Contract Sales Representative (Remote)

We 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.

• Conduct outbound outreach (email, phone, LinkedIn) to a provided list of leads
• Follow Upswing's sales messaging and outreach cadence
• Schedule demos for the sales team using our calendar tools
• Document all outreach activity and lead notes in the designated system
• Participate in training sessions and weekly check-ins
• Meet weekly KPIs related to demo generation and documentation completeness

• Based in the United States
• Experience in sales, lead generation, or outreach-focused roles preferred; experience in higher education or higher education sales a plus
• Strong communication and organizational skills
• Ability to follow structured processes and meet weekly targets
• Reliable time management and responsiveness
• Comfortable working remotely and independently

Contractors who excel during the 68 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.