Benefits Administration Technical Support Engineer - EST

Job Description
We're looking for a US Benefits Administration Customer Experience Engineer (CXE) to join our Customer Experience team.
In this role, you'll serve as the highest technical escalation point for Benefits Administration-related customer issues, partnering closely with Product, Engineering, Customer Success, and Support teams to investigate and resolve complex product challenges.
You'll analyze system behavior, reproduce issues, investigate data discrepancies, and identify root causes impacting customer workflows. While this is not a software engineering role, successful candidates should be comfortable working with technical concepts, reviewing logs and data, understanding integrations, and collaborating with Engineering teams to drive resolution.
This is a unique opportunity for someone who combines Benefits Administration knowledge with strong technical troubleshooting skills and a passion for solving complex customer problems.
The base salary range for this role is $103,000 - $129,000.
There is a strong preference to fill this role in NYC with a hybrid schedule out of our office, but we will consider exceptional candidates who are based in the EST time zone and open to working remotely.
Location Eligibility: While can be a remote position, HiBob is currently authorized to hire in the following states: CA. CO, CT, DC, FL, GA, IL, IN, KS, MA, MD, MN, NC, NH, NJ, NV, NY, OH, OK, OR, PA, RI, SC, TN, TX, UT, VA, WA.
Job Requirements

• 4+ years of technical support experience supporting Benefits Administration platforms, HRIS systems, or SaaS applications.
• Strong understanding of US Benefits Administration processes, including eligibility, enrollments, life events, carrier interactions, and benefits data flows.
• Experience in troubleshooting complex customer issues and performing root cause analysis.
• Experience supporting enterprise customers in a technical support or escalation environment.
• Experience working with APIs, integrations, webhooks, and data synchronization processes.
• Familiarity with SQL and database concepts, including the ability to query or analyze data during investigations.
• Experience investigating issues using logs, audit trails, reporting tools, and system-generated data.
• Experience working with Zendesk, Salesforce, Jira, Asana, or similar support platforms.
• Experience collaborating with Product and Engineering teams.
• Strong written and verbal communication skills.
• High level of ownership and accountability.

Nice to Have

• Experience with ACA, COBRA, ERISA, or other US benefits compliance requirements.
• Previous experience supporting payroll-related products.
• Experience in HR Technology environments.
• Basic scripting or HTML/CSS knowledge.
• Experience working in a high-growth SaaS environment.

Job Responsibilities

• Own Complex Customer Escalations
  • Act as the highest level of support for Benefits Administration-related product issues.
  • Investigate complex customer-reported problems that cannot be resolved by frontline support teams.
  • Take ownership of critical escalations from investigation through resolution.
  • Clearly communicate findings, impact, and next steps to customers and internal stakeholders.
• Technical Investigation & Troubleshooting
  • Reproduce customer-reported issues in test environments.
  • Analyze system behavior using logs, audit trails, APIs, reporting tools, databases, and internal platforms.
  • Investigate eligibility discrepancies, enrollment issues, carrier integration failures, benefits data inconsistencies, and unexpected product behavior.
  • Perform root cause analysis and provide Engineering teams with actionable findings, reproduction steps, and business impact.
  • Validate fixes and confirm issue resolution.
• Collaborate Across Teams
  • Work closely with Product, Engineering, Customer Success, Benefits Operations, and Support teams.
  • Participate in bug triage and technical investigations.
  • Advocate for customer impact during prioritization discussions.
  • Bridge the gap between customer-reported issues and technical investigations.
• Drive Continuous Improvement
  • Identify recurring issues and escalation trends.
  • Contribute to internal documentation and troubleshooting resources.
  • Help improve investigation processes, tooling, and support workflows.
  • Share technical knowledge across Customer Experience teams.

Benefits
At HiBob we are committed to creating an excellent employee experience. Our bobbers, culture, and additional benefits all make bob a great place to work, come join us! We offer a competitive compensation package that includes salary, benefits, and pre-IPO equity. We have a beautiful office located in NYC and remote bobbers coast to coast.

• 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)
• Fun and frequent social events, both in-person and virtual

Join HiBob and be part of a dynamic, people-centric organization where your impact will shape the future of work. Apply now and unleash your potential in a supportive, inclusive environment that celebrates your uniqueness.