Operations Associate / Operations Lead

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 This confusion stems from outdated systems and manual processes that lead to errors, delays, and widespread frustration.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

• 2-6 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 - $120,000; 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