Director of Enterprise Sales, CA

Sales Toronto, Ontario


The enterprise customer segment represents the biggest potential for Siteimprove as we drive towards hyper-growth. Siteimprove has found success with the SMB and MidMarket as we’ve continuously improved our platform and suite of products. Siteimprove already has a number of enterprise customers realizing tremendous value from our platform. It is the primary objective of the Enterprise Sales teams at Siteimprove to acquire and cultivate relationships with our most strategic customers through proactive targeted efforts by effectively aligning internal resources to their needs.

Siteimprove is currently seeking a Director of Enterprise Sales, CA, who brings deep experience and relationships with enterprise customers in Canada. This person will have responsibility for all of Siteimprove’s sales and business development within the most strategic segment of customers across Canada. The leader in this role will have the opportunity to hire, develop, and grow their own team of Enterprise Account Executives. The position is pivotal and will make a massive impact on the company’s growth, strategic direction, and market presence.

As a Sales Leader, you will be leading a team of Enterprise Account Executives selling the entire Siteimprove platform and suite of products. We are looking for a proven sales leader with great energy, leadership, and initiative to drive team performance and sales for our enterprise team. This is a hands-on role. The role of Director of Enterprise Sales, CA, encompasses both strategic and tactical functions; the breadth and scope of current growth opportunities require that we hire an experienced, high-caliber individual with a broad range of skills and a strong ambition to succeed. The team you lead will directly impact the growth of our overall organization. You will be masterful in client engagement and be naturally insightful and empathic, with excellent business acumen. You will coach your team to develop their careers and inspire your team to do their best work.

This role will partner with Marketing, Revenue Operations, Solution Engineering, Strategic Pursuit Advisors, Product Management, and Partner Alliances. Therefore, cross-company engagement and collaboration is an essential skill. The candidate will be a high-impact individual capable of driving outstanding business results and first-class employee development. The Sales Leader is fully responsible for developing and managing the team to generate revenue and achieve individual team and organizational quotas. Aligning to the sales strategy, you will lead your team to define and implement plans for the Enterprise Accounts across CA to achieve sales objectives.

What you will be doing

  • Responsible for net new and expansion revenue through enterprise customers

  • Development of a winning team, including recruiting, hiring, training, and ongoing coaching / mentoring

  • Coaching direct reports on strategies to drive sales wins

  • Support the team to identify key customer influencers, decision-makers, and executives, and help develop deep and wide relationships within each account or opportunity managed

  • Provide support and guidance to direct reports by participating and leading client and prospect meetings or engaging other resources - both regional and corporate, as required

  • Guide the team in leveraging resources across the region and company to accelerate deal progression

  • Accurate reporting on sales activity and forecasting to Regional Head of Sales for Europe

  • Consistent monitoring of the sales activity of the team and tracking results

  • Actively leading and monitoring demand generation activities

  • Leading initiatives to drive customer awareness and engagement

  • Develop and execute successful enterprise customer sales campaigns

  • Oversee/support CA-area business development activities and marketing events as required

  • Engaging at C-level in enterprise customer organizations

  • Speaking at conferences and key events to represent Siteimprove

  • Host strategic customer events

  • Develop required corporate relationships and executive engagement to support the success

  • Maintain a deep understanding of business, priority industries (manufacturing, information & technology, and retail), competitive landscape, and the CA market

  • Perform other related duties as assigned

What we require of you

  • 5+ years of sales leadership experience, managing teams of 6 or more quota-carrying software field salespeople to identify, pursue or manage enterprise accounts/opportunities of high 6-figure to 7-figure deal sizes

  • Proven successful experience in leading Enterprise Account Executives

  • Master team builder, willing and able to hire, train and mentor a world-class sales team, scaling with the business as it grows

What we'll love about you

  • Excellent presentation and executive management skills

  • Excellent negotiation skills

  • A self-starter that can thrive in a fast-paced environment

  • Strong leadership capabilities

  • Experienced in sales coaching and mentoring

  • Ability to achieve stretch goals in a fast-paced, team environment

  • Has a strong drive for results

  • Value-based selling experience

  • Is a trusted advisor to customers and colleagues

  • Prior experience working within the Software/Platform (SaaS/PaaS) space

What you'll love about us

Siteimprove is a people-centric company driven by the desire to make the internet better for all. We thrive on putting the customer first and developing the potential of our employees. Here, you’ll be surrounded by highly talented colleagues, which means there’s always someone to learn from. The many opportunities for personal growth that we offer are a direct consequence of the rapid growth we are experiencing as a company. Our amazing growth journey clearly shows that there’s big potential in creating a better and more inclusive web for all, which is what Siteimprovers do.

In addition, we hope you'll appreciate:

  • Great and inspiring company culture. Read more about the Siteimprovers and our inclusive, people-centric culture in this section here:

  • Rest and relaxation. 4 weeks of paid time off

  • Health benefits. Medical with paramedical, dental, vision, and competitive gym membership rates

  • Prepare for the future. Pension with company match

  • Corporate social responsibility. Siteimprove is a global thought leader within the field of digital inclusion, and we proudly give back to the community locally as well as globally.

How to apply

Click on the APPLY NOW button to submit your application.

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