Founding Account Executive

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 This confusion stems from outdated systems and manual processes that lead to errors, delays, and widespread frustration.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 a founding Account Executive at Clasp, your role will include prospecting, managing the 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 $120,000-$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!