Sales Development Representative

About Plansight:Plansight is the AI platform redefining how employee benefits brokers and consultants work. We automate the manual grind of renewals, spreadsheets, and repetitive tasks so teams can move faster, serve more clients, and grow revenue without growing headcount. Brokers using Plansight save hours per client while delivering a dramatically better experience to the employers they serve. We're in a breakout moment. Our platform is reshaping how the benefits industry operates, our customer base is expanding quickly, and we're adding new partners and agencies every month. This is a rare chance to join an AI company at the exact inflection point where category leadership is being decided. About the Role:We're hiring an Outbound Sales Development Representative (SDR) to help fuel our next stage of growth. You'll build pipeline by prospecting into employee benefits brokers, consultants, and agencies. As the first point of contact, you'll spark interest, qualify opportunities, and set meetings for our Account Executive team. This is a high-visibility seat on a fast-moving team. If you want to break into SaaS sales, learn AI-native selling, and build a career in a category that's being created in real time, this is the role. What You'll DoProspect into employee benefits brokers, consultants, and agencies via cold calls, email, and LinkedIn Identify and engage key stakeholders involved in RFPs, renewals, and client presentations Clearly communicate Plansight's value in language that resonates with brokers Qualify prospects based on need, timing, and fit Book and coordinate demos with our Account Executive team Personalize outreach based on firm size, structure, and workflows Track all activity and pipeline in HubSpot Consistently hit or exceed activity and meeting-setting goals What We're Looking For0 to 3 years of experience in sales, business development, or a customer-facing role Strong communication skills, especially the ability to simplify and clearly explain value Comfortable making cold calls and handling objections Highly organized and able to manage multiple prospects at once Coachable, competitive, and self-motivated Genuine interest in SaaS, AI, or the employee benefits space What Makes You Stand OutExperience selling into brokers or the employee benefits space Familiarity with RFP processes, renewals, or benefits workflows Experience with outbound prospecting tools like Outreach, Salesloft, Apollo, or Instantly Proven track record of hitting or exceeding activity or quota targets What You'll GetCompetitive base salary plus uncapped commission Clear path to Account Executive or other closing roles Hands-on training in SaaS and consultative selling Front-row seat to a fast-growing AI product in a high-demand market Collaborative, high-energy team environment where your work directly shapes the company's trajectory