The Clover Season 3 Calendar
Our Season 3 calendar brings together practical sessions, peer discussions and hands-on workshops for senior technology leaders. The focus stays the same as always: real-world insight from people doing the job, not vendor presentations.
🤖 4th September – AI Working Group: Season 3 Updates
Join the Clover AI Working Group for our quarterly update. We’ll open with a short briefing to frame the discussion, then move into Trevor’s AI Firehose Round-Up — a fast-paced look at the latest developments, tools and trends shaping the AI landscape. Richard Fridge of Adaptive Security will also join to discuss a key trend in AI-driven cyber incidents, and what he suggests you do about it.
🍳 Breakfast Clubs
No set topic, no agenda — just a relaxed start to the day with fellow tech leaders over something delicious. Off the back of great feedback over the summer, we’re continuing these twice a month, alternating between Mayfair and the City:
- City – 8th September, 13th October, 10th November, 9th December
- Mayfair – 22nd September, 20th October, 24th November
💬 18th September – Friday Online Session: Presentation Preparation
Community Manager Jamie Satterthwaite — a former actor and public speaking coach — walks us step-by-step through preparing for a big presentation, with plenty of room for questions and discussion. Plus, a five-minute update from Craig Felton on “The Death of PowerPoint.”
🔒 2nd October – Cyber Working Group: Season 3 Updates
Cybersecurity has never received more attention, or created more complexity. With an explosion of security solutions entering the market alongside an ever-evolving threat landscape, organisations face growing pressure to invest quickly, adapt constantly and stay ahead of emerging risks. But with so many overlapping tools, platforms and vendor promises, how can security leaders ensure their technology investments genuinely align with their cybersecurity roadmap? Join us as we explore the challenge of “security saturation” — from tool sprawl and fatigue to platform considerations and operational effectiveness — and discuss practical ways to build a security strategy that reduces risk without adding unnecessary complexity.
💼 23rd October – AI Risk Insurance w/ Testudo (Online)
Your organisation is deploying AI, but if it gets something wrong, who’s actually covered? As generative AI moves from pilot to production, the liability picture is shifting fast: many traditional policies are quietly adding AI exclusions, Testudo’s own data shows generative AI-related litigation up 137% year on year, and regulators across sectors, financial services included, are taking a much closer look at AI-driven decisions. We’re joined by Testudo, a Lloyd’s of London-backed start-up that came through the Lloyd’s Lab accelerator and specialises in underwriting AI risk, to explore how AI insurance can help enterprises get comfortable with that risk and keep innovating with confidence. Come with your questions, your war stories and your worries, and let’s work through it together.
🛠️ 5th November – Clover Hack: AI Agent Building
For our third Hack, we’re partnering with Dovetail. Each table will build a different AI agent to automate a specific business process — some even drawn from real processes within Clover Connect’s own Microsoft 365 environment, giving everyone a practical, hands-on challenge. Geoff from Dovetail has found that many corporate environments don’t allow teams to experiment freely with AI agents or sandbox environments, which is exactly why these workshops resonate. If you haven’t had the chance to play around with AI as much as you’d like, this one’s not to be missed — spaces are limited.
🚀 6th November – Innovator Showcase: Bring your own (Online)
Members bring the start-up or emerging vendor they rate, and give the room a short look at what it does and why it earned a place in their stack. Peer-picked, no sales pitches.
🤖 11th November – Clover Manchester: Human in the Loop
As AI moves deeper into the way our organisations run, the big question isn’t whether to use it, but where. Where should we automate, where should AI augment the people doing the work, and where must humans stay firmly in control? To mark the launch of the Clover Manchester Hive, we’re bringing senior technology leaders together for an evening of panels, talks and honest conversation about leading through uncertainty while making AI deliver real business impact. There won’t be a perfect playbook on offer, but there will be plenty of peers who’ve wrestled with the same decisions, so come ready to share what’s working, what isn’t, and what’s keeping you up at night.
☁️ 18th November – InTheClouds: AI Impact to Advantage
Our flagship event returns. A year on from “InTheClouds: AI, Hype to Impact,” we’re revisiting the question — has AI delivered on its promise, or has the hype outpaced the reality? More details to follow.
💼 20th November – Microsoft Licensing w/ Bytes (Online)
Microsoft eats a huge chunk of most IT budgets. This session looks at how members can optimise and future-proof their licensing. We’ll be joined by Bytes, who’ll share practical guidance on licence audits, Copilot rollout costs, and where members are finding the biggest savings without compromising security or compliance.
