Director of Enterprise Sales (New Business)

Loopio

7d • Remote

About The Position

Loopio is hiring a Director of Enterprise Sales to lead its existing team of Enterprise Account Executives and drive growth in the Enterprise segment, defined as organizations with more than 2,500 employees. Reporting directly to the VP of Sales, this leader will shape sales strategy and be responsible for acquiring new customers and achieving revenue targets. The role focuses on improving win rates, opportunity generation, deal velocity, and deal size; developing and scaling the sales team; recruiting and coaching enterprise talent; and establishing accurate forecasts and data-driven decision-making.

The Director will work closely with leaders and cross-functional partners in Marketing, Product, and Customer Success to align go-to-market strategy, identify new revenue opportunities, and help the sales team succeed. They will promote a culture of discipline, continuous learning, competitiveness, collaboration, and shared success; monitor market and competitive trends; and drive adoption of AI tools and automated workflows for pipeline generation, account intelligence, deal execution, and coaching.

This is a remote-first role. Candidates must reside in the Greater Toronto Area or surrounding areas and be able to access Loopio’s Downtown Toronto coworking space for occasional team gatherings. The company supports flexible coworking, virtual collaboration across regions, asynchronous work, and core sync hours.

Requirements

• 10 or more years of B2B software sales experience, focused on new business acquisition.
• 3 or more years of B2B Enterprise SaaS software leadership experience at Director level or above.
• Experience leading a team of Enterprise Account Executives.
• A track record of setting and exceeding targets.
• Strong analytical abilities and a metrics-driven approach.
• Strong understanding of the RFP response process and the challenges companies face.
• A clearly articulated leadership style.
• A relevant Bachelor’s degree, preferably in a technical or business function.
• Must reside in the Greater Toronto Area or surrounding areas and be able to access Loopio’s Downtown Toronto coworking space for occasional team get-togethers.

Nice To Haves

• Experience with MEDDPICC and Command of the Message.
• Experience selling to Sales and Marketing organizations.
• A history of published thought leadership.
• Experience scaling a sales team and contributing to organizational growth from $50M to $100M ARR.

Responsibilities

• Acquire new customers and achieve revenue targets.
• Create initiatives to improve win rates, opportunity generation, deal velocity, and deal size.
• Partner with Marketing to identify and develop revenue opportunities in new markets and industry segments.
• Oversee and scale a rapidly growing team of Enterprise sellers, including team structure, management hierarchy, communication mechanisms, and role specialization.
• Partner with Talent Experience to design and execute recruiting processes, participate in recruiting, and attract, hire, and close enterprise sales candidates.
• Improve onboarding and ongoing training to reduce ramp-up time and prepare team members to perform effectively.
• Coach team members by participating in calls, reviewing deal strategy, and providing actionable feedback using tools such as Gong and Lattice.
• Work with the Senior Leadership Team to set targets, develop sales forecasts, and report progress to the company and Board of Directors.
• Use analytics and data-driven decision-making to identify opportunities and mitigate risks.
• Foster a culture of discipline, continuous learning, competitiveness, collaboration, and celebrating success.
• Build strong cross-functional relationships with Product, Marketing, and Customer Success to align go-to-market strategy and support the sales team.
• Monitor team engagement, challenges, and well-being.
• Work with Loopio leaders to monitor customer, market, and competitive trends, and align Product Management and Sales.
• Stay current on SaaS software sales trends, tools, and best practices.
• Drive adoption of AI tools and automated workflows to accelerate pipeline generation, enhance account intelligence, and optimize deal execution and coaching.

Benefits

• Dedicated professional mastery allowance for learning and development.
• Health and wellness benefits supporting physical and mental well-being, starting on the first day.
• MacBook laptop for remote work.
• Monthly phone and internet subsidy.
• Work-from-home budget to set up a home office.
• Claude account for experimentation, automation, and building tools.
• Manager support through ongoing feedback and regular one-on-ones, using Lattice for one-on-ones and performance conversations.
• Opportunities to participate in town halls, AMAs, company celebrations, and four Employee Resource Groups.

What This Job Offers

• Job Type: Full-time
• Career Level: Director