Senior Services Engagement Director (AI/CCaaS)

Location: Greater Toronto Area, Ontario, Canada; virtual office with travel up to 50% based on customer and business requirements.

Salary: $140,200.00–$184,100.00 base compensation, with possible commission or performance-based bonus opportunities.

Company

hirify.global provides AI-powered experience orchestration and hirify.global Cloud solutions that connect people, systems, data, and AI for customer and employee experiences.

What you will do

• Own Professional Services revenue strategy and qualified pipeline creation across assigned strategic Canadian accounts.
• Lead complex services sales motions covering advisory, implementation, cloud migration, modernization, optimization, and transformation.
• Shape AI-powered customer experience, automation, analytics, orchestration, and data-driven transformation opportunities.
• Develop outcome-based proposals and executive messaging tied to customer objectives, business cases, and measurable value realization.
• Influence deal strategy, commercial structures, governance, risk, and investment decisions across complex multi-stakeholder environments.
• Align Account Executives, SDRs, Solution Consultants, Customer Success, and delivery leaders from opportunity development through retention and growth.

Requirements

• 5 to 7+ years of experience in SaaS, cloud software, enterprise technology, or Professional Services sales, including significant ownership of services-led sales motions.
• Demonstrated success selling complex Professional Services engagements in SaaS or cloud-based technology environments.
• Proven success building pipeline, negotiating, and closing complex, multi-stakeholder services opportunities with measurable revenue attainment.
• Experience selling on-premises-to-cloud transformation services, including migration, modernization, implementation, and optimization.
• Strong background in CCaaS, customer experience, or adjacent enterprise software markets, with knowledge of AI-enabled platforms, automation, analytics, or related technologies.
• Understanding of how Professional Services accelerate customer adoption, value realization, transformation outcomes, and long-term revenue growth.
• Established executive-level relationships and market knowledge across Canada's three major telecommunications companies and five major financial institutions.
• Strong account planning, opportunity management, commercial negotiation, executive stakeholder management, and executive communication capabilities.
• Track record of expanding services pipeline and revenue within existing strategic accounts while contributing to net-new growth, including experience with long-cycle enterprise sales involving business, technical, procurement, and executive stakeholders.
• Ability to travel up to 50% based on customer and business requirements.

Nice to have

• Experience positioning AI-enabled customer experience, automation, analytics, orchestration, or data-driven transformation services.
• Experience advising enterprise customers on AI adoption, governance, value realization, or transformation roadmaps.
• Knowledge of Canadian telecommunications, financial services, or other highly regulated enterprise markets.
• Familiarity with hirify.global Cloud or comparable enterprise CCaaS and customer experience platforms.

Culture & Benefits

• Comprehensive extended group health coverage and family-friendly benefits, including parental leave top-up and adoption assistance.
• Paid time off including vacation and personal leave, plus paid volunteer time and August Free Fridays.
• Retirement savings program with employer RRSP matching up to a prescribed maximum.
• Learning resources, mentorship, leadership development, education support, and internal mobility programs.
• Flexible ways of working, well-being resources, and regionally tailored programs for employees and families.

Hiring process

• Talent Acquisition and the hiring team review applications.
• Qualified candidates complete a Zoom interview, followed by interviews with the hiring manager and other interview team members.
• The process typically includes no more than five interviews, followed by final-step communication.