Director of PMO

About Wellfit:
Wellfit Technologies is the dental industry's fintech platform, removing financial barriers to care across patients, providers, employers, and payors. We are profitable, growing quickly, and building the workflows, data, and automation that power smarter execution across the healthcare financial ecosystem. We move fast, think practically, and value leaders who bring structure without slowing innovation.

About the Role:
Wellfit is hiring a Director of PMO to lead and mature our enterprise project and program management function. Reporting to the CTO, this leader will be a senior partner to the executive team and the PMO voice on the most strategic programs in the company.

This role is responsible for strengthening execution discipline, improving visibility across strategic initiatives, developing the PMO team, and evolving Wellfit's PMO from traditional delivery tracking toward outcome-based, AI-enabled operating rhythms. The right person operates credibly at the executive level and is equally comfortable getting into the details of project health, risk, and dependencies.

Key Responsibilities:
AI-First PMO Evolution:
Shape the next generation of PMO practices in an AI-enabled organization, applying AI to predictive risk detection, status synthesis, workflow automation, and decision support. Reduce manual data validation and reporting cycles through practical AI-enabled tooling.
Evolve PMO KPIs from activity-based measurements toward business outcomes, value delivery, and organizational impact.

PMO Leadership and Team Development:

• Lead and develop a team of [team size] project and program management professionals, including senior individual contributors with deep institutional knowledge.

• Build a culture grounded in accuracy, ownership, follow-through, and business partnership.
• Set clear expectations and development paths, and grow talent capable of meeting the demands of a fast-growing organization.

• Step in hands-on when needed to support project execution, stakeholder alignment, or coverage gaps.

• Partner with the CTO, executive leadership, and cross-functional stakeholders to ensure alignment across strategic initiatives.
• Communicate project health, risks, dependencies, tradeoffs, and business impact clearly and confidently at the executive level.

• Hold the line on accuracy and process when reporting to senior stakeholders, and escalate proactively when alignment is at risk.

• Translate complex project and program details into concise business narratives.

Enterprise Delivery Governance:
• Evaluate and improve PMO processes, ceremonies, reporting structures, and operating rhythms.

• Strengthen consistency around planning, prioritization, risk management, dependency tracking, and accountability.

• Ensure projects and programs have clear goals, owners, timelines, milestones, and measurable outcomes.

• Help teams balance speed, quality, and visibility without creating unnecessary bureaucracy.

Tools, Reporting, and Visibility:

• Own and improve PMO reporting practices using Jira, Confluence, and related tools.

• Develop dashboards and KPIs that provide meaningful visibility into execution and outcomes.

• Ensure project data is accurate, actionable, and consistently maintained, and use it to surface trends, risks, and bottlenecks.

•Bachelor's degree or equivalent experience.

• 7+ years of progressive project, program, or PMO leadership experience.

• 3+ years leading and developing project or program management teams.

• Experience in fintech, payments, healthcare technology, or another regulated, complex business environment.

• Strong executive communication skills and a track record of building trust across cross-functional stakeholders.

• Hands-on experience with Jira and Confluence or equivalent platforms.

• Demonstrated ability to improve PMO processes, define and track meaningful KPIs, and communicate project health and business outcomes.

•Experience in SaaS or technology-enabled services in regulated industries.

• Experience building or maturing a PMO function in a scaling organization.

• Practical experience using AI tools to improve productivity, reporting, documentation, or decision support.Familiarity with outcome-based delivery metrics beyond traditional activity or velocity tracking.

• PMP, Agile, Scrum, SAFe, or similar certification.

What Success Looks Like:
• In the first 90 days, this leader will build trust with executive and cross-functional stakeholders, assess the current PMO team, processes, tools, and reporting, identify immediate gaps in visibility and ownership, and begin developing a practical roadmap for maturing the function.
• Over time, this leader will create a stronger and more accountable PMO team, establish reporting that is clear and trusted across the business, shift the organization toward outcome-based execution metrics, introduce practical AI-enabled improvements to PMO workflows, and strengthen enterprise execution discipline without slowing innovation.

Why Join Wellfit
• Wellfit is building meaningful technology at the intersection of healthcare, fintech, and access to care. This role reports directly to the CTO with a seat at the executive table, real authority to shape the function, and the opportunity to apply AI in practical ways inside a company genuinely committed to AI-enabled delivery.

$180,000 - $205,000 a year