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Sales Executive, Pension Software

CalcAir

(Remote)

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: https://calcairebs.com/ 

➡️Gemini: https://www.csigemini.com/ 

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. 

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. 

A background in US pension administration is essential but full-cycle sales experience is not. If you know the industry, have previous customer facing experience and you're ready to bring that knowledge to a new role with the drive to learn the rest, we want to hear from you. 

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 

We're open to two kinds of candidates for this role: 

• You have 2–3+ years of experience in US pension administration/customer facing roles - you understand the lifecycle, you can speak the language, and you're ready to take that expertise into a client-facing sales role, or 
• You have full-cycle sales experience with a solid grounding in the US pension space — you've sold into this market before and you know how to move a deal forward 

Either way, you bring: 

• Genuine familiarity with US pension administration — TPAs, defined benefit and/or defined contribution plans, and the lifecycle that comes with them 
• Comfort with outbound sales activity —you need to be comfortable cold calling and following through, full ownership of the sales cycle  
• Strong communication skills and the ability to build trust with clients who take their work seriously 
• The organizational discipline to manage a pipeline and follow through consistently 
• Ability to travel within the US for trade shows and industry events 

Nice to Have 

• Experience with CalcAir or a comparable pension administration software platform 
• Prior experience at a TPA, pension plan administrators, or pension software company 

What's important to us at Gemini 🧲 

Make long term investments 

In people, technology, and customers. What goes around comes around and when possible, we try to pay it forward. 

Growth through learning 

Learning is the key to success. We encourage employees to share their expertise and best practices with their peers. That way, we all grow together. 

Autonomy 

Our staff operate independently in a decentralized structure. Whenever possible, we provide the independence required to drive growth and success. 

Trust comes first 

We believe in full transparency and ongoing communication; if there is a problem, we try to work collaboratively on solutions. 

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.

FLSA Designation (US Only):

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.

Other Compensation (US Only):

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.

Benefits (US Only):

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).

Time off (US Only):

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 Perseus_HR@constellationhbs.com.

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.

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