Account Executive

Wine and spirits retailers across the United States run their stores on our software: point of sale, inventory, purchasing, e-commerce, and reporting, all built specifically for their industry. As an Account Executive, you own the full sales cycle for our flagship products, WinePOS, WineCommerce and WinePayments, from finding the right prospects to closing the deal.

This is a full-cycle B2B sales role for a self-starter who can build a pipeline, run a compelling demo, and win the business. You will report to the VP of Sales and Marketing.

• Build pipeline. Generate new business through cold calling, direct outreach, referrals, and creative prospecting, both traditional and non-traditional.

• Qualify and prioritize. Identify strong-fit prospects for WinePOS and WineCommerce, and disqualify the ones that aren't, so your time goes where it counts.

• Demo the product. Present and demonstrate our solutions in person and remotely, tailoring each conversation to the prospect's specific needs.

• Close. Understand each prospect's system requirements, position the right solution, and win the business.

• Set up a clean handoff. Capture the core account details the Implementation Team needs to take it from there.

• Represent the brand. Be a visible ambassador for WinePOS at industry events and meetings.

• 3 to 5 years of full-cycle software sales, with a track record of turning leads into closed deals across both new prospects and warm referrals.

• Strong presentation and prospecting skills, and the ability to explain intangible services and solutions clearly to a range of audiences.

• Excellent written and verbal communication, and comfort in both formal and informal settings.

• A genuine self-starter who learns fast, works independently, and finishes what they start.

• A consultative listener who can accurately restate a prospect's needs and negotiate well when interests differ.

• Experience selling or supporting POS and/or e-commerce solutions.

• Experience in the wine, spirits, or wider liquor industry.

• Training in a structured sales methodology such as Sandler, SPIN, MEDDPICC, or Challenger.

• On-target earnings (OTE): $130,000 to $160,000 CAD, made up of base salary plus monthly commission on your sales, depending on experience and qualifications.

• Health, Dental, and Supplemental Insurance.

• Paid time off and vacation.

Work arrangement: Remote-first within Canada or the United States, with occasional on-site presence at our New Jersey office for events and training, plus approximately 10% travel within the US.

For over 40 years, ICS has served the retail beverage alcohol industry as a trusted, scalable solutions provider. Our core product, WinePOS, delivers point of sale, inventory, purchasing, and reporting to wine and liquor retailers across the United States, complemented by WineCommerce for online sales and WinePayments for integrated payments. ICS is an operating unit of Jonas Software.

That focus is your advantage: WinePOS is one of the few point-of-sale platforms built specifically for wine and spirits retail, so you sell on fit and expertise, not on price against generic systems. You get the backing and resources of Jonas Software with the focus of a specialized team, where your results are visible and rewarded.

Submit your resume through the application link. We would love to get back to everyone, but we only reach out to the candidates we would like to move forward with. If that is you, we will be in touch.

AI is used to help screen and assess applications for this role. A human always makes the final hiring decision.

Jonas Software is a leading provider of enterprise management software solutions, serving a wide range of vertical markets including hospitality, healthcare, construction, education, personal care, fitness, leisure, moving and legal services, to name a few. Within these markets, Jonas is comprised of over 65 distinct brands, each a respected leader in its domain.

Jonas’ vision is to be the branded global leader across these verticals and to be recognized by customers and industry stakeholders as the trusted provider of “Software for Life.” We are committed to technology, product innovation, quality, and exceptional customer service.

Jonas Software supports over 60,000 customers in more than 30 countries. We employ over 6,000 skilled professionals, including industry experts and technology specialists. Across our broader network, we support a global workforce of more than 30,000 employees.

Headquartered in Canada, Jonas Software has a global footprint with offices around the world. We’re a 100% owned subsidiary of Constellation Software Inc., based in Toronto, publicly listed on the TSX (CSU.TO), and a member of the S&P/TSX 60 Index.