CTO

Playroll was built to power a borderless economy. We help businesses and their people thrive, no matter where they're based. Since opening our doors in 2022, we've grown alongside the world of distributed work. What started with our Employer of Record solution has expanded into an integrated suite of HR solutions for companies of every size, covering contractor management, global employment, payroll, benefits and compliance. We're looking for talented people to help shape the future of work, today.

We're driven by a constant pursuit of excellence - building better products, better problem-solving, better ways to work across borders. If you thrive in fast-moving environments and want to help build what comes next, join our team to drive meaningful change.

Playroll is looking for a hands on, visionary CTO to lead our Engineering and Technology team. You'll define and drive our technology strategy, scale our multi product platform, and make sure everything we build is secure, reliable, and world class. This role sits at the heart of the Executive Team, owning the vision, architecture, and delivery of our core platform. You'll work closely with the Managing Director and Co Founder, shaping both strategy and execution. It's not just about setting direction - you'll be in the detail where needed, making key technical decisions and ensuring we build for speed, scale, and long term impact. As we grow globally, you'll build and lead a high performing Engineering team that's aligned, ambitious, and excited about the mission: enabling a truly borderless workforce. You'll push innovation, evolve our architecture, and make sure Playroll stays ahead of the curve.

• Define and execute the technology vision and strategy, ensuring architecture and systems scale with Playroll's global ambitions.
• Lead and inspire the Engineering organisation, building high-performing teams and fostering a culture of technical excellence, collaboration, and continuous learning.
• Own product and platform architecture decisions, balancing innovation, security, scalability, and speed to market.
• Partner with Product, Operations, and Commercial leaders to deliver a roadmap that unlocks customer value and competitive differentiation.
• Champion innovation and automation, embedding AI, tooling, and force multipliers that amplify impact across Playroll.
• Represent Playroll externally as a technology leader, building market reputation, attracting top talent, and shaping industry conversations.
• Coach and develop senior technical leaders, creating clear career pathways and succession across the engineering organisation.
• Ensure world class security and compliance, working with legal to maintain SOC 2 / ISO 27001 standards across systems and platforms.

• Demonstrate a growth mindset with a strong passion for learning, innovation, and continuous improvement in fast moving technical environments.
• Bring extensive senior technology leadership experience (CTO, VP Engineering, or equivalent) in high growth, product led organisations.
• Build and scale distributed systems, platforms, and cloud native applications designed for reliability, performance, and global scale.
• Apply hands on expertise with React, TypeScript, NodeJS, and NextJS, deployed within AWS cloud environments.
• Lead SOC 2 and ISO 27001 compliant environments, ensuring secure handling of sensitive personal and financial data.
• Implement modern engineering practices, including CI/CD, test automation, monitoring, and observability at scale.
• Balance long term strategic thinking with hands on technical problem solving and deep architectural understanding.
• Communicate clearly and compellingly, aligning technical and non technical stakeholders around shared outcomes.
• Influence and align cross functional teams through strong storytelling and stakeholder management skills.
• Drive technical excellence while remaining close to execution in high impact, fast paced environments.

• Experience scaling Engineering organisations globally, including hiring, mentoring, and developing diverse, high performing teams.
• Familiarity with complex HR, fintech, or SaaS product ecosystems.
• A strong eye for design and user experience, ensuring technology aligns seamlessly with product and customer needs.
• Demonstrated success leading organisations through periods of hyper growth and rapid change.