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 resume screening, drafting preliminary job descriptions, generating initial interview questions, transcription and occasionally sourcing prospective candidates. However, AI is never used to make final hiring decisions; our use of AI  serves to support repetitive and administrative tasks in order to streamline our hiring and recruitment workflows. We are committed to the responsible use of AI in our hiring practices, prioritizing both  an improved candidate experience and operational efficiency. Our standardized hiring practices remain focused on reducing biases, with all key hiring decisions  solely made by our team. We continuously review and refine our hiring practices to align with  industry best practices and evolving legal guidelines

AI Usage in Interviews 🤖 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. If AI-generated responses are identified during the interview, Loopio reserves the right to disqualify candidates from the interview process.

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.