Remote Workforce Development Jobs in Gary, IN (NOW HIRING)

Department : Partnerships

Reports To : Director – Business Development

Location : Remote – Chicago, IL preferred

Employment Type : Full-time

Travel : 25–35% (conferences and on-campus visits)

Compensation : Base $65K–$75K, + variable ; uncapped commission with accelerators.

About SkillUp Online

SkillUp Online is on a mission to skill 10 million people in 10 years. We deliver AI-readiness and tech workforce programs in partnership with IBM, Microsoft, and Google Cloud — embedded into degree pathways, continuing education, and workforce development channels at colleges and universities across the US and globally. We sit at the intersection of higher education, employer demand, and the certifications that move careers.

About the Role

We are hiring a senior Account Executive to own new business across the US higher education market. You will sell SkillUp's AI-readiness curriculum and certification partnerships into continuing education divisions, workforce development units, online learning programs, and academic colleges — institutions under pressure to launch credentialed pathways quickly without the in-house build capacity to do it alone.

This is a hunter role with long-cycle, multi-stakeholder deals. You will work with deans, provosts, VPs of workforce development, CIOs, and procurement — often on the same deal — and will need to navigate academic governance, RFPs, and curriculum committees while keeping deals moving.

What You'll Own

• New logo acquisition. Net-new business across US higher education: 4-year publics and privates, community college systems, state university systems, and consortia.
• Full-cycle sales. Prospecting through close, including discovery, solution design with our curriculum team, proposal and RFP response, contracting, and handoff to delivery.
• Pipeline generation. Outbound and conference generation.
• Account strategy and stakeholder mapping. Across academic affairs, workforce and continuing ed, IT, finance, and procurement.
• Curriculum partnership structuring. Packaging SkillUp programs into the institution's existing certificate, degree, or non-credit offerings.
• Conference and event presence. UPCEA, WCET, EDUCAUSE, ASU+GSV, AACC, and regional state association events.
• CRM discipline in HubSpot. Clean pipeline, accurate forecasting, and consistent activity logging.
• Cross-functional collaboration. Work with curriculum, partnerships, marketing, and admissions to bring the right offer to each opportunity.

What You Bring

• 5–8 years selling into US higher education with a track record of net-new wins at $250K+ ACV
• Direct experience selling to continuing education, workforce development, online learning, or academic colleges (preferred over pure SIS or LMS administrative selling)
• Demonstrated ability to navigate academic governance — curriculum committees, faculty senates, procurement cycles, RFPs
• Strong discovery and stakeholder-mapping skills in environments with five or more decision-makers
• Comfort presenting to deans, provosts, VPs, CIOs, and CFOs
• HubSpot or Salesforce fluency with clean CRM habits
• Bachelor's degree required

Bonus Points

• Existing relationships in continuing ed, workforce development, or community college networks
• Prior work selling or partnering with Microsoft, Google Cloud, or IBM certification ecosystems
• Familiarity with workforce funding mechanisms (WIOA, employer tuition reimbursement, state workforce grants)
• Experience selling OPM, bootcamp, or non-credit certificate offerings into higher ed
• Active participation in UPCEA, WCET, AACC, or similar associations

How We'll Evaluate Fit

• Walk us through a complex higher ed deal you led end-to-end — stakeholders, timeline, blockers, how you closed it
• Show us how you'd map and prioritize 50 target institutions in a given region
• Demonstrate discovery rigor in a live mock with our team

What We Offer

• Remote-first with Chicago-area preference
• Medical, dental, vision, life insurance, 401(k)
• Variable incentive plan with accelerators on overachievement
• Learning discounts and access to SkillUp certifications
• Direct line to senior leadership and a clear path to scale into a leadership role as the team grows
• Real ownership of a market segment with white space and active demand