Current Openings

About the Role

CalcFocus is seeking a Sales Executive for someone who wants to create momentum, not just manage a pipeline.

You will help expand an emerging Life & Annuity Insurtech platform that already delivers real value to clients and is ready for broader adoption. The foundation is in place: a strong product, satisfied clients, and clear market demand. The opportunity now is to turn that foundation into sustained revenue growth and deeper market presence.

You will own complex enterprise sales cycles, influence how the company shows up in the market, and help define the sales motion as the business scales.

What You Will Do

You will drive revenue growth by taking ownership of how opportunities are identified, shaped, and closed.

• Develop and convert a qualified pipeline of Life & Annuity carriers and providers through prospecting, networking, conferences, and industry engagement
• Lead long-cycle enterprise deals from early discovery through RFP, negotiation, and close
• Engage executive buyers and cross-functional stakeholders across IT, actuarial, underwriting, operations, and compliance
• Translate insurance and technology complexity into clear business outcomes and ROI
• Create and refine sales narratives, account strategies, and deal approaches that resonate with senior decision-makers
• Partner closely with product, marketing, and customer success to influence positioning, onboarding, and long-term adoption
• Bring market feedback into the business to sharpen differentiation and uncover new growth opportunities

What You Bring

You bring judgment, creativity, and comfort operating where structure is still evolving.

• 7+ years of B2B enterprise sales experience in Insurtech or Life & Annuity technology
• Familiarity with how carriers evaluate and purchase core systems (policy administration, illustration, underwriting, billing, etc.)
• Established relationships within carriers or insurance technology buyers
• Proven success prospecting, navigating complex buying committees and managing extended sales cycles
• Ability to think beyond the transaction and shape how solutions are positioned and sold
• High level of ownership, initiative, and comfort operating without rigid playbooks
• A collaborative approach and high integrity in how you represent the company in the market

Why Join Us

This role offers meaningful impact with room to grow.

• A product suite that already delivers value and is ready to scale
• The opportunity to influence go-to-market strategy, not just execute it
• Visibility into how sales, product, and customer success decisions are made
• Competitive compensation with performance-based incentives
• 100 percent employer-paid benefits
• A collaborative environment where ideas turn into action

About CalcFocus

CalcFocus is a people first company known for its flexible, collaborative, and truly supportive work environment. Our team is made up of talented, long tenured employees who stay because they feel valued, trusted, and empowered to do meaningful work.

We believe in balance, offering paid benefits, generous time off, and the space for employees to grow in both their careers and their personal lives.

At CalcFocus, teamwork isn’t just a value, it’s a daily experience. We foster an environment where great people learn from each other, support each other, and celebrate wins together. If you’re looking for a place where your ideas matter, your work is respected, and your contributions have real impact, join our team!