Senior Regional Account Executive - SaaS (Base upto $95K, OTE $450K)

Senior Regional Account Executive | SaaS New Business Sales

BoomerangFX

Location: Mississauga, Ontario — Hybrid

Reports to: Sales Leadership

Mandatory Experience

7 years of SaaS solution-selling experience, including a proven track record of managing the full sales cycle, achieving revenue targets and closing high-value deals in a fast-paced sales environment with short sales cycles. Experience selling into private healthcare, medical aesthetics or digital marketing is strongly preferred. Only applicants meeting the required sales experience will be considered for the role.

Why Join BoomerangFX?

BoomerangFX is a global healthcare technology company bringing SaaS, artificial intelligence and digital marketing together to help private-pay healthcare practices operate and grow. Recognized through Deloitte’s Technology Fast 500 program, we are building technology that simplifies practice management, strengthens patient engagement and helps healthcare businesses reach more people.

With operations in the United States, Canada, the United Kingdom, Australia and India, we are scaling internationally and working at the forefront of AI in healthcare. Our teams collaborate across countries and disciplines to turn new ideas into products and services that make a practical difference for customers.

Joining BoomerangFX is an opportunity to build your career alongside a growing global business. You will have meaningful responsibility, exposure to international markets and the opportunity to contribute ideas, develop your skills and see the impact of your work. We welcome people who take ownership, move quickly and want to help build what comes next.

The Role

The role is Senior Regional Account Executive - SaaS - Hybrid (OTE $450,000) at BoomerangFX, based in Mississauga, Ontario.

BoomerangFX is hiring a proven new-business closer who can help clinic owners make confident commercial decisions about technology, AI and practice growth. You will uncover operational and revenue challenges, quantify their business impact, recommend the right combination of solutions and own the sale through to a signed agreement.

This is a quota-carrying individual contributor role. Success requires consistent prospecting, commercially focused discovery, tailored demonstrations, disciplined follow-up and the confidence to ask for a buying commitment.

What You’ll Do

• Win new business. Own prospecting, qualification, discovery, demonstrations, proposals, negotiation and closing. Build your own pipeline alongside opportunities generated through business development and marketing.
• Diagnose the clinic’s business. Research each practice before the first meeting. Understand its services, growth priorities, current systems, lead response, consultation conversion, patient retention, staff workload and provider capacity. Identify the decision-makers, budget, timing and criteria for a purchase.
• Build a commercial case for change. Use the prospect’s information to quantify the impact of lost leads, unfilled appointments, inefficient processes and missed revenue opportunities. Explain the value of improvement with clear assumptions and realistic expectations.
• Demonstrate a tailored solution. Connect relevant workflows to the clinic’s priorities across RUN practice management, GROW lead management, AUVIA AI-assisted follow-up and booking, and ELEVATE digital marketing. Confirm the buyer understands how the recommendation addresses the problems discussed.
• Grow contract value through the right solution. Identify connected needs and recommend the appropriate combination of products and services. Establish value before negotiating price, and use approved commercial terms and incentives to secure a suitable, sustainable agreement.
• Lead the buying process and close. Resolve objections concerning price, competing suppliers, implementation, switching effort and timing. Agree concrete next steps, involve decision-makers early and ask directly for commitment when the business case and buying conditions are established.
• Compete with evidence. Understand alternative systems and the prospect’s experience with them. Use verified competitive information and public customer feedback to inform discovery, validate concerns with the buyer and demonstrate relevant differences accurately.
• Maintain sales discipline and a strong handoff. Keep HubSpot records current with business needs, decision process, deal value, next action and evidence supporting the close date. Participate in pipeline reviews and coaching, and coordinate with Customer Success to hand over the agreed scope, commitments and priorities.

Mandatory Qualifications

• SaaS sales experience. 7+ years of B2B SaaS solution-selling experience (mandatory), including personal ownership of the full sales cycle and a sustained record of achieving or exceeding individual new-business targets.
• A proven closing record. Experience winning multiple new customers each month in short sales cycles and selling five-figure annual agreements to business owners or senior decision-makers. Be prepared to explain your quota attainment, typical contract value, average sales cycle, monthly wins and share of pipeline personally generated.
• Commercial discovery and value selling. Ability to diagnose business problems, quantify their impact using customer information, develop a credible case for change and negotiate while protecting solution value.
• Prospecting and pipeline ownership. A demonstrated ability to create opportunities through outbound prospecting, progress qualified deals and maintain accurate forecasts and next steps in a CRM.

Only applicants who can demonstrate the required sales experience and individual closing results will be considered.

Additional Experience We Value

• Business and marketing understanding. Working knowledge of lead generation, paid advertising, conversion, customer acquisition costs and return on investment, with the ability to discuss these topics clearly with business owners.
• Communication and execution. Strong discovery, presentation, proposal-writing, negotiation and closing skills; effective prioritization; and a willingness to apply coaching and improve performance.
• Preferred background. Experience in private-pay healthcare, medical aesthetics, cosmetic surgery, dermatology, dental, vision, women’s health or adjacent vertical SaaS markets. HubSpot experience and practical application of consultative or Challenger-style selling are assets.
• Education. A degree in business, marketing or a related field is an asset. Equivalent relevant commercial experience will also be considered.

Compensation and Benefits

• Base salary: CAD $80,000–$95,000 annually.
• On-target earnings: Approximately CAD $400,000 annually.
• Quota: 7-10 deals /month average (average ACV $15,000-$20,000)
• Average Commissions Monthly: $10k - $15k
• Annual Bonus potential on Cumulative ACV: upto $150,000
• Benefits. Comprehensive health, dental and vision coverage, plus paid vacation.
• Career opportunity. Meaningful commercial responsibility and exposure to international markets within a growing healthcare technology business.

How to Apply

Submit your résumé with a brief summary of your individual sales results in your two most recent relevant roles. Include annual quota and attainment, typical annual contract value, average sales cycle, new customers personally closed and the proportion of pipeline you generated yourself. Anonymized figures or ranges are acceptable where confidentiality requires them.

Shortlisted candidates will complete a practical sales exercise covering discovery, a tailored solution recommendation, objection handling and closing. Candidates will receive a product brief in advance. Sales achievements and professional references may be verified, with the candidate’s consent.

Accessibility Statement

BoomerangFX is an equal opportunity employer committed to diversity and inclusion. We welcome applications from all qualified individuals and are dedicated to accommodating people with disabilities. If you require accommodation at any stage of the application process, please contact [email protected].