Senior Enterprise Account Executive

HighlightTA; Kitchener; Hybrid; CAD 125,000 - 150,000; Full time

Benefits offered by this job

Generous commission

Manulife benefits (Health, Dental, VIs

Equity – Stock Options

3 weeks vacation + 10 days holidays

Onsite gym at downtown office (Kitcher

Hybrid/Remote options

Job summary

RouteThis is seeking a Senior Enterprise Account Manager in Canada to drive new revenue through enterprise logos and existing account expansion. You will lead complex enterprise sales, manage large global accounts, and coordinate multi-disciplinary teams to close high six-figure deals.

You will articulate AI-driven value, translate technical capabilities into business outcomes, and build strong ROI-based business cases while navigating complex organizations and travel as needed.

Qualifications

• 8+ years in B2B SaaS sales at the Enterprise level.
• Experience selling complex, technical solutions including AI/automation.
• Ability to translate tech into business outcomes for Enterprise buyers.
• Proven track record selling to VP and C-level executives.
• Demonstrated ROI storytelling and value justification to customers.
• Strong written and verbal communication skills.
• Consistently close high six-figure deals and manage long sales cycles.
• Team-selling experience is a must-have; passport ready for global travel.

Responsibilities

• Understand RouteThis Value Drivers and translate AI offerings into business impact.
• Position and sell AI-driven solutions to Enterprise buyers focusing on outcomes.
• Educate customers on AI strategy and build business cases for adoption.
• Develop outreach and pipeline with marketing, leadership, and account teams.
• Navigate complex enterprises with multi-threaded stakeholder management.
• Lead conversations about automation, analytics, and AI transformation initiatives.
• Manage 6–12 month cycles with high six-figure deals; track opportunities in Salesforce.

Skills

Enterprise sales

AI/Analytics

C-level selling

ROI articulation

Team selling

Travel readiness

Degree required

Industry knowledge

Education

University or College degree/diploma

Tools

Salesforce

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.

The Role

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

Why RouteThis

Ownership. A COO who backs good ideas and gives real autonomy.

Timing. A 10-year-old business with a product that works, moving from SaaS to AI-native. You will shape how the team grows through it.

Team. A close, highly motivated team that prefers to promote from within.

Time off. Every long weekend, the Friday is off too. The company closes for a week between Christmas and New Year.

Package

• 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 options there is an onsite gym conveniently located at our downtown Kitchener office. In the office we offer weekly lunches. For those remote we offer other opportunities for social activities.

How We Hire

We use AI tools to support our recruitment process, including helping us organize applications and identify early matches based on role criteria. That said, every rejection decision is made by a human. We encourage candidates to apply authentically and avoid relying solely on AI-generated responses, especially during interviews.

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 RouteThis will work with you to address your needs.