Head of Technology

Formed in 2020, Pretty Technical serves the igaming industry with a range of software-based products, in addition to providing bespoke software development services and teams. We are a remote-first business with a global team, made up of passionate technologists. From Product and Project Managers to Engineers, we provide the full development lifecycle from inception to delivery through to operations. 

Why Pretty Technical? 

• Ambitious and driven business with a clear strategy. 
• Dynamic and fast-paced environment which values those who embrace empowerment. 
• Passionate about the ethos of agile software development. We value people before process, and collaboration over negotiation! 
• Remote-first - and always will be! You can work from home, or wherever you like. 
• Local timezone and flexible working day - structure your day in accordance with your team(s). 
• Collaborative, friendly and rewarding working environment. We’re good people! 

Head of Technology role

We are looking for an experienced technology leader to own the technical delivery and team health of Pretty Technical's entire technology function. You will lead four distinct teams - Front End practice, Tech Leads, QA and Infrastructure - and be responsible for everything from day-to-day sprint execution to long-term platform architecture across our UK and rest of the world projects.

Technologies:

•   Front End engineering - React, Next.js, TailwindCSS, Shadcn.
•   Back End engineering - APIs, integrations, event-driven architectures.
•   Cloud infrastructure - AWS, Terraform, Docker, Kubernetes, CI/CD.
•   Data platform - Data Vault 2.0, real-time processing pipelines.
• Claude / Claude Code

Looking for someone who is passionate about:

• Customer-facing project delivery.
• Thrives on translating business strategy into engineering roadmaps, architecture decisions and delivery execution.
• Has strong leadership and mentoring skills; able to grow engineers from mid-level through to principal, including developing Tech Leads.
• Has deep commercial awareness and enjoys working closely with clients, translating their needs into scoped, well-governed delivery.
• Is passionate about agile principles and what they mean for culture, delivery cadence and ways of working.
• Has a modern approach to the software development lifecycle - CI/CD, IaaC, observability, and security by design.
• Embraces AI-augmented development - actively champions tools such as Claude Code, GitHub Copilot and similar to accelerate team productivity.
• Thrives on ambiguity and embraces the challenge of working in a rapidly growing business, hungry for empowerment and autonomy.
• Has strong soft skills with excellent English, both written and verbal - comfortable representing engineering at exec and client level.
• Naturally takes ownership, makes decisions with conviction, and builds trust across technical and non-technical stakeholders.

Additionally,

• Experience in the gambling / iGaming industry is highly desirable.
• Familiarity with regulated environments such as UKGC or LOTBA (Argentina) is sought after.
• Experience with event-driven and data vault architectures is a bonus.
• Experience working within a remote, globally distributed environment is strongly valued.
• Spanish language skills are considered favourably.

Key Responsibilities

• Own the technology roadmap and delivery cadence across all four teams, ensuring alignment with product strategy and commercial commitments.
• Line-manage and develop Tech Leads and team leads; run regular 1:1s, set SMART performance targets, and support career progression across the function.
• Lead architectural decision-making for our products and ensure infrastructure scalability across AWS environments.
• Champion the use of AI and Agentic development/testing within the technology practice.
• Partner with the Customers to scope, staff and deliver client engagements on time and within budget, maintaining high satisfaction across our different markets.
• Define and uphold technology/engineering standards - code quality, security, testing, documentation - and embed AI tooling into the SDLC.
• Own technology hiring: define role profiles, lead technical interviews and build a diverse, remote-first global team.
• Manage technology budgets, AWS costs and tooling spend; surface trade-offs and build vs. buy recommendations to the exec team.
• Champion regulatory and compliance requirements within the technology team, ensuring certifiable and auditable builds.
• Drive incident response culture - establish runbooks, on-call practices and blameless postmortems across infrastructure and product teams.
• Represent technology in management meetings and with external stakeholders, including clients and regulators.
• Interface directly with senior client stakeholders, acting as a point of escalation and technical authority.
• Create and maintain overarching development architecture, roadmaps and comprehensive documentation.

What we offer

• Competitive salary benchmarked to senior UK technology leadership.
• Fully remote-first culture with a global, collaborative team.
• Real ownership and influence - you will shape the technology function from the ground up.
• Exposure to cutting-edge iGaming products and expanding international markets.
• Budget for professional development, conferences, and tooling.
• Flexible working and progressive HR practices.