Customer Care Systems Lead

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 70,000 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, GV, 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.

About The Role

Headway is looking for a Systems Lead with a strong background in CX analytics, AI adoption, and voice platform configuration to join our CX Systems team. Our CX team is the tip of the spear delivering affordable mental healthcare to millions — and you'll shape how that experience is measured, automated, and continuously improved.

This is a unique opportunity to own the intersection of data, AI, and voice in a fast-scaling CX organization. You won't just report on what's happening — you'll diagnose root causes, configure the systems that fix them, and drive adoption of the AI tools that help our agents and customers get to resolution faster.

You Will

Own CX systems metrics and reporting — design, maintain, and evolve dashboards that track key performance metrics (routing accuracy, system uptime, tool utilization) and translate data into clear operational recommendations for CX leadership

Lead AI adoption across the CX team — measuring impact rigorously; drive agent adoption through enablement and change management

Configure and optimize the voice/telephony platform — own IVR design, intelligent call routing, queue management, and voice bot scripting; ensure routing logic reflects current business priorities

Partner with Engineering, IT, Product, and BPO teams to translate CX business requirements into scalable technical configurations

Manage end-to-end technical programs — from scoping and vendor alignment through deployment and post-launch measurement

Proactively identify system, analytics, and process gaps; build the business case and drive improvements from idea to production

Represent the CX team in cross-functional initiatives and be the go-to expert on CX data, AI tooling, and voice systems

You’d be a great fit if…

You have 3–5+ years of experience in CX operations, analytics, or systems — ideally with exposure to all three

You've configured or optimized a voice/telephony platform (IVR, call routing, voice bots) — Five9, Genesys, Twilio, Amazon Connect, or similar

You're comfortable working with new tools, integrations, and configurations across the CX tech stack (CRM, QA, WFM) and can plug in when needed.

You've deployed or meaningfully improved an AI tool in a CX context — and have the adoption metrics to prove it

You're comfortable pulling and presenting data without relying on a dedicated analyst — SQL, Looker, Tableau, Metabase, or similar

You thrive in ambiguity and move fast without sacrificing quality; you know when to ship and when to wait

You're an analytical and creative problem solver: you dig into root causes, quantify impact, and build solutions that are elegant enough to scale

You communicate clearly to both technical and non-technical stakeholders, and know how to influence without formal authority

You're motivated by making an impact on one of our generation's defining problems — making mental healthcare affordable and accessible

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.

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

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.

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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 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.