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Customer Success Manager

June 18, 2026

Summary Join Us at PlanSource: Your Exciting Career Awaits!At PlanSource, a leading cloud-based provider of benefits administration technology and services, we are on a mission to simplify how people choose, use, and manage benefits through cutting-edge, AI-powered experiences. This is an incredible time to launch your career with us! The Customer Success Manager is responsible for leading customer relationships within the benefits administration industry that promotes customer satisfaction, loyalty, retention, and growth. The Customer Success Manager will support an operational foundation ensuring the proper support, consistency, and service excellence is delivered to each PlanSource customer. This role will work under the supervision of the Director of Customer Success. The Customer Success Manager is a key member of a team of subject matter experts who are involved in all activities related to benefits administration for their book of business. This role will work closely with all delivery groups within the PlanSource ecosystem to support customer success. Responsibilities include, but are not limited to:<ul><li>Serve as the primary point of contact for a portfolio of customers, ensuring seamless onboarding, implementation, and ongoing experience while driving adoption and outcomes leading to renewals, expansion, and advocacy across your portfolio.</li><li>Build and maintain strong, consultative relationships with HR, payroll, and benefits stakeholders within the customer’s organization.</li><li>Create and orchestrate ongoing documentation for customer specific processes.</li><li>Review SOP documentation as it is created and maintained.</li><li>Educate customers on the PlanSource products and system capabilities, industry best practices, and requirements related to system functionality.</li><li>Monitor customer health sentiment and proactively identify risks or opportunities to promote satisfaction.</li><li>Collaborate with internal resources to resolve customer concerns, project work, and ongoing delivery activities.</li><li>Consult and manage all Open Enrollment activities to include but not limited to requirements gathering, project management, EDI integration management, and payroll.</li><li>Manage and motivate to drive performance amongst support team members aligned to your book of business, with a strong eye toward customer satisfaction, efficiency, and employee engagement.</li><li>Develop and execute strategic business plans with our customers with a focus on renewing existing business.</li><li>Build and manage relationships with Sales, Business Development, and Operations teams.</li><li>Become an expert in PlanSource’s product offerings and how to position solutions for customers to meet their strategic goals.</li><li>Travel as requested (up to 25%) to visit partners and/or customers, to perform annual stewardship meetings, quarterly business review (QBR) presentations, complete training, and provide sales support.</li></ul>ScopeExecutes and guides all account activities to deliver an optimized, scalable, and quality-focused customer journey. Implements strategic plans and objectives for customers; supports tactical administrative duties. ComplexityProvides oversight for and directly contributes to strategic plans that ensure successful ongoing support for customers. These plans often leverage analysis of situations or data that requires an in-depth knowledge of the customer, competitive environment, technology and economic or social implications of organization activities. Health and Welfare domain expertise will be leveraged in support of these activities. DiscretionErroneous decisions and actions may impact or negatively influence the overall success of client relationships and company operations. InteractionRegularly interacts with executives and/or major customers, and key internal stakeholders across the organization. Interactions frequently involve highly visible activities such influencing and collecting feedback from customers, influencing other executives, and representing the organization on matters of great significance. SupervisionFunctions as an instrumental role within a complete functional team with deep domain and process expertise. About You Necessary Strengths, Skills, and Competencies<ul><li>8+ years of experience within the Health and Welfare Employee Benefits Administration industry, in an outsourcing environment, servicing clients of various size and complexity.</li><li>Career path that demonstrates consistency, increasing level of responsibility in scope and scale.</li><li>Health and Welfare domain knowledge that demonstrates expertise in enrollment technology configuration, employee benefits processes, benefit program requirements, carrier and payroll exchanges, and a firm understanding of benefit services (e.g. Open Enrollment, COBRA, ACA, Call Center, Billing).</li><li>General understanding of EDI data and file delivery management, including but not limited to requirements gathering, vendor file delivery, 834 and 5010 layouts, troubleshooting, and payroll file processes.</li><li>Strong problem-solving skills with a solution-oriented mindset.</li><li>Demonstrated mastery in project management and leading a team to successful and timely outcomes.</li><li>Illustrate the pursuit of excellence in partnership with experience among all customer delivery touchpoints: sales, implementation, and retention.</li><li>Exceptional data-driven and analytical problem-solving skills to identify trends as well as resolve complex inquiries from your customers and internal stakeholders.</li><li>Ability to manage large complex projects and guide both internal and external resources effectively.</li><li>Strong communication skills with great talent in driving clarity and solutions for customers; demonstrated resourcefulness in setting priorities and guiding investment in people and systems.</li><li>Demonstrates strong presentation skills with the ability to lead customer meetings and teams with little to no direction. Participate in sales support meetings as required.</li></ul> What We Offer At PlanSource, benefits are at the core of what we do, and we understand their impact on our employees and their families. That’s why we’ve designed our benefits program to support overall wellbeing across health, financial security, career growth, and work‑life balance.<ul><li>Comprehensive health coverage with multiple medical plan options - all covering 100% of in-network preventive care. </li><li>Employer‑funded Health Savings Account (HSA) - up to $1,000 annually for family coverage. </li><li>Dental & Vision plans with 100% coverage for routine dental care and $250 vision frame allowance, plus employee-only vision premiums at $0.</li><li>401(k) with immediate vesting and a 50% company match up to 6% of contributions.</li><li>Generous paid parental leave, adoption assistance, and fertility benefits.</li><li>Flexible PTO, paid holidays, a strong culture of work‑life balance and Flex Fridays in the summer.</li><li>Mental health & wellbeing support, including Employee Assistance Program (EAP), movement and wellness resources.</li><li>Rewards and recognition programs that celebrate employees through peer recognition, awards, and quarterly recognition initiatives.</li></ul>Top 5 Reasons to join PlanSource #5: Be part of what’s next in benefits technology Join a company redefining how benefits work. Backed by Vista Equity Partners, PlanSource is continuously investing in innovation, bringing together AI, automation, and human insight to simplify complex processes and deliver real outcomes. This is your opportunity to build the future of benefits at scale. #4: Make an impact with technology our customers trust Our platform powers some of the most complex benefits programs in the market, and our customers rely on us to get it right. From a unified benefits ecosystem to AI-driven decision support, everything we build is designed to deliver clarity, confidence, and measurable impact for the people who use it every day. #3: Be recognized, supported, and set up to thriveWe believe great work deserves recognition and real support. From meaningful rewards and recognition programs to a comprehensive approach to employee support, we invest in helping our people perform at their best and feel valued along the way. Recognized as a top workplace, PlanSource has earned multiple Great Place to Work certifications and numerous awards, including Best Company for Culture, Work-Life Balance, and Compensation, reinforcing our commitment to an exceptional employee experience. #2: Grow your career with intentionAt PlanSource, career growth doesn’t happen by accident. With a strong track record of internal mobility, structured development paths, and opportunities to take on new challenges, you’ll have the support and flexibility to build a career that evolves with you. #1: Be part of a culture built on connection and impactOur culture is rooted in connection, inclusion, and shared success. Guided by our S.O.U.R.C.E. values, we lead with service by putting others first, approach challenges with optimism, and act with urgency to drive meaningful outcomes. We hold ourselves accountable through reliability, continuously grow through curiosity, and operate with efficiency to maximize the impact of our work. Here, diverse perspectives are valued and they directly shape how we collaborate, innovate, and deliver an exceptional experience for our customers. NOTE: We will consider a remote employee for approved cities PlanSource can accommodate. If you’re selected, you’ll receive your offer and be asked to complete a background check. This will include a drug screen, criminal record search and verification of previous employment and/or education. Recruiting Scams: Unfortunately, scams targeting job seekers are common. To protect our candidates, we want to remind you that authorized representatives of PlanSource will only contact you from an email address ending in @plansource.com. PlanSource will never ask for personally identifiable information such as Date of Birth (DOB), Social Security Number (SSN), banking/direct/tax details, etc. via email or any other non-secure system, nor will we instruct you to make any purchases related to your employment. If you believe you’ve encountered a recruiting scam, report it to the Federal Trade Commission and your state’s Attorney General. REF 4828

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...