Key responsibilities include attending a 2-3 week long paid training program, meeting patients in the community, in the home, and in healthcare facilities to conduct needs assessments, helping patients with health-related social issues, and managing relationships with healthcare facility providers.

You will be part of a care team that includes licensed clinical social workers, pharmacists, and care coordinators. You will also be responsible for creating a directory of community resources, expanding your knowledge of community resources, and advocating for patients.

Minimum qualifications include being highly organized and self-motivated, having sound judgment and the ability to quickly analyze situations, and being able to work with a diverse community in an empathetic, passionate, and professional manner.

Preferred qualifications include having a Community Health Worker certification, being a long-time resident of the Round Lake area, and having experience conducting home visits and outreach.

In addition to salary, Waymark offers a comprehensive benefits package, including stock options, a work-from-home stipend, medical, vision, and dental coverage, life insurance, paid time off, parental leave, retirement savings, commuter benefits, and a professional development stipend.

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Key responsibilities include attending a 2-3 week long paid training program, meeting patients in the community, in the home, and in healthcare facilities to conduct a needs assessment, helping patients with health-related social issues, and managing relationships with healthcare facility providers.

Minimum qualifications include being highly organized and self-motivated, having sound judgment and the ability to quickly analyze situations, and being able to work with a diverse community in an empathetic, passionate, and professional manner.

Preferred qualifications include having a Community Health Worker certification, being a long-time resident of the Kane County area, and having experience conducting home visits and outreach.

In addition to salary, Waymark offers a comprehensive benefits package, including stock options, a work-from-home stipend, medical, vision, and dental coverage, life insurance, paid time off, parental leave, retirement savings, commuter benefits, and a professional development stipend.

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Key responsibilities include attending a 2-3 week paid training program, meeting patients in the community, in the home, and in healthcare facilities to conduct needs assessments and motivate patients to set and achieve health goals. You will also help patients with health-related social issues such as homelessness, substance use, and hunger.

In addition to these responsibilities, you will work with other CHWs and staff to create a directory of community resources, manage relationships with healthcare facility providers, and navigate technology systems to document patient encounters.

Minimum qualifications include being highly organized and self-motivated, having sound judgment and the ability to quickly analyze situations, and being able to work with a diverse community in an empathetic, passionate, and professional manner.

Preferred qualifications include having a Community Health Worker certification, being a long-time resident of the Carol Stream area, and having experience conducting home visits and outreach.

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You will personally own the models, build the reports, and stay deep in the details of our financials every day. As the source closest to the financials, you will be the primary point of contact for the Executive Leadership Team, Board, and investors, providing authoritative answers, updated projections, and rigorous ROI analyses to drive key decisions.

The ideal candidate will have 10+ years of progressive experience in Healthcare Finance, with meaningful exposure to both FP&A and Accounting. Prior VP Finance, Controller, or equivalent role at a growth-stage company is preferred, with direct experience overseeing or managing an accounting function.

Key responsibilities include building and maintaining FP&A systems for tracking and reporting on spend, owning and overseeing the accounting function, including GL creation and maintenance, and ensuring the budget operates efficiently within our Netsuite environment.

In addition to salary, we offer a comprehensive benefits package, including stock options, work-from-home stipend, medical, vision, and dental coverage, life insurance, paid time off, parental leave, retirement savings, commuter benefits, and professional development stipend.

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We are seeking a high-impact People Operations leader to join our team at Waymark. As a People Operations Manager, you will be responsible for owning and strategically scaling our core HR functions. You will thrive in a high-volume, rapidly evolving environment and be essential to driving the success of the People team.

Key Responsibilities:

• Continuous Process Transformation: Proactively identify, design, and implement end-to-end process transformations across the People team to ensure we can meet the demands of Waymark's rapid, sustained growth.
• Data management & HRIS: Configure, maintain, and optimize the Rippling HRIS for accurate data management and reporting. Enter employee changes and ensure payroll and HR systems are updated accordingly. Ensure employee files are maintained in a compliant and efficient manner.
• Payroll & Compliance: Collaborate closely with Finance to audit and execute accurate payroll processing, focusing on timely, accurate, and compliant reporting.
• Elevated Employee Experience & Support: Serve as the trusted, day-to-day subject matter expert, developing scalable and efficient processes to resolve inquiries across benefits and employment policies.
• Onboarding: Manage onboarding compliance steps (I-9s, systems setup, file creation). Ensure consistent and positive new-hire experience across all teams.
• LOAs: Manage LOAs in accordance with applicable state and federal laws, liaising between the LOA vendor, employees, manager and other internal People team members. Guide employees and managers through requirements and timelines.
• Strategic Benefits Program Management: Lead all day-to-day benefits operations (QLEs, 401(k), Open Enrollment), and actively partner with the VP, Head of People to evolve our total rewards strategy to remain highly competitive.
• Policy Ownership: Primary owner responsible for People team policies and SOPs.

Minimum Qualifications:

• 7+ years of progressive HR experience
• Bachelor’s Degree or equivalent experience
• Expert-level knowledge of employee benefits, LOAs, HR Compliance and employment-related laws and regulations
• Experience with HRIS (preferably Rippling)
• Proven track record and desire for process improvement.
• Superior written and verbal communication skills

Preferred Qualifications:

• Healthcare industry experience preferred.
• Combination of start up and established organization experience preferred
• SHRM-CP, SHRM-SCP, PHR, or SPHR Certification preferred

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.

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!

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Key Responsibilities:

• Serve as a dedicated thought partner and strategic advisor to leadership, driving organizational design, talent development, and proactive team performance management.
• Lead high-impact employee engagement strategies, translating survey data into concrete initiatives that champion a culture of belonging, feedback, high performance, and retention.
• Lead and guide managers through core talent processes, including performance management, talent reviews, succession planning, and compensation programs (merit, promotion, and salary structure updates).
• Provide essential coaching to managers on complex employee relations issues, reasonable accommodation requests, and offboarding, ensuring compliance, fairness, and empathy.
• Utilize data and people analytics to continuously identify and implement improvements that enhance the overall employee experience and operational efficiency of the People function.

Minimum Qualifications:

• 7+ years of progressive HR experience including 3+ years as a strategic Business Partner.
• Bachelor’s Degree or equivalent experience.
• Deep understanding of employment-related laws and regulations.
• Required industry experience includes healthcare; value-based care is preferred, and technology experience is a plus.
• Proven track record and desire for process improvement.
• Superior written and verbal communication skills.

Preferred Qualifications:

• Previous compensation administration experience strongly preferred
• Combination of start up and established organization experience preferred
• SHRM-CP, SHRM-SCP, PHR, or SPHR Certification preferred

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About this role:

As a Paralegal at Waymark, you will play a vital role in helping Waymark navigate the intersection of law and healthcare technology, ensuring our operations are compliant and efficient, enabling Waymark to transform care to patients with Medicaid benefits. Reporting to the General Counsel, you will help scale our legal infrastructure, becoming a go-to resource for internal teams on routine legal matters and process improvements.

Key Responsibilities:

• Own responsibility for Waymark’s corporate filings, monitor business licensing, patents, trademarks, and registrations; and maintain corporate records
• Maintain, organise and update legal and compliance related documents, templates, policies and procedures
• Operate and implement an agile legal intake process to manage legal requests that reduces friction for internal stakeholders
• Play a role in reviewing vendor contracts, and updating and maintaining contract management system
• Work cross-functionally with other departments to resolve issues and complete substantive tasks with moderate guidance.
• Conduct state and federal regulatory research to support our Medicaid business, develop processes to collect necessary paperwork to ensure compliance, assist with reporting and ad-hoc projects as assigned.

Minimum Qualifications:

• 3+ years of work experience as a paralegal or legal assistant at a law firm or in house legal department.
• Own and drive projects forward independently, demonstrating a strong “get things done” attitude and high attention to detail.
• Exceptional written and verbal communication skills, with a focus on delivering practical solutions.
• Ability to utilise legal technology tools (e.g., GC AI, Lexion (preferred), or other contract management system, Carta).
• Proven ability to manage multiple priorities and deadlines and thrive in a fast-paced environment.
• A strong value for teamwork and the ability to work effectively with diverse teams and perspectives.
• Proficient with healthcare regulatory laws.

Preferred Qualifications:

• Ability to work across a range of legal matters, transactional, regulatory, and compliance.
• Experience in a startup environment.
• Advanced proficiency in automating legal workflows.

Hourly Rate Range:

US Employees in San Francisco/Bay Area: $38.80 - $44.00/hour US Employees in Boston, Los Angeles, Seattle, Washington DC: $35.70 - $40.50/hour US Employees in Arlington, Denver, San Diego, Sacramento: $34.10 - $38.70/hour US Employees in Albany, Atlanta, Austin, Baltimore, Central/Southern Virginia, Charlotte, Chicago, Dallas/Fort Worth, Detroit, Houston, Las Vegas, Miami, Milwaukee, Philadelphia, Portland, Research Triangle, Salt Lake City, Twin Cities: $31.00 - $35.20/hour US Employees in Baton Rouge, Birmingham, Charleston, Cincinnati, Cleveland, Daytona Beach, Indianapolis, Nashville, New Orleans, Omaha, Phoenix, Pittsburgh, St. Louis, Tampa: $30.10 - $34.15/hour

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.

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!

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Vice President, West Provider Network Development & Technology Deployment

Job Description

Waymark is a mission-driven team of healthcare providers, technologists, and builders working to transform care for people with Medicaid benefits. We partner with communities to deliver technology-enabled, human-centered support that helps patients stay healthy and thrive.

We're designing tools and systems that bring care directly to those who need it most,removing barriers and reimagining what's possible in Medicaid healthcare delivery.

Key Responsibilities

• Drive top-of-funnel provider outreach, engagement, and pipeline management aligned with state and market growth goals, with an emphasis on West Coast expansion
• Drive our predictive analytics technology Go-To-Market strategy and full cycle sales
• Articulate Waymark's value proposition to primary care providers and provider groups, building strong relationships with key clinical and operational stakeholders
• Develop and execute market-specific outreach and contracting plans in collaboration with health plan partners during cohort design and market activation
• Lead provider sourcing, engagement, and contracting to expand Waymark's network and establish mutually beneficial financial incentives
• Partner with Legal, Operations, and Implementation to support efficient execution of provider agreements and onboarding
• Identify opportunities to improve provider contracting processes, network expansion strategies, and ongoing provider optimization to support medical cost performance
• Collaborate with Partner Success and Implementation to support growth planning with existing provider partners and ensure long-term success

Minimum Qualifications

• 10+ years of experience supporting providers and building high-performing provider networks
• Extensive experience selling enterprise SaaS, health tech, or digital health solutions with measurable outcomes
• Demonstrated ability to translate technical or platform capabilities into executive-level business value
• Deep commitment to improving healthcare for underserved populations, with experience across independent practices and health system-owned primary care providers
• Existing relationships with large provider systems, primary care groups, and the Medicaid provider community across multiple markets
• Strong understanding of value-based care models, including ACOs, PCMH, quality-based incentives, bundled payments, and Medicaid market dynamics
• High-energy, collaborative working style with strong process orientation
• Ability and willingness to perform hands-on provider development work while helping scale processes and team capacity
• Willingness to travel up to 50%

Preferred Qualifications

• Comfortable “sitting at the table” with clinical and operational executives to align on strategic outcomes
• Experience using a CRM to manage provider outreach and pipeline activity
• Knowledge of primary care practice types, including FQHCs, Look-Alikes, IPAs, and their respective financing models and operational needs
• Managed care experience (Medicaid preferred)
• Experience working with provider-sponsored or provider-owned Medicaid health plans

Salary and Benefits

The salary range for this role is $140,000 - $185,000 per year, depending on location. In addition to salary, we offer a comprehensive benefits package, including stock options, incentive program, work-from-home stipend, medical, vision, and dental coverage, life insurance, paid time off, parental leave, retirement savings, commuter benefits, and professional development stipend.

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About this role:

As the Director of MedEcon, you will be a key leader in the organisation covering claims-based analysis, actuarial science, and medical economics. This is a foundational finance role that requires both strategic vision and hands-on execution. You will be responsible for building out the next generation of actuarial and medical economics capabilities while simultaneously delivering critical analyses that drive our business and clinical strategy.

While your actuarial knowledge is important, your core focus will be combining financial data, claims data, and operational performance data to drive insightful analysis that help push the Waymark care model forward through deep collaboration with analytics.

Reporting to the Chief Revenue Officer (acting CFO), you will lead financial performance measurement and forecasting for value-based contracts. You will be a technical expert who ensures we accurately forecast performance, understand cost trends, identify opportunities for clinical impact, and communicate our value to partners.

This role requires someone who can both develop sophisticated analyses themselves and build the infrastructure to scale these capabilities. You will work at the intersection of finance, partnerships, clinical operations, and analytics,translating complex actuarial and medical economics concepts into actionable insights for both internal stakeholders and external health plan and health system partners. You must be as comfortable building an IBNR model or conducting a cost trend analysis as you are presenting financial projections to a health plan CFO or helping to guide contract negotiations.

Understanding the nuances of Medicaid is essential and an added bonus if you have experience with Medicare Advantage and Dual Eligibles. Healthcare data in these populations can be incomplete and inconsistent, and the regulatory environment is complex and varies by state. Your deep expertise in these markets, combined with your ability to build robust analytical frameworks despite data challenges, will be critical to our success.

Key Responsibilities:

• Own savings forecasts and monthly financial close for all value-based contracts, including shared savings accruals, reserves, and IBNR development • Build and maintain financial models capturing performance drivers under MLR-based and RCT-based contract structures; monitor cost trends and provide early warnings of variances with recommended actions • Serve as the technical authority on total cost of care projections, conducting and reviewing sophisticated analyses, cost trend studies, and actuarial modeling as needed • Lead year-end contract reconciliation with health plan actuaries and provide actuarial/financial guidance during contract negotiations • Develop underwriting frameworks (MLR targets, performance guarantees, risk corridors) and build methodologies to accurately measure organisational performance across contract structures • Perform deep-dive cost trend analyses to identify clinical impact opportunities; generate insights that drive clinical model innovation and support strategic planning across market opportunities and growth scenarios • Serve as the primary technical counterpart to health plan actuaries during data validation, reconciliation, and negotiations • Lead discussions to resolve methodology differences and communicate findings clearly to non-technical stakeholders • Develop compelling value narratives and analytical exhibits that translate complex medical economics findings into actionable recommendations • Build, grow, and lead a best-in-class medical economics and actuarial function • Develop analytical tools, data infrastructure, and reporting frameworks that improve team efficiency and scale capabilities • Dive deep into data quality issues and work cross-functionally to resolve discrepancies; write analytical memos and reports that communicate findings to senior leadership

Minimum Qualifications:

• Advanced degree in a quantitative field (actuarial science, statistics, mathematics, economics, public health, or related) • 10+ years of progressive experience in health actuarial science or medical economics, with at least 3-5 years in a leadership role • Demonstrable expertise in Medicaid, including capitation, risk adjustment, MLR requirements, and regulatory frameworks • Proven track record with value-based care arrangements, shared savings contracts, and risk-bearing models, including contract underwriting, performance forecasting, and financial reconciliation • Expert-level proficiency in actuarial and medical economics methodologies (reserving, pricing, trend analysis, total cost of care modeling); strong SQL, Python, and/or R skills; advanced Excel/financial modeling; and experience with large, complex healthcare datasets • Demonstrated ability to build and lead high-performing analytical teams in growth-stage organisations, with exceptional communication skills across technical and non-technical audiences • Equal parts strategic thinker and hands-on executor , able to build vision and infrastructure while personally conducting sophisticated analyses • Comfortable with ambiguity, fast-moving priorities, and building effective cross-functional partnerships

Preferred Qualifications:

• ASA credential or meaningful progress toward FSA • Deep Medicaid managed care experience, including state program variations, CMS regulations, and actuarial standards of practice (ASOP) • Understanding of care delivery models, clinical quality measures, and the relationship between clinical interventions and medical costs • Experience building analytical functions from the ground up in early-stage or high-growth companies • Genuine commitment to improving care for underserved populations and closing health equity gaps

Salary Range:

US Employees in San Francisco/Bay Area, New York City - $175,000 - $231,000

US Employees in Boston, Los Angeles, Seattle, Washington DC - $161,000 - $212,000

US Employees in Arlington, Denver, San Diego, Sacramento - $154,000 - $203,000

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 - $140,000 - $185,000

US Employees in Baton Rouge, Birmingham, Charleston, Cincinnati, Cl

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You are technical, a strong operator, and strategic thinker, looking to build, improve, and scale reliable security processes whenever possible. Your leadership of the information security program at Waymark will include all facets of cybersecurity, and the associated user experience of our remote teams, and community-based care workers. You will be responsible for security policy and implementation and operation of technical and administrative safeguards to support those policies. You will use your experience to inform sound judgement to achieve the appropriate management of security risks in a manner consistent with the company’s values. You will use your in-depth knowledge of security in a modern cloud based organization, to identify and address risks to the company, through a combination of hands-on technical contributions and directing and overseeing staff with security responsibilities. You will interact with the broader executive leadership team to communicate evolving needs, matching the security strategy to the size and stage of growth of the company and the information we safeguard.

This is a remote friendly position that can be located anywhere in the United States.

Key Responsibilities & Duties

• Oversee the internal cybersecurity program, road map, and strategy, which includes developing and implementing procedures and policies designed to protect Waymark communications, systems, and assets from internal and external threats and that safeguards health information.
• Oversee and manage Waymark’s MSSP and outsourced IT vendor, including responsibility for security and IT budgets, and IT tools used by Waymark.
• Partner with Product, Engineering, Legal, and Compliance leadership to determine risks and deploy risk management processes, supporting Waymark’s secure software development lifecycle and ensuring that our internally developed products and services meet the expectations of our patients, customers and regulators
• Own, define and oversee the necessary security operational functions such as Identity Management, Vulnerability Management, Incident Response, Security Awareness, and Vendor Risk Management
• Serve as Waymark’s HIPAA Security Officer, ensuring compliance with the HIPAA Security Rule, working closely with the legal team to document, review, maintain, and implement standards, policies, and procedures within security disciplines.
• Lead the strategy, implementation, and maintenance of industry-standard security certifications, including SOC2 Type II.
• Conduct research, analysis, and correlation across a wide variety of source data to identify and prevent compromise of our networks, host systems, and data.
• Track and report on network security to the Waymark executive leadership team

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