CTO - Project Based (Start up Consultancy)

Who we are:

Toucanberry Tech is a boutique software consultancy specialising in the reinsurance sector. We build innovative products and services by organizing cross-functional squads covering product, design, engineering, and data. We value autonomy, results, and cutting through bureaucracy.

The role:

You will embed within strategic client programmes as the senior technical authority, shaping direction, influencing executives, and ensuring large-scale transformation is structured, pragmatic, and deliverable.

• Act as the senior technical leader within complex client environments
• Shape and refine technology strategy alongside C-level stakeholders
• Translate business ambition into executable architectural direction
• De-risk large transformation programmes by breaking them into iterative value delivery
• Provide calm, credibly challenge and be grounded in delivery reality
• Ability to quickly identify and resolve any blockers as they arise
• Elevate and protect engineering teams so they can perform at their best
• Ability to report concisely both internally and externally

We are looking for an experienced consultancy technology leader that has worked across multiple delivery engagements with a breadth of solutions knowledge within Cloud and Data.

• Led large-scale digital transformations within consultancy engagements
• Influenced C suite executives including CTO’s, CIO’s and CDO’s amongst others
• Strong architectural judgement across modern cloud and data platforms, with hands-on architectural depth in AWS, Azure, GCP, Snowflake, and Databricks, is essential
• Experience navigating ambiguity in complex organisations
• The ability to balance influence, diplomacy, and commercial awareness
• Experience in a hands-on CTO or senior technology leadership role, including participating in engineering stand-ups and challenging delivery quality
• The ability to understand engineering discussions well enough to identify gaps and challenge technical decisions
• Experience owning solution delivery and ongoing managed service or maintenance support
• Very strong client management skills in senior advisory or delivery leadership roles
• The ability to define pragmatic software release processes for complex delivery environments
• Experience adapting quickly and remaining effective in startup environments where priorities change frequently
• The ability to manage prioritisation effectively in fast-changing startup environments
• Experience in insurance, reinsurance, financial services, or regulated industries is highly valuable.

• Fully Remote
• Outside IR35
• Long term contract