Senior Technical Project Manager, Engineering

About the role

Fleetio is seeking a foundational Senior Technical Project Manager to establish and lead project management practices within its product and engineering teams. This role will be instrumental in driving the success of critical technical initiatives, particularly those supporting enterprise client solutions and platform infrastructure. You will build and implement best-in-class project management processes from the ground up.

Key facts

What you'll do

• Establish project management frameworks, including cadence, tracking, and reporting, for the engineering organization.
• Oversee the delivery of custom technical solutions and integrations for major enterprise accounts, managing scope, timelines, and deliverables.
• Support platform engineering projects by managing milestones, dependencies, risks, and stakeholder communications.
• Provide regular project status updates to executive and senior leadership.
• Collaborate with customer success and solutions consulting teams to align expectations and ensure successful project outcomes.
• Evaluate and recommend improvements for project management tools and processes.

Requirements

• A minimum of 7 years in technical project or program delivery, with at least 3 years in a senior capacity.
• Demonstrated success managing multiple complex, cross-functional projects concurrently.
• Proven ability to build trust and alignment with a wide range of stakeholders, including executive leadership.
• Experience delivering technical projects within enterprise software settings, ideally with custom or statement-of-work engagements.
• Strong technical understanding to facilitate discussions on architecture, integrations, and dependencies.
• Excellent communication skills, capable of adapting information for technical and non-technical audiences.
• A proactive and self-directed approach to implementing project management methodologies.

Nice to have

• Prior experience in software engineering, infrastructure, or architecture.
• Experience managing teams composed of internal engineers and external contractors.
• Background supporting platform engineering, SRE, DevOps, or infrastructure teams.
• Experience building project management functions or implementing new tools in an organization.
• Familiarity with the fleet, transportation, or logistics industries, or B2B SaaS.

Skills & tools

• Project Management Methodologies
• Stakeholder Management
• Risk Management
• Communication Planning
• Technical Fluency

Practical notes

• Benefits include comprehensive health, dental, and vision insurance, incentive stock options, 4% 401(k) match, 4 weeks of PTO, 12 company holidays plus 2 floating holidays, paid parental leave, FSA/HSA options, disability insurance, and stipends for professional development, wellbeing, and business expenses.
• New hires receive a Mac laptop and equipment stipend.
• Fleetio has been a remote-friendly company since 2012.