this from Devin Reed). It happened a couple times that someone saw one 60-second clip, walked up to them at an event, and said “I love your show.” When they asked what their favorite episode is, they didn’t have one - they’ve only seen clips. Which is ok. Don’t aim for subscribers/followers, but moments that stick. 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

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