[Remote] Senior Technical Project Manager, Engineering

Note: The job is a remote job and is open to candidates in USA. Fleetio is a modern software platform that helps organizations manage fleet operations. The company is seeking a Senior Technical Project Manager to establish project management practices for its Engineering organization, lead strategic Solutions Engineering deliveries, and support complex Platform Engineering initiatives. The role will manage milestones, dependencies, stakeholder communication, risks, executive reporting, and customer-facing technical projects.

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)

Skills

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

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

Company Overview

Company H1B Sponsorship