Senior Technical Project Manager, Engineering

Fleetio

1d•Remote

About The Position

Fleetio is seeking a Senior Technical Project Manager to be the first project management hire within its Product and Engineering organization. This role will focus on supporting the Solutions Engineering capability, which delivers custom technical solutions, integrations, and statements of work for large enterprise accounts and strategic deals. The position will also support the Platform Engineering organization with infrastructure and platform initiatives. The ideal candidate will be experienced in building project management practices from scratch, comfortable operating in a less-defined environment, and motivated by delivering impact for major customers. This is a remote opportunity open to candidates in the United States, Canada, or Mexico.

Requirements

7+ years of technical project or program delivery experience.
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.
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.
A self-directed operating style: bring established PM best practices and implement them through your own discovery, thriving in environments where you define how projects are run.

Nice To Haves

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.

Responsibilities

Serve as the founding project manager for the Engineering organization, establishing project cadence, tracking, and reporting practices.
Drive delivery of Solutions Engineering projects for strategic enterprise accounts, including custom plans, integrations, and statement-of-work-based engagements.
Facilitate successful statement of work inception, ensuring proper scoping, deliverables, estimation, and milestone definition.
Support Platform Engineering initiatives with milestone tracking, dependency management, risk management, and stakeholder communication.
Deliver weekly business updates to executive and senior leadership.
Partner with Customer Success and Solutions Consulting to drive clear expectations and strong business cases.
Establish and maintain clear communication plans for all projects.
Assess project management tooling, work around existing gaps, and make recommendations for long-term tooling success.

Benefits

Multiple health/dental coverage options (100% coverage for employee, 50% for family)
Vision insurance
Incentive stock options
401(k) match of 4%
4 weeks PTO (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