The 2AM Club for CISOs, CIOs and Practitioners

Every vendor on earth is promising to solve "what keeps CIOs and CISOs up at night".  They think it's their category of software, missing dashboard, or shiny new AI feature that will do the trick,

At 2AM, IT and Security leaders are worrying about a very wide range of issues:  Your Board, navigating regulation from your particular sector, funding and budgets or AI governance with a stretched team, helping an ambitious executive understand the risk without sounding like a blocker, or figuring out if that £500k platform implementation you just signed off will properly integrate with your stack as the pitch and testing promised.

Even when everything is running perfectly, and you're beginning to exhale, it only takes a critical supplier to go down or be attacked as a point of entry, a regulator to change the rules, one person to click the wrong email, an AI agent going rogue, or a cyber attack on a critical part of your IT  infrastructure.

And then there are the things more personal in nature: the ability to engage with peers to solve a problem, mentoring a new CISO, a career move, moving up the ladder, progressing your career with a mentor or a quest for learning.

With the growth and development of others at its core, the 2AM Club is where technology leaders discuss what caught them off guard, the decisions that tested them, what they learned along the way and future aspirations, with options to enhance career development.

Because no matter how well prepared you are, there is always something waiting to ruin a perfectly good night’s sleep!
That’s why we created the 2AM Club

We're just starting out building this private network for CIOs, CISOs, and senior technology leaders from organisations of every shape and size, where mentorship,growth and development is at its core as a place to share experiences, compare decisions and learn from people facing similar pressures.
Membership is completely free

It's designed for those unable or unwilling to pay thousands of pounds to join a traditional executive peer group. Alongside candid conversations and career support, members can raise their profile, develop their network and earn money by contributing their expertise to activities funded by our technology Enablers should they choose and is line with their corporate policies.

There are no unsolicited sales pitches or hidden vendor agendas. Sponsored activities are clearly identified, and you decide whether to participate. If you opt in, you will be joining a genuine two-way conversation where your time, experience and opinions are recognised and valued.

Why Join the Club?

1. Peer-to-Peer Sanity Checks

Connect with practitioners across the UK who are dealing with the same operational headaches. Compare notes under Chatham House Rule on what’s working, what failed miserably, and what you’d do differently next time.

2. Mentoring and Growth

Learn from CISOs and CIOs who have done the hard yards and taken the knocks.  Learn how to progress your career based on real life experiences.

    Security & IT budget benchmarks: "Are my peers spending 1% or 6% of IT budget on security?"

    Tool rationalisation metrics: Learn what tools peers are decommissioning.

    Board deck frameworks: Plug-and-play templates that translate technical risk into executive language.

3. Build Your Personal Brand

Step up when you want to and share your hard-earned wisdom on executive panels, jump on podcasts, or contribute to research, building your profile as a pragmatic, forward-thinking leader.  If you wish, there will be opportunities for you to be sponsored for your input. 

Free to join.  What's the Catch?

At its heart is a committed group of CIOs, CISOs, CTOs and senior technology leaders who generously share their experience and provide a trusted sounding board for our peers who are navigating roles that are becoming more complex, visible and demanding.

We are supported by a carefully vetted group of technology Enablers: selected vendors, distributors and service providers that help fund our events, research and community infrastructure.

We will run both closed group meetings for the 2AM Club members, plus more open environments for Enabler participants who will have the opportunity to better understand the challenges we face
Our unshakeable Community Rules

      🚫 No vendor sales pitches in peer sessions if they are invited. Vendor sales decks are 
             not part of member events, even if  Enabler sponsors are present.

      🚫 Zero aggressive follow-ups. Enablers participate as industry supporters, not lead-
             hungry reps.

Ready to Sleep a Little Better?

Whether you're steering digital strategy, managing board expectations, trying to make sense of AI governance, or plotting your next career move,  you don't have to figure it out alone.

Apply for Free Membership: 

Exclusively for practising CIOs, CISOs, CTOs, and Senior Tech Practitioners in any size business

Support our 2AM Club Network: 

Engage with technology decision-makers through authentic dialogue and mutual learning

About the Founder and the 2AM Club

The 2AM Club was founded by Stuart Seymour with a two-fold mission:  To grow and develop the community to support talent in making the next step, and to bridge the gap between what's really bothering s CIOs and CISOs at night with what technology vendors think they need.

By aligning the mismatch, it creates the opportunity for greater understanding on both sides; it brings peers and providers closer to the outcome everyone wants: better decisions, stronger security and trusted relationships.