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.
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 This confusion stems from outdated systems and manual processes that lead to errors, delays, and widespread frustration.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
We're seeking early Product Engineers that want to own problems end to end, from architecture to shipping to the partner conversation that shapes what gets built next. You'll have autonomy and the room to make an outsized impact on the core product.
In this role, you’ll be responsible for:
Owning the transformation of our core products to best in class experiences from the benefit administration workflows and carrier integrations to embeddable user interfaces
Driving product direction as a critical member of the early product engineering team.
Establishing robust technical foundations that scale with our largest partners' needs and future growth.
Cultivating partner relationships to identify and shape our roadmap and feature development.
You could be a great fit if you:
Possess exceptional engineering skills to build complex systems with elegant design and robust architecture.
Collaborate effectively with customers and partners to solve complex problems.
Exhibit strong product sense and translate technical concepts to non-technical stakeholders effortlessly.
Learn quickly, motivate yourself, and execute rapidly while maintaining high quality standards.
Exhibit a profound curiosity for exploring overlooked nuances and niche areas within complex technical and industry domains.
Bonus:
Enjoy technical writing and sharing knowledge and your work with the broader team and wider community.
Bring 5+ years of experience designing and building systems through multiple lifecycles.
Have expertise in Django (Python) and/or React (TypeScript) - not required, but it will help you ramp quickly.
Value code maintainability, testability, and clarity highly.
Communicate excellently, especially with non-technical team members and customers.
We’re a team of ~15 and growing headquartered in NYC, with teammates between both coasts. Small enough that everyone knows what everyone else is shipping, but big enough that nobody’s alone on a problem. A few things that are true about working here:
You get to own the whole problem, not the ticket. Scoping, tradeoffs, and customer conversations all belong to the same person. Roadmaps are for direction, not instruction.
Quality is not negotiable, speed usually is. We ship fast when it's reversible and slowly when it isn't. Knowing which is which is most of the job.
We write things down. Decisions live in docs and public channels, not in DMs. It's how a team stays fast.
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, a stipend for home internet expenses, and unlimited PTO (with a 15-day minimum), among others.
Base compensation for this position ranges from $180,000-$220,000.
Final offer amounts are determined by experience and expertise and may vary from the amounts listed.
","descriptionPlain":"ABOUT CLASP\n\nWe'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.\n\nWe 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.\n\n \n\n\nTHE PROBLEM WE'RE SOLVING:\n\nEmployers 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.\n\nOur vision is to create an ecosystem where everyone benefits:\n\n - Brokers eliminate busy work and enhance their advisory roles\n\n - Employers receive a tailored, efficient benefits experience with better coverage and service, often at lower costs\n\n - Employees gain clear, accessible information about their benefits, leading to higher satisfaction and engagement\n\n - Partners like HR and payroll platforms expand their offerings effortlessly with our embeddable solutions\n\n\n\n\nWHAT WILL YOU DO IN THIS ROLE\n\nWe're seeking early Product Engineers that want to own problems end to end, from architecture to shipping to the partner conversation that shapes what gets built next. You'll have autonomy and the room to make an outsized impact on the core product.\n\n\n\nIn this role, you’ll be responsible for:\n\n - Owning the transformation of our core products to best in class experiences from the benefit administration workflows and carrier integrations to embeddable user interfaces \n\n - Driving product direction as a critical member of the early product engineering team.\n\n - Establishing robust technical foundations that scale with our largest partners' needs and future growth.\n\n - Cultivating partner relationships to identify and shape our roadmap and feature development.\n\n\n\n\nWHO YOU ARE\n\nYou could be a great fit if you:\n\n - Possess exceptional engineering skills to build complex systems with elegant design and robust architecture.\n\n - Collaborate effectively with customers and partners to solve complex problems.\n\n - Exhibit strong product sense and translate technical concepts to non-technical stakeholders effortlessly.\n\n - Learn quickly, motivate yourself, and execute rapidly while maintaining high quality standards.\n\n - Exhibit a profound curiosity for exploring overlooked nuances and niche areas within complex technical and industry domains.\n\nBonus:\n\n - Enjoy technical writing and sharing knowledge and your work with the broader team and wider community.\n\n - Bring 5+ years of experience designing and building systems through multiple lifecycles.\n\n - Have expertise in Django (Python) and/or React (TypeScript) - not required, but it will help you ramp quickly.\n\n - Value code maintainability, testability, and clarity highly.\n\n - Communicate excellently, especially with non-technical team members and customers.\n\n\n\n\nHOW THE TEAM WORKS TODAY\n\nWe’re a team of ~15 and growing headquartered in NYC, with teammates between both coasts. Small enough that everyone knows what everyone else is shipping, but big enough that nobody’s alone on a problem. A few things that are true about working here:\n\n - You get to own the whole problem, not the ticket. Scoping, tradeoffs, and customer conversations all belong to the same person. Roadmaps are for direction, not instruction.\n\n - Quality is not negotiable, speed usually is. We ship fast when it's reversible and slowly when it isn't. Knowing which is which is most of the job.\n\n - We write things down. Decisions live in docs and public channels, not in DMs. It's how a team stays fast.\n\n\n\n\nCOMPENSATION DETAILS\n\nWe 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, a stipend for home internet expenses, and unlimited PTO (with a 15-day minimum), among others.\n\nBase compensation for this position ranges from $180,000-$220,000. \n\nFinal offer amounts are determined by experience and expertise and may vary from the amounts listed."},{"id":"02480ac9-1040-4c0a-b8d6-223d64514416","title":"Account Executive","department":"Revenue","team":"Revenue","employmentType":"FullTime","location":"Remote - United States","secondaryLocations":[{"location":"New York Office (Hybrid)","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}}}],"publishedAt":"2025-06-23T18:54:24.590+00:00","isListed":true,"isRemote":true,"workplaceType":"Remote","address":{"postalAddress":{}},"jobUrl":"https://jobs.ashbyhq.com/clasp/02480ac9-1040-4c0a-b8d6-223d64514416","applyUrl":"https://jobs.ashbyhq.com/clasp/02480ac9-1040-4c0a-b8d6-223d64514416/application","descriptionHtml":"About Clasp
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.
Role Overview:
As an Account Executive at Clasp, your role will include prospecting, managing sales pipeline, and closing new business opportunities. You'll directly contribute to Clasp’s growth, collaborating with our growth, success, and product teams to ensure clients achieve transformative results.
This is a rare, ground-floor opportunity where you’ll have autonomy, ownership, and the ability to make a significant impact across the company and build the early foundations of a sales organization from the ground up.
Key Responsibilities:
Identify, prospect, and cultivate relationships with SMB brokers and payroll platform providers.
Lead engaging product demos and walkthroughs, articulating Clasp’s value proposition clearly and persuasively.
Manage the full sales cycle, from initial outreach to negotiation and successful deal closure.
Develop a deep understanding of Clasp’s product features, industry trends, and customer pain points.
Work collaboratively with internal teams (Growth, Customer Success, Product) to align GTM strategies and optimize client outcomes.
Achieve and exceed quarterly and annual revenue targets.
Requirements:
3+ years experience in SaaS sales, ideally selling into SMBs in verticals that are compliance-heavy.
Proven track record of consistently meeting or exceeding sales quotas.
Exceptional communication, presentation, and negotiation skills.
Comfort and ability to navigate complex sales processes with multiple stakeholders.
Highly organized, self-motivated, and proactive.
Familiarity with CRM platforms and revenue ops tooling.
Nice to Have:
Prior experience or familiarity with benefits administration, HR technology, payroll systems, or insurance brokerage industries.
Experience selling AI-driven or automation-based products.
Compensation
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 $200,000-$300,000 OTE.
Final offer amounts are determined by experience and expertise and may vary from the amounts listed.
Come build the future of benefits with us!
","descriptionPlain":"About Clasp\n\nWe’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.\n\nWe 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. \n\n\nThe problem we’re solving:\n\nEmployers 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.\n\nOur vision is to create an ecosystem where everyone benefits:\n\n - Brokers eliminate busy work and enhance their advisory roles.\n\n - Employers receive a tailored, efficient benefits experience with better coverage and service, often at lower costs.\n\n - Employees gain clear, accessible information about their benefits, leading to higher satisfaction and engagement.\n\n - Partners like HR and payroll platforms expand their offerings effortlessly with our embeddable solutions.\n\n\n\nRole Overview:\n\nAs an Account Executive at Clasp, your role will include prospecting, managing sales pipeline, and closing new business opportunities. You'll directly contribute to Clasp’s growth, collaborating with our growth, success, and product teams to ensure clients achieve transformative results. \n\nThis is a rare, ground-floor opportunity where you’ll have autonomy, ownership, and the ability to make a significant impact across the company and build the early foundations of a sales organization from the ground up.\n\n\n\nKey Responsibilities:\n\n - Identify, prospect, and cultivate relationships with SMB brokers and payroll platform providers.\n\n - Lead engaging product demos and walkthroughs, articulating Clasp’s value proposition clearly and persuasively.\n\n - Manage the full sales cycle, from initial outreach to negotiation and successful deal closure.\n\n - Develop a deep understanding of Clasp’s product features, industry trends, and customer pain points.\n\n - Work collaboratively with internal teams (Growth, Customer Success, Product) to align GTM strategies and optimize client outcomes.\n\n - Achieve and exceed quarterly and annual revenue targets.\n \n\nRequirements:\n\n - 3+ years experience in SaaS sales, ideally selling into SMBs in verticals that are compliance-heavy.\n\n - Proven track record of consistently meeting or exceeding sales quotas.\n\n - Exceptional communication, presentation, and negotiation skills.\n\n - Comfort and ability to navigate complex sales processes with multiple stakeholders.\n\n - Highly organized, self-motivated, and proactive.\n\n - Familiarity with CRM platforms and revenue ops tooling.\n \n\nNice to Have:\n\n - Prior experience or familiarity with benefits administration, HR technology, payroll systems, or insurance brokerage industries.\n\n - Experience selling AI-driven or automation-based products.\n\n\nCompensation\n\nWe 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.\n\n\n\nBase compensation for this position ranges from $200,000-$300,000 OTE.\n\nFinal offer amounts are determined by experience and expertise and may vary from the amounts listed.\n\n\n\nCome build the future of benefits with us!"},{"id":"759f1a9d-e4de-45c0-a8ea-71cee7d66c98","title":"Strategy & Operations","department":"Operations","team":"Operations","employmentType":"FullTime","location":"New York Office (Hybrid)","secondaryLocations":[],"publishedAt":"2026-06-17T17:56:52.532+00:00","isListed":true,"isRemote":null,"workplaceType":null,"address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}},"jobUrl":"https://jobs.ashbyhq.com/clasp/759f1a9d-e4de-45c0-a8ea-71cee7d66c98","applyUrl":"https://jobs.ashbyhq.com/clasp/759f1a9d-e4de-45c0-a8ea-71cee7d66c98/application","descriptionHtml":"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.
","descriptionPlain":"ABOUT CLASP\n\nWe'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.\n\nWe 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.\n\n\n\nThe problem we're solving:\n\nEmployers 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.\n\nOur vision is to create an ecosystem where everyone benefits:\n\n - Brokers eliminate busy work and enhance their advisory roles\n\n - Employers receive a tailored, efficient benefits experience with better coverage and service, often at lower costs\n\n - Employees gain clear, accessible information about their benefits, leading to higher satisfaction and engagement\n\n - Partners like HR and payroll platforms expand their offerings effortlessly with our embeddable solutions\n \n \n\n\nROLE OVERVIEW\n\nAs 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.\n\n\n\n\nKEY RESPONSIBILITIES\n\n - 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\n\n - Stand up new processes: when something has no process yet, design it, document it, and make it repeatable enough to hand off\n\n - 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\n\n - Act as PM when needed: write the requirements, prioritize, and drive delivery with Engineering whenever a project needs a product manager to carry it\n\n - Bring the analysis: use data and models to decide where to focus, size the impact, and prove what is working\n\n\nREQUIREMENTS\n\n - 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\n\n - Analytical and quantitative: fluent in spreadsheets and modeling, and able to turn ambiguity into structured analysis and a clear recommendation\n\n - A structured thinker: you scope projects from an ambiguous problem to analysis to execution, and think in frameworks and first principles\n\n - A cross-functional leader: you manage internal and external stakeholders and drive projects to completion, often without direct authority\n\n - 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\n\n - A builder and an operator: high ownership, low ego, energized by ambiguity, and happiest shipping rather than just advising\n\n\nNICE TO HAVE\n\n - Exposure to benefits, insurance, payroll, HR-tech, fintech, or healthcare\n\n - Background in management consulting, investment banking or finance, strategy and operations, BizOps, or chief of staff\n\n\nCOMPENSATION\n\nWe 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.\n\nBase compensation for this position ranges from $100,000-$170,000, plus meaningful early-stage equity.\n\nFinal offer amounts are determined by experience and expertise and may vary from the amounts listed."},{"id":"6b3788a0-5ff9-4f97-b1ad-2f4bd1e6822f","title":"Account Management Lead","department":"Revenue","team":"Revenue","employmentType":"FullTime","location":"New York Office (Hybrid)","secondaryLocations":[],"publishedAt":"2026-08-12T15:44:04.760+00:00","isListed":true,"isRemote":null,"workplaceType":null,"address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}},"jobUrl":"https://jobs.ashbyhq.com/clasp/6b3788a0-5ff9-4f97-b1ad-2f4bd1e6822f","applyUrl":"https://jobs.ashbyhq.com/clasp/6b3788a0-5ff9-4f97-b1ad-2f4bd1e6822f/application","descriptionHtml":"We are a team of builders on a mission to transform the health insurance industry by modernizing and automating the entire benefits experience. Founded in 2023, we are backed by Base10 Partners, Terrain, Conversion Capital, and SemperVirens, investors behind companies like Ramp, Rippling, and Blend from the seed stage.
Employers spend over a trillion dollars on benefits every year, yet more than 85% of employees find their benefits confusing. Outdated systems and manual processes create errors, delays, and frustration. We are building an ecosystem where everyone wins: brokers shed busy work and elevate their advisory role, employers get a tailored and efficient benefits experience, employees finally understand their coverage, and HR and payroll platforms expand their offerings with our embeddable solutions.
As our first dedicated Account Management Lead, you will own Clasp’s most important client relationships and build the foundation for how we manage accounts at scale. We need someone senior enough to own these relationships, and capable enough to eventually build and lead the function.
Upon starting, you’ll embark on a crash course through our core implementations and product surface area, shadow the current primary account managers for our largest clients, and then become the primary relationship owner for those clients within 90 days. As we scale, you hire and mentor the AM team and help scale the Account Management function at Clasp.
Own our key client relationships. Serve as the primary point of contact for key clients, including our largest accounts: driving client strategy, weekly syncs, QBRs / contract renewals, and high-touch coordination across internal cross functional teams to support
Operate at the executive level. Own the room with client leadership and carry that same trust down through every level of their org, from HR admins to support reps, so you're the person clients call when something matters
Build the AM function from the ground up. Define how account management works at Clasp: the playbook, the templates, the escalation frameworks, the QBR and reporting cadence, and the account health metrics that turn AM from individual heroics into a repeatable function the next hire steps into
Turn client signal into product insight. Spot recurring patterns in feedback and operational friction, and bring RnD / Ops the problem, the impact, and your recommendation
Build the team. As we scale, hire and mentor junior AMs, define the team structure, and evolve from player-coach to Head of Account Management
5 to 8+ years in account management, client success, or strategic partnerships at a B2B SaaS, fintech, insurtech, or benefits/HR technology company; you have managed complex, high-touch accounts, not just a book of SMBs
The most senior AM in the room. Formally a manager or not, you are the person others look to when an account is on fire; you have de-escalated tense situations and kept trust through difficult periods
Operationally deep. You understand the product, the workflows, and the technical details well enough to diagnose issues and drive solutions without waiting for a translator
A builder. We do not have an AM playbook yet; you will be writing it, and you thrive in environments where you build the processes rather than follow them
An exceptional communicator across registers. Credible and clear with partner executives, support reps, internal engineers, and carrier vendor contacts alike
Organized under load. You track multiple accounts, dozens of open threads, and competing deadlines without letting things fall through
Experience with benefits administration or payroll/HRIS platforms
A startup chapter where you defined your own role and built processes from zero
Comfort with data: pulling reports, spotting trends, and using numbers to tell the story of account health
Base compensation ranges from $120,000 - $200,000 OTE; 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
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