CX 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 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.

About The Role

Every month, hundreds of thousands of patients and providers interact with Headway's support systems. Today, those interactions move through a patchwork of tools and configurations that weren't built to scale with us — and as we scale our operations and embed AI across the agent workspace and customer experience, we need someone to own how it all comes together.

As CX Systems Lead, you'll own the platform behind Headway's customer experience. You'll shape how our voice and chat systems route, how our AI tools augment our agents, and how the data tells us what to fix next. You will design and configure CX systems, deploy the AI tooling that lives inside it, and establish the feedback loops that connect support insights to the rest of the company.

You will: 

• Own the voice platform from the CX side — configure and continuously evolve IVR design, intelligent routing, queue management, and voice bot logic. Partner with engineering on the platform migration and underlying integrations.

• Operationalize AI across the agent workspace — deploy, configure, and tune the AI tooling that augments our agents (agent assist, auto-summarization, suggested responses, intelligent triage). Drive adoption rigorously and measure what's actually moving the needle.

• Configure and scale the broader CX tech stack — Zendesk, CRM, QA, WFM, and the integrations that connect them; translate business requirements into scalable configurations that hold up as we grow.

• Run technical programs end-to-end — from scoping and vendor alignment through deployment and post-launch measurement. Build the business case for new investments and shepherd improvements from idea to production.

• Own CX systems performance and reporting — design the dashboards that track what matters (routing accuracy, AI tool utilization, deflection, system uptime), and turn the data into the next system change rather than the next report.

• Be the connective tissue across CX, Product, Engineering, and IT partners — represent CX systems in cross-functional initiatives, surface gaps proactively, and be the go-to operational expert on voice, AI tooling, and CX configurations.

You’d be a great fit if…

• You have 4+ years across CX systems, CX operations, contact center platform, or technical CX program management — and are comfortable picking up new tools, integrations, and configurations as the stack evolves.

• You've configured and optimized a voice/CCaaS platform from the operational side — AWS Connect, Genesys, Five9, Twilio, NICE, or similar — including IVR design, intelligent routing, and voice bots.

• You're operationally minded but build-oriented — you ship through configuration, low-code, and well-scoped specs.

• You're AI-native in a CX context. You've deployed agent assist, auto-summarization, chat/voice AI, or similar tooling.

• You're an analytical and creative problem solver: you dig into root causes — using Hex, SQL, Looker, Tableau, Metabase, or similar — quantify impact, and build solutions elegant enough to scale.

• You thrive in ambiguity and move fast without sacrificing quality — you know when to ship a "good enough for now" configuration and when to wait for the right architecture.

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

• Bonus: experience in healthcare, insurance, or other regulated industries with complex customer interactions; experience migrating between contact center platforms.

Compensation and Benefits:
The expected base pay range for this position is $105,280-$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.