Sales Executive - Leaves Solutions (Leave Management)

Location: Deerfield, Illinois, United States of America

Salary: $175,000–$185,000 per year, plus bonus and/or incentive eligibility as applicable.

Company

hirify.global helps organizations build healthier and more financially secure workforces through health, wealth, wellbeing, navigation, and absence-management solutions.

What you will do

• Lead mid- to large-market leave-of-absence sales opportunities and manage the full RFP lifecycle from intake through final submission.
• Own relationships with specialty leave brokers, qualify opportunities, gather prospect intelligence, and identify decision makers and influencers.
• Develop win strategies, pricing inputs, value-engineering approaches, and solution positioning for Leave Solutions.
• Prepare and lead finalist meetings with the required subject-matter experts, leaders, and aligned messaging.
• Coordinate proposal inputs across product, operations, implementation, legal, account, and sales teams.
• Support contract terms, communicate realistic deal timing, and maintain achievable pipeline close dates, typically within 3–4 months.

Requirements

• 3–5+ years of sales experience in leave management.
• Proven success managing large, complex sales cycles involving multiple stakeholders.
• Strong presentation skills and confidence leading finalist meetings.
• Experience working with brokers, consulting houses, or channel partnerships.
• Ability to navigate complex buying committees, craft win strategies, and align internal stakeholders.
• Clear, confident communication and strong executive presence.
• Ability to identify issues early and coordinate solutions across cross-functional teams.
• Understanding of leave-industry trends, the competitor landscape, and hirify.global’s capabilities.
• Collaborative approach with Product, Implementation, Operations, and other sales teams.

Nice to have

• Understanding of leave regulations, disability management, FMLA/ADA, or the HRIS/HCM ecosystem.
• Familiarity with Salesforce, sales methodologies, and pipeline-management best practices.

Culture & Benefits

• Inclusive culture centered on purposeful, human, united, and growth-minded values.
• Health, dental, and vision coverage starting on Day One.
• Wellbeing programs, retirement plans with contribution matching, generous time off, and parental leave.
• Continuing education, training, and career-growth opportunities.
• Flexible working arrangements where possible; occasional travel to a physical office location may be required.
• Virtual interviews are conducted by video, with a camera-on culture.

Hiring process

• Virtual interviews are conducted by video and may require the camera to remain on.
• Offers are contingent on successfully completing a background check, which may include identity, education, employment, criminal, sanctions, credit, or drug screening checks depending on the role.
• Applicants must have work authorization in the employing country without requiring current or future visa sponsorship.