Senior Technical Project Manager, Engineering

Fleetio is a modern software platform that helps organizations manage their fleet operations. They are seeking a Senior Technical Project Manager to define and implement project management practices within their Engineering organization, focusing on delivering custom technical solutions for enterprise accounts.

Responsibilities:

• 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
• Support Platform Engineering initiatives with the same delivery discipline: milestone tracking, dependency management, risk management, and clear stakeholder communication
• Deliver weekly business updates to executive and senior leadership across product and engineering, including the VP of Engineering and directors
• Partner closely with Customer Success and Solutions Consulting — the customer-facing owners of day-to-day relationships — to drive clear expectations, well-organized asks, and strong business cases; join customer calls directly when brought in
• Establish and maintain a clear communication plan for every project so no stakeholder is left guessing
• Assess our project management tooling, work effectively around gaps while they exist, and make recommendations on how to set up our tooling for long-term success (with support teams available for configuration)

Requirements:

• 7+ years of technical project or program delivery experience, with at least 3 years operating at a senior level
• Proven ability to run multiple complex projects in parallel across cross-functional teams
• Demonstrable track record of building broad stakeholder alignment and trust from scratch, including regular reporting to and interaction with executive leadership
• Experience delivering customer-impacting technical work in enterprise software environments — ideally including professional services, SOW-based, or custom-delivery engagements with repeat clients
• Strong technical fluency: able to facilitate architecture and integration trade-off discussions, manage technical dependencies, and hold your own in rooms with senior engineers and technical customer stakeholders
• Excellent written and verbal communication, with the ability to tailor project status, risk, and impact to any audience from engineers to executives
• A self-directed operating style: you bring established PM best practices with you and implement them through your own discovery, thriving in environments where you get to define how projects are run
• Hands-on background in software engineering, infrastructure, or architecture
• Experience coordinating blended delivery teams (internal engineers + external contractors)
• Experience supporting platform engineering, SRE, DevOps, or infrastructure organizations
• Experience standing up project management practices or tooling in an organization that didn't have them
• Familiarity with fleet, transportation, logistics, or adjacent B2B SaaS domains