Head of Sales

About Vouch
Vouch is the insurance broker that powers ambition.

We're a tech-enabled insurance advisory and brokerage purpose-built for growing companies in technology, life sciences, and professional services. Our clients are ambitious leaders building complex businesses, and we help them manage risk with tailored advice, smart coverage, and responsive service.

Backed by over $225M from world-class investors, Vouch combines deep industry expertise with AI-powered tools to deliver a better insurance experience. Our digital workflows reduce friction, speed up decisions, and give our clients the confidence to move faster.

*Why should you join our team and Vouch?*
Not only is this an exciting and growing team where you can drive a real impact on our operational scalability, but Vouch is also the preferred insurance provider to customers of Y Combinator, Brex, Carta, and WeWork. We're a quickly growing startup that believes in transparency and acknowledgment with our team members and cultivating a values-driven company. Our values are "Put People First," "Listen, Challenge, and Grow," "Face challenges head-on and win as a team," and "Serve clients with integrity and excellence."

*What does a work environment look like at Vouch?*
Vouch has employees located across the U.S., with offices in San Francisco, Chicago, and New York City. This role is based in San Francisco (preferred) or New York City and our core collaboration hours are 8:30 am-2:30 pm Pacific Time. (When most internal meetings are held)

What You'll Do

• Define and execute Vouch's overall sales strategy, aligned to revenue goals and the Vouch 2.0 trust strategy
• Lead, manage, and scale a team of producers and BDRs, fostering a culture of ambition, accountability, and trust
• Refine and operationalize a repeatable GTM motion across inbound and outbound segments
• Build and manage a Center of Influence (COI) partner strategy to expand market reach, leveraging industry partners, advisors, and key influencers to accelerate lead generation and client acquisition.
• Ensure sales teams deliver a high-trust, high-NPS client experience at every step of the journey
• Collaborate with RevOps, Marketing, Client Management and Placements to strengthen cross-functional impact
• Partner with executive leadership on forecasting, planning, and new market/segment expansion
• Personally lead or support select large, complex opportunities and partnerships

About You

• 10+ years in sales, with 5+ years leading and scaling revenue teams
• Proven track record of managing quota-carrying teams with $20M+ revenue responsibility
• Demonstrated success in fast-growth, entrepreneurial environments
• Exceptional leadership and coaching ability — you build high-performing teams that people want to join and stay with
• Deeply data-driven, with strong forecasting discipline and process orientation

Nice To Have

• Experience in commercial P&C insurance or adjacent financial services
• Background in startups, SaaS, or fintech, with GTM scaling experience
• Exposure to partnership-driven sales models (channel, referral, etc.)

What Success Looks Like (12–18 Months)

• Drive 30%+ YoY new business revenue growth
• Increase average revenue per client through product expansion
• Hire, ramp, and retain a high-performing sales org
• Deliver accurate and reliable forecasting for executive planning
• Strengthen trust & alignment across Marketing, Placements, and Client Management

*Vouch provides several benefits to help you bring your best self to work:*

• Competitive compensation and equity packages
• Health, dental, and vision insurance
• Parental leave
• Flexible vacation time
• Wellness allowance ($80/month)
• Technology allowance ($100/month)
• Professional Development ($500/Yr)
• Home office setup (One-time $500)
• L&D: Partnerships with Ethena and monthly Lunch & Learns
• Employee Groups: Vouch supports various employee groups to foster an inclusive, equitable workplace and create affirming, empowering, employee-centered spaces for conversation, community, and support. These groups include Pride @ Vouch, Women @ Vouch, Black @ Vouch, Virtual Connections, Pop Culture, Pets of Vouch, Skincare, Astrology, Plants, etc.
• Wellbeing: Voucher's have access to many wellbeing perks, including Peloton, Fetch, OneMedical, SoFi, etc.
• Bi-Annual performance reviews with quarterly check-ins: Vouch conducts bi-annual performance discussions with all team members, offering goal setting and check-ins, development discussions, and promotion opportunities.

What To Expect In a Typical Interview Process
(Please note these steps may vary slightly depending on the role)

• 30-minute phone call with our recruiting team
• 30-45 minute video interview with the hiring manager
• Case study/technical screen
• Meet the team 30-45 min 1:1 video discussion with 3-4 team members you'd work closely with in the role
• Executive chat

Compensation Philosophy
Our salary ranges are based on paying competitively for our size and industry and are part of our total compensation package, which also includes benefits and other perks. We also include stock options in all compensation packages and believe all Vouch employees should have the opportunity to become owners in the company. Individual pay decisions are based on a number of factors, including qualifications for the role, experience level, skill set, location, and business need. The pay range provided is subject to change and may be modified in the future.

Vouch believes in putting our people first, and building a diverse team is at the front of everything we do. We welcome people from different backgrounds, experiences, perspectives, and ranges of abilities. We are an equal-opportunity employer and celebrate the diversity of our growing team.
If you require reasonable accommodation to complete this application, interview, complete any pre-employment testing, or otherwise participate in the employee selection process, please direct your inquiries to

.