Principal Project Manager

First Stop Health; Chicago (IL); Remote; USD 100,000 - 150,000; Full time

Job summary

First Stop Health is looking for a Principal Project Manager to lead strategic initiatives across departments in a remote-first environment. This role involves designing project plans, managing resources, and ensuring alignment among stakeholders to achieve measurable outcomes. Join a mission-driven company that prioritizes delightful healthcare delivery and offers a comprehensive benefits package.

Benefits

Flexible paid time off

Summer Fridays

401k employer match

Monthly phone stipend

Qualifications

• 10+ years of experience leading cross-functional projects.
• Strong track record of driving enterprise-wide initiatives.
• Experience leading integrations with third-party systems.

Responsibilities

• Lead end-to-end planning and execution of initiatives.
• Align stakeholders on project scope and success criteria.
• Track and report project KPIs to executive stakeholders.

Skills

Leadership

Communication

Project Management

Strategic Thinking

Stakeholder Engagement

Education

Bachelor’s degree

PMP or PgMP certification

Tools

Project Management tools

Job description

Description

About Us:

On a mission to deliver affordable, delightful healthcare for all, First Stop Health provides connected, whole-person virtual care to employers 24/7 through app, website, or phone in all 50 states. First Stop Health prioritizes an engaging and easy-to-use experience, setting people on healthier journeys through care at multiple stages.

First Stop Health offers a comprehensive benefits package that includes various health and medical coverage options, dental and vision coverage, disability and life coverage, making healthcare easily accessible. For those that choose to waive medical coverage a monthly medical waiver allowance will be provided.

First Stop Health offers a remote-first work environment and flexible paid time off, including Summer Fridays. Furthermore, the employer match 401k plan and monthly phone stipend demonstrate the company's commitment to employee financial well-being. The First Stop Health membership benefit is another added perk for employees and provides our virtual care solutions - Urgent Care, Mental Health, and Primary Care - from their very first day!

Job Description

First Stop Health is seeking a Principal Project Manager to lead high-impact, cross-functional initiatives that span departments. Initially reporting into senior leaders, this role is both a strategic program leader and a cross-company integrator, responsible for driving operational clarity, accountability, and execution excellence across the organization. This individual will be instrumental in aligning teams, removing roadblocks, and ensuring we deliver on our most important priorities.

Responsibilities

• Lead end-to-end planning and execution of company-wide initiatives, with a focus on delivering measurable outcomes aligned to strategic goals
• Act as a thought partner to the CEO, helping translate vision into project plans, roadmaps, and operating cadences
• Align stakeholders across departments on project scope, risks, timelines, and success criteria, with an emphasis on communication
• Design and implement change management strategies to ensure successful adoption of new systems and workflows
• Develop and manage comprehensive project plans, clearly articulating milestones, timelines, dependencies, and risks
• Track and report project and portfolio-level KPIs to executive stakeholders; surface insights to improve decision-making
• Oversee project budgets; identify opportunities for cost efficiency and improved ROI
• Serve as a cross-functional “air traffic controller”, connecting the dots between teams, projects, and priorities
• Coach and model best-in-class project and program management practices to raise the bar across the organization
  
  

What Success Looks Like In The First 90 Days

• A clear, prioritized portfolio of in-flight and upcoming projects is documented and aligned with key stakeholders
• A defined rubric for what projects belong with this role versus managed within departments
• Operating cadences and reporting structures are established for Senior Leadership visibility and cross-functional coordination
• Project management standards and best practices are in motion and adopted across core teams.
• Early wins delivered—examples may include unblocking a high-stakes integration or streamlining execution for an important initiative.
  
  

Qualifications

• 10+ years of experience leading cross-functional projects or strategic programs, ideally in health tech or SaaS
• Strong track record of driving enterprise-wide initiatives with multiple stakeholder groups and visible business impact
• Proven success acting as a trusted partner to C-suite leadership, translating vision into action
• Experience leading integrations with third-party systems or platforms (e.g., EHRs, digital health tools, APIs)
• Skilled in project portfolio management and modern PM tools
• Strong command of KPI definition, reporting tools, and strategic measurement frameworks
• Experience coaching or mentoring teams in project and program management best practices
• Bachelor’s degree required; PMP, PgMP, or other relevant certifications strongly preferred
  
  

First Stop Health is committed to diversity, equity, inclusion, and belonging. Research shows that women, people of color and other historically underrepresented groups tend to only apply to jobs in which they meet all of the job requirements. Unsure if you check every box? Apply. We’d love to consider your unique experiences and how you could make First Stop Health even better.

To learn more about First Stop Health, visit https://www.firststophealth.com/ and if you require any assistance during the application process or have questions, please don't hesitate to contact our talent acquisition team via email at [e-mail].