Director of Enterprise Sales (New Business)

Take your career to new heights with Loopio! ✨

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).

 

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, opportunity 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 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 flexible co-working locations available to Loopers in ON and BC. Those based in ON have the option of working out of our convenient co-working space located in the heart of Downtown Toronto and a 12-minute walk from Union Station. BC Loopers have the option to work centrally in Vancouver. It is whatever works best for you!

• You’ll collaborate with your teams virtually across the UK, India, and North America (we’re just a Zoom call and Slack message away!) with core sync hours and focus time for headsdown work during the workday

• We encourage asynchronous collaboration to effectively work as a global #OneTeam!

 

Why You’ll ♥️ Working at Loopio

• 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 offer a wide range of health and wellness benefits