Vice President, Sales

ISA Cybersecurity•Toronto, ON

18h•CA$200,000•Remote

About The Position

Reporting to the CEO, the Vice President, Sales leads the day-to-day performance, structure, and growth of ISA Cybersecurity's sales organization. This role translates corporate revenue goals into an executable sales strategy across our enterprise, mid-market, and managed services segments, and leads a team through the complex, multi-stakeholder sales cycles typical of enterprise cybersecurity, from technical evaluation and security assessment through RFP, procurement, and executive sign-off. The ideal candidate is a strong, consultative seller with experience selling IT and/or cybersecurity services, paired with strong people leadership skills to build a high-performing, well-coached sales team. This person drives discipline across forecasting, pipeline management, and CRM data integrity, and evolves the sales function thoughtfully as the business grows. About Us: 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 are Certified as a Great Place to Work 2026-2027. This certification, based directly on feedback from our own employees, reflects the kind of workplace culture we've built and continue to invest in, and adds to a strong track record of employer recognition ISA has earned over the past several years. 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

8-12 years of experience in sales leadership, including building and leading high-performing sales teams.
Experience leading a sales team through complex, multi-stakeholder cybersecurity (or other technical/security solution) sales cycles at enterprise organizations, including technical evaluations, security assessments, RFPs, and procurement and legal/compliance review.
Deep understanding of the enterprise cybersecurity buying landscape, including CISOs, IT security, risk, and compliance stakeholders, and how enterprise security purchasing decisions get made.
Experience selling vendor-agnostic consulting or professional services, in addition to product or staff augmentation sales.
Strong track record of sales operations discipline: forecasting, CRM management, quota setting, and compensation management.
Experience designing and administering sales compensation plans and identifying the performance drivers that motivate desired seller behavior.
Demonstrated ability to lead a sales team through evolving business needs and organizational change.
A clear point of view on how AI and broader market shifts are changing enterprise selling.
Strong communication, coaching, and people leadership skills.
Ability to build trust and work collaboratively across sales, marketing, and delivery functions.
Bachelor's degree or equivalent relevant experience.

Responsibilities

Own the sales strategy, structure, and coverage model across enterprise, mid-market, and managed services segments, with a focus on winning complex, multi-stakeholder cybersecurity sales cycles at enterprise organizations.
Bring structure and discipline to pipeline and funnel management, forecasting, CRM data integrity, quota setting, and compensation management.
Oversee pipeline and deal execution, from opportunity and proposal development, technical evaluations, and security assessments through RFx responses, quoting, order processing, and renewals.
Manage vendor and technology partner relationships in support of active sales opportunities.
Hire, onboard, coach, and manage the performance of the sales team, building a clear development path for sellers.
Manage the sales function's budget in line with company growth targets and financial discipline.
Partner cross-functionally with Marketing, Service Delivery, and Solution Architecture to ensure sales commitments are achievable and the client experience remains strong end-to-end.
Represent the Sales function in company planning, budgeting, and leadership discussions.
Bring strong change management skills to help the sales team adapt and evolve as the business grows.

Benefits

Flexible sick and personal days for all employees
Generous health plan with enhanced mental health resources and virtual care
Professional development opportunities and education reimbursement up to $2,000 annually for all employees and access to LinkedIn Learning
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
Service anniversary recognition and generous five-year milestone service awards
Annual President’s Club recognizing special achievement awards
Spot rewards providing opportunities for instant peer recognition
Annual kick-off meeting to communicate our strategic priorities
Quarterly town hall meetings
Regular team get togethers and client events
Scheduled employee feedback surveys and goal setting focus groups