Strategy & Operations

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 This confusion stems from outdated systems and manual processes that lead to errors, delays, and widespread frustration.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

As one of our first Strategy & Operations hires at Clasp, you will run highly operational work across our products and own it end to end. This is a high-autonomy, ground-floor role: you'll establish new processes where none exist, act as the general manager of a new vertical, coordinate with R&D to build the tooling that scales it, and step in as the product manager when a project needs one. You'll have the autonomy, ownership, and surface area to make a significant impact across the company, with the strategy living in how you decide a function should work and then build it.

• Operate across the business: take on the highest-priority operational work across Clasp's products, from benefits and ACA to 401(k), HSA, carrier connections, and new lines as they launch

• Stand up new processes: when something has no process yet, design it, document it, and make it repeatable enough to hand off

• Act as GM of a new vertical: own a line end to end, the strategy, the operations, and the outcomes, and decide how it should work and scale

• Act as PM when needed: write the requirements, prioritize, and drive delivery with Engineering whenever a project needs a product manager to carry it

• Bring the analysis: use data and models to decide where to focus, size the impact, and prove what is working

• Proactively solves problems: you see what needs to be done and do it, working around obstacles to reach an outcome without waiting to be told

• Analytical and quantitative: fluent in spreadsheets and modeling, and able to turn ambiguity into structured analysis and a clear recommendation

• A structured thinker: you scope projects from an ambiguous problem to analysis to execution, and think in frameworks and first principles

• A cross-functional leader: you manage internal and external stakeholders and drive projects to completion, often without direct authority

• High-caliber, fast-paced background: 2 to 6 years at a place that trusted you with hard problems early, such as top consulting, banking or finance, a high-growth startup, or a similarly selective environment

• A builder and an operator: high ownership, low ego, energized by ambiguity, and happiest shipping rather than just advising

• Exposure to benefits, insurance, payroll, HR-tech, fintech, or healthcare

• Background in management consulting, investment banking or finance, strategy and operations, BizOps, or chief of staff

We offer competitive salaries in line with years of experience and work location. Our benefits include health insurance that is 100% covered, a $5K office budget, and unlimited PTO, among others.

Base compensation for this position ranges from $100,000-$170,000, plus meaningful early-stage equity.

Final offer amounts are determined by experience and expertise and may vary from the amounts listed.