Sales Executive - Leaves Solutions

Alight • Deerfield, IL

9d • $175,000 - $185,000

About The Position

The Sales Executive within Leave Solutions leads and closes mid- to large-market leave-of-absence sales opportunities. The role owns the end-to-end RFP lifecycle, broker engagement, prospect intelligence, solution positioning, finalist meeting orchestration, and deal execution. Sales Executive IIs serve as subject-matter experts in Leave & Disability Management and play a central role in advancing Alight’s “One Alight” go-to-market strategy.

The position works with brokers, Strategic Account Executives, Enterprise Sales, and cross-functional teams to develop cohesive sales strategies, position solutions, prepare proposals and finalist meetings, and support contract close. It also provides prospect insights and field feedback to inform go-to-market approaches and future product considerations. Alight notes that occasional travel to a physical office location may be required. Virtual interviews are conducted on video.

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.
• Ability to navigate complex buying committees, develop win strategies, and align internal stakeholders.
• Clear, confident communication and strong executive presence.
• Ability to identify issues proactively and coordinate solutions across cross-functional teams.
• Understanding of leave industry trends, competitor landscape, and Alight’s capabilities.
• Collaborative approach across Product, Implementation, Operations, and sales teams.

Nice To Haves

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

Responsibilities

• Lead the RFP process from intake through final submission, aligning proposals with prospect needs and internal delivery capabilities.
• Serve as the primary point of contact for brokers on leave-related opportunities, with only one sales executive engaging each broker.
• Qualify opportunities and gather prospect pain points, objectives, industry insights, and competitive intelligence.
• Own relationships with specialty leave brokers throughout the sales cycle.
• Collaborate with enterprise sellers when prospects have local broker relationships and define an appropriate engagement model.
• Identify decision makers, buyers, and influencers, and align them to the win strategy.
• Partner with Strategic Account Executives and Enterprise Sales on “One Alight” positioning.
• Develop win strategies, including pricing inputs, value engineering, and solution alignment.
• Craft sales narratives using AWL utilization, call volume insights, and broader platform value to differentiate Leave Solutions.
• Lead preparation and delivery of finalist meetings, ensuring appropriate subject-matter experts, leaders, and aligned messaging are present.
• Coordinate proposal inputs across product, operations, implementation, legal, and account teams.
• Ensure messaging reflects current product capabilities and accurately represents the roadmap.
• Work with Strategic Account Executives, Enterprise Sales, Product, and Market Maker roles where defined to build cohesive strategies and avoid misalignment.
• Provide prospect insights and field feedback to influence go-to-market motions and future product considerations.
• Partner with Legal and Sales Operations on contract terms, including leave-specific addenda or indemnities.
• Communicate realistic deal timing and ensure pipeline close dates are achievable, typically 3–4 months.

Benefits

• Health coverage starting Day One
• Dental coverage starting Day One
• Vision coverage starting Day One
• Wellbeing programs
• Retirement plans with contribution matching
• Generous time off
• Parental leave
• Continuing education and training
• Career growth opportunities
• Competitive total rewards package

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed