Customer Care Systems Lead

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 $99280-$146000  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

What We Do

Headway’s mission is a big one – to build a new mental health care system everyone can access. We’ve built technology that helps people find great therapists with the first software-enabled national network of providers accepting insurance. 1 in 4 people in the US have a treatable mental health condition but the majority of providers don’t accept insurance making therapy too expensive for most people. Headway is building a new mental healthcare system that everyone can access by making it easy for therapists to accept insurance and scale their practice. Headway was founded in 2019. Since then we’ve grown into a diverse national network of over 60000 mental healthcare providers across all 50 states who run their practice on our software and have served over 1 million patients. We’re a Series D company with over $325m in funding from a16z (Andreessen Horowitz) Accel GV (formerly Google Ventures) Spark Capital Thrive Capital Forerunner Ventures and Health Care Service Corporation.

Why Work With Us

The demand for mental health care has never been higher underscoring the need for solutions like Headway that increase accessibility to clinical care. 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.

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