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Senior Director, Leaves Strategy and Execution

May 27, 2026

Our storyAt 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 BenefitsWith 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 WorkingSo 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 WorkThanks 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 <a href="http://www.alight.com/about" target="_blank" rel="noopener noreferrer">Click Here.</a>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 <a href="https://careers.alight.com/us/en" target="_blank" rel="noopener noreferrer">careers.alight.com</a>. The Senior Director of Leave Solution Strategy & Execution is a senior leader responsible for driving the end-to-end execution of Alight Leave Solutions’ growth agenda. This includes product and platform transformation, go-to-market acceleration, distribution expansion, and strategic initiatives such as partnerships and acquisitions.This role operates as the bridge between strategy and outcomes, partnering across Product, Engineering, GTM, and Corporate Development to translate priorities into measurable growth. The leader owns complex, cross-functional initiatives and ensures execution delivers business impact revenue growth, client expansion, and market differentiation.Key Responsibilities:Transformation & Growth Execution<ul><li>Lead enterprise-wide initiatives (e.g., claims modernization, platform transformation, operating model evolution)</li><li>Translate executive strategy into clear, outcome-driven programs tied to growth, efficiency, and client impact</li><li>Drive execution across product, delivery, and GTM to ensure initiatives land in market not just in roadmap</li></ul>Product, Engineering & Platform Alignment<ul><li>Partner with Product and Engineering to align roadmap priorities with business and GTM needs</li><li>Drive modernization across workflows, automation, data integration, and experience</li><li>Own cross-functional execution of key platform initiatives, including AI-enabled capabilities within product and operations</li><li>Remove systemic blockers to improve speed, quality, and predictability of delivery</li></ul>Go-To-Market & Distribution Expansion<ul><li>Partner with Commercial and GTM leadership to ensure solutions are market ready, differentiated, and scalable</li><li>Lead execution of new distribution partnerships (e.g., worker’s compensation partners)</li><li>Help operationalize partner models (offerings, enablement, integration, joint value proposition)</li><li>Support development of clear packaging, positioning, and value articulation tied to growth</li></ul>Strategic Initiatives <ul><li>Support evaluation, planning, and execution of partnerships and inorganic growth opportunities</li><li>Act as execution lead for integration planning (product, GTM, operations)</li><li>Ensure acquired capabilities or partnerships are effectively embedded into the broader solution and GTM motion</li><li>Partner with corporate strategy and finance to link deals to measurable outcomes</li></ul>Client Health & Experience<ul><li>Partner with GTM and Client Success to improve retention, expansion, and satisfaction</li><li>Ensure transformation initiatives translate into tangible client experience improvements</li></ul>Execution & Governance<ul><li>Lead complex, multi-workstream programs with clear ownership and accountability</li><li>Establish lightweight governance to drive speed and transparency</li><li>Provide regular updates to Executive Leadership on progress, risks, and business impact</li></ul>Success Metrics<ul><li>Improved alignment between Product, Engineering, and Delivery teams</li><li>Improved product-market alignment and GTM effectiveness</li><li>Increased client retention, expansion, and satisfaction</li><li>Reduction in delivery friction and operational inefficiencies</li><li>Launch of new distribution channels and partnerships</li></ul>Qualifications<ul><li>10+ years leading complex, cross-functional initiatives across product, GTM, or operations</li><li>Proven track record executing enterprise-scale transformation and growth initiatives</li><li>Experience with partnerships, distribution models, or M&A integration strongly preferred</li><li>Strong executive presence and ability to influence without authority</li><li>Experience in SaaS, HR tech, insurance, or adjacent markets preferred</li><li>Demonstrated ability to translate strategy into execution and results</li></ul>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. Please be aware that Alight is a camera-on culture and may require occasional travel to one of our physical office locations.Our commitment to InclusionWe 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 <a href="mailto:alightcareers@alight.com" target="_blank" rel="noopener noreferrer">alightcareers@alight.com</a>. Equal Opportunity Policy StatementAlight 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 CountryApplicants 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 RangeMinimum :186,000.00 USDMaximum :227,000.00 USDPay 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: <a href="https://leplb0920.upoint.ap.alight.com/ah-angular-afirst-web/#/web/alight/cp/wellbeing_and_benefits_selector_page" target="_blank" rel="noopener noreferrer">Wellbeing and Benefits Selector Page - Alight</a> 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.

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...