Sales Vertical Director - Retail at Windfall – San Francisco, California

We’re hiring a Director of Retail to own and build this vertical. The short version: you’ll carry a bag, you’ll build a team, and you’ll help define how Windfall goes to market across luxury retail, e-commerce, consumer brands, and adjacent retail segments.

This is a player/coach role - intentionally so. You’ll personally lead outreach and engagement across our top 50–100 Retail accounts while simultaneously hiring, developing, and managing the AEs who will eventually scale this into a standalone business. Windfall’s wealth data unlocks high-impact use cases for retailers - identifying HNW customers, personalizing outreach, powering loyalty programs, and driving clienteling at scale. You’ll help retailers understand why that matters and build the motion to close it.

You’ll work directly with our co-founders, product, and marketing to shape Windfall’s Retail strategy - what we build, how we position it, and who we prioritize. If you want a job where you just manage, this isn’t it.

Our mission is to change how organizations perceive and use people data. We hold true to our core values of: (1) Be an excellent communicator; (2) Operate with transparency; (3) Provide leverage, not optimization; (4) Make a difference every day; and (5) Act with integrity and trust.

• Account ownership: Direct outreach, pipeline development, and deal execution across Windfall’s top 50-100 Retail accounts, you’re not handing this off - you’re running it
• Team leadership & buildout: Hire, coach, and develop the AE team for the Retail vertical - from first rep to full team, you set the bar and hold it
• Vertical strategy: Partner with co-founders, product, and marketing to define ICP, messaging, product priorities, and go-to-market motion for Retail, this is a seat at the table, not a consulting exercise
• Revenue accountability: Own the Retail number - new bookings, retention, and expansion, the vertical’s performance is yours
• Cross-functional influence: Translate retail market dynamics into product feedback, competitive positioning, and partnership priorities, you’re the voice of the customer inside the building

• Bachelor’s Degree
• 5+ years of enterprise SaaS sales experience, with a demonstrable track record of closing complex, multi-stakeholder deals
• 3+ years of sales leadership experience - you’ve built or managed a team and have the scar tissue to show for it
• Deep fluency in retail - whether you’ve sold into the space or operated within it, you understand the buyer, the workflow, and how decisions get made across marketing, loyalty, and digital teams
• Familiarity with luxury retail, e-commerce, department stores, specialty retail, or consumer brands is a strong signal
• Experience selling data, analytics, or customer intelligence solutions is a meaningful plus
• You think in systems and build them that way - you know how to create a repeatable motion, not just close deals
• You’re direct, organized, and not precious about being a player in a player/coach role
• Based in or willing to relocate to San Francisco