Chief Commercial Officer

Insurify • Cambridge, MA

123d

About The Position

Insurify is one of the America’s fastest-growing MIT FinTech startups and has been recognized as one of Inc. 5,000’s fastest-growing private companies in America of 2023, 2022 and 2021, Forbes Fintech 50 List for 2023, 22, 21, Forbes Next Billion Dollar Startups of 2022 global and Top 100 InsurTech company. We’re changing the way millions of people compare, buy and manage insurance with artificial intelligence, technology, and superior product design. Our company vision is to be recognized as the preeminent and most trusted digital agent for insurance comparison, purchase, and management. Our team is critical to achieving our vision and fostering the right culture is essential to our team’s success. We’re hiring a CCO to own Insurify’s commercial engine end‑to‑end—partner economics, pricing & yield, performance strategy, RevOps, and lifecycle—delivering profitable, durable growth across consumer and B2B/white‑label channels.

Requirements

• 15+ years driving revenue in marketplace/fintech/insurtech or adjacent regulated categories; ownership of a $1.0B+ multi‑channel P&L.
• Proven pricing/yield optimization and partner/carrier negotiation track record.
• Leadership of teams across Partnerships, RevOps/Analytics, and Enterprise/B2B.
• Data fluency: strong SQL literacy and BI familiarity (Looker/Tableau/Mode); experimentation at scale.

Nice To Haves

• P&C insurance/MGA exposure.
• Contact‑center sales leadership.
• Deploying AI/agent assist in sales or QA.

Responsibilities

• Own the numbers: Net Revenue, Contribution Margin, unit economics, LTV, and forecast accuracy.
• Lead the commercial engine end-to-end: Partnerships/Supply, Strategic Demand Partnerships, Proprietary Products & Monetization, Pricing & Yield, LTV, Revenue Operations & Analytics, Lifecycle/CRM, Policy & Monetization Experiments, and Agency Operations (Insurify call & service center).
• Strengthen supply & demand: Improve carrier economics, state coverage, vertical expansion and B2B partnerships to acquire qualified traffic and monetize it efficiently.
• Level up conversion: Partner with the CPO and CTO to ship pricing/ranking experiments, funnel improvements, and raise quote to bind and cumulative contribution margin per visit/user/lead/call.
• Implement performance management systems: Implement robust KPIs and OKRs to track and enhance company performance.
• Build the operating system: Single‑source revenue truth model, RevOps dashboards, weekly revenue council cadence, and rigorous experiment governance.
• Lead & develop talent: Hire/mentor a high‑caliber org, establish comp plans tied to margin gates, and enforce clear goals.
• Carrier Partnerships: Commercial ownership of carrier relationships. Develop C-level relationships with carrier partners to grow share of wallet, improve economics (commission, bonuses, incentives), expand state coverage, and drive SLA adherence/compliance.
• Strategic Partnerships: Source and scale partners whose brands/audiences drive qualified traffic. Structure co‑branded flows, revenue‑share models, data‑sharing and measurement, and improve partners’ monetization with insurance.
• Proprietary Products & Monetization: Manage and expand Insurify’s product portfolio across segments and verticals (e.g., auto, home, renters, bundled). Define packaging/pricing, cross‑sell/upsell modules, partner APIs/white‑label offerings, and new revenue lines.
• Agency Operations (Call & Service Center): Own daily performance of Insurify’s agency/contact center: staffing and WFM, conversion/QC/QA targets, scripting/coaching, compliance, and vendor management. Partner with Product to deploy AI/assist and with Legal/Compliance for controls.
• Pricing & Yield: Optimize take rate, prioritization/ranking levers, marketplace incentives, and discount/bonus frameworks; run controlled tests to maximize cumulative contribution margin per visit/user.
• Revenue Operations & Analytics: Forecasting, partner reporting, servicing, and analytics.
• Policy & Monetization Experiments: Design/run A/B and multivariate tests across quote flows, call routing, incentive structures, and pricing/ranking; enforce guardrails and experiment reviews, in partnership with product, marketing, and engineering.

Benefits

• Competitive compensation
• Generous stock options
• Health, Dental Coverages
• 401K plan with match
• Unlimited PTO
• Generous company holiday calendar
• Learning & Development Stipends
• Paid Family Leave
• Social impact volunteer time
• Catered lunches in the office

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: Bachelor's degree
• Number of Employees: 101-250 employees