Benefits Administration Technical/Customer Support Engineer - EST

HiBob•,

3d•$103,000 - $129,000•Hybrid

About The Position

HiBob helps modern, mid-size businesses transform the way they manage people. Our HR platform, Bob, provides powerful tools for HR, payroll, workforce planning, benefits administration, and employee engagement. Since launching in 2015, we've grown rapidly and now serve thousands of businesses worldwide. We're building a company where great people can do their best work while helping our customers create exceptional employee experiences. We're looking for a US Benefits Administration Customer/Technical Support Engineer (CXE) to join our Customer Experience team. In this role, you'll become the technical and operational expert for HiBob's Benefits Administration product, helping customers navigate complex benefits challenges while partnering closely with Product, Engineering, Payroll, and Customer Success teams. You'll investigate escalated customer issues, troubleshoot benefits administration workflows, support integrations with carriers and third-party systems, and help drive improvements across our product and support experience. This is a unique opportunity for someone who combines deep knowledge of US benefits administration with strong problem-solving and technical troubleshooting skills.

Requirements

4+ years of experience in Benefits Administration and/or HR Technology. This is a hard requirement.
Strong knowledge of US benefits administration processes, including eligibility, enrollments, life events, and carrier interactions.
Experience supporting customers in a SaaS environment.
Exceptional troubleshooting and problem-solving skills.
Ability to investigate issues across multiple systems and identify root causes.
Excellent communication skills and ability to explain complex topics clearly.
Experience working cross-functionally with technical and non-technical stakeholders.
A proactive, customer-first mindset with strong ownership and accountability.

Nice To Haves

Experience with ACA, COBRA, ERISA, or other US benefits compliance requirements.
Experience with Benefits Administration platforms, HRIS systems, or payroll solutions.
Familiarity with APIs, integrations, webhooks, or data troubleshooting.
Experience with Zendesk, Salesforce, Jira, Asana, or similar support tools.
Enterprise customer support experience.
Experience in a high-growth SaaS environment.

Responsibilities

Act as the highest level of support for Benefits Administration-related issues.
Investigate and resolve complex customer challenges involving enrollments, eligibility, life events, carrier connections, and benefits data.
Manage critical issues from investigation through resolution while keeping customers informed and confident.
Develop deep expertise in HiBob's Benefits Administration offering.
Guide customers on best practices for benefits configuration and administration.
Support customers through Open Enrollment, life events, eligibility changes, and compliance-related processes.
Analyze system behavior using logs, APIs, reporting tools, integrations, and internal platforms.
Investigate data discrepancies and synchronization issues between HiBob and benefits providers.
Perform root cause analysis and partner with Engineering on long-term solutions.
Work closely with Product, Engineering, Payroll, Customer Success, and Support teams.
Advocate for customer needs during bug triage and product discussions.
Help identify opportunities to improve product functionality and customer experience.
Identify recurring issues and systemic challenges.
Create documentation, troubleshooting guides, and enablement materials.
Help scale support operations through automation, process improvements, and knowledge sharing.

Benefits

Stock options in a scaled, high-growth SaaS leader
Comprehensive medical, dental, and vision coverage from day one
401(k) with a 3% company match effective the month following your start date
Hybrid working model for Bobbers in the NY metro area
Temporary remote work-from-anywhere in the world for up to 2 months(after 6 months of employment)
Monthly wellness stipend to invest in your physical, mental, and overall wellbeing
Work from home allowance to set up your home office
Bob balance days - 4 additional days within a calendar year - Enjoy a company-wide long weekend at the beginning of each quarter
We love birthdays - take the day off and receive a special gift
Two social impact days each year - to volunteer and give back to causes you care about
Annual Headspace subscription and wellness benefits
$2,500 employee referral bonus (plus ambassador incentives)