Sales Executive II (Leave Solutions)

Location: Virtual, Illinois, United States; occasional travel to physical office locations may be required.

Salary: USD 135,000–165,000 per year, with potential bonus and/or incentive eligibility.

Company

hirify.global provides benefits, wellbeing, health, wealth, navigation, and absence-management solutions that help organizations build healthier and more financially secure workforces.

What you will do

• Lead the end-to-end RFP lifecycle for mid- to large-market leave-of-absence sales opportunities.
• Manage relationships with specialty leave brokers and prospects, identifying decision-makers and shaping win strategies.
• Develop solution positioning, pricing inputs, value engineering, and differentiated sales narratives.
• Prepare and lead finalist meetings with subject-matter experts, leaders, and cross-functional teams.
• Coordinate Product, Operations, Implementation, Legal, Account, and Sales teams to deliver accurate proposals.
• Support contract terms, leave-specific addenda, pipeline accuracy, and deal closure.

Requirements

• 3–5+ years of sales experience in leave management.
• Proven success managing large, complex sales cycles with multiple stakeholders.
• Strong presentation skills and confidence leading finalist meetings.
• Experience working with brokers, consulting houses, or channel partnerships.
• Strategic selling, executive communication, proactive problem solving, and cross-functional collaboration skills.
• Applicants must already have United States work authorization that does not now or in the future require visa sponsorship.

Nice to have

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

Culture & Benefits

• Flexible working arrangements and a virtual work setup.
• 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.
• Inclusive workplace with reasonable accommodations available during hiring and employment.

Hiring process

• Virtual interviews are conducted by video and may require cameras to be on.
• Offers are contingent on successfully completing a background check, which may include employment, education, identity, criminal, sanctions, credit, or drug screening depending on the role.