Senior Technical Project Manager, Engineering

Fleetio

Senior Technical Project Manager leading project management for engineering at Fleetio. Defining project management excellence in a growing organization with custom solutions for enterprise accounts.

Posted 7/22/2026full-timeRemote • 🇺🇸 United StatesSeniorWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates extensive experience in technical project management, with a focus on delivering complex projects in enterprise software environments. Capable of building stakeholder alignment, facilitating technical discussions, and providing clear communication across all levels of an organization.

Highest-signal resume keywords

Technical Project ManagementStakeholder CommunicationEnterprise Software DeliveryRisk ManagementCross-Functional Team Leadership

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Project Cadence TrackingMilestone DefinitionDependency ManagementTechnical FluencySOW-Based EngagementsEstimation TechniquesIntegration Trade-Off DiscussionsProject ReportingCustomer Impact AssessmentAgile Methodologies

Soft Skills

Excellent Written CommunicationExcellent Verbal CommunicationSelf-Directed Operating StyleRelationship BuildingTrust Establishment

Tools & Technologies

Project Management ToolingStakeholder Communication ToolsReporting SoftwareCollaboration Platforms

Industry Keywords

Solutions EngineeringProfessional ServicesCustom Delivery EngagementsEnterprise AccountsTechnical Dependencies

About the role

Key responsibilities & 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 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

What you’ll need

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.

Benefits

Comp & perks

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 #LI-Remote