About the Role:

The Senior Director, Managed Services will drive the growth of ISA’s Managed Cybersecurity and Managed AI Agent offerings by owning the entire business development lifecycle - from strategic hunting to deal closure. This role is responsible for building a robust sales pipeline, crafting go-to-market strategies, orchestrating pursuit teams, and negotiating high-value multi-year contracts. The ideal candidate is an enterprise sales leader with deep experience in cybersecurity or managed services, skilled in translating technical solutions into compelling business value for CISOs, CIOs, and executive stakeholders. Success in this role means expanding ISA’s recurring revenue footprint, accelerating sales velocity, and ensuring seamless handoff to delivery teams for outstanding client outcomes.

Key Responsibilities:

• Generate and qualify pipeline opportunities through proactive prospecting, intent data, industry events, and partner channels.

• Lead responses for new Managed Services RFPs, including win theme development, technical solution alignment, and pricing strategies.

• Develop and refine data-driven GTM plans targeting high-potential verticals and accounts.

• Define value propositions and campaign themes to maximize market visibility and client engagement.

• Orchestrate cross-functional teams (account managers, architects, delivery leads) throughout the sales cycle.

• Deliver accurate monthly forecasts, meet or exceed Annual Recurring Revenue (ARR) and Total Contract Value (TCV) targets, and maintain strong pipeline discipline.

• Lead negotiations for multi-year managed service agreements and SOWs to secure profitable, risk-mitigated contracts.

• Create sales playbooks, competitive battle cards, and objection-handling guides to enhance deal velocity.

• Build and manage alliances with vendors and strategic partners to uncover joint go-to-market opportunities.

• Ensure seamless client transition from sales to service delivery and establish success metrics for onboarding.

• Partner with delivery teams to identify upsell and cross-sell opportunities within existing accounts.

• Monitor emerging threats, competitive offerings, and industry trends to inform pricing, positioning, and product roadmaps.

About Us:

We are proud to be recognized as a top employer for multiple years in a row, we currently hold the distinctions of Canada’s Top Small and Medium Employers 2025, Greater Toronto’s Top Employers 2025 and are Certified Great Place to Work 2025-2026.

At ISA Cybersecurity, our mission is to help clients achieve their privacy and security goals, and to be proactive in the fight against security threats. ISA is Canada’s leading cybersecurity-focused company, with three decades of experience delivering cybersecurity services and people you can trust. We provide our clients with comprehensive counsel on complex, evolving, and multi-faceted issues related to cybersecurity and breach incident response.

ISA Cybersecurity also offers a world-class 24/7 by 365 SOC 2 Type II certified CIOC (cybersecurity intelligence operations center), giving our clients deeper insights and earlier warnings about coordinated cyber-attacks. ISA strategically partners with many of the most respected security technology firms in the world. Through these relationships, our clients can gain access to a broad portfolio of industry-leading cyber solutions best suited to protect their corporate assets and customer data.

In today’s volatile world of digital threats, we help Canadian companies to better understand their current security posture and how to mitigate risks.

Environment:

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.

Qualifications:

• Enterprise Sales Expertise: Proven track record in meeting or exceeding quotas for complex cybersecurity or XaaS solutions.

• 5+ years in quota-carrying roles managing full sales cycles in MDR, MSSP, MSP, or managed services environments.

• Strong understanding of cybersecurity and AI concepts; ability to whiteboard SOC workflows, SIEM/MDR architectures, and AI use cases.

• Exceptional verbal and written skills; ability to simplify technical concepts for executive audiences.

• Experience running discovery workshops, live demos, and PoCs.

• Skilled at structuring multiyear agreements balancing customer satisfaction and profitability.

• Hands-on experience with Microsoft Dynamics CRM or similar tools for forecasting and pipeline management.

• Eligible for Government of Canada Reliability Status or higher.

Preferred:

• Certifications: CISSP, CISM, CISA, GCIH, or equivalent.

• Bachelor’s degree in business, Computer Science, Engineering, or related field.

Why Join Us?

At ISA Cybersecurity we lead with our "Why". Our Why is to make people feel safe. This not only applies to the result of services that we provide to our clients, but how people feel when interacting with us. Whether you're an employee of ISA or a client we want you to feel safe and supported. Each one of our team members is expected to uphold this leadership quality and embrace it through consistent demonstration of our core values of Explore, Persevere, Adapt and Uplift.

We are proud to offer a variety of employee friendly programs that enable our team to perform at their best.

Highlights of our programs and policies include:

• 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

We also place great value on celebrating the contributions of all employees through the following service recognition programs:

• 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

Information-sharing and team-building initiatives include:

• Annual kick-off meeting to communicate our strategic priorities

• Informal staff events like pizza lunches or games day

• Quarterly town hall meetings

• Regular team get togethers and client events

• Scheduled employee feedback surveys and goal setting focus groups

Thank you for your interest in joining ISA Cybersecurity. Our team looks forward to reviewing your application. We will be reaching out to you directly if your experience matches our needs.

Accessibility:

ISA Cybersecurity is committed to providing accommodations for applicants with disabilities. If you require specific accommodation because of a disability or medical need, please inform ISAs Human Resources team (hr@e-isa.com) so arrangements can be made for appropriate accommodation to be in place during the recruitment process.