You bring one thing keeping you up.
Architecture that won't scale, an AI bet you can't undo, a first senior engineering hire, a vendor that's failing, a migration that's stuck.
Stuck on a technical decision you can't afford to get wrong?
Bring it to two senior CTOs who've already made the same call. A live session, straight talk.
In medicine, Grand Rounds is where difficult cases get reviewed by a panel of specialists. This is the same thing, for technology.
One case. Two vetted CTOs. A direction you can act on.
Architecture that won't scale, an AI bet you can't undo, a first senior engineering hire, a vendor that's failing, a migration that's stuck.
They ask the questions you didn't think to ask yourself, challenge what you've taken for granted, and share how they solved the same thing before, leaving you with a clear direction you can act on.
A short written summary of what the panel found, what they disagreed on, and what they recommend you do next. Clear enough to act on.
When founders bring a case, we don't hand them a generalist. We take a look at their domain and choose the two or three people who have been there:
Not résumés. The decisions, scars and turning points behind them,
so you know
exactly who's reviewing your case.
Fujitsu, Wipro, BT, Sopra Steria, Capita
Neil's first job was computer operator. Thirty-eight years later he led the £500m Digital, Data, Integration, AI & Cloud transformation on BT's £1.5bn programme - finding £800m of hidden value in a 27-petabyte data estate, and was Chief Architect on a national health platform covering 400 million citizens.
In between: CTO for the UK's Home Office and criminal justice system, fractional CTO building a challenger bank from a blank page, startup work spanning Banking, Media, Health & Wellbeing, Security & Public Safety, Retail and Textiles, and the only non-IBM person ever invited to present at IBM's Distinguished Engineers global event.
When an adult sees something new, they pick up the manual. A kid just starts playing with it. Startups need that mentality - read the manual later. Learn, don't fail. Learn, move forward. Try next, try next, try next.
Technology strategy, delivery recovery and engineering leadership
Jerome MacGillivray has spent more than twenty-five years leading global technology teams and delivering digital platforms across regulated, customer-facing and operationally complex environments. His experience spans fintech, retail, travel, cybersecurity, robotics and AI, with roles covering CTO leadership, engineering scale-up, vendor management, platform delivery and technical recovery. He works with founders, boards and leadership teams to make technology decisions clearer, delivery more predictable, and engineering more closely aligned with business priorities.
Jerome helps organisations move from technical uncertainty to practical, well-governed delivery, while identifying where technology can create commercial value and growth.
Good technology leadership is about understanding why something should be built, how it will be delivered, and where it can create new value for the business.
Co-Founder - ex-TransUnion
Carlos spent 14 years inside TransUnion, moving from software developer to DevOps engineer to Product Owner, learning exactly how large financial institutions think, what slows them down, and where the cracks are. Then he left to help founders build things faster than those institutions ever could.
Today he works hands-on with early-stage founders: taking what they've already built, often a scrappy MVP or a lovable prototype, and turning it into something that can actually scale. He's co-founded a fashion reverse logistics platform, built an AI-powered interviewer from scratch including voice, analytics and payments, and cut a founder's lead times by over 50% by re-engineering a handful of manual processes into a clean web application.
His edge is the intersection: he speaks enterprise fluency when a founder needs to close a corporate pilot, and moves like a startup when they need to ship.
The more domain expertise a founder has, the more solid the idea becomes. I come in assuming I know absolutely nothing - and ask every question until the real problem surfaces.
It's like a hackathon for your real business problems. You bring your challenges and bright minds work on them - with no obligation, no pressure. I walked away with perspectives on investors, encryption solutions, and a connection that could directly benefit my product. Honestly, why rely on one mind, when you can have many?
It was an incredibly welcoming space to connect with senior technical minds I wouldn't normally have access to as a non-technical founder. A fantastic opportunity to get real, honest answers to the challenges I was facing - and to walk away with meaningful connections who continue to support me.
CTO Grand Rounds was the best event by far. This is where the founder world and the tech world actually merge, with real introductions instead of leaving people to stay siloed. I was deep in a conversation about cybersecurity and feedback loops - practical advice I could act on immediately.
What I valued most was the mix of CTO styles at the table - some all-in on AI, others more measured. As a founder, you don't want someone else's answer, you want enough perspectives to make your own call. I walked away with two strong contacts - people who hit the mark on build support, strategic fit, and investor credibility. The relaxed format made room for real technical conversation, not just quick decisions. Worth coming back for.
David came to Grand Rounds with two open questions he wanted pressure-tested before taking them to investors: how Euryan should handle LLM and cloud strategy across different client environments, and whether the core product wedge, dynamic FMEA/8D automation, was the right foundation to build the rest of the roadmap on.
I was surprised by the seniority of the CTOs and the breadth of scope of discussion, with great debate around both technical, architectural topics, as well as business planning for future funding rounds.
I find open networking of limited value, but this format has opened my eyes to a potential route that helps Euryan's validation in the future. I am already connecting with both Neil and Edoardo to discover future opportunities to collaborate.
Two cases per session, selected for quality and relevance. Tell us about your technical problem — we'll confirm within a few days.
Book 20 minutes with Jane, who runs Grand Rounds.
Tell her what you're wrestling with, and she'll line up the two CTOs who've solved it before.
If it's not a fit, she'll tell you straight and point you somewhere better.
Pick a timeGrand Rounds is run by Dinarys. We build and scale software. This is how we meet founders and CTOs around an actual problem instead of a cold sales email. Some of the people we meet here become clients later. Most don't. Nobody sells you anything in the room.
If after the session you want hands to build something, we have them and we'll say so plainly. If you don't, the advice stands on its own. Either way, it never changes a word of what the independent CTOs tell you to your face.
Companies with a product in production and a technical problem they haven't been able to solve internally.
Technical crises: architecture not scaling, vendor failure, migration stuck, velocity collapsed, post-acquisition integration chaos, AI strategy without a path. Organisational engineering problems: team restructuring, CTO-founder conflict, engineering hiring breakdown. The panel is strongest on problems at the intersection of technical and organisational - which is most of them.