PlanPILOT, LLC Lead Client Services Associate Chicago, IL · Full time Company website

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PlanPILOT takes a comprehensive approach to defined contribution retirement plan consulting, focused on minimizing fiduciary risk for plan sponsors and their oversight teams, as well as minimizing the risk of negative participant outcomes. We provide pro-active, value-adding services to our clients, their plan committee(s) and their employees. Our Mission: We aim to deliver comprehensive advisory services that help plan sponsors exceed fiduciary duties by providing risk management solutions and independent advice you need. Our Services: No two plans are alike. Our experienced consultants customize and design tailored solutions to help meet and exceed plan sponsors’ specific goals and objectives. Our Insights: Stay up to date on the latest retirement plan and benefits-related news and trends. Find key market insights through our articles, publications and other thought leadership.

A Role With Impact

At PlanPILOT, client service is a key part of shaping better retirement outcomes for working Americans. In this role, you will partner closely with senior consultants to support retirement plan committees and strengthen your expertise in service delivery and governance processes. You’ll enhance your skills in professional judgment, project management, communication, and strategic client support, while your work supports executive leaders at our client organizations operate their retirement plan more effectively. Experience gained in this role drives long-term career growth in consulting environments.

Who You Are

This role is ideal for candidates who thrive in a supportive, growth-oriented environment and take pride in creating structure, solving problems, and elevating the experience of both clients and colleagues. You are highly organized and detail-oriented and are motivated by summiting new challenges, delivering impact, increasing your skills, and strengthening collaboration.

• You naturally take ownership and prefer proactively solving problems.
• You communicate professionally and confidently with both internal teams and external client contacts.
• You are energized by building better processes, improving workflows, and helping teams operate more efficiently.

Why You Might Stand Out From the Crowd

• Experience supporting retirement plans, wealth management, institutional consulting, or other regulated financial service environments.
• Demonstrated success building or improving operational processes, SOPs, workflows, or cross-functional systems.
• Strong analytical capabilities with experience interpreting data and transforming it into meaningful client-facing reporting.
• Ability to manage projects and competing priorities while maintaining exceptional responsiveness, accuracy, and professionalism.
• A service mindset that combines strategic thinking, operational discipline, and genuine care for client outcomes.

Responsibilities

• Lead day-to-day execution for a dedicated client portfolio, serving as a strategic partner to senior consultants by applying best practices, managing partner/co-vendor relationships, driving deliverables, engaging directly with key client contacts, and ensuring consistent, high-quality service outcomes.
• Onboard assigned clients to PlanPILOT systems through data management and project planning
• Serve as the operational leader for the client services department, owning process architecture, documentation, and implementation. Drive alignment across teams by identifying inefficiencies, developing scalable solutions, and leading initiatives that improve the employee experience, service delivery, and organizational effectiveness.
• Provide quality assurance for department SOPs and training materials
• Own fiduciary document workflows, including monitoring DocuSign, collaborating with other Client Services team members to execute annual disclosures, tracking client meeting follow up items, and proactively advising Senior Consultants on timing, impacts, and needed updates.
• Prepare and analyze client reports (e.g., participant balances, average deferral rates, fee benchmarking reports), thoughtfully aligning outputs to client objectives, proactively researching and incorporating relevant data, and partnering with senior consultants to deliver clear, insightful reporting.
• Lead proposal development by partnering with senior consultants to understand prospect priorities and service expectations, then curating compliant proposal content and metrics from internal libraries. You act as the primary driver of proposal assembly, positioning our value, with outputs refined through collaboration and review.
• Provide quality assurance and support of team technical administration:
• Maintenance of Client Services Dashboard – architecture of improvements and data-pulling
• Execution of annual Client Survey
• HubSpot operations by collaborating with team members to maintain clean data and optimize platform efficiency
• Optimize and maintain systems for data storage including user access, records, and documentation in Dropbox and Revver
• Provide direct support for inbound client requests, as well as secondary support for Senior Consultant requests including plan compliance-related requests.
• Support Client Service Manager in leading prospect outreach projects and coordinate materials for new business development including campaigns, email newsletters, and events.
• Onboard assigned clients to PlanPILOT systems through data management and project planning

Compensation & Benefits

• $69,000 - $77,000 annual base salary, compensation commensurate with experience
• Medical Insurance, HSA plans available (employer funds $600 towards total premium cost)
• Dental Insurance
• FSA
• Commuter Benefit
• 10 days paid time off, 15 days after 3 years tenure
• Sick leave in accordance with local law
• 9 company paid holidays

Work Location

The Lead Client Services Associate will be expected to work from PlanPILOT's Chicago, IL office Tuesday - Thursday weekly.