Senior Customer Experience Specialist - Benefits

Job requirements

• Strong experience supporting Benefits products, benefits administration, or customer operations within an HRIS, Payroll, or SaaS environment.

• Demonstrated expertise in Benefits processes, product functionality, and customer support best practices.

• Proven experience managing complex customer escalations and driving issues to resolution through cross-functional collaboration.

• Experience working closely with Engineering and Product teams to investigate defects, validate fixes, and improve the customer experience.

• Experience conducting quality assurance reviews and providing constructive coaching to improve team performance and service consistency.

• Experience onboarding, mentoring, and enabling colleagues through training, knowledge sharing, and continuous learning initiatives.

• Strong organizational and prioritization skills, with the ability to manage multiple complex cases simultaneously.

• Excellent problem-solving skills with a proactive, customer-focused, and solutions-oriented approach.

• Strong communication and stakeholder management skills, with the ability to work effectively across Customer Experience, Implementation, Managed Services, Product, and Engineering.

• Passion for coaching others, sharing expertise, and fostering a culture of operational excellence and continuous improvement.

Job responsibilities

• Act as the primary subject matter expert for the Benefits product, associated processes, and customer support best practices.

• Own and coordinate the resolution of complex Benefits escalations originating from Customer Experience, Implementation, and Managed Services teams.

• Partner closely with CX Engineering, Product, and other cross-functional teams to investigate issues, identify root causes, and drive timely customer resolutions.

• Provide expert guidance and day-to-day coaching to Customer Experience Specialists, enabling them to confidently resolve complex Benefits enquiries.

• Conduct regular quality assurance reviews of customer interactions and case handling, providing actionable feedback to improve service quality and consistency.

• Support the onboarding and training of new team members by delivering product, process, and operational knowledge.

• Develop and maintain internal knowledge resources, documentation, and best practices to improve team capability and self-sufficiency.

• Participate in feature validation, user acceptance testing (UAT), and bug-hunting activities for new Benefits functionality, ensuring customer scenarios are thoroughly assessed prior to release.

• Work with Product and Engineering teams to reproduce customer issues, validate fixes, and provide customer-focused feedback to improve product quality.

• Identify recurring customer issues, operational trends, and product gaps, making recommendations for process improvements and product enhancements.

• Champion operational excellence by ensuring adherence to established support processes, quality standards, and service expectations.

• Support continuous improvement initiatives that enhance customer experience, operational efficiency, and first-contact resolution.

• Collaborate with Customer Experience, Implementation, Managed Services, Product, Engineering, and other internal stakeholders to deliver seamless customer outcomes.

• Act as a trusted escalation point for complex Benefits queries, balancing customer needs with operational priorities to achieve timely resolutions.

• Promote a collaborative, knowledge-sharing culture by mentoring colleagues and contributing to the continuous development of the wider Customer Experience organization.

Job benefits

• Equity in a global, high-growth HR tech SaaS leader

• 401(k) with a 3% company match effective the month following your start date

• $2,500 employee referral bonus

• Medical, dental, and vision coverage from day one

• $1,920 annual wellness stipend to support your physical and mental wellbeing

• Annual Headspace membership and expanded wellness benefits

• Hybrid working model for Bobbers in the NY metro area

• Temporary work from anywhere for up to 2 months per year (after 6 months)

• Generous paid time off and company holidays to rest, recharge, and enjoy

• Bob Balance Days – 4 additional days within a calendar year - Enjoy a company-wide long weekend at the beginning of each quarter

• Your birthday off — plus a special gift from us

• Home office allowance to set up your ideal workspace

• Two paid Social Impact days each year to give back to causes you care about

• Frequent team and company social events, both in-person and virtual