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 health