Director, Technical Support
•Ada18· 23h
🎧 Support⏰ Full-time👔 Executive🇨🇦 Canada
23h ago
Contentsquare·14 days ago
About the Role
We are looking for a strategic and operationally exceptional Head of Support to lead our global Support organization. This leader will own the strategy, operational execution, and transformation of Support into an AI-first, scalable, multi-product function that delivers fast, consistent, value-creating outcomes for every customer.
This role oversees Support delivery across all products and regions, the AI and automation roadmap, the global hybrid and vendor delivery model, tooling modernization, services performance management, and organizational design.
The ideal candidate is a strategic and operational leader with deep SaaS Support experience, strong financial acumen, and a proven ability to transform Support organizations through automation, scalable delivery models, and technology innovation. You will partner cross-functionally with Customer Success, Professional Services, Product, Engineering, and Sales to ensure customers realize maximum value from the Contentsquare platform.
This role is critical in driving customer retention, satisfaction, scalability, and operational maturity as Contentsquare continues its global growth journey.
Support Strategy & Leadership
Lead and scale a global Support organization across EMEA, North America, and APAC.
Define and execute the Support strategy aligned with company growth objectives, retention targets, and customer outcomes.
Lead the transformation of Support into an AI-first, scalable, multi-product function.
Establish regional operating models and leadership structures that improve delivery consistency and operational accountability.
Drive organizational alignment and integration initiatives following structural or product changes.
AI & Automation Strategy
Set and execute the roadmap for AI-driven deflection, triage, and resolution across all products.
Lead the implementation of AI-powered support tools, chatbots, and operational agents.
Make automation the default, not the exception, and scale containment without compromising customer experience.
Position Support automation as a driver of both cost efficiency and customer satisfaction.
Multi-Product Service Delivery & Operational Excellence
Oversee end-to-end Support delivery across Contentsquare, Heap, Hotjar, and Loris.
Run Support across Free, Growth, Pro, and Enterprise tiers with clear, enforced service standards for each.
Own SLAs, CSAT, first contact resolution, deflection rate, and cost to serve.
Implement operational cadences, KPI frameworks, and business review processes that improve visibility and execution.
Lead the Support side of the Hotjar migration and build the playbook for absorbing future product transitions without service disruption.
Partner with Product and Engineering to build support readiness for new AI-powered product features, ensuring the team is trained, tooling is in place, and ticket intake forecasts account for new product complexity before general availability
Global Hybrid & Vendor Delivery Model
Build and manage a hybrid delivery model across in-house teams and outsourced partners.
Develop tiered delivery frameworks leveraging internal teams, regional partners, and remote delivery models.
Lead partner negotiations and vendor management initiatives to improve delivery capacity and cost efficiency.
Establish governance models and performance standards across internal and external delivery teams.
Technology & Systems Transformation
Lead the modernization of Support tooling, systems, and operational infrastructure.
Evaluate, negotiate, and implement platforms that improve customer visibility, case resolution, and KPI reporting.
Partner with Product and Engineering on integrations and workflow automation across the Support lifecycle.
Voice of the Customer & Growth Contribution
Turn ticket data into product insight through a structured feedback loop into Product and Engineering, so we fix root causes, not just symptoms.
Build the motion for Support to surface trial activations, upsell signals, and expansion opportunities to Customer Success and Sales.
Contribute operational insights that improve product adoption, retention, and long-term customer value.
Cross-Functional Collaboration
Partner closely with:
Customer Success and Professional Services on customer lifecycle alignment
Product and Engineering teams on implementation challenges and customer feedback
Sales leadership on support positioning and tier definition
Finance on budgeting, forecasting, and cost-to-serve management
Support strategic customer escalations and complex engagements where executive oversight is required.
Leadership & Talent Development
Build high-performing Support leadership and delivery teams across regions.
Build a team that is technically fluent, customer-obsessed, and comfortable working alongside AI agents.
Create career paths across products, not within silos.
Drive clear accountability structures, communication frameworks, and performance management practices.
Lead teams through organizational transformation and operational scaling while maintaining execution focus and team alignment.
10+ years of experience in Customer Support, Customer Operations, or SaaS Services leadership roles.
Proven track record leading large-scale Support transformation initiatives
Proven experience scaling AI-driven support tools (chatbots, deflection engines, automation agents) from pilot to enterprise-wide deployment, with measurable containment and satisfaction outcomes.
Demonstrated experience managing a global incident management process including on-call rotations, priority protocols, external status page communications, and post-mortem disciplines.
Strong experience running multi-product or multi-business-unit Support in a SaaS environment, ideally through an acquisition or integration.
Demonstrated expertise managing hybrid delivery models across in-house and outsourced teams.
Experience implementing Support tooling, automation platforms, and scalable delivery frameworks.
Strong financial and operational acumen with experience managing Support budgets, forecasting, and cost to serve.
Experience leading global or regional teams in fast-paced, high-growth environments.
Strong executive communication, stakeholder management, and organizational leadership capabilities.