Sales Executive, Pension Software

At Calc Air, we've been helping employee benefit professionals breathe easier for over 50 years — and we're just getting started. As a trusted name in benefits software and services, we blend deep industry roots with a forward-thinking mindset. Calc Air is part of the Gemini Group, one of the operating groups within Constellation Software Inc. (CSI). Being under CSI—a global leader in vertical market software—means we benefit from the stability, innovation, and long-term investment philosophy of a world-class software organization, while still operating with the agility and culture of a specialized team.

Join a team where experience meets innovation, and where your work truly shapes the future of how people work, plan, and retire. If you're ready to make an impact, grow your career, and have a little fun along the way, Calc Air might be the perfect fit.

Learn more about us here:
Calc Air:  Gemini:

Calc Air is looking for a Sales Executive, Pension Software to grow our client base and deepen relationships with existing clients. This is a full-cycle sales role, from cold outreach and lead qualification through demos, proposals, and closing, and it sits at the intersection of pension expertise and client-facing sales. Represent a mission-critical compliance platform that organizations legally cannot operate without.

With an established customer base, exceptional client loyalty, strong referral-driven growth, and long switching costs that reinforce long-term partnerships, you'll spend less time creating demand and more time closing business and expanding relationships. You'll be the face of Calc Air: building relationships with TPAs, plan sponsors, and industry contacts, representing us at trade shows and conferences, and helping prospective clients understand how Calc Air can make their work easier.

You'll work closely with our support and marketing teams, but this role requires someone who can own their pipeline and isn't afraid to pick up the phone. If you know how to prospect, build relationships, and close — and you're motivated by a specialized market with real commission upside — we want to hear from you. Knowledge of the US retirement industry is a genuine asset and will help you hit the ground running, but it's your sales instinct and drive that matter most.

Important:
To be considered, you must have experience working in the US pension space. Candidates without this experience will not be considered.

• Prospecting and cold outreach: identifying new leads, making calls, and building relationships with TPAs, plan sponsors, and others in the pension community
• Managing the full sales cycle from first contact through close, including demos, proposals, and contract execution
• Owning and tracking pipeline activity and reporting on sales progress
• Representing Calc Air at US industry trade shows and conferences — planning, attending, generating leads, building relationships, and following up
• Maintaining and growing relationships with existing clients
• Collaborating with support and marketing teams to surface new opportunities and ensure a strong client experience

You bring:

• 3+ years in a customer facing role
• Proven sales acumen — you're comfortable prospecting, cold calling, and owning a pipeline from first contact to close
• Experience with a CRM (Hub Spot or similar) and the discipline to manage your sales cycle without being pushed
• A consultative approach: you build trust, ask the right questions, and know when to move a deal forward
• Strong communication skills and the confidence to engage clients who take their work seriously
• Willingness and excitedness to learn about the US retirement industry
• Ability to travel within the US for trade shows and industry…