Scheduling Lead, Workforce Management

1 in 4 people in the US have a treatable mental health condition, but most providers don't accept insurance, making therapy too expensive for most people. Headway’s mission is to fix this by building a new mental healthcare system everyone can access. We started by solving the biggest barrier to care: insurance. The admin work - credentialing, claims, payment reconciliation - is a nightmare. We've automated that.

But we're going further. Over 75,000 providers across all 50 states run their practice on our software, serving over 1 million patients. We are building the best tools for therapists to run their entire practice, reimagining the experience of finding a therapist, and investing in the platform foundations to enable this at scale. We aren't just a billing layer; we are becoming the platform where care actually happens.

We're a Series D company with $325M+ in funding (a16z, Accel, Spark Capital, etc.), looking for exceptional people to help us achieve this mission. We want your time here to be the most meaningful experience of your career. Join us, and help change mental healthcare for the better.

Workforce Management keeps every patient and provider who contacts Headway answered on time — at a cost that falls as we scale. We forecast demand, schedule the people to meet it, and manage the day in real time across Headway's internal team and our BPO partners — with a growing agent support operation. We run it as a lean, senior, AI-empowered team: the mechanical work goes to the machine; judgment, exceptions, and relationships stay human.

You'll be Headway's first dedicated scheduler — the owner of a function responsible for building, optimizing, and publishing schedules that keep our contact center staffed to demand, govern rosters across the network. This critical work makes our staffing spend defensible and helps make sure we scale the workforce efficiently. You'll report to the WFM Manager and partner daily with our Real-Time and Capacity Planning leads.

You Will

You'd be a great fit if…

• Build and publish agent schedules against demand in Verint on an 8-week horizon — absorbing training classes, PTO, and overtime
• Balance rigorous SLA targets with agent well-being — design sustainable shift templates that reduce burnout and help us retain top talent
• Own network-wide roster and headcount data across Headway's internal (Core) and CX teams, including complex, high-variability shift patterns
• Reconcile scheduled hours against invoiced/productive BPO hours — the control that keeps staffing spend accountable
• Handle exceptions (time-off, swaps, coverage gaps) and partner with Real-Time on intraday adjustments and adherence
• Drive scheduling-optimization strategy through quarterly project cycles; set policy and standardize templates so the function scales with new sites and lines of business
• Adopt, test, and help shape AI-assisted scheduling — acting as the human-in-the-loop who governs automated drafts, which frees you to focus on higher-level optimization strategy
• You have 3+ years in contact-center workforce management with direct ownership of scheduling
• You've worked hands-on in an enterprise WFM platform (Verint strongly preferred; NICE IEX / Aspect / Playvox welcome)
• You're fluent in staffing math — occupancy, shrinkage, coverage — and comfortable defending a number with data
• You've built complex, multi-shift rosters that held SLA, ideally in a multi-vendor or BPO environment
• You're a translator — the bridge between WFM and Operations — who can communicate the "why" behind the scheduling math and trade-offs to agents and senior leaders alike (you operate independently and set policy)
• You're excited to build a function from scratch and to work alongside AI tooling rather than around it

Compensation and Benefits

The expected base pay range for this position is $99,280 - $146,000 based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

We believe a team's strength is in its people, and we cannot achieve this mission without a team that reflects the diversity of this problem – across race, ethnicity, gender, sexuality, age, national origin, religion, family status, disability, military status, and experience. Headway is committed to the full inclusion of all qualified individuals. As part of this commitment, Headway will ensure that persons with disabilities are provided with reasonable accommodations. If reasonable accommodation is needed to participate in the job application or interview process, to perform essential job functions, and/or receive other benefits and privileges of employment, please inform the recruiter when they contact you to schedule your interview.

Headway participates in E-Verify. To learn more, click here. https://www.e-verify.gov/sites/default/files/everify/posters/EVerifyParticipationPoster.pdf

A notice to Headway applicants: To protect yourself against phishing and recruitment fraud, please note that Headway only accepts applications through our official careers page at https://headway.co/careers. Headway will never refer you to external websites, ask for payment or personal information, or conduct interviews via messaging apps. All official communication will come from a @findheadway.com http://findheadway.com email address. If you are contacted by someone claiming to be from Headway via an unofficial channel, please do not share any information and report it as spam.

• Benefits offered include:
• Equity compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development