Remote Enterprise Sales Director, Canada

Location: Toronto, Ontario, Canada - Remote

Who Are We?

About Airlock Digital:

The Enterprise Sales Director is responsible for leading and scaling the sales function within their assigned region, with a focus on acquiring and growing relationships with the organization's largest and most strategic accounts (7,500+ employees). This role owns the full sales cycle for enterprise-level engagements — from pipeline development and stakeholder mapping through negotiation and closing — while translating company-wide sales strategy into actionable regional plans.

As the Sales Director for your territory, you will help set the tone for the team's approach to complex, high-value deals and navigating multi-stakeholder buying committees, long sales cycles, and enterprise procurement processes, positioning the company as a strategic partner rather than a vendor.

Success in this role requires a combination of strategic thinking, hands-on deal leadership, and cross-functional collaboration with marketing, customer success, product, and legal teams to ensure smooth deal execution and long-term account health. The Enterprise Sales Director is ultimately accountable for revenue targets, forecast accuracy, and the overall health and growth of the enterprise book of business.

Key Responsibilities:

Strategy & Market Growth

• Develop and implement effective sales strategies for the region, aligned with overall company objectives and revenue targets


• Identify target accounts, key customers, partners, and sales channels to maximize revenue growth and market penetration

Sales Execution

• Manage the full sales cycle, from prospecting through to on-boarded customers


• Work closely with prospects and customers to understand their business needs and goals, advising on relevant product capabilities


• Qualify leads and work with the sales team to overcome obstacles to achieving sales goals


• Negotiate commercial terms with customers


• Ensure a seamless handover of new customers to Customer Success and Customer Support

Relationships & Representation

• Build and maintain strong relationships with key customers, strategic partners, and stakeholders in the region


• Attend conferences and industry events to promote Airlock Digital

Cross-Functional Collaboration

• Collaborate across the business on messaging, pricing strategy, and business models to support revenue goals


• Provide insights and recommendations to Airlock Digital leadership on sales strategy and product enhancements

Reporting & Analysis

• Prepare regular sales reports, including revenue forecasts, pipelines, and performance metrics


• Analyze sales data to identify trends, opportunities, and areas for improvement

Required Skills & Qualifications:

• 8+ years of technology sales experience, with a proven track record of consistently meeting or exceeding quota


• Must live within and have an established sales history/network in Canada (Toronto)


• Deep understanding of the cybersecurity industry, market landscape, and emerging trends


• Experience executing go-to-market strategies and managing complex, multi-channel sales cycles


• Strong understanding of SaaS business models, sales cycles, and solution/value-based selling methodologies


• Established relationships with and/or ability to network with business owners, CISOs, and technology leaders across organizations of all sizes


• Excellent verbal, written, and presentation communication skills, with the ability to build rapport and negotiate effectively at the executive level


• Skilled in pipeline management and forecasting, with proficiency in CRM tools (e.g., Salesforce)


• Proactive, self-motivated, and results-oriented, with a strong drive to exceed sales targets


• Bachelor's degree or equivalent practical experience


• Willingness to travel as needed within the territory

What We Offer:

We don’t think money is everything, but we know it is an important part of your decision to apply for a role. Additional factors considered in extending an offer include responsibilities of the job, education, location, experience, knowledge, skills, abilities, and internal equity, alignment with market data, or applicable laws.

At Airlock Digital we offer a wide range of benefits to our eligible team members. Our benefit programs vary by location and can include Medical, dental, and vision insurance – 401K Plan with 4% Company Match – Life and Disability Programs – Paid Parental Leave - Paid time off and Paid Holidays – Volunteer and Birthday Time off – Home Office Allowance

Our Commitment:

We believe in supporting our team members both personally and professionally. Named one of the USA’s Greatest Places to Work in 2024 and 2025, we value flexibility, trust, and a work environment that empowers our team to do their best work.

We will be assessing applications as they come in, so we encourage you to send your resume through to us as soon as possible. All official job offers from our company are extended directly by our recruitment team and will be sent through an official BambooHR document for your review and signature. Please be aware that we do not ask for any personal information in the process of extending offers of employment, such as financial details or social security numbers. Upon acceptance of any offer, we will request such information as part of the onboarding process prior to or on your first day of employment, and only after completing a background check through an authorized third-party vendor. If you receive any communication asking for personal details outside of these processes, please contact us immediately to verify the authenticity of the request. Your security is important to us, and we are committed to a safe and transparent hiring experience. No contact from recruitment agencies, thank you #LI-AF1 #LI-Remote