Group CTO — Deck2 Capital / The Cove

Deck2 Capital buys good businesses with untapped potential and makes them exceptional, combining an operator's hands-on intensity with an investor's discipline. We take majority positions in digital companies that distribute insurance, sometimes with strategic co-investors, and grow and transform our assets via Cove, our wholly-owned operating entity, applying a shared platform of technology, data, talent, and playbooks to each business we acquire. Deck2 was founded in 2024 by CEO Chris Bayley, the Co-Founder of insurtech pioneer and embedded insurance specialist Cover Genius, and executives from other high profile fintech unicorns.

Our singular focus is on growing and improving our companies once acquired. They are always digital companies and usually direct to customer. We will only consider those with genuine high growth, high achievement, D2C experience.

The Group CTO is the technical engine of Deck2's unique "long term hold and operate" model: a hands-on, AI leader who owns the technology agenda across the group, from the diligence that underwrites an acquisition to the integration, consolidation, and growth that follow. This is not a governance seat or a slide-deck role and you'll be judged on deployment, outcomes and results. You'll build and lead versatile engineering, data, and AI teams operating under genuine complexity and real speed-to-market pressure. 90% of Cove are engineers and our approach requires "radical centralisation", an operating model that's unique to Deck2 and lauded operator/investor Bending Spoons.

We're open to a proven CTO,



or an exceptional senior Product or Tech leader ready to step into the mandate; what matters is verifiable evidence you can do great work in a high growth setting. We set the bar high.

We’re looking for these capabilities

- Hands-on AI leadership: Personally set and drive the applied-AI agenda, shipping it into products and operations rather than sponsoring it from a distance.
- Hands-on oversight of acquisitions: Lead technical assessment and due diligence, then own the arc post-close: buy, integrate, assess, consolidate, and grow, turning disparate companies into an integrated platform of assets.
- High-growth D2C product experience: Bring hard-won experience building and scaling direct-to-consumer products with millions of customers and demanding conversion, reliability, and unit-economics bars.
- AI-based operational automation: Re-engineer how the group runs, automating core operations (pricing, supply, support, back-office) so human judgment and machine intelligence reinforce each other.
- Strategic technical oversight: Own architecture, performance, security, and cost across the portfolio, and design the org itself: team structure, the hiring bar, and the leadership needed to deliver outsized results from small, autonomous teams.
- Speed and versatility: Run lean teams that solve hard problems fast, ship relentlessly, and simplify complexity instead of adding to it.

If you recognise the model and you're excited to operate at this high bar, we'd like to hear from you. If you think you could excel over time, don't self-reject.

📌 Group CTO (Sydney)
🏢 Deck2 Capital
📍 Sydney