Enterprise Account Executive, Upper Mid-Market

Location: Chicago, IL – US-based candidates only, no visa sponsorship available.

About the role

This role supports revenue growth through customer focus, relationship development, and disciplined commercial execution. You will collaborate with sales, customer, product, and operational partners to identify opportunities, solve problems, and improve outcomes in a technology-driven environment.

Responsibilities

• Own new business sales for 200-300 accounts, primarily sourced through outbound efforts
• Lead full-cycle Enterprise deals, coordinating across multiple stakeholders
• Engage prospects to quantify their pain and impact financial decisions through real-time ROI modeling
• Negotiate and finalize annual contracts ranging from $50K to $1M
• Plan for post-sale activation by setting ramp milestones and targets prior to closure
• Utilize AI tools for account research, pipeline management, and prospecting tasks
• Foster internal champions to facilitate resource access and approvals when necessary
• Travel for in-person meetings with prospects and clients

Qualifications

• Proven track record in closing new Enterprise accounts with complex organizational structures
• Self-sourced outbound sales ability, not just dependent on inbound leads
• Experience selling to EVPs/CXOs and end-users simultaneously
• Ability to quantify business value and create ROI cases for prospects
• Experience managing post-sale handoff and ramp planning in volume-based pricing models
• Resourcefulness in problem-solving without waiting for assistance from other departments
• Operational experience using AI tools to enhance sales output
• Strong written and verbal communication skills to convey complex ideas simply
• Experience selling B2B solutions, particularly to HR buyers
• A decisive, action-oriented attitude with resilience in ambiguous situations

Pay

$252,697 – $297,290 annually

Benefits

• Fast-paced, collaborative work environment
• Learning and development allowance for professional growth
• Competitive compensation structure with cash and equity components
• Comprehensive coverage for medical, dental, and vision health
• Generous reimbursement opportunities for fertility, adoption, and parental services
• Flexible PTO to maintain a healthy work-life balance
• Monthly wellness stipend to support well-being
• In-office perks including meals and snacks for on-site employees
• Potential relocation assistance for moving to a hub location