VP of SalesOveralls • Chicago, IL, US
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VP of Sales
Overalls • Chicago, IL, US
[job_card.30_days_ago]
[job_preview.job_type]
- [job_card.full_time]
[job_card.job_description]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 usthe startup growth journey does. Leadership presence : Ready to be part of Overalls' leadership team, contributing to company-wide strategy and culture. 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
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
- Own the sales motion : Transition Overalls from founder-led selling to a scalable, repeatable sales process.
- Be hands-on early : Act as an individual contributor in the near-term, driving deals while building the playbook for scale.
- Design the sales framework : Introduce and instill best practices from proven models like MEDDIC, Challenger Sales, SPIN, or others you've mastered.
- Build the team : Recruit, mentor, and lead a sales team over timesetting structure, process, and culture.
- Drive predictable growth : Establish pipeline discipline, forecasting accuracy, and performance metrics that align with company goals.
- Be our sales SME : Serve as the company's subject matter expert on all things sales strategy, training, and enablement.
- 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
Why Join Us
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Vp Of Sales • Chicago, IL, US
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