Entry Level Operations Jobs in West Chester, PA (NOW HIRING)

Who Are We Looking For?
Vestwell is expanding and we're excited about growing our Operations team with entry-level Operations Associates who are passionate about our mission to change the retirement Fin-Tech space. At a high level, we're looking for someone who has insane levels of attention to detail and proven ability of juggling multiple priorities at once. You will be key to powering transactions on the platform and ensuring it runs at full speed while exercising independent judgment in resolving complex, high-impact operational issues that directly affect client outcomes and regulatory compliance.

We're a startup… so a self-starter mentality comes first and foremost. You are someone who will dive into whatever challenge is placed in front of you, and find creative ways to solve problems by evaluating multiple courses of action and determining appropriate resolution paths within established operational and regulatory frameworks.

What Will You Be Doing?

This role regularly exercises independent judgment on matters of significance that materially affect payroll accuracy, participant eligibility, deferrals, data integrity, and client outcomes. While operating within established operational, regulatory, and ERISA-related frameworks, the Operations Associate is responsible for independently identifying, investigating, and resolving complex, high-priority issues; evaluating multiple potential courses of action; assessing risk, urgency, and business impact; and determining appropriate remediation and escalation paths. The role requires discretion in how policies and standards are applied to fact-specific situations, how work is prioritized and communicated, and how resolutions are driven to completion, including through direct interaction with internal partners and external stakeholders. Although decisions and recommendations may be subject to review and do not include unilateral policy-setting authority, the consistent and recurring exercise of judgment is a central and essential function of the role and directly supports Vestwell's compliance obligations, operational continuity, and client experience.

Day-to-Day, You May Also Be Expected To:

• You're flexible, creative, team-oriented, and results-driven, exercising independent judgment within established guidelines while collaborating effectively with both internal and external stakeholders on matters that materially impact payroll accuracy, participant eligibility, deferrals, and overall data integrity.
• Develop and maintain internal and client-facing knowledge bases; independently identify opportunities for incremental process improvements and raise recommendations through appropriate channels based on investigative analysis, trend identification, and assessment of operational risk and efficiency.
• Support and guide team members by monitoring workload volume, exercising discretion in day-to-day prioritization, and ensuring timely and accurate remediation of a high volume of complex operational issues in accordance with established standards including determining urgency, client impact, and appropriate escalation paths.
• Collaborate with teams across the Vestwell organization to surface operational insights, document trends, and contribute input on platform enhancements and procedural efficiencies informed by firsthand analysis of recurring issues and fact-specific operational scenarios.
• Maximize team efficiency through timely completion of assigned tasks and projects, using independent judgment to triage, sort, and assign incoming work across platforms based on urgency and service-level expectations rather than applying predefined or rote outcomes.
• Identify, investigate, and resolve discrepancies in high-priority payroll, deferrals, eligibility, and related activities by applying established processes and exercising discretion in analysis, escalation, and resolution to ensure data accuracy and compliance with ERISA and related regulatory requirements as applied to specific factual situations.

Requirements
The Necessities

• Strong Excel proficiency (e.g., pivot tables, VLOOKUPs) to analyze data and support operational decision-making within defined parameters including evaluating risk, prioritization, and remediation options.
• Comfort working in a start-up environment with autonomy over task execution and prioritization, while operating within established policies and procedures that require judgment in interpretation and application, rather than mechanical execution.
• Exceptional analytical and detail-oriented aptitude; a high degree of accuracy and sound judgment is required as the role regularly affects compliance outcomes, client experience, and operational continuity.
• Ability to manage time effectively, balance competing priorities, and meet deadlines with minimal supervision while independently determining sequencing and urgency of work.
• Strong verbal and written communication skills to clearly document findings, explain recommendations, and escalate issues appropriately based on assessed risk, complexity, and business impact.
• Problem-solving skills, including the ability to research, analyze, and apply judgment to determine appropriate next steps or escalation paths recognizing that decisions may be subject to review but require meaningful discretion.
• Bachelor's degree or equivalent combination of formal education and work experience.
• 1 year of relevant experience in Financial Services, Operations, or SaaS industries.

The Extras

• Payroll system experience
• Proficiency with productivity tools, especially JIRA
• Retirement industry experience including exposure to ERISA-governed processes or regulated operational environments

This role will be based in either the New York City, Austin, King of Prussia, or Scottsdale office, and will be part of Vestwell's hybrid in-office operation.

The expected base salary range for this position is $60K - $72K base. This position is eligible to participate in the Company Bonus Pool and is eligible to receive new hire equity in the Company. Please note that salary bands are based on NY and other similar metro areas and may differ based on where the role is ultimately hired.