Sr. Specialist, Benefits Systems

Job Description

Insight Global is seeking a Sr. Specialist, Benefits Systems for a leading retail organization. This individual will serve as a key player on a lean, high-impact benefits team, acting as the right-hand support for financial analysis and operational management of employee benefit programs. The role blends HR and finance, requiring someone who can manage billing, build reports, and partner with FP&A to support forecasting and strategic decision-making. This is an excellent opportunity for a detail-oriented, analytical professional with early career experience in benefits, payroll, or finance who is looking for strong exposure to leadership and long-term growth within Total Rewards.

Day-to-Day:

Manage benefits financial operations including billing reconciliation and payments

Pull and analyze reports for benefits plans and financial tracking

Support financial forecasting and projections alongside FP&A partners

Partner cross-functionally with Finance, FP&A, and HR leadership

Assist in budget tracking and ongoing financial management of benefit plans

Work closely with leadership (including exposure up to CFO-level discussions)

Maintain and analyze large datasets across multiple systems

Act as the right-hand support to senior benefits leadership, helping keep the lights on operationally

We are a company committed to creating diverse and inclusive environments where people can bring their full, authentic selves to work every day. We are an equal opportunity/affirmative action employer that believes everyone matters. Qualified candidates will receive consideration for employment regardless of their race, color, ethnicity, religion, sex (including pregnancy), sexual orientation, gender identity and expression, marital status, national origin, ancestry, genetic factors, age, disability, protected veteran status, military or uniformed service member status, or any other status or characteristic protected by applicable laws, regulations, and ordinances. If you need assistance and/or a reasonable accommodation due to a disability during the application or recruiting process, please send a request to ... learn more about how we collect, keep, and process your private information, please review Insight Global's Workforce Privacy Policy:

Skills and Requirements

1+ years of experience in Benefits, Payroll, Finance, or HR-related analytical role

Strong financial acumen (billing, reporting, budgeting exposure, forecasting support)

Intermediate Excel skills (VLOOKUPs, Pivot Tables, data consolidation)

Ask about their experience consolidating data from different sources (multiple systems, Excel sheets, etc.)

Highly detail-oriented and analytical mindset

Strong communication skills / articulation (will interact with leadership up to CFO level)

Exposure to benefits fundamentals (deductibles, plans, terminology)

Proven stability in work history (no frequent job hopping)

Ability to work in a fast-paced, lean team environment Bachelors degree preferred OR equivalent relevant experience

Experience participating in budgeting or financial planning cycles

Background with mid-to-large enterprise organizations

Prior exposure to Benefits systems or administration

HR degree with strong analytical coursework or internship experience

Experience consolidating data from multiple systems/sources