Account Executive

At CalcAir, we've been helping employee benefits 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:
Constellation Software:

CalcAir Employee Benefit Systems, Inc. is seeking a motivated and results-driven Account Executive to build out our sales motion, foster growth, drive client retention, and expand our customer base.

Joining our team means becoming part of a dynamic environment where your sales expertise will make a real impact. You'll have the opportunity to collaborate closely with support and marketing professionals, leveraging your skills to drive growth and build lasting client relationships. As we continue to innovate and expand our platform's capabilities, your contributions will be crucial in delivering high-quality solutions and empowering organizations to achieve confident, compliant retirement plan management at scale.
 

We're looking for someone who thrives in a proactive sales environment—someone who is energized by self-sourcing opportunities, cold outreach, and full-cycle ownership of the sales process from prospecting to close.
 

• Build and maintain strong relationships with both existing and prospective clients to promote service adoption and long-term partnerships

• Source and develop your own pipeline through cold calling, outbound email campaigns, and strategic networking activities

• Manage the full sales cycle, from lead generation and discovery through demos, negotiation, and close

• Identify and pursue new sales leads to expand the customer base

• Develop and implement sales strategies aimed at increasing client retention

• Collaborate with support and marketing teams to uncover new sales opportunities

• Gather and communicate customer feedback to inform cost-effective product enhancements

• Monitor competitor activities and market trends to inform sales tactics

• Plan, attend, and represent CalcAir at industry trade shows, conferences, and networking events

• Manage sales and marketing projects from initiation to completion

• Track and report on product sales and associated costs

• Research and evaluate competing product offerings

• Prepare, analyze, and present sales reports to support strategic decision-making

• At least three years of sales or business development experience, including strong outbound prospecting and self-sourced pipeline generation, with a minimum of one year in a full-cycle role

• Proficiency in Microsoft Office Suite (Word, Excel, PowerPoint, Outlook)

• Excellent verbal and written communication skills

• Strong analytical skills and experience with sales metrics reporting

• Ability to work collaboratively with cross-functional teams to achieve shared goals

• Outstanding organizational and project coordination abilities

• Skills in direct marketing, marketing research, and project management

• Demonstrated creative initiative, motivation, and experience in budget and forecast management

• Bonus: previous experience selling retirement plan administration

• A base salary of around $60,000 CAD, plus a performance-based commission plan designed to reward your results and growth, for a competitive total on-target earnings (OTE)

• A comprehensive benefits package

• Vacation and floater days

• Access to Profit Sharing through our bonus programs

• The opportunity to participate in the CSI Employee Stock Purchase Plan
   

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
 

Applicants with disabilities who would like to require a reasonable accommodation related to any part of the application process may contact us at