Senior Enterprise Account Executive

Jaide Health; Toronto; On-site; CAD 125,000 - 150,000; Full time

Benefits offered by this job

Generous commission structure

Medical, Dental, Vision, Life Insurance

Employee Assistance Program

Stock Options

3 weeks vacation plus 10 additional days

Social activities for remote workers

Job summary

Jaide Health is seeking a Senior Enterprise Account Manager in Toronto, Canada. This role is essential for driving revenue through both new and existing enterprise accounts. The ideal candidate will have over 8 years of B2B SaaS sales experience, specifically within complex technical solutions. You will educate customers on AI applications and develop outreach strategies. The salary range is CAD 125,000 - 150,000, plus commission and competitive benefits. Join us to innovate in a rapidly evolving market.

Qualifications

• 8+ years in B2B SaaS sales at the Enterprise level.
• Experience selling complex, technical solutions, ideally including AI.
• Demonstrated excellence selling to VP and C-level executives.

Responsibilities

• Understand and articulate RouteThis Value Drivers to customers.
• Position and sell AI-driven products by translating technical functionality.
• Manage multiple enterprise sales cycles with 6 to 12 month purchasing cycles.

Skills

B2B SaaS sales experience

Technical solution selling

Communication skills

Quota achievement

Education

University or College degree/diploma in Sales, Marketing, Business, or Communications

Tools

Salesforce.com

Job description

RouteThis is on a mission to revolutionize technical support. We build AI‑powered solutions that help Internet Service Providers and Smart Home companies solve connectivity and WiFi problems—before the subscriber ever needs to call.

Our customers already benefit from our SaaS solutions today and we aim to magnify that value by building autonomous agents into our solutions. As we continue to advance our AI solutions, we’re looking for a Senior Enterprise Account Manager.

RouteThis is looking for a highly motivated individual to fill this key role in driving new revenue through new Enterprise logos and existing customer expansion. In this role you will be leading complex Enterprise Sales, drawing on your previous Enterprise sales expertise.

You will be provided with the autonomy and opportunity to manage large global accounts, working to solve complex customer challenges, leading large virtual account teams, navigating complex organizations, and driving deals to closure. You will work closely with a team of professionals to continuously increase market penetration, disrupt an industry that is ripe for disruption, and drive significant revenue. You will be maniacally focused on building a strong pipeline, developing unique value propositions, driving account teams to deliver successful outcomes, and creating value in a space where companies might not easily associate your solutions to solve their pains.

What You'll Do:

• Understand, articulate, and navigate the unique RouteThis Value Drivers we deliver to customers and prospective clients, including our AI‑powered solutions and how they drive measurable operational and customer experience impact.
• Position and sell AI‑driven products and capabilities by clearly translating technical functionality into business outcomes for Enterprise buyers.
• Educate and guide customers on the strategic application of AI within their organizations, helping them build internal business cases for adoption.
• Develop and execute on an outreach strategy for your target accounts with the assistance of marketing, sales leadership, etc.
• Exceed pipeline and revenue goals on a quarterly basis.
• Effectively navigate Enterprise organizations, multi‑threading through key stakeholders at all levels and developing champions who are “selling” on our behalf.
• Lead complex conversations around innovation, automation, analytics, and AI transformation initiatives.
• Manage multiple enterprise sales cycles with 6 to 12 month purchasing cycles, with typical deal sizes in the high six figures.
• Track all opportunity details including use cases, AI applications, Value Drivers, accurate timing, next steps, dollar amounts, forecasting, etc. in Salesforce.com.
• Work closely with marketing and product teams to provide feedback based on customer interactions, especially related to AI capabilities, competitive positioning, and market demand.
• Maintain balance in your pipeline (early/mid/late) as well as pipeline velocity and conversion rates.
• Manage the client and internal teams through the customer journey, ensuring alignment on AI implementation expectations and outcomes.
• Partner with customer success to ensure high satisfaction, adoption, and expansion within your accounts.

What You Bring:

• 8+ years in B2B SaaS sales at the Enterprise level.
• Demonstrated experience selling complex, technical solutions, ideally including AI, analytics, automation, or data‑driven platforms.
• Comfort discussing AI concepts (machine learning, predictive analytics, automation workflows, data insights) with both technical and business stakeholders.
• Demonstrated excellence selling to VP and C‑level executives.
• Proven ability to translate emerging technologies into clear ROI and business value.
• Superior written and verbal communication skills.
• Consistently deliver high 6+ figure deals.
• Thrive in a fast‑paced, self‑starting environment.
• Have the ability to efficiently prioritize time.
• Validated quota achiever (top 10% in your company).
• Team‑selling experience is a must‑have.
• Telecommunications experience is helpful but not required.
• Ability to travel to meet prospects, customers, and for occasional internal meetings. Passport must be up‑to‑date; we are a global business.
• University or College degree/diploma with excellence in your field of study, ideally: Sales, Marketing, Business, or Communications.

Package Overview:

• This role offers a base salary range of $125,000 - $150,000 CAD.
• In addition, this position includes a generous commission structure with significant earning potential for high performers.
• Competitive benefits through Manulife – Medical, Dental, Vision, Life Insurance.
• Employee Assistance Program.
• Equity – Stock Options.
• 3 weeks vacation plus an additional 10 days around statutory holidays to make long weekends longer.
• For those working hybrid, there is a gym conveniently located at our downtown Kitchener office and we offer weekly lunches; for those remote we offer other opportunities for social activities.

RouteThis is an Equal Opportunity Employer and considers applicants for employment without regard to race, colour, religion, sex, orientation, national origin, age, disability, genetics or any other basis forbidden under federal, provincial, or local law. Please let us know if you require an accommodation due to a disability and we will work with you to address your needs.