VP Of Sales - Remote Eligible

Vice President of Sales

Location: Flexible / Remote Compensation: $150–$185k base + competitive OTE, strong equity, and comprehensive benefits

About Overalls

Overalls is on a mission to transform how people experience benefits and support at work. We're building a category-defining company, and we're now ready to accelerate growth with the right sales leadership.

We're looking for a Vice President of Sales to help Overalls evolve from a founder-led sales motion to a predictable and repeatable revenue engine. This is a high-impact leadership role on our executive team, where you'll both sell directly and lay the foundation for a world-class sales organization that takes us to the next stage of growth.

What You'll Do

1. Own the sales motion: Transition Overalls from founder-led selling to a scalable, repeatable sales process.
2. Be hands-on early: Act as an individual contributor in the near-term, driving deals while building the playbook for scale.
3. Design the sales framework: Introduce and instill best practices from proven models like MEDDIC, Challenger Sales, SPIN, or others you've mastered.
4. Build the team: Recruit, mentor, and lead a sales team over time—setting structure, process, and culture.
5. Drive predictable growth: Establish pipeline discipline, forecasting accuracy, and performance metrics that align with company goals.
6. Be our sales SME: Serve as the company's subject matter expert on all things sales strategy, training, and enablement.
7. Deeply understand the buyer: Lead sales into HR and benefits decision-makers, while expanding our footprint into insurance carriers, unions, and associations.

What We're Looking For

• Proven growth experience: You've successfully helped scale a startup, either leading the charge or riding shotgun as a senior sales leader.
• Sales methodology mastery: You've studied and practiced structured approaches like MEDDIC, Challenger Sales, or similar, and know how to operationalize them.
• Domain expertise: Strong track record selling into HR and benefits leaders; experience with carriers, unions, and associations is a plus.
• Hands-on leader: Comfortable starting as an IC, then evolving into a team-builder and organizational leader.
• Startup DNA: You thrive in ambiguity. Big-company logos on your resume don't impress us—the startup growth journey does.
• Leadership presence: Ready to be part of Overalls' leadership team, contributing to company-wide strategy and culture.

Why Join Us

• A mission-driven company at the inflection point of growth
• Competitive compensation: $150–$185k base + strong OTE + meaningful equity
• Comprehensive benefits and perks
• The opportunity to build something category-defining from the ground up
• A seat at the leadership table shaping Overalls' trajectory