Billing Specialist

About the Billing Specialist (Insurance A/R) at Headspace:

The Billing Specialist (Insurance A/R) is responsible for ensuring timely and accurate insurance A/R resolution across a complex claims portfolio. This role sits at the center of execution and problem-solving—driving follow-up, denials and underpayment resolution, cash acceleration, and process improvements that improve collections outcomes and reduce operational friction.

You will be expected to effectively and independently drive project execution, recommend solutions to enhance existing processes, prioritize between competing deliverables with sound judgment, and communicate assumptions up front to minimize rework.

What you will do:

Insurance A/R Follow-up & Resolution

• Work assigned worklists of complex and high-risk accounts, meeting productivity and quality targets while driving timely A/R resolution.
• Own key insurance collections workflows (e.g., recoupments) and billing / coding accuracy processes (e.g. coding and billing quality audits) end-to-end, driving complete, accurate, and SLA-compliant execution.
• Resolve claim issues across rejections, denials, and underpayments through payer portal review, payer outreach, documentation review, and escalation pathways.
• Research, review, and resolve exceptions and escalations surfaced by teammates and cross-functional partners, bringing issues to closure with strong documentation.
• Maintain high-quality claim notes and documentation standards to ensure auditability, continuity, and efficient handoffs.
• Conduct special projects (e.g. targeted payer issue review, A/R clean-up, etc.) and provide “SWAT” support for high-risk billing areas when needed to reduce write-offs and address aging risk.

Cash, Reporting, and Operational Rigor

• Support weekly / monthly reporting and reconciliation activities and ensure accurate tracking of collections progress and payer behavior.
• Assist with monitoring workload and KPIs, and contribute to the design and implementation of system / process changes and improvement initiatives.
• Contribute to productivity and quality reporting processes, flagging gaps, trends, and opportunities to improve operational performance.
• Partner in delivering team training and strengthening SOP documentation to drive standardized, high-quality execution.
• Actively identify and advance AI and automation opportunities within collections workflows, partnering on pilots and driving adoption to improve efficiency and accuracy.
• Conduct ongoing coding and billing accuracy reviews, implement corrective actions as needed, and partner with Clinical and QA teams to identify retraining and performance improvement opportunities.

Process Improvement & Cross-Functional Problem Solving

• Identify trending claim issues and root causes (rejections, denials, underpayments) and recommend practical remediation strategies to improve collections performance.
• Recommend solutions to enhance existing workflows and leverage available resources to overcome unforeseen issues (e.g., payer constraints, system limitations, unclear routing).
• Prioritize between competing work and project deliverables with sound judgment, communicating assumptions and clarifying requirements up front to minimize rework.
• Identify opportunities to standardize, automate, and reduce manual processes across collections workflows; support testing and adoption of improvements.
• Partner with Product and Engineering on testing and validation of RCM workflow enhancements (e.g., UAT support, requirements feedback) when needed.
• Work cross-functionally with internal teams (e.g., Clinical, Provider Ops, Client/Account partners, Member Support, etc.) to implement and optimize workflows for new and existing health plans, clients, and members.

What success looks like:

• Insurance A/R worklists are executed with speed, accuracy, and strong documentation, resulting in improved aging and collections outcomes.
• Trends and root causes are surfaced early, with clear recommendations that reduce repeat issues and prevent avoidable denials or write-offs.
• Competing priorities are handled with good judgment and proactive communication, minimizing rework and protecting team throughput.
• Workflows become more standardized and efficient through practical improvements and automation support.

What you will bring:

Required Skills:

• 5+ years of Revenue Cycle Management experience with strong knowledge of medical claims and health plan/EAP rules.
• Strong claims follow-up skills across denials, rejections, and underpayments; ability to independently drive resolution to closure.
• Strong root-cause problem solving and attention to detail; high bar for accuracy and documentation.
• Ability to prioritize effectively across competing work and communicate assumptions/needs early to reduce rework and unblock progress.
• Proficiency in Excel and comfort using data to support reporting, reconciliation, and operational decision-making.
• Strong communication and interpersonal skills; ability to collaborate cross-functionally in a fast-paced environment.

Preferred Skills:

• Behavioral health / mental health service line and telehealth billing experience.
• Professional coding certification.
• Experience with process improvement and automation initiatives in RCM operations.
• Experience in B2B2C healthcare environments.

Location:

We are currently hiring this role remotely in the US and Hybrid for San Francisco (SF). Candidates must permanently reside in the US full-time.
For candidates with a primary residence in the greater SF area, this role will follow our hybrid model. You’ll work 3 days per week from our office, allowing for impactful in-office collaboration and connection, while enjoying the flexibility of remote work for the rest of the week. Your recruiter will share more details about our hybrid model.

Pay & Benefits:

The anticipated new hire hourly range for this full-time position is $31.00-$39.00/hour + equity + benefits.

Our pay ranges are based on the job, level, and location, and reflect the lowest to highest geographic markets where we are hiring for this role within the United States. Within this range, individual compensation is determined by a candidate’s location as well as a range of factors including but not limited to: unique relevant experience, job-related skills, and education or training.
Your recruiter will provide more details on the specific salary range for your location during the hiring process.

At Headspace, base salary is but one component of our Total Rewards package. We’re proud of our robust package inclusive of: base salary, stock awards, comprehensive healthcare coverage, monthly wellness stipend, retirement savings match, lifetime Headspace membership, generous parental leave, and more. Additional details about our Total Rewards package will be provided during the recruitment process.

About Headspace

Headspace exists to provide every person access to lifelong mental health support. We combine evidence-based content, clinical care, and innovative technology to help millions of members around the world get support that’s effective, personalized, and truly accessible whenever and wherever they need it.

At Headspace, our values aren’t just what we believe, they’re how we work, grow, and make an impact together. We live them daily: Make the Mission Matter, Iterate to Great, Own the Outcome, and Connect with Courage. These values shape our decisions, guide our collaborations, and define our culture. They’re our shared commitment to building a more connected, human-centered team—one that’s redefining how mental health care supports people today and for generations to come.

Why You’ll Love Working Here:

• A mission that matters—with impact you can see and feel
• A culture that’s collaborative, inclusive, and grounded in our values
• The chance to shape what mental health care looks like next
• Competitive pay and benefits that support your whole self

How we feel about Diversity, Equity, Inclusion and Belonging:

Headspace is committed to bringing together humans from different backgrounds and perspectives, providing employees with a safe and welcoming work environment free of discrimination and harassment. We strive to create a diverse & inclusive environment where everyone can thrive, feel a sense of belonging, and do impactful work together.

As an equal opportunity employer, we prohibit any unlawful discrimination against a job applicant on the basis of their race, color, religion, gender, gender identity, gender expression, sexual orientation, national origin, family or parental status, disability*, age, veteran status, or any other status protected by the laws or regulations in the locations where we operate. We respect the laws enforced by the EEOC and are dedicated to going above and beyond in fostering diversity across our workplace.

*Applicants with disabilities may be entitled to reasonable accommodation under the terms of the Americans with Disabilities Act and certain state or local laws. A reasonable accommodation is a change in the way things are normally done which will ensure an equal employment opportunity without imposing undue hardship on Headspace. Please inform our Talent team by filling out this form if you need any assistance completing any forms or to otherwise participate in the application or interview process.

Headspace participates in the E-Verify Program.

Privacy Statement

All member records are protected according to our Privacy Policy. Further, while employees of Headspace (formerly Ginger) cannot access Headspace products/services, they will be offered benefits according to the company's benefit plan. To ensure we are adhering to best practice and ethical guidelines in the field of mental health, we take care to avoid dual relationships. A dual relationship occurs when a mental health care provider has a second, significantly different relationship with their client in addition to the traditional client-therapist relationship—including, for example, a managerial relationship.

As such, Headspace requests that individuals who have received coaching or clinical services at Headspace wait until their care with Headspace is complete before applying for a position. If someone with a Headspace account is hired for a position, please note their account will be deactivated and they will not be able to use Headspace services for the duration of their employment.

Further, if Headspace cannot find a role that fails to resolve an ethical issue associated with a dual relationship, Headspace may need to take steps to ensure ethical obligations are being adhered to, including a delayed start date or a potential leave of absence. Such steps would be taken to protect both the former member, as well as any relevant individuals from their care team, from impairment, risk of exploitation, or harm.

For how how we will use the personal information you provide as part of the application process, please see: https://www.headspace.com/applicant-notice

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