CX Quality Assurance Lead

Headway

1d•$95,200 - $140,000•Remote

About The Position

Headway is seeking an experienced QA Lead to enhance quality assurance within its CX organization. This role focuses on evolving from manual evaluations to a continuous insight-generating system that identifies behavioral trends and drives improvements for agents and customer service. The position is within the Agent Success team in Customer Experience, aiming to make CX agents more effective, consistent, and supported. The QA function is undergoing a transformation from a manual, sampling-based model to a specialized, insight-driven system, and the hired individual will play a key role in its development. The role offers ownership over specific areas such as calibration and framework governance, AI-powered analytics and insights, or vendor and partner quality oversight. This is not a traditional QA role focused on manual interaction grading; instead, it involves designing systems, analyzing signals, and identifying patterns to influence operational changes. The work will provide CX leadership with consistent and reliable visibility into performance, processes, and operations, enabling informed decision-making.

Requirements

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

Responsibilities

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

Benefits

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