About Waymark

About this Role

The Director of Implementation serves as the senior operational leader responsible for the end-to-end planning and delivery of Waymark implementations including new geographies, managed care organization (MCO) contract launches, and provider group contract launches. Reporting to the Head of Operations, this leader is accountable for the implementation function, ensuring implementations are delivered on time, in scope, and to a consistently high standard through direct contribution and team management.

This is a hands-on program leadership role for a seasoned project management professional. You will own, build, and run the implementation function's core infrastructure — project plans, workplans, governance structures, status reporting, risk and issue management, and repeatable playbooks — while personally leading the most complex, high-stakes launches. You and your team will be the connective tissue between Waymark's internal teams (clinical, product, engineering, analytics, quality, compliance, and regional market leadership) and our external partners (MCOs, provider groups), managing stakeholders at every level from working teams to executives. This role is a unique opportunity to build and scale the implementation function from the ground up, allowing you to define the strategic and operational roadmap and evolve the team as Waymark grows.

Key Responsibilities

• Implementation Project Planning & Delivery
• Own end-to-end delivery of large, complex, multi-workstream implementations — new market expansions and MCO and provider contract launches — from kickoff through stabilization and handoff to ongoing operations.
• Develop and maintain comprehensive project plans, including detailed workplans, milestone schedules, resource plans, dependency maps, and critical path analyses for each implementation.
• Establish and run implementation governance: project charters, RACI/decision-rights frameworks, working group cadences, executive status reporting, and stage-gate reviews.
• Proactively identify, track, and mitigate risks, issues, and dependencies; drive timely escalation and resolution to keep implementations on schedule and in scope.
• Manage scope, timeline, and budget across concurrent implementations, making clear trade-off recommendations to leadership when priorities conflict.
• Lead post-launch retrospectives and translate lessons learned into improved processes, tools, and playbooks.
• External Stakeholder Management
• Serve as the senior implementation point of contact for MCO and provider partners — leading presentations and joint implementation meetings with clients and prospective clients, aligning on delivery timelines and data exchange requirements, and managing executive-level communications and escalations.
• Guide MCO and provider partners through onboarding, workflow integration, and adoption of Waymark's care model and technology.
• Build durable, trust-based relationships with external partners that position Waymark for contract expansion and long-term partnership success.
• Internal Stakeholder Management & Cross-Functional Leadership
• Orchestrate cross-functional implementation teams spanning clinical, product, engineering, analytics, quality, compliance, regional market leadership, partnerships, and finance — driving alignment on scope, sequencing, and accountability without direct authority.
• Partner with Regional VPs and market leaders to translate contract requirements into executable local launch plans, balancing standardization with market-level flexibility.
• Partner with product and analytics teams to plan and sequence Signal and other data product deployments and facilitate adoption by care teams.
• Champion internal stakeholder alignment, bringing teams along through transparent, proactive communication regarding implementation roadmaps, trade-offs, and fluid deliverables to foster full cross-departmental buy-in.
• Provide clear, concise, and candid status reporting to executive leadership, including progress against milestones, risks, and decisions needed.
• Implementation Infrastructure & Team Leadership
• Build the implementation function's core toolkit: standardized playbooks, templates, launch checklists, success metrics, and operating rhythms that make implementations repeatable, transparent, and scalable.
• Define and track implementation KPIs (time-to-launch, milestone attainment, partner satisfaction) and use them to drive continuous improvement.
• Build, lead, and mentor a high-performing implementation team; develop project management capability across the broader organization.
• Foster a culture of accountability, collaboration, and continuous learning.

Required Qualifications

• Experience: 7+ years in healthcare services implementation, program management, or operations — ideally in tech-enabled care delivery or value-based care — with a track record of leading large, complex, multi-stakeholder implementations from planning through launch.
• Project & Program Management: Deep expertise in formal project management disciplines — workplan development, milestone and dependency management, risk/issue tracking, governance, and status reporting — with demonstrated success delivering complex programs on time and in scope.
• External Stakeholder Management: Proven ability to manage relationships with health plans, provider groups, and other external partners at all levels, including executive sponsors; skilled at navigating competing priorities, negotiating timelines, and managing escalations.
• Cross-Functional Leadership: Demonstrated success leading matrixed, cross-functional teams in fast-paced environments, driving alignment and accountability without direct authority.
• Communication: Exceptional written and verbal communication skills, with the ability to distill complex programs into clear, decision-ready updates for executives and external partners.
• Data & Technology: Experience implementing or deploying technology platforms and using data to guide operational decisions; fluency with project management tools.

Preferred Qualifications

• Passion for improving care for Medicaid patients.
• Experience with Medicaid managed care, including MCO contracting and data exchange.
• Experience launching new markets, contracts, or service lines in early-stage, high-growth environments.
• Formal project management certification (PMP or Lean Six Sigma).
• Track record of building implementation functions, playbooks, and teams from the ground up, with a focus on individual development.

Hiring Range

US Employees in San Francisco/Bay Area, New York City - $160,000 - $229,000

US Employees in Boston, Los Angeles, Seattle, Washington DC - $147,000 - $211,000

US Employees in Arlington, Denver, San Diego, Sacramento - $141,000 - $201,000

US Employees in Albany, Atlanta, Austin, Baltimore, Central/Southern, Charlotte, Chicago, Dallas/Fort Worth, Detroit, Houston, Las Vegas, Miami, Milwaukee, Philadelphia, Portland, Research Triangle, Salt Lake City, Twin Cities - $128,000 - $183,000

US Employees in Baton Rouge, Birmingham, Charleston, Cincinnati, Cleveland, Daytona Beach, Indianapolis, Nashville, New Orleans, Omaha, Phoenix, Pittsburgh, St. Louis, Tampa - $124,000 - $177,000

In addition to salary, we offer a comprehensive benefits package. Here’s what you can expect:

Stock Options: Opportunity to invest in the company’s growth.

Work-from-Home Stipend: A dedicated stipend for your first year to help set up your home office.

Medical, Vision, and Dental Coverage: Comprehensive plans to keep you and your family healthy.

Life Insurance: Basic life insurance to give you peace of mind.

Paid Time Off: 20 vacation days, accrued over the year, plus 11 paid holidays.

Parental Leave: 16 weeks of paid leave for birthing parents after six months of employment, and 8 weeks of bonding leave for non-birthing parents.

Retirement Savings: Access to a 401(k) plan with a company contribution, subject to a vesting schedule.

Commuter Benefits: Convenient options to support your commute needs.

Professional Development Stipend: A dedicated stipend supports professional development and growth.

Offer of employment is contingent upon successful completion of a background check. Employment history and advance degree verification (when applicable) are included as part of the standard background check process. 

Don’t check off every box in the requirements listed above? Please apply anyway! Studies have shown that some of us may be less likely to apply to jobs unless we meet every single qualification. Waymark is dedicated to building a supportive, equal opportunity, and accessible workplace that fosters a sense of belonging – so if you’re excited about this role but your past experience doesn’t align perfectly with every preferred qualification in the job description, we encourage you to still consider submitting an application. You may be just the right candidate for this role or another one of our openings!