Join Our Team!Location: Ashburn, VA (Onsite)
Shape the Future of Benefits at SSP AmericaWe are seeking a strategic, analytically minded
Director of Benefits to lead the design, governance, administration, and continuous improvement of our employee benefits and retirement programs across the United States and Canada. Reporting to the Vice President, People, this leader will build and execute a benefits strategy that is compliant, competitive, cost effective, and aligned with workforce engagement, employee wellbeing, and talent attraction and retention.
This is an ideal opportunity for a leader who enjoys shaping program strategy, managing vendor partnerships, using data to control cost and improve outcomes, and building a team that delivers an exceptional employee experience.
What You'll Do:As the
Director of Benefits, you will serve as SSP America's subject matter expert and strategic advisor for health and welfare plans, retirement programs, and wellness initiatives.
Key responsibilities include:- Developing and executing the organization's employee benefits and retirement strategy, ensuring alignment with company goals, workforce needs, and market competitiveness.
- Directing the administration, governance, and optimization of health, welfare, retirement, leave, wellness, and ancillary benefit programs across the U.S. and Canada.
- Overseeing retirement programs, including 401(k), defined contribution, and other retirement plans, with accountability for fiduciary governance, compliance, employee engagement, and vendor performance.
- Leading vendor selection, contract negotiations, service level agreements, and ongoing relationship management with brokers, consultants, third-party administrators, retirement providers, and insurance carriers.
- Ensuring compliance with federal, state, provincial, and local regulations, including ERISA, ACA, HIPAA, COBRA, IRS and DOL requirements, and retirement plan governance standards, along with benefits audits, regulatory filings, and annual disclosures.
- Partnering with Finance on annual benefits budgets, financial forecasts, reserve planning, and cost containment strategies.
- Analyzing benefits utilization, claims experience, demographic trends, and market data to identify program enhancements, operational efficiencies, and return on investment.
- Leading annual open enrollment strategy, education, communication, and implementation, and ensuring accurate administration of enrollments, eligibility rules, retirement contributions, payroll interfaces, and HRIS processes.
- Leading and mentoring the Benefits team, serving as the senior escalation point for complex benefits and retirement matters affecting employees, leaders, HR partners, and union stakeholders, and providing leadership during mergers, acquisitions, and organizational change.
- Building a culture of accountability, service excellence, innovation, and continuous improvement aligned with SSP America's Core Values of Ownership, Teamwork, Curiosity, and Passion.
What We're Looking For:We're looking for a leader who pairs deep technical benefits expertise with financial acumen and a passion for improving employee wellbeing.
Required Qualifications- Minimum of 8 years of progressive experience in employee benefits and retirement administration, including strategic plan design, vendor management, compliance, and program leadership.
- Minimum of 3 years of leadership experience managing teams.
- Extensive experience overseeing retirement plans, including fiduciary governance, plan administration, retirement compliance requirements, and vendor oversight.
- Demonstrated experience developing and implementing benefits strategies that balance employee experience, compliance, and financial stewardship.
- Advanced knowledge of ERISA, ACA, HIPAA, COBRA, IRS regulations, retirement plan governance, fiduciary responsibilities, and related employment laws.
- Strong analytical and financial acumen, with experience managing benefits budgets, forecasting costs, evaluating claims trends, and presenting recommendations to executive leadership.
- Proven ability to negotiate vendor agreements and manage complex third-party relationships.
- Exceptional communication, presentation, influencing, and relationship management skills, including the ability to partner with executive leadership on strategic recommendations.
- Advanced proficiency with HRIS platforms, benefits administration systems, retirement plan administration tools, and Microsoft Office applications.
- Ability to establish and maintain eligibility to work in the United States without sponsorship.
- Ability to travel approximately 10% within the U.S. and Canada, including overnight extended stay. If required, SSP will support work authorization.
- Ability to pass and maintain a criminal background check and, as required, meet airport security requirements such as Transportation Security Administration (TSA) clearance, Federal Aviation Administration (FAA), Transport Canada, and other applicable clearances.
Preferred Qualifications- Bachelor's degree (or international equivalent) in Human Resources, Business Administration, Finance, Accounting, Economics, or a related field.
- Professional credentials such as CEBS, CBP, PHR, SPHR, SHRM-CP, SHRM-SCP, or equivalent certification.
- Experience supporting both U.S. and Canadian employee populations.
- Experience in hospitality, restaurant, travel, aviation, retail, or other multi-unit environments.
- Experience leading benefits integration through mergers, acquisitions, and organizational change.
You'll Be Successful If You:- Balance employee wellbeing, compliance, and financial stewardship in every program decision.
- Use claims data, utilization trends, and benchmarking to drive decisions and contain cost.
- Track legislative developments, market trends, and emerging technology, and act on what you learn.
- Hold vendors accountable and get measurable value from every partnership.
- Translate complex plan rules into clear, useful communication for employees and leaders.
- Build trusted partnerships across Human Resources, Finance, Payroll, Legal, and operations.
Why Join SSP America?This role owns programs that reach every employee at SSP America. You'll shape how we invest in health, retirement readiness, and financial wellness across a complex, growing organization, with direct access to executive leadership and real influence over strategy, spend, and program design.
If you're passionate about benefits strategy, retirement plan governance, financial stewardship, and building programs that employees genuinely value, we'd love to hear from you.
Apply today and help us build the future of Benefits at SSP America. 
