Demo

Sales Executive II

Alight Solutions
Chicago, IL Full Time
POSTED ON 6/10/2026
AVAILABLE BEFORE 8/10/2026

Come make a difference and consider this unique opportunity to step into a rewarding career.

Amazing Opportunity and Great Place to Work!

Our story

At Alight, we believe a company's success starts with its people. At our core, we Champion People, help our colleagues Grow with Purpose and true to our name we encourage colleagues to "Be Alight." We are passionate about connecting purpose with impact. Alight empowers clients to build a healthier and more financially secure workforce by unifying the benefits ecosystem across health, wealth, wellbeing, navigation, and absence management.

Our Benefits

With a comprehensive total rewards package, Alight offers programs and plans that support your mind, body, wallet, and life. Benefits include health, dental and vision coverages starting Day One. Additionally, Alight colleagues enjoy wellbeing programs, retirement plans with contribution matching, generous time off, parental leave, continuing education, and career growth opportunities - all within a thriving global organization.

Flexible Working

So that you can be your best at work and home, we consider flexible working arrangements wherever possible. Alight has been a leader in the flexible workspace and "Top 100 Company for Remote Jobs" 6 years in a row.

Great Place to Work

Thanks to the work of every colleague, Alight has received multiple awards of recognition including "Great Place to Work" for the past 7 years and Fortune's "Best Companies to Work For." To learn more about our company culture and awards Click Here.

If you, Champion People, seek to Grow with Purpose, and embody the meaning of Be Alight - We invite you to join our team! Learn more at careers.alight.com.

Position Summary

The Sales Executive II (SE II) within Leave Solutions is responsible for leading and closing mid to largemarket leaveofabsence sales opportunities. This role owns the endtoend RFP lifecycle, broker engagement, prospect intelligence, solution positioning, finalist meeting orchestration, and deal execution. SE IIs serve as subjectmatter experts in Leave & Disability Management and play a central role in advancing Alight's "One Alight" gotomarket strategy.

Key Responsibilities

1. RFP & Deal Leadership

  • Lead the entire RFP process from intake to final submission, ensuring alignment with prospect needs and internal delivery capabilities.
  • Serve as the primary point of contact for brokers on leaverelated opportunities (explicit requirement: only one sales exec engages the broker).
  • Drive opportunity qualification, gather prospect pain points, objectives, industry insights, and competitive intelligence.

2. Broker & Prospect Relationship Management

  • Own relationships with specialty leave brokers throughout the sales cycle.
  • Collaborate with enterprise sellers when prospects have local broker relationships; define the appropriate engagement model.
  • Identify key decision makers, buyers, influencers, and align them to the win strategy.

3. Sales Strategy & Value Engineering

  • Partner with Strategic Account Executives (SAEs) and Enterprise Sales on "One Alight" positioning.
  • Develop win strategies, including pricing inputs, value engineering (administer, integrate, personalize, guide), and solution alignment.
  • Craft narratives using AWL utilization, call volume insights, and broader platform value to differentiate Leave Solutions.

4. Finalist Meetings & CrossFunctional Coordination

  • Lead preparation and delivery of finalist meetings, ensuring the right SMEs, leaders, and message alignment are present.
  • Coordinate inputs across product, operations, implementation, legal, and account teams to ensure seamless delivery of proposals.
  • Ensure messaging reflects both current product capabilities and roadmap truthtelling.

5. Internal Alignment & Collaboration

  • Work closely with SAEs, Enterprise Sales, Product, and Market Maker roles (where defined) to build cohesive strategies and avoid misalignment.
  • Provide prospect insights and field feedback to influence gotomarket motions and future product considerations.

6. Contract & Close Support

  • Partner with Legal and Sales Operations on contract terms, including leavesspecific addenda or indemnities.
  • Communicate realistic deal timing and ensure pipeline reflects achievable close dates (typically 3-4 months).

Qualifications

Required

  • 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.

Preferred

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

Key Competencies

  • Strategic Selling: Ability to navigate complex buying committees, craft win strategies, and align internal stakeholders.
  • Influence & Communication: Clear, confident communicator with strong executive presence.
  • Proactive Problem Solving: Ability to identify issues early and coordinate solutions across cross-functional teams.
  • Market & Product Insight: Understanding of leave industry trends, competitor landscape, and Alight's capabilities.
  • Collaboration: Embodies "One Alight" through partnership with Product, Implementation, Operations, and other sales teams.

Application and Interview

By applying for a position with Alight, you understand that, should you be made an offer, it will be contingent on your undergoing and successfully completing a background check consistent with Alight's employment policies. Background checks may include some or all the following based on the nature of the position: SSN/SIN validation, education verification, employment verification, and criminal check, search against global sanctions and government watch lists, credit check, and/or drug test. You will be notified during the hiring process which checks are required by the position.

Alight requires all virtual interviews to be conducted on video.

Our commitment to Inclusion

We celebrate differences and believe in fostering an environment where everyone feels valued, respected, and supported. We know that diverse teams are stronger, more innovative, and more successful.

At Alight, we welcome and embrace all individuals, regardless of their background, and are dedicated to creating a culture that enables every employee to thrive. Join us in building a brighter, more inclusive future.

As part of this commitment, Alight will ensure that persons with disabilities are provided reasonable accommodations for the hiring process.If reasonable accommodation is needed, please contact alightcareers@alight.com.

Equal Opportunity Policy Statement

Alight is an Equal Employment Opportunity employer and does not discriminate against anyone based on sex, race, color, religion, creed, national origin, ancestry, age, physical or mental disability, medical condition, pregnancy, marital or domestic partner status, citizenship, military or veteran status, sexual orientation, gender, gender identity or expression, genetic information, or any other legally protected characteristics or conduct covered by federal, state, or local law. In addition, we take affirmative action to employ disabled persons, disabled veterans, and other covered veterans.

Alight provides reasonable accommodations to the known limitations of otherwise qualified employees and applicants for employment with disabilities and sincerely held religious beliefs, practices and observances, unless doing so would result in undue hardship. Applicants for employment may request reasonable accommodations/modifications by contacting their recruiter.

Authorization to work in the Employing Country

Applicants for employment in the country in which they are applying (Employing Country) must have work authorization that does not, now or in the future, require sponsorship of a visa for employment authorization in the Employing Country and with Alight.

Note, this job description does not restrict management's right to assign or reassign duties and responsibilities of this job to other entities; including but not limited to subsidiaries, partners, or purchasers of Alight business units.

We offer you a competitive total rewards package, continuing education & training, and tremendous potential with a growing worldwide organization.

Salary Pay Range

Minimum :

135,000.00 USD

Maximum :

165,000.00 USD

Pay Transparency Statement: Alight considers a variety of factors in determining whether to extend an offer of employment and in setting the appropriate compensation level, including, but not limited to, a candidate's experience, education, certification/credentials, market data, internal equity, and geography. Alight makes these decisions on an individualized, non-discriminatory basis. Bonus and/or incentive eligibility are determined by role and level. Alight also offers a comprehensive benefits package; for specific details on our benefits package, please visit: Wellbeing and Benefits Selector Page - Alight


DISCLAIMER:


Nothing in this job description restricts management's right to assign or reassign duties and responsibilities of this job to other entities; including but not limited to subsidiaries, partners, or purchasers of Alight business units.

Alight Solutions provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, creed, sex, sexual orientation, gender identity, national origin, age, disability, genetic information, pregnancy, childbirth or related medical condition, veteran, marital, parental, citizenship, or domestic partner status, or any other status protected by applicable national, federal, state or local law. Alight Solutions is committed to a diverse workforce and is an affirmative action employer.

 

Salary.com Estimation for Sales Executive II in Chicago, IL
$78,137 to $108,693
If your compensation planning software is too rigid to deploy winning incentive strategies, it’s time to find an adaptable solution. Compensation Planning
Enhance your organization's compensation strategy with salary data sets that HR and team managers can use to pay your staff right. Surveys & Data Sets

What is the career path for a Sales Executive II?

Sign up to receive alerts about other jobs on the Sales Executive II career path by checking the boxes next to the positions that interest you.
Income Estimation: 
$80,062 - $120,119
Income Estimation: 
$104,680 - $202,844
Income Estimation: 
$122,633 - $166,569
Income Estimation: 
$116,413 - $176,962
Income Estimation: 
$129,120 - $252,029
Income Estimation: 
$80,062 - $120,119
Income Estimation: 
$104,680 - $202,844
Income Estimation: 
$122,633 - $166,569
Income Estimation: 
$116,413 - $176,962
Income Estimation: 
$129,120 - $252,029
Employees: Get a Salary Increase
View Core, Job Family, and Industry Job Skills and Competency Data for more than 15,000 Job Titles Skills Library

Job openings at Alight Solutions

  • Alight Solutions Atlanta, GA
  • Our story At Alight, we believe a company’s success starts with its people. At our core, we Champion People, help our colleagues Grow with Purpose and true... more
  • 10 Days Ago

  • Alight Solutions Atlanta, GA
  • Amazing Opportunity and Great Place to Work! Are you a fast learner who is fascinated by Client interactions? Our story At Alight, we believe a company’s s... more
  • 12 Days Ago

  • Alight Solutions Illinois, IL
  • Are you looking for a new opportunity to work in a goal-oriented team? Are you excited by the prospect of creatively solving problems? Our story At Alight,... more
  • 12 Days Ago


Not the job you're looking for? Here are some other Sales Executive II jobs in the Chicago, IL area that may be a better fit.

  • Executive Recruiting Associates Zurich, IL
  • Sales Engineer – mechanical engineering ; heavy trucks Lake Zurich, IL area $85k-$120k plus commissions International motion control manufacturer needs a S... more
  • 1 Day Ago

  • Expert Executive Recruiters (EER Global) Chicago, IL
  • Territory Sales Manager – Automotive Technology – North America Our client, a globally active leader in the Automotive Technology space, is looking for a (... more
  • 1 Day Ago

AI Assistant is available now!

Feel free to start your new journey!