Contract Sales Representative (Remote)

Job Title: Contract Sales Representative (Lead Generation & Demo Scheduling)Location: U.S.-based (Remote)Contract Type: 1099 ContractorDuration: 6-8 week trial with potential transition to part-time or full-time roleCompensation: Hourly (via Upwork)About UpswingUpswing is an education technology company focused on improving student success and retention through engagement tools, academic support, and actionable insights. We partner with colleges, universities, and nonprofits to help empower students to achieve their goals.Role OverviewWe are seeking highly motivated Contract Sales Representatives to support our outreach efforts. In this role, you will be responsible for generating scheduled demos from a provided list of leads. You'll receive targeted sales training covering our messaging, buyer personas, product positioning, and outreach workflow.This role is ideal for candidates who are self-starters, highly organized, and excited about contributing to a meaningful mission in higher education.ResponsibilitiesConduct outbound outreach (email, phone, LinkedIn) to a provided list of leadsFollow Upswing's sales messaging and outreach cadenceSchedule demos for the sales team using our calendar toolsDocument all outreach activity and lead notes in the designated systemParticipate in training sessions and weekly check-insMeet weekly KPIs related to demo generation and documentation completenessQualificationsBased in the United StatesExperience in sales, lead generation, or outreach-focused roles preferred; experience in higher education or higher education sales a plusStrong communication and organizational skillsAbility to follow structured processes and meet weekly targetsReliable time management and responsivenessComfortable working remotely and independentlyAdvancement OpportunityContractors who excel during the 6-8 week trial period may be invited to transition into a part-time or full-time role such as Jr. Account Executive or Account Executive, with expanded responsibilities including full sales cycle management.

Created: 2026-04-02