Co-Founder & CEO, Ivo. San Francisco (ex-New Zealand). Former corporate lawyer who taught himself to code. Building AI contract intelligence for enterprise legal teams.
Why he's VIP: Series B ($55M at $530M valuation) closed January 2026. London and New York offices opened March 2026. Headcount tripling from 97 to 180. Lawyer and engineer founding team with no finance function. Three major financial complexity triggers hit simultaneously.
The play: Lead with the expansion problem, not funding congratulations. Everyone is emailing about the Series B. Reference the London/NY office announcement as the trigger.
The hook: When I saw you opened London and New York last week, the first thing I thought was: does Ivo have someone modeling the FX exposure, UK employer NIC, and entity transfer pricing, or is that landing on your desk between sales calls?
Offer: £3-6K/month Fractional CFO Retainer. Ivo just closed a $55M Series B at $530M valuation with 150+ enterprise customers including Uber, Shopify, IBM, and Canva. Headcount is tripling from 97 to 180. London and New York offices are opening. There is no CFO. The founders are a lawyer and an engineer. This is exactly the company Leo's Fractional CFO service was built for.
Why it works: Min-Kyu is the decision-maker and he has no finance background. The company has the revenue and the raised capital to afford a Fractional CFO easily. The 6x ARR growth means enterprise contract revenue recognition is getting complex fast. Multi-currency exposure from NZ, UK, and US operations adds FX risk they are not managing. Board reporting for Series B investors demands financial sophistication they do not yet have. Start with the free Round Readiness Audit to show the gaps, then propose the 30-Day Sprint (£3K) as the pilot, then move to Fractional CFO retainer.
Risk: Min-Kyu may assume finance is handled by their accountant or that the Series B itself validates they are fine. Leo needs to show the difference between bookkeeping and financial architecture - and why every week without a CFO at this growth rate costs more than the retainer.
Min-Kyu's arc tells a story in a single sentence: "I was a lawyer. I taught myself to code. I cold DM'd a YC partner. I built a $530M company." The willingness to leap from law to engineering - and succeed at it - is the same quality that makes him a founder who responds to sharp, specific pitches. He did not take the safe path. He will not dismiss an unconventional approach from Leo. The challenge is not getting his attention - it is leading with a problem he recognises as urgent rather than congratulations he has heard a hundred times.
Series B, $530M valuation, 97 employees scaling to 180, two international offices opening, no CFO. CEO is the direct decision-maker with no finance background. This is Leo's textbook ICP at peak urgency. Stage: 10/10. Finance literacy: 3/10. Geography: 8/10. Timing: 10/10.
The core gap - no finance function at $530M valuation with international expansion burning - is a financial architecture problem, not a product problem. Min-Kyu is a lawyer. Jacob is an engineer. Neither can run board-level finance. That gap is Leo's exact lane. Start with the free Round Readiness Audit, move to the 30-Day Sprint (L3K), land the Fractional CFO retainer (L3-6K/month).
Each angle is a standalone way in. Jamie should pick the one that feels most natural and lead with massive free value.
What Jamie does: Record a 10-minute Loom walking through castellum.ai. Apply his framework: "Who is this for? Is the customer's problem stated above the fold, or is it all about the product?" Show the gap between Castellum's compliance language ("AML/KYC screening," "watchlists," "false positive reduction") and the actual story ("We correct the UN's sanctions data. Our AI passed the professional certification exam. We stop financial criminals using AI"). The homepage tells the technical story. It should tell the human one.
Why it works: Peter is a compliance expert, not a marketer. He thinks in data quality and regulatory frameworks. Jamie thinks in positioning. The Loom delivers immediate, specific value - showing Peter that his own website undersells his most compelling asset: the founder story. Compliance officers buy from people they trust. The story builds trust faster than any product demo.
What Jamie does: Send a thoughtful LinkedIn message: "Peter - I read your PYMNTS interview. 'We actually correct governments on a regular basis.' That is one of the most audacious things a startup CEO has ever said. But it's buried in a fintech trade publication. That line should be in Forbes, not PYMNTS. Your story - Afghanistan, Treasury, building an AI that passes the CAMS exam - is bigger than the audience that's currently hearing it. I think there's a strategic conversation worth having about that."
Why it works: It names the thing Peter probably already feels. He has done PYMNTS, AlleyWatch, FinovateFall - but none of those reach the general business audience. Jamie is not criticizing his media strategy - he is pointing out that the story deserves a bigger stage. That is flattery and insight combined.
What Jamie does: Create a one-page PDF: "5 Things That Break After an $8M Series A - and the one most compliance tech founders miss." Not about Castellum specifically - about the pattern Jamie sees across post-Series A companies in vertical SaaS. Send it with a personal note: "I wrote this after working with 20+ founders at your exact stage. Number 4 (the messaging ceiling) might be relevant given what I am seeing at Castellum."
Why it works: It positions Jamie as someone who understands the post-Series A challenge without being salesy. The PDF gives Peter something concrete to evaluate. The "Number 4 might be relevant" creates curiosity without being presumptuous.
What Jamie does: Frame the conversation around the CUSO expansion: "You have 130+ credit unions in your investor base through Curql. Their compliance officers don't read TechCrunch. They listen to podcasts recommended by peers and attend industry events. Your story - the former OFAC officer who now helps credit unions stay compliant with AI - is the perfect trust-builder for that audience. But it needs to live on mainstream platforms they encounter outside their compliance bubble."
Why it works: It connects Jamie's value to Peter's most urgent business priority: converting the 130+ credit unions in Curql's network into customers. By framing founder visibility as a customer acquisition tool for the credit union channel, Jamie makes the conversation about revenue, not ego.
Jamie should pick ONE of these and record a 5-10 minute Loom. The goal: deliver so much free value that he has to respond.
Hit multiple channels in the same week. The goal is not to be annoying - it is to be impossible to miss. Each touchpoint delivers value, not asks.
Send a connection request with a short, specific note (not a pitch):
Record the Website Positioning Audit (Loom 1 above). Keep it under 10 minutes. Be specific about the compliance-language-vs-story gap. End with actionable advice. This is the centerpiece of the entire outreach.
Do NOT send it via LinkedIn. Hold it for the email on Day 3-4.
Send a personal email (not from a campaign - from Jamie's personal email) with the Loom embedded:
Look for mutual connections through the fintech/credit union ecosystem. Curql, BTech, Framework Venture Partners all have networks Jamie can tap:
If no response, send a brief follow-up with a new piece of value:
Send a physical package to Castellum's New York office. Pattern interrupt. Ideas:
These are not templates. They are starting points Jamie should rewrite in his own voice. The specific details are what make them work.
Peter Piatetsky is a dream lead for Jamie's Unstuck Growth Intensive. He has the budget ($8.5M Series A just closed), the decision-making authority (he is the CEO), and a crystal-clear positioning problem that Jamie is built to solve: Castellum's story is trapped in compliance niche media when it should be a mainstream business narrative.
The website positioning audit is the way in. Jamie pulls up castellum.ai and shows Peter the gap between compliance jargon and the extraordinary story underneath - Afghanistan, Treasury, correcting the UN, an AI that passed the CAMS exam. That Loom will be impossible to ignore because it reveals something Peter already knows but has not articulated: his website undersells the most interesting company in compliance tech.
Even if Peter does not buy the $15K Intensive immediately, getting Jamie in front of this founder opens the credit union and fintech ecosystem - Curql (130+ credit unions), BTech (12+ banks), Framework (RBC). One conversation with Peter creates access to hundreds of potential referrals. This lead is worth the personal attention.