Loopio is seeking a proven Director of Enterprise Sales to lead our team into its next chapter of growth. If you're a proven sales leader who consistently beats quota, builds high-performing teams, and thrives in fast-moving, results-driven environments, we want to talk. Reporting directly to the VP of Sales, you’ll shape the company's strategic direction.

You’ll lead an existing team of Account Executives and work closely with leaders across Loopio to achieve our ambitious growth targets in the Enterprise segment (organizations with over 2,500 employees).

Ultimately, you are responsible for acquiring new customers, and achieving our revenue targets

Partner with the Marketing Team to explore and unlock new revenue opportunities, including new markets and industry segments Team Management: Evolve and scale team structure, management hierarchy, and communication mechanisms

Build Your A-Team: Partner with our Talent Experience team to design and execute a rigorous interview process to attract and hire seasoned enterprise sales talent and high-potential future stars. Be an active participant in recruiting, from leveraging your network to closing top candidates.

Accelerate Performance: Optimize the onboarding and continuous training programs to decrease ramp-up time and ensure every team member is equipped to excel.

Forecast with Precision: Work with the Senior Leadership Team to set ambitious targets, develop accurate sales forecasts, and report on progress to the company and the Board of Directors.

Embrace Data: Make data-driven decisions the standard across the sales organization, using analytics to identify opportunities and mitigate risks. Foster a strong, collaborative relationship with Product, Marketing, and Customer Success to ensure our GTM strategy is cohesive and our sales team is set up for success.

Work with other Loopio leaders to monitor trends in customers, market, and competitive landscape

Ensure strong alignment between Product Management and Sales to set your team up for success

Keep a pulse on trends, new tools,



and best practices in SaaS software sales Drive the adoption of AI tools and automated workflows across the team to accelerate pipeline generation, enhance account intelligence, and optimize deal execution and coaching.

10+ years in B2B software sales, with a focus in current business acquisition

3+ years in B2B Enterprise SaaS software leadership (Director level and above)

Experience leading a team of Enterprise Account Executives

Relevant Bachelor’s degree, preferably in a technical or business function

Strong assets: Experience selling to Sales and Marketing organizations

Experience in scaling a sales team and contributing to organizational growth from $50M to $100M ARR. Loopio is a remote-first workplace because we recognize the advantages of working flexibly. We are HQ’d in Canada, with established hub regions around the world where we hire from.

The majority of our team is based in ON and BC, which means these employees live and work remotely within a 300km radius of Toronto (within Ontario) and Vancouver (Within BC).

We offer adaptable co-working locations available to Loopers in ON and BC. with core sync hours and focus time for headsdown work during the workday

Your manager supports your development by providing ongoing feedback and regular 1-on-1s, we leverage Lattice for our 1:1s and performance conversations

You will have the opportunity to elevate your craft and the opportunity to explore your creativity, with a dedicated professional mastery allowance for more learning support! We encourage experimentation and innovative thinking to drive business impact.

We’ll set you up to work remotely with a MacBook laptop, a monthly phone and internet subsidy, and a work-from-home budget to help get your home office all set up.





We’ll give you a Claude account to experiment with, automate your routine tasks, and build tools so you can work smarter every day.

You’ll be joining a supportive culture that has thoughtfully built out opportunities for connections in a remote first environment.

You’ll be a part of an award-winning workplace with an opportunity to make the big impact on the business.

We understand that a resume can only showcase so much during the applicant stage, so we've created prompts in the application for you to share more about yourself. At Loopio, we leverage artificial intelligence (AI) technology to enhance our recruitment process. These tools assist with tasks such as resume screening, drafting preliminary job descriptions, generating initial interview questions, transcription and occasionally sourcing prospective candidates. our use of AI serves to support repetitive and administrative tasks in order to streamline our hiring and recruitment workflows.

We continuously review and refine our hiring practices to align with industry best practices and evolving legal guidelines The Loopio interview process is designed to help us better understand your professional experiences, as well as your unique perspective and approach to delivery and collaboration. To ensure a fair and accurate assessment, we expect candidates to refrain from using AI-generated content to produce responses to our interview questions during the live interview, as our goal is to evaluate your own knowledge and problem-solving abilities - not those of an AI assistant. For specific roles that include a take-home assignment, our AI Interviewee Policy allows the use of AI for initial support; however, the final submission must be a true reflection of your personal insights, skills and decision-making.

Loopio is an equal opportunity employer that is deeply committed to building equitable workplaces that are diverse and inclusive. com) should you require accommodations at any point during our virtual interview processes. #

📌 Director of Enterprise Sales (New Business) (Toronto)
🏢 Loopio
📍 Toronto