Head of Sales

Why Join Insuraviews? 

●      Build something that matters. Our mission is to revolutionize the insurance industry and every person on this team has a direct hand in that mission. You will see your work shape decisions that affect real carriers and their customers.

●      A culture built on real values. We lead with Integrity, Responsibility, and Trust. That means we follow through on what we say we'll do, own our mistakes, and treat everyone's time and ideas with respect.

●      Innovation is an expectation, not a perk. Creativity and AI is woven into how we work and what we build. You’re expected to experiment, bring better approaches back to the team, and out-think a fast-moving market.

●      Mentorship and real ownership from day one with a path toward growth, not just a title. We are startup focused on growing together, supporting one another, and helping everyone expand their skills. 

●      Competitive compensation and comprehensive benefits, including paid holidays, paid time off, and company benefit plans (e.g. medical, dental)

●      Flexible and hybrid work options designed around outcomes, not hours.

About the Role

Insuraviews is ready for a dedicated leader to own the company’s revenue number. As Head of Sales, you will put in place the practical processes that make revenue repeatable and forecastable, and you will help hire the sales and customer success team members who support the company’s growth.

Reporting to the CEO and working side-by-side with the Chief Actuary and Head of Operations, you will lead a small team of direct sellers and Customer Success, own the sales process from pipeline through renewal, and be accountable for new business, renewal, and expansion ARR. You will also carry a personal quota on a select set of named accounts and strategic deals, building executive-level relationships with actuarial, product, and underwriting leaders at carriers and representing Insuraviews at industry conferences and client meetings.

You will thrive here if you are a hands-on seller who still enjoys closing, likes coaching a team, and is comfortable in a lean, early-stage startup where priorities shift quickly and everyone wears multiple hats. If you are credible with actuarial, product, and underwriting buyers and ready to own the number, we would love to meet you.

Location

●      Remote in WI, IL, MN or FL

●      In-Office / Hybrid in Eau Claire, WI (Optional)

Compensation

●      Base Salary (see below) + bonus based on team achievement and company targets + commission on named accounts and strategic deals

●      Equity grant upon hire, subject to board approval. Equity amount based on experience

Responsibilities

1. Revenue Ownership & Team Leadership

●      Own overall quota and ARR achievement for the revenue team, including new business, renewal, and expansion revenue.

●      Lead and coach a small team of direct sellers and Customer Success, guiding them through regular pipeline reviews, deal coaching, and clear goals.

●      Drive attainment across all quota-carrying and revenue focused roles, including direct sellers, Customer Success, and the Chief Actuary.

●      Serve as the escalation point for complex deals, pricing exceptions, and at-risk renewals.

●      Help hire future sales and customer success team members as the company grows.

2. Strategic & Named Account Selling

●      Carry a personal quota for a select set of named accounts and strategic deals.

●      Build and lead executive-level relationships with actuarial, product, underwriting, and competitive intelligence leaders at target and existing carrier clients.

●      Structure and negotiate enterprise agreements, in partnership with the CEO and Head of Operations.

●      Partner with the Chief Actuary on technically complex opportunities, pairing commercial leadership with actuarial credibility.

3. Sales Process & Forecasting

●      Own the end-to-end sales process, from lead qualification and pipeline management through close, handoff, renewal, and expansion, keeping it practical and right-sized for a small team.

●      Own the sales forecast, delivering accurate, regular pipeline and forecast reporting to the CEO and leadership team.

●      Track core sales metrics, including pipeline coverage, win rate, sales cycle length, average contract value, and net revenue retention.

●      Partner with the Head of Operations on sales operations, including CRM hygiene, quoting and order processing, security reviews, and reporting.

●      Create simple, practical sales tools, including talk tracks, demo flows, and proposal templates that the team can put to use right away.

4. Customer Success, Retention & Expansion

●      Lead the Customer Success function, ensuring clients are onboarded effectively, adopt the platform, and realize measurable value.

●      Own renewal and expansion outcomes across the customer base, including renewal forecasting and proactive management of at-risk accounts.

●      Ensure a clean, consistent handoff from sales to Customer Success following contract execution.

●      Partner with Customer Success and the Chief Actuary to define and monitor client health metrics.

5. Planning & Go-to-Market

●      Collaborate with the CEO and Head of Operations on annual sales planning, budgeting, and quota setting.

●      Help shape go-to-market priorities, including target segments, ideal customer profile, and account prioritization, and provide input on pricing and packaging.

●      Collaborate on marketing campaigns, messaging, and lead generation that build a healthy pipeline.

●      Bring market, customer, and competitive feedback to the product team and leadership to inform the roadmap and positioning.

6. Industry Presence & Market Engagement

●      Represent Insuraviews at industry conferences, carrier meetings, and partner events.

●      Travel to conferences, plus client meetings as needed.

●      Build and maintain relationships across the P&C carrier, MGA, and consulting ecosystem.

Required Qualifications

●      8+ years of B2B sales experience, including SaaS, with at least 2 years leading or coaching others (as a sales manager, team lead, or player-coach) and a track record of meeting or exceeding quota.

●      A hands-on seller who still enjoys closing and who is comfortable personally owning complex enterprise deals while coaching a small team.

●      Direct experience selling into insurance carriers, MGAs, or other insurance organizations, with working knowledge of how insurance products are created, priced, filed, and brought to market. An actuarial credential is not required.

●      Experience running a sales process, including pipeline management, forecasting, and sales metrics, in a CRM-driven environment.

●      Experience navigating multi-stakeholder buying committees, long procurement cycles, security reviews, and enterprise contract negotiations.

●      Experience owning or directly influencing renewal and expansion revenue in partnership with Customer Success.

●      Comfortable in a lean, early-stage startup where priorities shift quickly and everyone wears multiple hats.

●      Exceptional written and verbal communication skills, with the ability to engage credibly with C-suite executives and highly technical practitioners such as actuaries and product managers.

●      Comfortable using AI tools to improve the quality or efficiency of day-to-day work, with curiosity about emerging capabilities in their domain.

●      Willingness to travel to industry conferences approximately 5 to 10 times per year, plus client meetings as needed.

●      Bachelor’s degree in Business, Marketing, Economics, Finance, Actuarial Science, Mathematics, or a related field. Relevant experience will be considered in lieu of a degree.

Nice to Have

●      Experience selling SaaS, data, or analytics platforms to P&C carriers, particularly to actuarial, pricing, product, or competitive intelligence teams.

●      Established relationships with actuarial, product, and underwriting leaders at P&C carriers.

●      Experience at an early-stage or venture-backed startup, ideally helping build a sales motion from an early stage rather than inheriting an established one.

●      Familiarity with multi-state rate and form filing processes, SERFF, or insurance regulatory environments.

●      Experience with Pipedrive, HubSpot, or Salesforce, and with sales engagement or conversation intelligence tooling.

●      Experience selling alongside actuarial or other technical subject-matter experts.

●      CPCU, AINS, or other insurance-related certification or credential.

Insuraviews is an equal opportunity employer and values diversity at our company. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status. We are committed to creating an inclusive environment for all employees.