Strategic Account Executive

ENTERPRISE Vertical based

Wingmate develops technology that provides a business’ front line employees with an easy-to-use mobile platform from which they can capture timely revenue opportunities in the field.

Our platform helps organizations out-team the competition by engaging ALL staff to drive new sales, streamline service & communicate in real-time.

Wingmate is based out of Toronto, Canada is cash flow positive and growing rapidly.

Wingmate is seeking a bright, driven, and passionate Strategic / Enterprise Account Executive to drive top-line growth in North America.

As an Enterprise Account Executive at Wingmate, you will have the freedom to work independently, showcasing your strong initiative while taking on the responsibility of identifying and targeting large corporate accounts across North America. We expect you to leverage your expertise in building and nurturing relationships with C-level executives, utilizing your existing network and establishing new connections.

Reporting directly to the President & CEO of Wingmate, this role offers a unique opportunity to contribute to the strategic growth plans of the company and shape its future direction.

This role is based in the vibrant city of Toronto, ON.


We are looking for individuals who embody the following qualities:

Proven experience selling to C-level executives, demonstrating a deep understanding of their needs and challenges.

Track record of identifying pain points and generating interest with key decision makers.

Proven track record of consistently meeting or exceeding sales quotas.

Minimum of six years of experience selling enterprise software (preferably with established CRM software companies like HubSpot, PipeDrive, etc.).

Startup experience in the SaaS sales industry, with a passion for embracing an entrepreneurial spirit in a dynamic startup environment.

Proficiency in working with a CRM system (preferably HubSpot) and a consistent track record of achieving monthly targets.

A genuine passion for building and nurturing relationships with customers and prospective clients.


At Wingmate, we provide an exceptional environment for talented professionals to thrive. Here’s why you should consider joining our team:

Growth: Wingmate is experiencing rapid expansion, with our revenue doubling year over year for the past four years. As an Enterprise Account Executive, you will have ample opportunities to grow alongside the company. We value self-starters who demonstrate strong initiative.

Culture: Our team consists of talented and energetic individuals who are passionate about their work. We foster a culture of open communication and collaboration, striving to create a supportive and inclusive work environment.

Impact: At Wingmate, your efforts will have a tangible impact on our business and our customers. We are dedicated to helping businesses make sales and service a team sport, and you will play an integral role in making that happen.

Benefits: We believe in recognizing and rewarding our employees for their contributions. In addition to a competitive base salary and uncapped commissions, we offer health and dental benefits, opportunities for professional development, and flexible work arrangements to promote a healthy work-life balance.

This is an outstanding opportunity for a self-starter who wants to make a significant impact on a growing company while working independently. If you thrive in a fast-paced environment and are passionate about building relationships and driving revenue, we encourage you to apply.

For any inquiries, please feel free to contact us at


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