Founding Senior Technical PM - Enterprise Delivery

Fleetio; United States; Remote; USD 120,000 - 160,000; Full time

Benefits offered by this job

401(k) match

PTO 4 weeks

Remote-friendly since 2012

Job summary

Fleetio is seeking a Senior Technical Project Manager, Engineering, to found and shape our project management practices as part of the first PM hire. You will lead critical enterprise initiatives, coordinating engineers and external contractors where needed, while building a repeatable delivery playbook.

You will report to the VP of Engineering and collaborate with Solutions Engineering and Platform Engineering to drive on-time delivery and measurable impact for major customers.

Qualifications

• 7+ years of technical project or program delivery experience with at least 3 years at senior level.
• Proven ability to run multiple complex projects in parallel across cross-functional teams.
• Track record of building stakeholder alignment and reporting to executive leadership.
• Experience delivering customer-impacting technical work in enterprise software environments (SOW-based or custom-delivery).
• Strong technical fluency: facilitate architecture/integration trade-offs and manage dependencies.
• Excellent written and verbal communication tailored to engineers and executives.
• A self-directed operating style with established PM best practices.

Responsibilities

• Serve as founding PM for the Engineering organization, establishing cadence, tracking, and reporting from day one.
• Drive delivery of Solutions Engineering projects for enterprise accounts, including custom plans and integrations.
• Facilitate SOW inception: ensure scoping, deliverables, estimation, milestones, and accountability.
• Support Platform Engineering with milestone tracking, risk management, and stakeholder communication.
• Deliver weekly business updates to executive and senior leadership, including VP of Engineering.
• Partner with Customer Success and Solutions Consulting to drive clear expectations and strong business cases.
• Establish and maintain a clear project communication plan for all stakeholders.
• Assess tooling; propose setups and improvements with internal support teams.

Skills

Senior project management

Stakeholder alignment

Executive reporting

Cross-functional coordination

SOW-based / professional services

Enterprise software delivery

Technical fluency

Communication

Self-directed PM

Job description

Fleetio is seeking a Senior Technical Project Manager, Engineering, to found and shape our project management practices as part of the first PM hire. You will lead critical enterprise initiatives, coordinating engineers and external contractors where needed, while building a repeatable delivery playbook.

You will report to the VP of Engineering and collaborate with Solutions Engineering and Platform Engineering to drive on-time delivery and measurable impact for major customers.