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FleetioFleetio

Senior Technical Project Manager, Engineering

Founding Senior Technical Project Manager for Fleetio's Engineering org. Drive delivery of complex Solutions Engineering projects and Platform initiatives for enterprise customers, establishing PM practices from scratch while facilitating technical discussions and executive reporting.

About the job

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.
  • 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 the 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).

Your Experience

  • 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.

Considered a Plus

  • 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.

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

Skills

Project Management, Technical Project Delivery, Stakeholder Management, Risk Management, Dependency Management, Technical Fluency, Enterprise Software, Sow Management, Platform Engineering, DevOps

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