Job Description: 

Key Responsibilities

• Drive net-new revenue by prospecting, qualifying, and closing new WinePOS, WineCommerce, and WinePayments opportunities across target accounts and market segments.
• Own the full sales cycle from outreach and discovery through proposal, negotiation, close, and handoff to implementation, with minimal oversight.
• Lead consultative sales conversations by identifying each prospect's operational, inventory, ecommerce, and payments requirements and aligning the right ICS solution set to those needs.
• Deliver compelling, tailored demonstrations remotely and, when needed, in person, adapting presentations to the prospect's business model, growth goals, and technical environment.
• Manage more complex or strategically important opportunities, including multi-stakeholder deals, competitive takeaways, and higher-value accounts.
• Actively develop and manage pipeline through outbound efforts, inbound leads, referrals, industry events, partner relationships, and existing-customer expansion.
• Maintain strong opportunity discipline in HubSpot, including next steps, forecast accuracy, activity tracking, close plans, pipeline hygiene, and inspection readiness.
• Coordinate a high-quality internal handoff by gathering accurate business, technical, and operational information required for implementation and go-live planning.
• Stay engaged post-sale through key implementation milestones and early customer adoption, helping protect the customer relationship and identify additional revenue opportunities.
• Represent ICS professionally at trade shows, conferences, and customer meetings as a senior brand ambassador for WineSuite solutions.
• Contribute market insight, messaging feedback, and practical field input to help sharpen sales plays, positioning, and go-to-market execution.
• Support less experienced sales team members through example, collaboration, and shared best practices, even without direct people management responsibility.

AI and Operating Expectations

ICS is actively investing in AI across operations, product development, and go-to-market execution. Senior Account Executives are expected to use approved AI tools as part of their daily workflow to improve speed, quality, consistency, and deal execution.

• Use approved to prepare for calls, research accounts, personalize outreach, summarize meetings, draft follow-up communication, and improve sales productivity.
• Leverage AI to reduce administrative work, improve account preparation, and strengthen deal execution while maintaining a high standard of judgment, accuracy, and professionalism in customer-facing output.
• Verify AI-generated content before using it externally, and exercise sound judgment with customer data, confidential information, pricing details, and internal materials.
• Adopt new workflows and process improvements that support ICS's broader AI-enabled operating model and help raise team effectiveness.
• Contribute ideas and best practices on how AI can improve prospecting, discovery, demos, proposal generation, account planning, and account management.

Required Qualifications

• 5+ years of experience in B2B sales, SaaS sales, software sales, payments sales, POS sales, or another full-cycle consultative sales environment, with a track record of meeting or exceeding quota.
• Demonstrated success prospecting consistently, building pipeline, and closing new business in a disciplined, metrics-driven environment.
• Strong discovery, needs analysis, presentation, negotiation, and deal strategy skills, including the ability to manage complex sales cycles.
• Clear written and verbal communication skills with the ability to tailor messaging to business owners, operators, and senior decision-makers.
• Comfort presenting software and payments solutions in formal and informal settings, both remotely and in person, with strong executive presence.
• Strong organizational discipline and follow-through, with the ability to manage multiple opportunities at different stages simultaneously and maintain forecast accuracy.
• Ability to learn new products, workflows, and industry-specific requirements quickly and translate them into business value for prospects.
• Comfort using CRM systems, sales automation, and modern productivity tools in a structured sales process.
• Self-starter mindset with energy, resilience, sound judgment, and accountability for results.

Preferred Qualifications

• Experience selling into retail, beverage alcohol, hospitality, payments, ecommerce, or multi-location merchant environments.
• Experience selling a combination of software and payment processing solutions, ideally in a vertical or operationally complex market.
• Familiarity with HubSpot or similar CRM and sales automation platforms, including disciplined opportunity and forecast management.
• Experience using AI tools in a business setting to improve prospecting, preparation, documentation, communication, or pipeline management.
• Prior experience selling larger, consultative, or multi-solution deals with longer sales cycles.
• Degree, technical diploma, or equivalent combination of education and relevant sales experience.

What Success Looks Like

• Consistently builds qualified pipeline and advances opportunities with urgency, discipline, and strong deal control.
• Wins new logo business while also identifying cross-sell and upsell opportunities across the existing customer base.
• Maintains accurate CRM data, reliable forecasts, and strong internal communication across sales, leadership, and implementation teams.
• Uses AI and sales tools effectively to work faster and smarter without sacrificing quality, judgment, or customer trust.
• Represents ICS with professionalism, builds trust with prospects and customers, and sets a strong example for sales process discipline.

Compensation and Benefits

Senior Account Executives are paid a base salary plus commissions, along with a benefits package that includes health, dental, supplemental insurance, 401(k), and paid time off.

                                                                                    

Business Unit: 

                                                                                    

Scheduled Weekly Hours:

40

                                                                                    

Number of Openings Available: 

1

                                                                                    

Worker Type: 

Regular

                                                                               

More About Jonas Software:

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.