Major Account Executive - Chicago, IL

About the Role

The Major Account Executive is a high-impact, full-cycle sales role responsible for driving new customer revenue through strategic prospecting and disciplined execution. This is a true hunter position, focused on landing and growing mid-market, multi-site, and national accounts across OpenWorks’ core industries, including Medical, Education, Logistics, Manufacturing, and other recession-resistant verticals.

In this role, you will own the entire sales process, from outbound prospecting and discovery through proposal development, negotiation, and close while partnering closely with internal teams to ensure long-term client success. Success requires strong prospecting skills, comfort engaging senior decision-makers, experience navigating RFP and procurement processes, and the ability to manage complex, multi-stakeholder deals.

What You'll Do

• Own the full national sales cycle, from prospecting through close, within OpenWorks’ ideal customer profile
• Drive both new logo acquisition and expansion within existing national accounts (land-and-expand model)
• Use the OpenWorks “OW Way” – a consultative, customer-first sales approach – to uncover needs and deliver tailored facility service solutions
• Lead complex, multi-stakeholder sales processes, including discovery, solution design, pricing, proposals, and contract negotiation
• Build and execute account strategies to engage decision-makers from VP to C-suite
• Develop customized proposals and deliver compelling virtual and in-person presentations
• Partner closely with Operations, Strategic, and Pricing teams to deliver accurate, competitive solutions
• Ensure smooth handoff of new clients to Operations after close
• Share best practices, insights, and market feedback to continuously improve our sales organization

What You Bring

• 6+ years of B2B sales experience, including national or enterprise-level selling
• 3+ years of experience selling services across multi-state or multi-region territories
• Proven success as a full-cycle hunter, consistently achieving $2M–$6M+ in annual revenue
• Strong experience selling in competitive, outbound-focused (“cold”) markets
• Proven experience using HubSpot (or comparable CRM) to manage pipeline, forecast accurately, and drive deal strategy
• Strong ability to leverage sales technology, automation, and AI-powered tools to improve efficiency, insight, and performance
• Demonstrated ability to collaborate with cross-functional and strategic partner teams
• Track record of building trusted relationships with senior leaders and executives
• High personal accountability, strong work ethic, and a growth-oriented mindset
• Excellent communication, negotiation, and consultative selling skills

Why OpenWorks?

• Contribute to projects and initiatives that directly shape our company’s success
• Collaborate with diverse teams and stakeholders across the organization
• Contribute to projects and initiatives that directly shape our company's success
• Collaborate with diverse teams and stakeholders across the organization
• Competitive compensation, benefits, and the opportunity to grow your career in a forward-thinking and inclusive Environment