CX Systems Lead

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