Revenue Strategy and Operations Lead, Headway

Insights & AI

$105.4-155k

Offers equity

SQL

Mid and Senior level

Remote from US

Therapist-by-insurance marketplace

Be an early applicant

Therapist-by-insurance marketplace

1001+ employees

HealthcareB2CB2BMarketplaceMental healthWellbeing

Be an early applicant

$105.4-155k

Offers equity

SQL

Mid and Senior level

Remote from US

1001+ employees

HealthcareB2CB2BMarketplaceMental healthWellbeing

Company mission

To build a new mental healthcare system, rewired for access and affordability.

Job

Company

Role

Who you are

You're AI-fluent, having applied AI tools to tackle real operational problems
You're a strategic initiative driver: you can scope ambiguous problems, build structured analyses, and bring stakeholders to a decision
You have strong analytical depth: data modeling, trend diagnosis, and forecasting (SQL knowledge a plus)
You have 3-6 years in strategy, sales operations, or analytics at a growth-stage company; experience supporting a high-velocity sales team is a strong plus

What the job involves

Headway's Provider Growth team is one of the largest and highest-performing sales organizations in mental health. We drive new provider activation across the country, supported by an established playbook, performance infrastructure, and a growing AI-enabled stack
We're hiring an Insights & AI Lead to own and push that foundation further. You'll generate insights that drive decisions, build tools reps and managers rely on, and see strategic work through from analysis to execution
This role reports directly to the Senior Manager of RevOps Insights and has a direct line to Revenue leadership
Identify and build AI-powered tools that help PGAs prioritize providers, optimize outreach, and convert effectively
Deliver proactive strategic analysis on funnel trends, pipeline health, and cohort performance; own the initiatives that action these insights
Support the WBR and executive operating cadence with analytical inputs and data-driven recommendations
Build tools that let Sales leaders self-serve performance questions

Our take

In the US, 1 in 4 citizens are living with treatable mental health conditions. But a vast majority of people are unable to access the care they need, often due to cost. Headway connects clients with therapists who accept insurance as payment, and provides independent practitioners with the tools and resources needed to both serve their patients and manage administrative workloads.

Headway’s concept is timely, with national mental health under particular strain following recent events. The company facilitates over 600,000 appointments per month and has attracted backing from the likes of Accel and Google Ventures. It is working to broaden its presence across the US while building out its product and pursuing the application of AI in health care.

Freddie

Company Specialist at Welcome to the Jungle

Insights

Top investors

64% employee growth in 12 months

Glassdoor (3.7)

Trustpilot (3.3)

Company

Funding (last 2 of 6 rounds)

Jul 2024

$100m

LATE VC

Oct 2023

$125m

SERIES C

Total funding: $327m

Company HQ

Tribeca, New York, NY

Leadership

Andrew Adams

(Founder & CEO)

Prior to founding Headway in 2017, Andrew was a Product Analyst at Spring Inc.

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