Enterprise Account Executive - Insurance

About FeatheryFeathery is the AI Operating & Decisioning system for financial services. Our customers — including Fortune 500 insurers like Allstate — use Feathery to power mission-critical workflows across insurance underwriting, quoting, submission intake, claims, and customer onboarding. Why We’re HiringAs Feathery grows, we’re expanding our footprint across the insurance industry and engaging with more enterprise carriers and insurance organizations that require a consultative, high-touch sales process. We’re hiring an Enterprise Account Executive with deep insurance industry experience to drive revenue growth and help define our enterprise sales motion within insurance. This role is ideal for someone who thrives in a full-cycle sales environment, enjoys building pipeline, and wants to play a key role in shaping how Feathery goes to market and wins within the insurance <industry.As> an early member of the team, you’ll have significant ownership over pipeline, deals, and how we win in the enterprise. About the RoleThis is a high-ownership role that blends:Full-cycle enterprise sales across the insurance industryPipeline generation and deal executionStrategic, consultative sellingCross-functional collaboration with product, marketing, and leadershipYou’ll own the entire sales process — from sourcing opportunities to closing deals — while helping define how Feathery scales its enterprise revenue engine. What You’ll DoPipeline Generation & ProspectingProspect and develop new enterprise accounts across the insurance industryReach out to prospects via email, phone, and LinkedInExperiment with messaging, targeting, and channels to generate new opportunitiesAttend insurance industry conferences and events to build relationships and source pipelineOwn pipeline generation strategy and continuously refine outbound approachesDeal Execution & Sales ProcessManage the full sales cycle from initial outreach through closeHandle inbound and referred leads and convert them into qualified opportunitiesConduct discovery to understand customer needs and business challengesDeliver tailored demos and presentations for different stakeholdersNavigate complex buying processes and multi-stakeholder dealsSales Strategy & Cross-Functional CollaborationHelp define and refine sales playbooks, positioning, and processesPartner with product and engineering to communicate customer needs and influence roadmapCollaborate with marketing on campaigns and demand generation initiativesContribute to product launches and go-to-market strategy About YouExperience selling enterprise SaaS into the insurance industry, or deep insurance industry experience in a commercial roleExperience with enterprise deals ($100K–$1M+ ARR)Track record of high achievement in quota-carrying rolesStrong consultative selling skills and ability to engage senior stakeholdersExcellent communication and storytelling abilities with high customer empathyExperience building pipeline through outbound prospectingBuilder mindset with a desire to shape processes and strategyHighly motivated, resilient, and comfortable operating in a fast-paced environmentPassion for understanding customer problems and helping solve them BonusExisting network within the insurance industryExperience selling complex or technical productsExperience attending or sourcing pipeline through industry conferencesBackground at a high-growth B2B SaaS or InsurTech company What We OfferCompetitive compensation and equityHealth, dental, and vision coverageUnlimited PTODowntown Toronto office locationOffice snacks and monthly catered lunchA supportive, low-ego team that values ownership and growthCompany offsite to connect and rechargeFeathery is an equal opportunity employer and does not discriminate on the basis of race, religion, color, national origin, sex, sexual orientation, age, veteran status, disability, genetic information, or any other legally protected characteristic. We’re committed to building an inclusive team and provide reasonable accommodations upon request.