About this role.
Fleetio seeks an Engineering Manager to lead two Growth Engineering squads focused on product-led growth outcomes across activation, adoption, engagement, retention, conversion, and monetization. The manager will oversee roughly seven direct reports initially, build the second squad, develop engineers, and recruit additional talent as the organization grows. This role partners closely with Product, Design, Data, Analytics, and Engineering leadership to prioritize experiments and translate customer and usage insights into roadmap decisions. Success requires strong people leadership alongside practical expertise in experimentation, event instrumentation, analytics, SaaS web development, and balancing rapid delivery with engineering quality.
Role DNA
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Job Complexity
5/5Pace & Pressure
5/5Autonomy Level
5/5Communication Load
5/5Salary analysis
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Core skills
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Sample interview questions
I start by aligning teams on a measurable growth objective and a small set of primary and guardrail metrics. I establish a repeatable process for hypothesis formation, instrumentation review, experiment design, statistical analysis, and decision documentation, then use learnings to inform the roadmap rather than treating experiments as isolated tests.
I separate reversible, low-risk experiment paths from foundational work that requires stronger architecture and testing. By defining technical guardrails, feature-flag practices, observability expectations, and clear ownership up front, the team can move quickly while avoiding data-quality issues, reliability regressions, and unmaintainable short-term solutions.
I would create a shared outcome-oriented roadmap, clarify each squad’s domains and interfaces, and establish regular planning and learning rituals across both teams. I would manage dependencies actively, use common metrics and engineering standards, and give individual engineers clear ownership so collaboration does not dilute accountability.
I would verify that event definitions map to meaningful user behaviors, properties are consistently named and documented, and critical events are tested and observable from source through the analytics warehouse. I would also review identity handling, duplicate-event risks, data latency, and whether the metric definitions used by Product, Engineering, and Analytics are consistent.
I use regular one-on-ones, timely feedback, and tailored development plans that connect technical work to customer and business outcomes. I encourage engineers to participate in discovery and experiment reviews, own metrics alongside implementation, and progressively lead initiatives while receiving coaching on judgment, communication, and technical quality.
A little about us…Fleetio is a modern software platform that helps thousands of organizations worldwide manage their fleet operations. Transportation technology is a hot market, and we’re leading the charge with raving fans and new customers signing up every day. We raised $450M in our Series D funding round in March of 2025 and are on an exciting trajectory as a company. Fleetio is also a proud founding member of the Rails Foundation!
More about our team and company:
- Fleetio overview video: https://www.youtube.com/watch?v=YoXyXTFWbkg
- Our careers page: https://www.fleetio.com/careers
Job Description
Fleetio is looking for an Engineering Manager to lead our Growth Engineering squads and accelerate the delivery of customer and business impact through product-led growth. This leader will be responsible for building and developing high-performing engineering teams that own activation, adoption, and monetization initiatives across Fleetio’s customer journey.
You’ll inherit an established Growth squad and continue building out Growth 2, creating a unified engineering organization with a shared growth mission, high technical standards, and a culture centered on experimentation, customer value, and continuous improvements. We’re looking for a leader who views engineering as a strategic driver of growth, not simply a delivery function. You’ll partner closely with Product, Design, Data, and Engineering leadership to shape strategy, identify high-leverage opportunities, and ensure our teams are running high-quality experiments that translate into measurable business outcomes.
This role requires a leader who has directly managed engineering teams running structured growth and experimentation programs and understands how to balance speed with engineering excellence and customer experience. You have deep experience with experimentation, analytics, event instrumentation, and product development. You should also be able to coach engineers on engineering quality and partner effectively with PM, Design, and Data analytics without a long ramp-up period.
If you are an engineering leader with strong technical judgment, strong people leadership skills, and experience leading growth-focused engineering teams in a B2B SaaS environment, we would love to connect with you.
More About Our Engineering Team
- Watch our culture videos: https://fleet.io/culture
- Engineering culture, interview process, and videos: https://www.fleetio.com/careers/engineering
- Fleetio Go overview video: https://www.fleetio.com/go
- More about the Fleetio platform: https://www.fleetio.com/features
- API docs: developer.fleetio.com
- Test drive Fleetio to get an even better feel for what we’re building: https://www.fleetio.com/register
This is a remote opportunity and is open to candidates in the United States, Canada, or Mexico.
Who you are
You are an experienced engineering leader who believes great engineering teams are measured by the customer and business outcomes they create, not simply the features they ship.
You have successfully led growth-focused engineering organizations that use experimentation, analytics, and rapid iteration to improve activation, engagement, retention, monetization, or other key business metrics. You understand that experimentation is more than running A/B tests. It’s about creating fast learning loops, making high-quality decisions, and continuously improving the customer experience.
You possess a blend of engineering leadership, growth experimentation expertise, data fluency, and strong people management skills.
You understand event instrumentation, product analytics, experimentation platforms, and statistical fundamentals well enough to challenge assumptions, ask thoughtful questions, and coach engineers to produce trustworthy data and scalable implementations. You have hands-on familiarity with usage and event analytics tooling such as Snowflake, Segment, Growthbooks, , or similar systems, and can partner with Product and Analytics while coaching engineers on high-quality instrumentation.
You care deeply about engineering excellence.You hold a high bar for quality while continuously improving engineering velocity. You create systems that allow teams to move quickly without compromising maintainability, reliability, or customer experience.
You have experience managing and developing engineers, setting clear expectations, sustaining team engagement, and helping teams deliver measurable outcomes. You communicate clearly, make thoughtful tradeoffs, and create clarity across multiple stakeholders.
Your impact
- Lead both the Growth 1 and Growth 2 engineering squads against a shared growth mission and roadmap.
- Act as a strategic thought partner to Product, Design, Data, and Engineering Leadership, proactively identifying technical opportunities, sequencing work for maximum leverage, and shaping roadmap priorities based on engineering insight and experimentation learnings.
- Optimize engineering execution by proactively identifying dependencies, removing bottlenecks, sequencing work effectively, and ensuring teams deliver value with urgency and focus.
- Help the teams run structured experimentation programs that improve activation, adoption, conversion, engagement, or retention.
- Raise the bar for engineering excellence by coaching engineers on code quality, testing practices, observability, experimentation discipline, and product-minded engineering while enabling teams to ship quickly and confidently.
- Translate experiment results, usage data, and customer insights into engineering priorities and roadmap recommendations.
- Manage roughly 7 direct reports initially, with a model that may scale toward 8 engineers as the squads build out. Coach and develop engineers into exceptional growth engineers with strong product intuition, analytical thinking, experimentation discipline, and a deep sense of ownership.
- Develop and mentor engineers through regular 1:1s, feedback, coaching, and performance conversations.
- Foster a high-performing, accountable engineering culture where engineers are empowered to solve customer problems, challenge assumptions, and continuously improve how the team works. Communicate progress, risks, lessons learned, and trade-offs clearly to stakeholders.
- Recruit, hire, and retain exceptional engineering talent that raises the technical, analytical, and collaborative bar across the Growth organization.
Your experience
- 2+ years of experience leading engineering teams as an Engineering Manager or technical people leader.
- Proven experience leading engineering organizations focused on product-led growth, experimentation, onboarding, activation, adoption, engagement, retention, monetization, or conversion optimization
- Deep experience designing and operating experimentation programs, including A/B testing, guardrail metrics, statistical significance, experiment analysis, and translating learnings into product strategy.
- Hands-on familiarity with analytics and event-data tooling such as Snowflake, Segment, Growthbooks, or similar platforms.
- Experience coaching engineers on experimentation, engineering quality, execution speed, and long-term maintainability.
- Experience partnering closely with Product, Design, Data, and Analytics as a strategic thought partner rather than an execution partner.
- Experience managing SaaS web application engineering teams; Ruby on Rails and React experience preferred.
- Strong track record of developing engineers, setting clear expectations, and helping teams deliver measurable outcomes.
- Excellent written and verbal communication skills.
Benefits
- Multiple health/dental coverage options (100% coverage for employee, 50% for family)
- Vision insurance
- Incentive stock options
- 401(k) match of 4%
- PTO – 4 weeks (increases at year two!)
- 12 company holidays + 2 floating holidays
- Parental leave – birthing parent (16 weeks paid) non-birthing (4 weeks paid)
- FSA & HSA options
- Short and long term disability (short term 100% paid)
- Community service funds
- Professional development funds
- Wellbeing fund – $150 quarterly
- Business expense stipend – $125 quarterly
- Mac laptop + new hire equipment stipend
- Fully stocked kitchen with tons of drinks & snacks (BHM only)
- Remote working friendly since 2012 #LI-Remote
Fleetio provides equal employment opportunities to all employees and applicants and prohibits discrimination and harassment. We celebrate diversity and are committed to creating an inclusive environment for all. All employment is decided on the basis of qualifications, merit and business need.
This application is not intended to and does not create a contract or offer of employment. Employment with Fleetio is at will.
If you have a disability or a special need that requires an accommodation to fill out the online application, please let us know by calling (205) 718-7500.
Annual salary information is not provided for this position. Explore salary ranges for similar roles in our Salary Directory ›
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