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 them
Genuine conviction about AI in engineering — you've moved teams beyond AI as a curiosity to AI as a core capability multiplier
Strategic technical depth — you can engage credibly with senior engineers on architecture without needing to be the smartest technologist in the room
Experience with SaaS product companies — you understand how engineering decisions compound into product and commercial outcomes
Comfort with complexity — you've navigated hybrid environments combining legacy systems and modern platforms, and you've made that transition well
Strong presence and communication — you lead in person, you build trust quickly, and you make hard decisions with clarity
Collaborative by default — you partner well with Product, Commercial, and the wider leadership team to create alignment, not just agreements
Travel 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 Off
Comprehensive medical, dental, vision package with 100% employer paid options
Additional 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 App
401k/Retirement Plan with 6% employer match
Generous Parental Leave Program
Paid Volunteer Leave Days
Public Holiday Exchange Scheme
Talent Referral Program – get rewarded for referring a friend to join our team!
Diverse training & internal networking opportunities across all of our product lines
Opportunities for career progression and development
Service recognition awards
Click 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.
Skills Required
- Proven track record building and leading high-performing engineering organisations at scale
- Demonstrated experience embedding AI into engineering workflows and product (AI-first mindset)
- Strong technical credibility and ability to engage on architecture across legacy and modern systems
- Experience at SaaS product companies with product-driven engineering outcomes
- Experience managing migrations from monoliths (AWS EC2) to microservices (AWS EKS)
- Experience with multi-platform products (web, mobile) and diverse stacks (C#/.NET, JS frameworks, mobile native/hybrid)
- Strong presence, in-person leadership, and excellent communication skills
- Ability to hire, develop, and retain engineering talent globally
- Based in Miami and able to lead on-site
- Willingness to travel to global offices (including Colombia, UK, Canada, Australia)
Simpro Software Group Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Simpro Software Group and has not been reviewed or approved by Simpro Software Group.
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Wellbeing & Lifestyle Benefits — Feedback suggests a four-day work week is a standout perk that supports work-life balance and can offset slightly lower market pay for some roles.
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Parental & Family Support — Feedback suggests parental leave is notably generous, including extended paid leave for primary and secondary caregivers along with return-to-work support.
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Inclusive Benefits Coverage — Feedback suggests benefits include unusually broad medical-travel support, including a dedicated travel-expense grant for medical procedures, which strengthens perceived inclusivity.
Simpro Software Group Insights
What We Do
Simpro is the total business management software for commercial trade service businesses. From job quoting and scheduling to inventory tracking, invoicing and everything in between, Simpro's smart technology solutions and expert long-term support help businesses build, repair and power their future with complete control over operations. Led by CEO Gary Specter and headquartered in Brisbane, Australia, Simpro supports more than 8,000 businesses and 200,000 users worldwide in the electrical, plumbing, HVAC, security and fire protection industries with 400+ employees in six global offices. In November 2021, Simpro acquired Clockshark, a US-based timesheeting and scheduling platform and AroFlo, an Australian-based job management software provider. Our company is seeing tremendous growth globally and especially in the US. As our team grows, so do our opportunities! Join us! We'd love to have you along for the ride!
Why Work With Us
We are ONE Team. No heroes. No egos. Just a diverse community of passionate people rolling up their sleeves and working hard to deliver exceptional technology, service and outcomes to each and every customer every day. Our values guide us: We are One Team We Innovate We Own It We Care We Have Fun We Understand
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