Retirement Plan Jobs in Chicago, IL

Entry‑level plan administrators and compliance analysts earn $60k–$80k. Mid‑level consultants and portfolio managers range $90k–$120k. Senior analysts and senior managers command $130k–$170k, while directors and VP‑level executives earn $180k–$250k, depending on company size and geographic location.

Key certifications include Certified Financial Planner (CFP), Certified Management Accountant (CMA), Retirement Plan Specialist (RPS), and Chartered Financial Analyst (CFA). Technical proficiency in plan software (Fidelity Plan Center, Vanguard Plan Services), data tools (Tableau, Power BI, SQL), and Excel modeling is mandatory. Knowledge of ERISA, IRS 401(k) rules, and fiduciary standards is essential.

Remote work is common for roles that focus on data analysis, compliance monitoring, and client advisory, such as Portfolio Managers and Compliance Analysts. Plan Administrators and Payroll Specialists often require on‑site access to sponsor records, but many firms offer hybrid arrangements with periodic in‑office meetings.

A typical trajectory moves from Analyst to Manager, then to Director of Retirement Services, and ultimately to VP or Chief Retirement Officer. Advanced roles include Plan Sponsor Advisor, consulting engagements for multiple firms, or leadership in fintech companies developing plan‑management platforms.

The sector is moving toward zero‑based budgeting, ESG‑aligned investment options, and AI‑driven analytics for plan health. Increased regulatory scrutiny, especially around fiduciary duty and data security, creates demand for compliance experts. The rise of defined‑contribution plans and employee ownership models expands opportunities for advisors skilled in investment strategy and participant education.