Senior Benefits Specialist - Operations

Company: Stitch PEO
Location: Brentwood
Posted on: February 13, 2026

Job Description:

Job Description Job Description Position Description: About Stitch PEO Ready to stitch together a revolution in healthcare? Join the Stitch PEO movement. We're not your average PEO. We're redefining the game for independent healthcare groups, backed by the visionary minds of Redesign Health and fueled by a rocket ship of growth. We're not just scaling up, we're exploding onto the scene, and we need YOU to join the ride. Forget the corporate grind. At Stitch PEO, your expertise is celebrated, your drive is infectious, and your passion for our clients (and each other) is the thread that binds us. This is a place where you can own your work, make a real impact, and build something legendary alongside a team of rockstar teammates.Think you've got the chops? Deep domain expertise: You know healthcare inside and out. You understand the challenges, the opportunities, and the secret sauce that makes it tick. Drive to succeed: You're not content with "good enough." You push the boundaries, chase ambitious goals, and leave a trail of wins in your wake. Dedication to the team: You're a collaborator, a cheerleader, and a co-pilot. You lift others up, celebrate their victories, and believe in the power of "we." If this sounds like your jam, then step into the Stitchverse and: Work alongside passionate healthcare veterans and tech-savvy innovators. Craft solutions that empower independent groups to thrive. Make a real difference in the lives of patients, providers, and communities. Work alongside passionate healthcare veterans and tech-savvy innovators. Craft solutions that empower independent groups to thrive. Make a real difference in the lives of patients, providers, and communities. Experience the thrill of building a game-changing company from the ground up. Enjoy a culture that's as dynamic, supportive, and fun as it is results-driven. So, are you ready to stitch your talents into something extraordinary? Go ahead, take the leap. We've got the needle and thread, you bring the magic. P.S. We offer competitive salaries, killer benefits, and a chance to be part of something truly special. Just sayin'.StitchPEO HealthcareRevolution JoinTheMovement.Location: Chicago, SF, or NYC (REMOTE)About the JobAs a growing PEO, we are seeking a highly skilled and experienced Senior Benefits Administrator who is licensed to sell health insurance products. This position will play a pivotal role in leveraging their expertise to expand our client base, particularly within the independent medical practice sector. You will report to, and work with the Stitch PEOs Director of Operations. The position can be fully remote within the United States. As the Senior Benefits Administrator, you will be responsible for managing and enhancing our benefits administration processes and strategies. Your primary focus will be to sell health insurance products and services, including medical, dental, vision, and ancillary benefits, to independent medical practices. In addition to driving sales, you will also play a crucial role in advising clients on benefit options, regulatory compliance, and best practices. Your exceptional knowledge of health insurance products, sales experience, and applicable certifications will position you as a key resource within our organization.Health Insurance Sales:Design our Benefits Strategy for the short-term including Client Sponsored-Stitch Administrated Offering, Broker-based Plan Design and, eventually, Master Plans with several national or local carriers.Leverage your health insurance license to sell a wide range of health insurance products and services, including medical, dental, vision, and ancillary benefits, to independent medical practices.Cultivate and maintain relationships with key decision-makers at medical practices to understand their benefit needs and present customized solutions.Develop and execute effective sales strategies to achieve revenue targets and expand the client base.Collaborate with the sales team to identify potential clients, develop sales pitches, and participate in client presentations.Benefits Administration:Oversee the end-to-end administration of employee benefits programs, ensuring accurate and efficient delivery of services.Assist clients with plan design, implementation, and ongoing management of employee benefits programs.Educate clients on industry trends, compliance requirements, and best practices related to benefits administration.Collaborate with internal teams to develop innovative benefit offerings and ensure the alignment of benefits programs with client needs and organizational goals.Stay up-to-date with relevant industry regulations, trends, and changes in benefit plans to provide proactive guidance to clients.Prism HR setup and electronic onboarding.Client Relationship Management:Serve as the primary point of contact for clients regarding benefit plan inquiries, escalations, and issue resolution.Conduct regular benefit plan reviews and audits to ensure compliance, cost-effectiveness, and employee satisfaction.Build and nurture strong, long-lasting relationships with clients by providing exceptional customer service and anticipating their needs.Conduct client training sessions to educate and empower HR administrators and employees on benefits enrollment, utilization, and self-service tools.Compliance and Reporting:Ensure compliance with federal, state, and local regulations pertaining to benefit plans, such as HIPAA, ERISA, ACA, and COBRA.Prepare and distribute required benefits-related communications, including Summary Plan Descriptions (SPDs), Annual Notices, and enrollment materials.Collaborate with the compliance team to conduct periodic audits, assessments, and internal reviews to maintain adherence to regulatory standards.Generate regular reports on benefits utilization, cost analysis, and program effectiveness for internal and external stakeholders.What youll need:You have 10 years of experience working with employer benefits plansLicensed as a Broker to sell Health Insurance products in State of domicile (and/or reciprocal in all States) is strongly preferred. 10 years of operational leadership experience in a high growth environmentYou have experience managing outside business partners and creating partnershipsYou have experience with buy v. build decision thinking; understanding of how to make those decisions and what it will take to integrate various vendorsExperience with PrismHRExperience tracking operational performance metrics (e.g., call volume, client NPS) and recommending strategic initiatives based on trends and resultsExperience establishing brand new processes and collateral for internal stakeholders and clients (e.g., implementation process client manual)What you'll bring to the table: You have the ability to create, operationalize, and manage manual and automated processes for a tech-enabled employer benefits or HR solutions company You have experience designing business processes to accommodate varying customer requirements across geographies (e.g., state-level regulations) You have a metrics-driven approach with an ability to establish and utilize KPIs to improve performance and streamline processes; leverages data and metrics to drive decision making across a businessYou have the ability to thrive in ambiguity and build-out new metrics, tools, and technology to support workforceYou have the proven ability to evaluate & prioritize user needs to develop thoughtful operational plans and provide data-driven product roadmap inputYou have the ability to launch and operationalize new products/services, markets, projects, etc.Who you are: Behavioral CompetenciesResourcefulness. You marshal resources (people, funding, material, support) to get things done, and understand how to orchestrate multiple activities simultaneously to accomplish a goal. You get the most out of limited resources, and apply your knowledge of internal structures, processes and culture to resourcing efforts.Manages Complexity. You ask the right questions to accurately analyze situations and uncover root causes to difficult issues. Through acquiring data from multiple and diverse sources, you are able to make sense of complex, high-quantity, and sometimes contradictory information to solve problems.Drives Results. You persist in accomplishing objectives and exceeding goals despite obstacles and setbacks, while also helping others to achieve results.Builds Effective Teams. You form teams with an appropriate and diverse mix of styles, perspectives, and experience, establishing common objectives and a shared mindset. You foster open dialogue and collaboration, creating a feeling of belonging and a strong team morale.You can work out of one of the following locations - REMOTERemote: Alabama, Arizona, Arkansas, California, Colorado, Connecticut, Delaware, District of Columbia, Florida, Georgia, Idaho, Illinois, Indiana, Iowa, Kansas, Kentucky, Louisiana, Maine, Maryland, Massachusetts, Michigan, Minnesota, Mississippi, Missouri, Montana, Nebraska, Nevada, New Hampshire, New Jersey, New Mexico, New York, North Carolina, North Dakota, Ohio, Oklahoma, Oregon, Pennsylvania, Rhode Island, South Carolina, South Dakota, Tennessee, Texas, Utah, Vermont, Virginia, Washington, West Virginia, Wisconsin, WyomingAdditional InformationFull-time base salary range of $70,000 - $90,000 Benefits and Equity. Knowledge, Skills and Abilities: Benefits Sourcing - Sourcing of Benefits - Build an appropriate portfolio of benefits that would be attractive to our clients. Medical Insurance, Dental, Vision, STD, LTD, 401K, Life Insurance, HSA/FSA, Commuter, Discount Rx, Life & Wellness benefits Selling Benefits - Help prospective clients assess different benefits. Act as a Subject Matter Expert to support the sales team team to add benefits for each client. Have to be a licensed producer and be able to sell medical/health insurance products in various Go-to-market States including IL, CA, NY-NJ-CT, DC-VA-MD-PA Implementing & Administration of Benefits - Conduct Open Enrollment session(s), Prepare Employee-facing guide(s), support the implementation to ensure all enrolled Employees can use their benefits. Also support ongoing administration for qualifying life events (QLEs). $70,000.00 - $90,000.00 Annually

Keywords: Stitch PEO, Watsonville , Senior Benefits Specialist - Operations, Sales , Brentwood, California