Middle Sales Executive, Pension Software

At CalcAir, 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.

CalcAir 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, CalcAir might be the perfect fit.

Learn more about us here:

➡️CalcAir:

➡️Gemini:

About the Role

CalcAir 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 high 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 CalcAir: building relationships with TPAs, plan sponsors, and industry contacts, representing us at trade shows and conferences, and helping prospective clients understand how CalcAir 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.

What You'll Be Doing

• 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 CalcAir 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

About You

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 (HubSpot 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 events

Nice to Have

• Familiarity with the US retirement industry — TPAs, defined benefit/defined contribution plans, recordkeepers, or investment house account management

• Experience at a TPA, pension plan administrator, recordkeeper, or investment house

• Experience with CalcAir or a comparable pension administration platform

Human-Centered, AI-Supported: We may use AI tools to support and streamline parts of our recruitment process, such as scheduling, application review, and note-taking. AI helps us work more efficiently and consistently, but it never replaces human judgment. All hiring decisions are made by people not machines. Interviews are conducted by real team members who want to get to know you and your experience. AI is used to reduce bias, improve fairness and streamline processes, while keeping human connection and individual stories at the heart of our process.

Trust Comes First: We aim to be transparent about our pay practices. We post what we reasonably expect to pay for this position at the time of posting, based on factors such as role scope, market data, internal equity, and experience. Beyond base salary, we offer a comprehensive total rewards package that may include health and wellness benefits, paid time off, learning and development opportunities, and other employee programs designed to support your well-being and growth. This role also includes a commission plan.

Exempt

Salary Range:

The estimated base salary range for this role is USD$63,000.00 - USD$77,000.00 per year. We include salary ranges in job postings only where required by applicable pay transparency laws, based on the jurisdictions in which the role may be performed. The posted range is a good faith estimate and reflects factors that are subject to change. Final offer amounts may vary based on job-related factors, including work location, candidate experience and expertise, and other relevant considerations. This role will also be eligible for participation in a Company profit sharing bonus plan. Sales positions may be eligible to participate in the business commission plan. Plan details will be provided to you upon hire. Full time employees will also be eligible for enrollment in a wide range of choices of benefits , including medical, dental, vision, basic life insurance, short/long term disability, 401(k) participation (with company match). The Company provides a minimum of 10 days of vacation for new employees , sick time based on state requirements, 8 Company-paid holidays and 2 personal holidays per year. We recognize the value and importance of diversity and inclusion in our communities and in the workplace. We celebrate diversity and one of our goals as an employer is to create an inclusive work environment for all employees. We are an equal opportunity employer and do not discriminate against any employee or applicant because of race, religion, sex, sexual orientation including gender identity or expression, pregnancy, national origin, age, marital status, veteran status, disability status, or any other category or characteristic protected by law. Applicants with disabilities who would like to require a reasonable accommodation related to any part of the application process may contact us at . NOTE: If an applicant is selected to receive a conditional offer of employment, and in accordance with applicable law, a criminal background check may be conducted before the offer becomes final and employment begins. Pursuant to the San Francisco Fair Chance Ordinance, and other applicable laws, we will consider for employment qualified applicants with arrest and conviction records. #Calcair