Director of Engineering

Job Context Simpro Group is at an inflection point. As a pioneer of AI-powered field service software now serving over 250,000 users worldwide, we're not done making big changes. We've just launched Simpro Group Lightning — an AI intelligence layer that deploys autonomous agents across field service operations — and we need a Director of Engineering to lead the teams building what comes next. Headquartered in Miami — one of the largest field service software networks in the world — Simpro Group has been transforming how trades and field service businesses operate since 2013. Our platform connects jobs, people, and performance across plumbing, HVAC, fire & security, facilities management, electrical contracting, and more. Trusted by over 2,200 high-growth businesses, we've processed billions in invoiced work and scheduled tens of millions of jobs. We've featured multiple times on the Sunday Times Tech Track 100, and we're just getting started with AI. Simpro Group Lightning represents the next chapter: AI agents that act as virtual business partners, trainers, documentation specialists, and customer success functions — delivering the headcount the economics never previously supported. What You’ll Do THE ROLE This is a senior in-person leadership position based in Miami. You'll lead the engineering organisation responsible for Simpro Group's product suite — from the legacy monolith to our rapidly evolving microservices platform and mobile applications — while embedding an AI-First engineering culture that makes every engineer more capable, every delivery faster, and every customer outcome stronger. You will report to executive leadership and be a key voice in shaping the technical future of one of the world's most recognised field service technology businesses. What You'll Own Team Leadership Build, mentor, and inspire high-performing engineering teams. Drive a culture of ownership, craft, and continuous improvement from squad level to organisational level. Develop engineering managers and create clear career pathways for individual contributors and leaders alike. AI-First Culture Champion the integration of AI into every layer of how we build — from developer tooling and CI/CD intelligence to the AI agents at the heart of Simpro Group Lightning. This isn't about adopting tools; it's about fundamentally changing how engineers work and what they can achieve. Engineering Strategy Partner with Product and the C-suite to shape the technical roadmap. Balance velocity on new capabilities with architectural health across a hybrid legacy and modern stack. Translate business goals into clear engineering priorities. Platform Evolution Oversee the continued migration from AWS EC2 monolith toward AWS EKS microservices. Make the architectural decisions that protect reliability and security while enabling rapid innovation and scale. Delivery Excellence Own engineering velocity, quality, and predictability. Build the processes and metrics that let teams move fast without creating tomorrow's technical debt. Hold the bar on engineering standards without becoming a bottleneck. Hiring & Talent Attract and retain exceptional engineering talent across the globe. Make Simpro Group the kind of engineering organisation that people choose over the obvious alternatives. Be the reason great engineers want to stay. What We're Looking For Proven track record leading high-performing engineering teams at scale — you've built, grown, and developed engineering organisations, not just managed themGenuine conviction about AI in engineering — you've moved teams beyond AI as a curiosity to AI as a core capability multiplierStrategic technical depth — you can engage credibly with senior engineers on architecture without needing to be the smartest technologist in the roomExperience with SaaS product companies — you understand how engineering decisions compound into product and commercial outcomesComfort with complexity — you've navigated hybrid environments combining legacy systems and modern platforms, and you've made that transition wellStrong presence and communication — you lead in person, you build trust quickly, and you make hard decisions with clarityCollaborative by default — you partner well with Product, Commercial, and the wider leadership team to create alignment, not just agreementsTravel to our various offices across the globe including Colombia, UK, Canada, and Australia — this is an on-site leadership role OUR TECHNOLOGY LANDSCAPE You won't be hired for any one technology — you'll be hired for how you lead engineers across all of them. Our current stack spans multiple technologies across product lines: Client Side – Mobile Angular, Kotlin, Swift React, Angular, Ionic/Capacitor Application and Database Stack WebForms, jQuery, C# / .NET 4.6.2 MS SQL, Postgres, MongoDB Cloud Deployment AWS EC2, S3, EKS, AWS ELB Jenkins, Terraform New Relic, Pager Duty, Github, LaunchDarkly Cloudflare, Sentry Additional Services Auth0, Mongo Realm, Twilio Fivetran, Snowflake, Github Enterprise, Redis Engineering Tools Visual Studio Pro, VSCode JIRA, Azure DevOps Pagerduty AI-DLC Github copilot, Claude, Cursor The right leader adapts to the stack in front of them. We value engineering judgement over technology loyalty. What You’ll Bring What We Can Offer You Responsible Time OffComprehensive medical, dental, vision package with 100% employer paid optionsAdditional benefits including Health Savings Account; Flexible Spending Account; Critical Illness Insurance; Hospital Insurance; Accident Insurance; Life Insurance and AD&D; and Disability Insurance available to purchase. Wellness Challenge App, Diabetes Prevention App, and Health Hub App401k/Retirement Plan with 6% employer matchGenerous Parental Leave ProgramPaid Volunteer Leave DaysPublic Holiday Exchange SchemeTalent Referral Program – get rewarded for referring a friend to join our team!Diverse training & internal networking opportunities across all of our product linesOpportunities for career progression and developmentService recognition awardsClick here to find out more about working at Simpro Group! Our Core Values We Are One Team We Are Customer Centric We Are Growth Minded We Are Accountable We Celebrate Success Simpro, AroFlo, BigChange & ClockShark are equal opportunity employers with a best-of-class onboarding program and supportive team environments. This means that we want everyone to feel welcome with us and to provide equal opportunities for everyone, regardless of age, disability, gender reassignment, marriage and civil partnership, pregnancy and maternity, race, religion or belief, sex or sexual orientation, or any other non-performance factor. If you'd like to join a fun and progressive organization, where there are opportunities to develop your career, please apply now with your CV/resume. Please note, no agencies will be accepted in the recruitment of this role.