Job Description
We are seeking a Director of Sales who is both a top-tier closer and a builder of systems, people, and process. This is a player-coach role, responsible for owning key deals while mentoring a small team, creating stand up repeatable sales motions across direct and broker channels, and partnering tightly with Marketing to drive pipeline and learnings.
Responsibilities:
* Own revenue: Prospect, run full-cycle deals, and close new business while setting standards for discovery, demos, negotiation and forecasting
* Build the engine: Design and implement our sales strategy, operating cadence, and playbooks partnering with the broader team where necessary (e.g. ICP, messaging, qualification, pricing, proposals, and objection handling)
* Enable the sales team to close deals at market-leading rates
* Scale the team: Recruit, onboard and coach the sales team; establish goals, enablement, and performance management
* Broker & partner channels: Activate and grow benefits brokers and PEOs in partnership with our VP of Partnerships and Sales Consultants; create tiered engagement plans, trainings, and co-marketing
* Process & metrics: Stand up rigorous pipeline hygiene, stage definitions, and forecasting rhythm; create dashboards for conversion, win rates, sales cycle and channel ROI
Requirements
Our ideal candidate will have:
* Startup experience: Success establishing a sales team at an early stage startup in SaaS, insurtech, or similar B2B business
* Player-coach DNA: Proven full-cycle closer who has also hired, coached, and scaled small teams (Series A ? Series B)
* Domain expertise: B2B rewards/HRtech or health insurance background preferred; experience with benefits brokers/consultants a plus
* Channel expertise: Experience building broker/partner programs (brokers, PEOs, marketplaces) and running trainings, spiffs, and joint plans
* Builder mindset: Comfortable creating process, not just running it—CRM architecture, playbooks, comp plans, territories, and quarterly business reviews
* Strategic + analytical: Can segment markets, size opportunities, set targets, and use data to iterate
Benefits
As a member of our team, you can expect:
* Competitive base + variable + equity
* Paid parental & family leave
* Opportunity to build a category-defining company with real social impact