Director of Engineering

USA Simpro Software Ltd.; Miami (FL); On-site; USD 190,000 - 260,000; Full time

Benefits offered by this job

Medical, dental, vision package

401k with employer match

Parental Leave

Paid Volunteer Leave

Job summary

Simpro Group in Miami is seeking a Director of Engineering to lead the engineering organization responsible for the product suite, from legacy monolith to microservices and mobile apps, while embedding an AI-first culture.

You will report to executives, shape the technical future, drive platform evolution, and hire top talent globally; travel to offices worldwide is expected.

Qualifications

• Proven track record leading high-performing engineering teams at scale.
• Experience with SaaS product companies and hybrid environments.
• Strong communication and leadership presence.
• Ability to shape technical roadmap with C-suite.
• Advocacy for AI as a core capability multiplier.
• Willingness to travel to offices globally.

Responsibilities

• Build, mentor, and inspire engineering teams.
• Drive ownership and continuous improvement.
• Embed AI into developer tooling and milestones.
• Shape the technical roadmap with Product and executives.
• Oversee migration from AWS EC2 monolith to AWS EKS microservices.
• Attract and retain top engineering talent globally.

Skills

Team leadership

AI in engineering

SaaS familiarity

Hybrid architecture

Strategic thinking

Communication skills

Tools

AWS

Kubernetes

Terraform

Jenkins

Azure DevOps

GitHub Copilot

Job description

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

• 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

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

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.

Welcome to Simpro! Together with AroFlo, BigChange and ClockShark we are one team made up of many nationalities. We are customer‑centric, always putting our customers and teammates first. We take accountability, owning both our innovations and our mistakes. We’re growth‑minded, constantly learning and evolving. And most of all, we celebrate our successes together! Simpro Group provides best-in-class SaaS field service management solutions to trade and field service businesses worldwide. The group comprises four industry‑leading companies, Simpro, AroFlo, BigChange and ClockShark, with offices across North America, Australia, New Zealand and the UK. Simpro, AroFlo & BigChange provide comprehensive field service management software for growth‑minded trade and field service businesses, while ClockShark specializes in time‑tracking and scheduling software solutions. Together, these companies seek to drive businesses forward with solutions that empower teams to work smarter, provide foundations for business scaling, and offer data‑driven insights to fuel decision‑making. Simpro Group serves over 22,000 businesses and over 400,000 users worldwide and has a global workforce of more than 600 employees.

Ready to transform your business? Explore our products at simprogroup.com, aroflo.com, bigchange.com and clockshark.com.