Stride

Sales Development Rep

• Stride is the first portable benefits platform designed for the nearly 60 million American independent workers who do not receive employer-based benefits. The Stride platform offers access to insurance — health, dental, vision, life and other supplemental insurance — as well as financial tools to track income, mileage and other deductible expenses to manage their tax obligations, all via a single app.\n• The Role: Cash compensation range: $88,000 - $107,000 USD/annually + equity\n• We, at Stride, are seeking a Sales Development Representative (SDR) to drive top-of-funnel growth for our Enterprise SaaS pipeline. In this role, you’ll generate awareness of portable benefits and Stride’s unique offerings. You’ll work closely with the Business Development, Marketing, and Partnerships teams to build and execute outbound campaigns, conduct research to identify and map prospects, and ensure inbound inquiries are properly triaged. You’ll be essential in evolving our pipeline mix from 100% outbound to a healthier balance of 70% outbound and 30% inbound. Additional responsibilities include, but are not limited to:\n• Identifying target companies and buyer personas, and conducting in-depth research to build contact maps and strategic outreach plans\n• Owning outbound outreach using tools like LinkedIn Sales Navigator and HubSpot and creating personalized 1:1 messages and sequences\n• Collaborating with Marketing on outbound campaign content and strategy\n• Triaging and qualifying inbound interest, ensuring leads are properly routed\n• Building and managing structured follow-up systems to re-engage prospects at the right time\n• Supporting the broader BD team by providing market insights and prospecting materials\n• Tracking and reporting on outreach performance, adjusting strategies as needed\n• Contributing to a feedback loop that improves Stride’s messaging, targeting, and go-to-market strategy

Sales Development Representative, SDR