About the Role

Headway is looking for an experienced QA Lead to evolve how quality works across our CX organization as we move from manual evaluation to a system that generates insights continuously, surfaces behavioral trends at scale, and drives the decisions that make our agents better and our customers better served.

This is a customer support quality assurance role focused on agent evaluation, conversation analytics, and AI-powered quality measurement — not software testing, test automation, or CI/CD engineering

You'll be joining the Agent Success team within Customer Experience, a function focused on making our CX agents more effective, more consistent, and better supported. QA is in active evolution here; we're moving from a manual, sampling-based model to a specialized, insight-driven system, and the people we hire will have a direct hand in building it. Your role will have real ownership over a defined area of the QA program — calibration and framework governance, AI-powered analytics and insights, or vendor and partner quality oversight, depending on role fit.

This isn't a traditional QA role where you spend your days manually grading interactions. You'll design the systems, analyze the signals, and surface the patterns that change how we operate, with clear ownership over outcomes.

Your work will give CX leadership consistent, reliable visibility into performance, process, and operations — and the context to act on what they find.

You will:

• Own a defined area of the QA program end-to-end (calibration and rubric governance, AI-powered analytics, or partner quality) and drive it from signal to action
• Set quality standards and rubric logic for your area; ensure consistent application across channels and partners and recommend framework updates based on outcomes
• Configure and continuously improve AI-QA tooling (ObserveAI or similar) with set scoring logic, monitoring accuracy, and ensuring the platform delivers consistent, actionable output
• Build automation into QA workflows to reduce manual overhead and expand coverage; establish AI-assisted processes for status updates, reporting, and initiative recaps
• Analyze quality and conversation data to surface DSAT drivers, behavioral trends, escalation patterns, and workflow gaps by going beyond what happened to understand why
• Design and maintain dashboards that track key quality metrics; translate findings into clear operational recommendations for CX leadership
• Produce structured insight reports (clear signal, root cause, recommended action) and ensure findings flow into training, content, coaching, and product decisions
• Contribute QA input to WBR/MBR cycles and cross-functional planning; give leadership consistent visibility into program health and customer experience impact
• Partner with BPO teams and CX stakeholders to align on standards, drive calibration, and keep expectations consistent across every channel and partner
• Collaborate with Enablement, Knowledge, and Programs to ensure quality signals drive decisions across training, content, and coaching and deliver initiatives that measurably improve agent quality and customer satisfaction

You'd be a great fit if...

• 4–7 years in CX operations, QA, or analytics — you've genuinely owned a program (not just contributed to one) and have specific, measurable outcomes to point to
• Comfortable pulling and analyzing data without a dedicated analyst (Looker, Metabase, Hex, or similar; SQL is a plus)
• You've worked with QA and conversation intelligence tools (ObserveAI, Rippit, Level AI, Klaus, or similar) and know how to configure, calibrate, and get meaningful output from them
• You use AI as part of how you actually work with automations, workflow improvements, faster paths to insight
• You've produced insight reports that moved real decisions, where training shifted, processes changed, policy updated
• You don't just identify problems, you design the processes that prevent them from recurring
• You can translate quality data for non-QA audiences and influence decisions without formal authority
• You are comfortable in ambiguity and move fast without sacrificing rigor, and you're fine building the playbook as you go
• You are fluent in quality evaluation methodologies, calibration processes, and QA framework design
• You have a track record coordinating across operations, training, content, and technology teams to deliver shared goals
• You are a strong communicator, demonstrated with clear status reports, insight briefs, and stakeholder presentations
• You are motivated by the mission: making mental healthcare affordable and accessible

Compensation and Benefits:

The expected base pay range for this position is $95,200-$140,000, 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