Contract Sales Representative (Remote)

Job Title: Contract Sales Representative (Lead Generation & Demo Scheduling)

Location: U.S.-based (Remote)

Contract Type: 1099 Contractor

Duration: 6–8 week trial with potential transition to part-time or full-time role

Compensation: Hourly (via Upwork)

About Upswing

Upswing 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.

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.

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  Conduct outbound outreach (email, phone, LinkedIn) to a provided list of leads
  
  

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  Follow Upswing’s sales messaging and outreach cadence
  
  

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  Schedule demos for the sales team using our calendar tools
  
  

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  Document all outreach activity and lead notes in the designated system
  
  

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  Participate in training sessions and weekly check-ins
  
  

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  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 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.