Take your career to new heights with LoopioLoopio 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).
Note: This is an existing vacancy on the team
What You’ll Be Doing
Revenue
Ultimately, you are responsible for acquiring new customers, and achieving our revenue targets
Continually create initiatives to optimize win rates, chance generation, deal velocity, and deal size
Partner with the Marketing Team to explore and unlock new revenue opportunities, including new markets and industry segments
Team Management:
Oversee a rapidly growing team of Enterprise sellers
Evolve and scale team structure, management hierarchy, and communication mechanisms
Empower the team to achieve greater focus and efficiency by exploring and implementing strategic role specialization.
Talent Acquisition, Development & Coaching:
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.
Lead from the Front:
Roll up your sleeves to actively coach your team through participating in calls, reviewing deal strategy, and providing actionable feedback using tools like Gong and Lattice.
Forecasting & Reporting
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.
Culture
Foster and scale a culture of discipline, continuous learning, competitiveness, collaboration, and celebrating success — what’s missing?
Champion Cross-Functional Alignment:
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.
Actively work to keep a pulse on the engagement, challenges, and well-being of your team
Research & Awareness
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
AI & Automation:




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.
What You’ll Bring to the Team
10+ years in B2B software sales, with a focus in new business acquisition
3+ years in B2B Enterprise SaaS software leadership (Director level and above)
Experience leading a team of Enterprise Account Executives
Track record of setting and exceeding targets
Deep analytical abilities and metrics-driven approach
Strong understanding of the RFP response process and the challenges that companies face
Well-defined leadership style that can be articulated clearly
Experience with MEDDPICC and Command of the Message would be ideal
Relevant Bachelor’s degree, preferably in a technical or business function
Strong assets:
Experience selling to Sales and Marketing organizations
History of published thought leadership
Experience in scaling a sales team and contributing to organizational growth from $50M to $100M ARR.
Where You’ll Work
We are currently only looking for candidates who reside in the Greater Toronto Area and surrounding areas and can access our co-working space in Downtown Toronto for the occasional Team get-together.
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.
Our employees (or Loopers, as we call ourselves) live and work in Canada (British Columbia and Ontario), US, India (specifically in Gujarat, Maharashtra, and Bengaluru), and London.
The majority of our team is

📌 Director Of Enterprise Sales (Canada)
🏢 Loopio
📍 Canada