Sales Vertical Director - Retail

San Francisco, California, United StatesOnsiteFull TimeDirectorPosted 2 months agoVisa sponsorship available

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Role summary

Windfall is seeking a Director of Retail to lead and build its retail vertical. This player/coach role involves direct account ownership, pipeline development, and deal execution for top retail accounts, alongside hiring, coaching, and managing a team of Account Executives. The Director will collaborate with co-founders, product, and marketing to define the retail strategy, including ICP, messaging, product priorities, and go-to-market motion. Revenue accountability for new bookings, retention, and expansion is key, as is translating market dynamics into product feedback and competitive positioning. The ideal candidate has 5+ years of enterprise SaaS sales experience, 3+ years of sales leadership, and deep fluency in the retail industry.

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.

We’re on a mission to change how organizations perceive and use people data. And we hold true to our core values of: (1) Be an excellent communicator; (2) Operate with transparency; (3) Provide leverage, not optimization; (4) Win When Our Customers Win; and (5) Act with integrity and trust.

Responsibilities:

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

Requirements:

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

Additional Information:

The range displayed on each job posting reflects the minimum and maximum target for new hire salaries for the position across California. Within the range, individual pay is determined by work location and additional factors, including job-related skills, experience, and relevant education or training. We also offer a comprehensive benefits package, which you can explore on our careers site

Compensation range:

About Windfall

Windfall is a people intelligence and AI company that gives go-to-market teams actionable insights. By democratizing access to people data, organizations can intelligently prioritize go-to-market resources to drive greater business outcomes. Powered by best-in-class machine learning and artificial intelligence, Windfall activates insights into workflows that engage the right people for each respective organization. More than 1,500 data-driven organizations use Windfall to power their business. For more information, please visit www.windfall.com.

We comply with CCPA. For more information on how we comply, review our privacy notice.

Windfall is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees.

We may use AI tools to assist parts of the hiring process, such as reviewing applications or analyzing resumes. These tools assist our team and do not replace human judgment. Final hiring decisions are made by people.

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