Director of Sales

ISA Cybersecurity•Toronto, ON

18d•Remote

About The Position

The Director, Sales is an operational leadership role within ISA Cybersecurity's Sales organization. The incumbent will be responsible for the day-to-day management, performance, and development of sellers and client experience. This role serves as the operational engine of the sales team, ensuring KPIs are tracked and acted upon, sales processes are consistently executed, CRM data is accurate, and the team is well-coached and enabled to achieve its revenue targets. The Director, Sales reports to the Executive Vice President, Sales. We are proud to be recognized as a top employer for multiple years in a row and are Certified Great Place to Work 2026-2027. ISA Cybersecurity is a proudly Canadian cyber and AI services and solutions provider. Trusted by over 500 clients from SMB to global enterprise, we empower organizations to safeguard their most critical assets and adopt AI securely. Through our highly customizable Cyber 360 and AI 360 offerings, we deliver a comprehensive range of governance, assurance, engineering protection, detection, and response services for the public and private sectors. Backed by over three decades of operational experience and a vast network of highly specialized and certified experts, we leverage cutting-edge technologies and AI to ensure that clients achieve their privacy, security, and business goals. We operate in a remote-first environment. Office presence is typically less than 20% of the time, varying by role and work requirements. Our office space, located at Bloor and Islington, is a collaborative space designed for in-person meetings and drop-ins. We enjoy hosting in-person quarterly townhalls and social events throughout the year to encourage teambuilding and collaboration.

Requirements

University Degree in Business (Commerce or Business Administration), or equivalent combination of education and experience.
Minimum 5 years of progressive sales experience, with at least 2–3 years in a sales management or team lead role.
Demonstrated experience managing sales performance through data — including pipeline metrics, KPI dashboards, forecasting, and CRM reporting.
Proven ability to coach, mentor, and develop quota-carrying Account Managers.
Strong CRM proficiency (Microsoft Dynamics, Salesforce, HubSpot, or equivalent); experience enforcing CRM discipline and data hygiene across a team.
Ability to communicate and present effectively to internal stakeholders at all levels, including senior leadership.
Background in cybersecurity, IT services, or managed services sales is strongly preferred.
Experience managing a Client Experience, Customer Success, or Post-Sales team in addition to an outbound sales team.
Familiarity with ISA's service catalogue including cybersecurity advisory, managed detection & response (MDR), and professional services offerings.
Experience with sales enablement tools and methodologies (e.g., MEDDIC, SPIN Selling).
Track record of building and scaling operational reporting frameworks to drive predictable revenue.

Responsibilities

Provide day-to-day management and coaching of Account Directors
Conduct regular 1-on-1s to review individual KPIs, pipeline health, and activity metrics
Identify and remove obstacles to individual and team performance
Manage and support the Client Experience team to ensure high-quality client touchpoints
Drive renewal readiness and post-sale satisfaction across the portfolio
Define, track, and report on key sales metrics including pipeline coverage, win rates, average deal size, cycle time, quota attainment, and forecast accuracy
Use performance data to drive continuous improvement across the sales team
Own the integrity and adoption of Microsoft Dynamics CRM data within the sales team
Ensure all opportunities, activities, and client records are accurately maintained
Deliver regular pipeline and forecast reports to the EVP, Sales
Maintain an accurate monthly sales forecast
Conduct regular pipeline reviews with Account Directors to assess deal progression, risks, and accelerators
Enforce consistent use of ISA's sales methodology across the team
Identify process adherence gaps and address them through targeted coaching and enablement
Lead onboarding for new sales hires
Build and execute development plans for Account Directors in areas such as solution selling, cybersecurity knowledge, and executive communication
Act as the operational bridge between Sales, Service Delivery, Alliances, and Sales Operations
Coordinate on client escalations, resource requirements, and deal support needs
Provide operational oversight and guidance for RFX responses and proposal submissions
Ensure timeliness and quality standards are consistently met
Support the VP, Sales in territory planning, quota setting, and execution of annual and quarterly sales plans
Contribute to achieving overall revenue targets
Serve as an escalation point for key client issues raised by Account Directors
Ensure timely resolution and retention of strategic accounts
Support adoption and optimization of sales tools including CRM, sales intelligence platforms, and enablement resources
Maximize team productivity through effective use of available technology

Benefits

Flexible sick and personal days for all employees
Generous health plan with enhanced mental health resources and programs
Professional development opportunities and education reimbursement up to $2,000 annually for all employees
Maternity and parental leave top-up
Employee referral bonus of $2,000
Competitive salaries complemented with RRSP matching and bonus programs
Distance remote working policy
LinkedIn Learning access for all team members
Service anniversary recognition and generous five-year milestone service awards
President’s Club recognizing special achievement awards: Team Member of the Year for Sales, CIOC and Cyber Services, the Rich Uhrich Founder’s Award that is nominated on by all employees and four President’s Awards (Risk Taker, Lost Without You, Money Maker and On the Rise)
Spot rewards providing opportunities for instant peer recognition