Senior Technical Project Manager, Engineering - Fleetio

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!

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. 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.

Who You Are

• Experienced: 7+ years of technical project or program delivery experience, with at least 3 years operating at a senior level.
• Proven: Demonstrable track record of building broad stakeholder alignment and trust from scratch, including regular reporting to and interaction with executive leadership.
• Technical: Strong technical fluency, able to facilitate architecture and integration trade-off discussions, manage technical dependencies, and hold your own in rooms with senior engineers.
• Self-Directed: Brings established PM best practices with you and implements them through your own discovery.

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.
• Facilitate successful statement of work inception: ensure the right people are in the room for scoping, deliverables, estimation, and milestone definition.
• Support Platform Engineering initiatives with milestone tracking, dependency management, risk management, and clear stakeholder communication.
• Deliver weekly business updates to executive and senior leadership across product and engineering.
• Partner closely with Customer Success and Solutions Consulting to drive clear expectations and strong business cases.
• Assess project management tooling and make recommendations for long-term success.

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 (16 weeks paid for birthing parent, 4 weeks paid for non-birthing)
• FSA & HSA options
• Short and long term disability
• Community service & professional development funds
• Quarterly wellbeing fund ($150) and business expense stipend ($125)
• Mac laptop + new hire equipment stipend
• Remote working friendly since 2012