Senior Customer Experience Specialist - Benefits

HiBob•,

4d•$106,250 - $135,250•Hybrid

About The Position

The Senior Customer Experience Specialist – Benefits is responsible for providing expert operational and product support across the Benefits offering, acting as the subject matter expert for customer-facing teams and ensuring the consistent delivery of high-quality customer outcomes. As the Benefits subject matter expert, the Senior Specialist develops and maintains deep expertise in both benefits processes and product functionality. They enable and coach Customer Experience Specialists through knowledge sharing, guidance, and ongoing support, helping to improve confidence, consistency, and first-contact resolution across the team. Requirements are often considered a measure of how equipped you are to do the job, but sometimes, they aren’t the only factor. If you don’t have nearly enough experience or not all the skills, we’d still like to hear from you. This could be the perfect fit for you and us.

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.

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.

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