Remote Senior Enterprise Account Executive

Bilinguallink; Winnipeg; Hybrid; CAD 125,000 - 150,000; Full time

Benefits offered by this job

Stock options

Health benefits

Employee Assistance Program

Vacation + holidays

Job summary

RouteThis is seeking a Senior Enterprise Account Manager to drive new revenue with large global accounts and existing expansions. You will lead complex enterprise sales, multi-threaded stakeholder management, and craft compelling ROI cases around AI-driven solutions.

You will manage 6–12 month purchasing cycles, collaborate with marketing and product, and stay focused on building a robust pipeline. A hybrid/work-flexible model is supported in a fast-growth tech environment.

Qualifications

• 8+ years in B2B SaaS enterprise sales.
• Experience selling complex technical solutions including AI/analytics.
• Comfort discussing AI concepts with both technical and business stakeholders.
• Proven ability to translate emerging technologies into clear ROI and business value.
• Strong written and verbal communication skills.
• Consistently deliver high six-figure deals.
• Thrives in a fast-paced, self-starting environment.
• 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.
• University or College degree/diploma in Sales/Marketing/Business/Communications.

Responsibilities

• Understand, articulate, and navigate the RouteThis value drivers for customers and prospects.
• Position and sell AI-driven products by translating functionality into business outcomes.
• Educate customers on AI strategy and ROI for adoption.
• Develop and execute outreach strategies for target accounts.
• Exceed pipeline and revenue goals quarterly.
• Navigate enterprise organizations with multi-threading and champions.
• Lead conversations around innovation, automation, analytics, and AI.
• Manage multiple enterprise sales cycles with 6–12 month cycles and high six-figure deals.
• Track opportunity details in Salesforce and feed feedback to product/marketing.
• Maintain balanced pipeline and velocity.
• Coordinate with customer success to ensure adoption and expansion.

Skills

Enterprise sales

B2B SaaS

Executive outreach

Team selling

ROI storytelling

Communication

Travel readiness

Education

University/College degree

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.

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 are 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 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.

Why RouteThis?

Opportunity: As a rapidly evolving startup, we are constantly facing new challenges and opportunities, while working with us, you can jumpstart and shape your career.

Team: At RouteThis you will be working on a highly-motivated team, each team member has been carefully selected to ensure there is a fit with our values of One Team, Customer First, Innovate and Own It.

Fun: We believe that work should be fun and engaging. We host social events both in person and virtual.

Total Rewards: We offer a total compensation package that includes competitive salaries, stock options, extended long weekends, and a comprehensive benefits package.

Location: Located in the "Silicon Valley of the North" we are proud members of the Waterloo-region in downtown Kitchener. We offer flexible work arrangements.

We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.