Now Hiring: Part-Time Sales Lead at REACH Pathways

Reports to: Head of Employability  

Location: Remote (U.S. based)  

Hours: 20 hours per week  

Compensation: $30–$45/hour depending on experience  

Start Date: ASAP 

About REACH Pathways 

REACH Pathways is an award-winning platform reimagining how young people explore careers, build skills, and connect with opportunity. Built with and for youth, REACH delivers gamified skill-building, AI-powered personalization, and near-peer mentorship to prepare the next generation for a workforce transformed by technology and change. 

Backed by 30 years of proven outcomes through Chicago Scholars and recognized by Fast Company’s World Changing Ideas List, SXSW Pitch, and the Chicago Innovation Awards - REACH is bridging the gap between potential and placement. 

Position Summary 

REACH is seeking a mission-driven, results-oriented Part-Time Sales Lead to drive our B2B sales and partnerships strategy. This role will lead outreach, prospecting, and deal management with employer and campus partners, working directly with the Head of Employability and President/Founders to grow our national footprint. The ideal candidate is a strong communicator, experienced in consultative sales or partnership development, and excited to lead a strategic sales function in a growing start-up. 

Key Responsibilities 

Lead Generation & Sales Execution 

• Drive the corporate and campus partnership pipeline from lead generation through to deal closure 

• Identify and prioritize high-potential prospects through research, market insights, and strategic networking 

• Draft and personalize outreach emails to secure discovery meetings with new leads 

• Prepare and tailor pitch decks, proposals, and sales collateral to specific partner needs 

• Build and maintain relationships with key decision-makers in HR, DEI, career services, and student affairs 

• Track outreach activity, open rates, and conversion metrics to evaluate and optimize engagement strategies 

• Manage and maintain accurate records in HubSpot, including deal stages, meeting notes, and follow-up actions 

• Lead partner discovery calls and support negotiation and closing processes in collaboration with the Head of Employability 

  
  

Sales Strategy & Systems Development 

• Co-develop quarterly sales and outreach strategies aligned with REACH’s revenue and growth goals, and provide input on goals based on sales data and partner conversations 

• Conduct market research and competitor analysis to inform strategic positioning and differentiation 

• Support pricing, packaging, and pilot design to align offerings with partner needs 

• Recommend messaging and value proposition improvements based on audience feedback and trends 

• Refine and document scalable sales workflows to support a growing customer base 

• Optimize HubSpot CRM setup, including deal pipelines, templates, reporting, and automations 

• Track and analyze key sales metrics (e.g., response rates, conversion rates, deal velocity) to drive continuous improvement 

  
  

Partnership and Communications Support 

• Support the Head of Employability in preparing proposals, meeting recaps, and summary reports 

• Assist in timely follow-up communications after partner meetings and conferences 

• Help develop and maintain a partnership tracker with contact notes, statuses, and next steps 

• Stay informed on trends in EdTech, employer engagement, and career readiness 

  
  

Qualifications 

• 3+ years of experience in B2B sales, business development, or partnerships (EdTech or workforce preferred) 

• Strong relationships with school districts and/or universities highly preferred 

• Proven ability to close deals and meet or exceed sales targets 

• Exceptional written and verbal communication skills 

• Familiarity with HubSpot or other CRM tools 

• Strong organizational and follow-up skills 

• Passion for educational equity and creating pathways for under-resourced students 

• Comfortable working independently in a fast-paced, entrepreneurial environment 

To Apply

Please email your resume and cover letter to info@reachpathways.com by July 18th. Applications will be reviewed on a rolling basis.