Salesperson

Company Description Tobie transforms complex benefits documents—such as SPDs, riders, union contracts, and open enrollment FAQs—into clear, employee-friendly experiences. The platform powers branded microsites, an AI assistant that answers only from approved materials, explainer videos, and automated campaigns aligned with enrollment windows. Designed around real-world HR workflows, Tobie helps manage late-breaking plan changes, short enrollment periods, and recurring employee questions, while surfacing actionable insights for HR. All answers are sourced from client documents, not the open internet, with a full audit trail, HIPAA awareness, and SOC 2 readiness. Tobie typically delivers a working demo from a benefits guide within 48 hours.Role Description This is a remote contract role for a Salesperson at Tobie. The Salesperson will identify and qualify leads, focusing on HR teams, benefits leaders, and brokers who manage complex benefits communication. Daily responsibilities include conducting outbound outreach, running discovery calls, delivering product demos tailored to prospect needs, and managing opportunities through the sales pipeline. The role involves collaborating with marketing and product teams to refine messaging, gathering feedback from prospects, and updating CRM records accurately. The Salesperson will also negotiate terms within established guidelines, support onboarding handoffs to customer success, and consistently work toward meeting and exceeding sales targets.Qualifications Proven experience in B2B sales, preferably selling SaaS or HR/benefits technology solutions.Strong skills in prospecting, lead qualification, and managing a consultative sales cycle from discovery to close.Ability to deliver compelling product demos and translate complex concepts into clear, value-focused conversations.Comfort using CRM tools, sales engagement platforms, and basic productivity software to manage pipeline and reporting.Excellent written and verbal communication skills, with a professional, inclusive, and customer-focused approach.Experience selling to HR, benefits, or employee experience stakeholders is highly beneficial.Self-directed, comfortable in a fast-paced, remote environment, and able to prioritize effectively with minimal supervision.Bachelor’s degree in Business, Communications, or a related field, or equivalent practical experience.