VP of Sales

VP/Head of Sales at Cover Force

At Cover Force, we're redefining how insurance is bought and sold. Our mission is simple: to make business insurance faster, easier, and fully digital. Thousands of insurance agents and corporate customers rely on our platform to streamline quoting, comparing, and purchasing policies.

We partner with leading insurers like Travelers, Liberty Mutual, and Chubb to reduce underwriting and sales time by 60%, setting a new standard for efficiency in the industry.

Our solutions power the future of insurance distribution:
Quote & Bind Platform – Used by Top 100 insurance distributors to generate quotes instantly and eliminate paperwork. Embedded Commercial Product – Enables platforms like Walmart, Gusto, and Uber to embed business insurance seamlessly into their customer journeys. Insurance's API Layer – We're building the Plaid of commercial insurance, providing frictionless access to policies through APIs and modern software.

We're looking for a VP/Head of Sales to lead and scale the revenue engine s is a senior leadership role reporting directly to the CEO, with a true seat at the table and significant influence over the company's next phase of growth. You'll own the full go-to-market motion, shape our sales strategy, and build the team, processes, and systems needed to scale revenue to $50M+ ARR and beyond.

This is a hands-on leadership role for someone who wants to be close to the business. You'll carry a bag, close strategic deals, and work directly with the CEO and leadership team to shape how Cover Force wins in the market. You'll have the autonomy to make decisions, build the organization around you, and play a defining role in the company's growth trajectory.

This position is based in-person in New York City or Denver.

• Own the full sales function: pipeline, forecasting, team hiring, and quota attainment

• Personally close mid-market and enterprise deals alongside your team, staying close to the customer throughout the cycle

• Build and iterate on the sales process, playbooks, and tooling; CRM hygiene, pipeline rigor, and a forecasting methodology you'd stake your number on

• Hire, coach, and develop a team of AEs; establish a high bar for performance and a culture of accountability

• Partner directly with the CEO to set GTM strategy, shape pricing and packaging, and identify the highest-leverage markets and segments

• Work closely with Marketing to develop demand-gen programs, partner with CS to ensure strong retention and expansion, and influence the product roadmap based on what you hear in the field

• Build the operational muscle the sales org will need at scale; territory design, comp plans, onboarding, and enablement infrastructure

Cover Force is at a clear inflection point. We've built the platform, signed the carriers, and proven out the model with a growing base of agency networks, wholesalers, and embedded insurance partners. The infrastructure is in place. What comes next is building the sales organization that takes us from traction to category leadership, and we want the right person to own that.

• 8–12+ years of B2B SaaS or technology sales experience, including at least 3–5 years in a sales leadership role

• Track record of building and scaling sales teams at an early-stage company ($3M–$20M ARR); you've done this before and have the scar tissue to show for it

• You've personally carried a bag and closed deals at some point in your career, and you're willing and eager to get back in the field alongside your team

• Experience selling into a market where you had to create the category or educate the buyer, not just capture inbound demand

• Proven ability to build from scratch: process, playbooks, hiring rubrics, and forecasting models

• Strong operator; comfortable in a spreadsheet, rigorous about pipeline health, and capable of presenting a credible number to the board

• Insurance or fintech experience is a plus, but not a requirement; what matters more is the ability to learn a complex domain quickly and translate it into a compelling sales narrative

• Competitive pay including equity

• Unlimited PTO

• Home office stipend

• Full healthcare coverage for you and your family

• Parental leave for all types of parents including adoption and foster care