We're a team of builders, united by our passion for simplifying the most complex industries. At Clasp, we're on a mission to transform the health insurance industry by modernizing and automating the entire benefits experience.
We started in 2023 backed by investors such as Base10 Partners, Terrain, Conversion Capital, and SemperVirens, firms that have led investments and helped grow companies like Ramp, Rippling, and Blend from the seed stage.
The problem we're solving:
Employers collectively spend over a trillion dollars on benefits every year, yet more than 85% of employees find their benefits confusing. This confusion stems from outdated systems and manual processes that lead to errors, delays, and widespread frustration.
Our vision is to create an ecosystem where everyone benefits:
Brokers eliminate busy work and enhance their advisory roles
Employers receive a tailored, efficient benefits experience with better coverage and service, often at lower costs
Employees gain clear, accessible information about their benefits, leading to higher satisfaction and engagement
Partners like HR and payroll platforms expand their offerings effortlessly with our embeddable solutions
About the role
This is a hands-on operations seat at the center of how Clasp delivers every day. You will own frontline execution across customer support, employer implementations, carrier connections, ACA compliance work, and other new verticals, partnering directly with our BizOps and R&D teams to keep the machine running and to make it run better.
Upon starting, you’ll embark on a crash course through our core implementations and product surface area and then become the primary lead on these functions across key client accounts. As we scale, you help hire and mentor the Operations team and help scale the Support / Implementation function at Clasp.
What you'll do
Customer support: own the support queue end to end: triage, investigate, resolve, and escalate issues across employers, partners, brokers, and carriers, hitting our SLA and quality targets
Implementations: onboard new employer groups: collect and validate censuses and plan documents, configure plans and rates, run enrollment data quality checks, and coordinate go-live with partners
Carrier connections: stand up and maintain EDI and API feeds: manage carrier and vendor build queues, work discrepancy reports to resolution, and keep connections healthy after go-live
ACA and compliance: run the ACA implementation process, data collection and reconciliation, and filing review cycles alongside our compliance tooling and vendors
Process building: document what you learn into runbooks and SOPs, spot the recurring failure modes, and work with BizOps and engineering to automate them away
Cross-functional support: be the operational voice into R&D: reproduce bugs, define edge cases, test fixes, and translate customer pain into product requirements
What we're looking for
2-4 years in operations, support, implementations, or account management at a fintech, HR-tech, benefits, insurance, or similar operationally-intensive company
High ownership: you chase issues to resolution across email threads, carrier portals, and spreadsheets without being asked twice
Sharp written communication: you will spend much of your day writing to employers, partners, and carriers, and precision matters
Comfort with messy data: confident in spreadsheets (lookups, pivots, data cleaning); SQL or scripting is a plus, not a requirement
Process instinct: you notice when the third ticket looks like the first two and go fix the root cause
Thrives on volume and pace: this is a doing role at a fast-moving startup, and the work is concrete, daily, and measurable
What success looks like
By 30 days: independently resolving the majority of support tickets within SLA and running implementation checklists with light oversight
By 90 days: owning a slice of the connections or ACA book end to end, with updated processes you wrote yourself
By 6 months: operating as the go-to owner for support or implementations and ready to formally lead that function as it scales
Base compensation ranges from $70,000 - $100,000; final offers depend on experience and expertise and may vary from the amounts listed
Competitive equity stock options
Health insurance 100% covered, a $5K office budget, unlimited PTO, and more
Skills Required
- 2-4 years in operations, support, implementations, or account management at a fintech, HR-tech, benefits, insurance, or similar operationally-intensive company
- High ownership and ability to drive issues to resolution across multiple channels
- Sharp written communication for employer, partner, broker, and carrier correspondence
- Comfort with messy data and confident in spreadsheets (lookups, pivots, data cleaning)
- Process instinct: identify recurring failure modes and implement root-cause fixes
- Thrives in high-volume, fast-paced startup environments
- Experience with SQL or scripting
- Experience standing up or maintaining carrier connections (EDI/API) and vendor build queues
- Familiarity with ACA implementation, data reconciliation, and compliance tooling
What We Do
Health benefits infrastructure for HR, payroll, and benefits brokers.
