Senior Technical Project Manager, Engineering

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

Fleetio's Engineering organization is looking for a Senior Technical Project Manager to be the founding project management hire supporting our most strategic technical delivery work. This is a day-zero role: the position does not exist today, and you will be the one to define how world-class project management operates inside our product and engineering organization.

Your primary focus will be supporting our Solutions Engineering capability — a new team that delivers custom technical solutions, integrations, and statements of work for our largest enterprise accounts and most strategic deals. This work is central to Fleetio's growth strategy: landing our biggest prospects and retaining the customers most important to our business. You will secondarily support our Platform Engineering organization, bringing the same delivery rigor to complex, cross-functional infrastructure and platform initiatives.

Your mandate is project management excellence, executed at a senior level: driving accountability, setting and tracking milestones, managing dependencies, maintaining clear communication plans, and ensuring the projects you run land on time. You will bring your own proven playbook — along with the trust and autonomy to implement it from day one.

If you are an experienced technical project manager who is energized by building from scratch, comfortable operating scrappy while you stand up better systems, and motivated by delivering visible impact for major customers, we would love to connect with you!

This is a remote opportunity and is open to candidates located in the United States, Canada, or Mexico.

More About Our Engineering Team and Company

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

Who You Are

You are a seasoned technical project manager with a bias for action and an intrinsic motivation to build — even when the environment isn't perfect yet. You have deep experience delivering in enterprise software organizations, and you pair that with the flexibility and growth mindset to thrive where processes and tooling are still being defined. You run your own discovery, identify what a project needs to succeed, and put it in place.

You are credible in highly technical rooms. Your strength is facilitation: you lead trade-off conversations between engineers and customers, manage technical dependencies with confidence, and translate technical constraints into clear business communication for executives. You build trust quickly across a broad stakeholder base — from individual engineers to executive leadership — and you have a track record of delivering multiple concurrent projects on time, delighting customers along the way.

This role reports to the VP of Engineering.

Your Impact

Serve as the founding project manager for the Engineering organization, standing up project cadence, tracking, and reporting practices from day one.

Drive delivery of Solutions Engineering projects for our most strategic enterprise accounts — custom plans, integrations, and statement-of-work-based engagements involving internal engineers, external contract engineers, or a blend of both.

Facilitate successful statement of work inception: ensure the right people are in the room for scoping, deliverables, estimation, and milestone definition, and hold the project accountable to what was committed.