VP of Sales

Headway•San Francisco, NY

4d•$171,360 - $201,600

About The Position

Headway’s mission is a big one – to build a new mental health care system everyone can access. We’ve built technology that helps people find great therapists with the first software-enabled national network of providers accepting insurance. 1 in 4 people in the US have a treatable mental health condition, but the majority of providers don’t accept insurance, making therapy too expensive for most people. Headway is building a new mental healthcare system that everyone can access by making it easy for therapists to accept insurance and scale their practice. Headway was founded in 2019. Since then, we’ve grown into a diverse, national network of over 60,000 mental healthcare providers across all 50 states who run their practice on our software and have served over 1 million patients. We’re a Series D company with over $325m in funding from a16z (Andreessen Horowitz), Accel, GV (formerly Google Ventures), Spark Capital, Thrive Capital, Forerunner Ventures and Health Care Service Corporation. 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 Team & Role The Provider Sales team at Headway is a 200 FTE organization focused on SMB sales, with deals typically closing in 1–2 meetings at an ACV of approximately $5,000. On average, each rep closes around 20 new providers per month, with key sales motions focused on solo providers (~70%), prescribers (~15%), and group practices (~15%). The team is supported by Revenue Enablement (10 FTEs) and Project Management (3 FTEs). This role is focused on building and leading the Provider Sales organization and partnering with leadership to continue defining Headway’s go-to-market strategy. Areas outside the scope of this role include provider demand generation, Revenue Operations (which works across multiple teams), CFN collaboration, R&D/Product, Product Marketing, Business Operations, and the Clinical team. The role reports to Headway’s Chief Revenue Officer , who oversees the Revenue team (including Revenue Marketing, Sales, and CS), a total of roughly 300 FTEs within Headway’s 900-person organization.

Requirements

Scale large, fast-growing sales orgs
Have led organizations of 100–200+ sellers with ~100 hires per year
Demonstrate the ability to manage rapid scaling and high hiring velocity without quality decay
Bring deep SMB / high-velocity sales DNA
Have built or led teams in short sales cycle, low–mid ACV, high-velocity environments (e.g., Uber, Toast, Shopify, HubSpot, DoorDash, Yelp, Podium, Mindbody, Thumbtack, Opendoor)
Understand motions that mirror Headway’s volume-driven provider acquisition
Operate comfortably in multi-motion complexity
Have managed multiple segments or sub-motions (e.g., solo, group, prescriber) or similar SMB segmentation models (small biz, mid-market, partner-led)
Can design nuanced org structures and tailor playbooks to each motion
Know how to integrate Product-led / PLG motions
Have partnered closely with Product to build in-product nudges, self-serve flows, and human handoff systems
Understand how to build strategies using levers beyond Sales alone , collaborating with Product to deliver the right solution
Match Headway’s shift toward product-led sales
Bring stage-relevant operational maturity
Understand WGLL (what great looks like) for a company entering its next phase of growth
Have experience inside mature or public environments (e.g., Uber, Toast, Shopify, HubSpot, DoorDash, Mindbody)
Bring strong operational rigor , forecasting discipline , and cross-functional alignment experience

Responsibilities

Invest in product-led sales motion
Enable provider self-serve onboarding with optional human support
Metric: Increase Activated Providers per PGA from [x] → [y] via higher funnel conversion
Enhance PGA tooling to reduce manual work and improve efficiency
Metric: Increase Activated Providers per PGA from [x] → [y] by reducing time per opportunity
Make PGAs count where it matters most
Prioritize high-leverage funnel moments (Referrals, Ranking, PEM, port support, Re-engagement)
Metric: Increase PGA-driven RICs from [x] → [y] per month
De-average the motion at scale
Customize PGA workflows by territory, channel, provider type; consider introducing a BDR team
Use AI for just-in-time knowledge and sharper interactions
Adjust motions using predicted provider value (opportunity scoring) to optimize ROI
Metric: Increase Activated Providers per PGA from [x] → [y] via higher funnel conversion
Uplevel team performance
Standardize and enforce best-in-class playbooks; reduce variance across performers
Metric: Improve P90/P10 ratio from 2.0x → 1.5x
Hire, develop, and retain top talent (PGA + TL + PGM); strengthen onboarding, development, and career paths
Metrics: Successfully onboard [100] new PGAs
Increase engagement scores from [x] → [y]
Continually iterate with changing offerings (supervisory billing, packaging, EHR) and new motions

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