Contract Sales Representative (Remote) - SAAS - Remote

Mon, 09 Mar 2026 02:32:30 -0500

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.

Role Overview

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.

Responsibilities

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

Qualifications

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

Advancement Opportunity

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.