VP of Sales

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. 

You Will 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

You’d be a great fit if you…

• 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

Compensation and Benefits:

The expected base pay range for this position is $161,280 - $252,000, 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