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 to support your physical and mental well-being, starting day 1️⃣ with Loopio.

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.

Participate in 🎤 townhalls, AMA (Ask-Me-Anything), and company celebrations to celebrate the big wins and milestones as #oneteam!

Our four Employee Resource Groups offer opportunities for employees to learn and connect year-round.

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

Questioning your qualifications? Read this ‼️ Hi there, we recognize that all too often, potential candidates don’t apply for a position simply because they don’t hit every single criteria included in the job description—particularly members of underrepresented groups.

Whether or not your experience ✅ checks off all the boxes on a job posting, we still encourage you to apply to ensure that your application receives a review from our team. 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. If you've made a career transition (or a few!), you’re self taught in a new role, or you have skills/experience you’d like to highlight, we want to hear more about what you could bring to the table.

AI in Recruitment 👩🏻‍💻 At Loopio, we leverage artificial intelligence (AI) technology to enhance our recruitment process. These tools assist with tasks such as