Interview #8 of our St. Patrick's Day series, and we're heading to London.

Jack Stenson is the founder of Charrlie, an AI-powered platform that helps corporate venture teams and investors scout, diligence, and manage startups. Think of it as an always-on, evidence-first Chief of Staff for the deals that matter. Built from over a decade of doing that work manually, Charrlie is Jack's answer to a problem he lived every day.

Stay tuned for the remaining interviews over the coming weeks and keep an eye out for our St. Patrick's Day newsletter, where we reveal the full results of our survey with over 120 Irish founders across the globe.

I’m Jack Stenson, an Irish founder building an “agentic Chief of Staff” platform for corporate venture and VCs called Charrlie. I’m from Galway, spend most of my time in London, and I’ve worked in Dublin and New York where I’m still in the innovation communities. Professionally, I’ve spent over a decade at the intersection of strategy, venture, and startup execution: nine years in strategy and innovation consulting (including a spin-off venture I founded in New York), two years as commercial lead for startups, four years in corporate venture at BT Corporate Ventures across areas like drones, health tech, fintech and energy, and as Head of Ireland for the SF VC Plug and Play’s where I supported UK and Irish corporate innovation programmes and invested in Irish startups.

That mix matters because Charrlie is, in many ways, over a decade of work I used to do manually poured into one product. It finds startups globally, pressure-tests claims, pulls together evidence and diligence, and turns a messy dealflow stream with data spewn across spreadsheets, emails and files into one workspace where busy executives can stand behind their decisions. I built Charrlie because I could see AI automating big chunks of that “consulting layer” and because most of the tools people were using were still too ad hoc: you could get an answer, but you couldn’t always trust it, repeat it, collaborate with colleagues, or show your working. I recently had a call with an old client who would have previously paid for a manual eight week scouting process. In 20 minutes Charrlie found the startup they invested in and some others the team didn’t come across at the time. Sure, I automated my old job, but the exciting thing about agentic means you can go further. Charrlie had more in-depth research, suggested questions, and could invite the company to a meeting with the click of a button in 20 minutes. 

Charrlie is an evidence-first platform that helps corporate venture/innovation teams, and investors scout, diligence, and manage engagement with startups. The emphasis is on reliability and provenance: structured workflows, transparent evidence, and outputs you can bring to a meeting. In practice that means: curated scouting that produces a high-quality longlist; due diligence workflows that turn pitch decks, spreadsheets and meeting transcripts into structured analysis and questions; pipeline management that keeps teams aligned; and, over time, more automation around follow-ups, meeting orchestration, and ongoing monitoring. It’s an extra all-knowing person on the team.

I went full-time on Charrlie in September 2025. Since then, the focus has been turning it from a strong product beta into a real business: getting it into the hands of the right buyers, living in the problem, proving repeatable value, and building a foundation that can scale beyond founder-led delivery.

Yes, but not in a starry-eyed way.

I’m optimistic because the underlying demand is real: innovation teams and investors are being asked to do more with less. The bar for diligence is also increasing. When money is tighter and scrutiny is higher, “good story” stops being enough; you need evidence, you need speed, and you need a workflow you can defend. That’s exactly where Charrlie sits.

I’m also optimistic because we’re entering a phase where “AI tools” are no longer novelty software. Buyers are separating: (1) tools that create impressive text, from (2) tools that reliably change outcomes inside an organisation. The second category is harder to build, but it’s where durable companies get made. Charrlie is designed to be in that second category - less about clever answers, more about repeatable, decision-grade work.

The reason my optimism is conditional is simple: execution is everything. There’s plenty of noise in the market and a lot of over-claiming and AI hype. The companies that win won’t be the ones that say “agentic” the loudest; they’ll be the ones that prove they can shorten cycles, reduce risk, and materially improve decision quality without breaking trust. That means staying grounded in customer outcomes, not AI theatre.

My priorities for the next year are about turning Charrlie into a product that’s not just impressive, but indispensable and doing that with discipline.

1) Nail the wedge and make everything easy and delightful for the buyer.
Charrlie can support multiple workflows (scouting, diligence, proactive nudges, organising meetings), but early-stage focus matters. The near-term priority is to win with a wedge that’s painfully clear: a buyer who feels the problem weekly, has budget authority, and can adopt without a six-month internal process. The product needs to map cleanly to their reality: time pressure, credibility pressure, and the need to show evidence. Luckily from years of being on the buyer/investor side of the table (and for those who know me, longer as a cheerleader for founders watching the table) I’ve seen a thousand go-to-market approaches. For example, I’ve designed Charrlie to not need any IT integration to avoid lengthy scrutinisation and make ‘yes’ easy. 

2) Build repeatable distribution.
Most early products don’t die because they’re bad; they die because distribution never becomes predictable. Over the next 12 months, I want a repeatable go-to-market motion that doesn’t depend on me carrying every deal: clearer ICP targeting, sharper messages, stronger proof points, and a process that turns conversations into pilots and pilots into renewals. Right now I’m focused on the turf I worked in - corporate venture/innovation and VC.

3) Improve product reliability
Because Charrlie is evidence-first, quality isn’t a nice-to-have; it’s the product. I had two key litmus tests for finding the right time to begin BD; 1) can it perform better than an LLM at the individual tasks it stitches together, and 2) if I saw it in a previous job would I want to use it? It’s performing beyond expectations on both fronts. Now the focus is continuing to expand and harden the workflows while making sure it’s always explaining where it got its evidence and how it made a call. 

The biggest challenge right now is converting clear interest into repeatable, paid adoption - in other words, crossing the gap between “this is impressive” and “we need this”.

In this category, it’s easy to get pulled into theatre: demos that look great, pilots that are exciting, conversations that feel warm, and then nothing sticks because the tool isn’t embedded into a real workflow with a real owner and a clear success metric.  

So the challenge is building trust at speed. Not just trust in the AI output, but trust in the product as a system: it won’t hallucinate sources, it won’t drift, it won’t hide uncertainty, and it won’t break in the middle of a live decision cycle. That’s why “evidence-first” is more than positioning for me - it’s the line between a tool you play with and a tool you pay for.

There’s also a personal version of that challenge: as a founder, you’re constantly balancing product depth with commercial urgency. If you over-build, you run out of time; if you under-build, you can’t retain customers. The job is to make the right bets, sequence them well, and keep focus.

Being Irish has helped - but in practical ways, not sentimental ones.

First, it’s helped through network effects. Ireland has an unusually strong diaspora in business and tech, and I’ve seen first-hand how quickly a conversation can move when there’s shared context and mutual trust. My work with Digital Irish, the Irish innovation community, in London and New York has been a genuine advantage in terms of introductions and credibility with people who can open doors.

Second, Irishness has helped because Ireland is a small market that forces global thinking early. If you want to build a meaningful tech company, you’re pushed quickly towards international customers and standards. That shapes how you build: you design for export, for enterprise credibility, and for buyers who won’t cut you slack just because you’re local. There’s American-English in Charrlie for a reason!

Third, it’s helped culturally in how I approach relationships: direct, fast rapport, low ego in conversations, and an instinct to be practical rather than performative. That matters when you’re selling something new particularly in areas like venture and corporate innovation where everyone has seen a hundred “next big things”.

But I’m also clear on what being Irish doesn’t do. It doesn’t replace product-market fit. It doesn’t shorten procurement on its own. And it doesn’t substitute for proof. At best, it gets you in the room faster after that, the work has to stand on its own merits.

If I had to summarise it: being Irish has been a tailwind for building relationships and building ambition. The company still lives or dies on execution.

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