Senior Director, Technical Support

Zendesk•Madison, WI

6d•Hybrid

About The Position

Zendesk is seeking an experienced, strategic Senior Director to lead its Technical Support organization, which handles tickets escalated to human agents after the AI support tier. The leader will set the operating strategy, develop a strong technical leadership team, and deliver reliable, high-quality technical resolutions while improving operational efficiency and scalability. A central focus is transitioning human support agents into a proactive workforce aligned with AI teams, including leading cultural and operational change and evolving human-AI workflows. The role owns service performance across customer segments and channels, develops scalable global coverage and workforce models, and guides the design of support offerings and service commitments. It uses customer and operational insights to influence product and process improvements and communicates performance, risks, investment needs, and opportunities to executive leadership. The Senior Director represents customers and the support organization in senior-level discussions, including complex escalations and strategic customer reviews, and partners across the company to align support with customer needs, commercial strategy, and product priorities. The position requires extensive senior leadership experience in technical support, customer support, or service delivery at a high-growth SaaS or enterprise technology company. The successful candidate will have experience scaling complex global organizations, leading leaders, integrating AI and automation into support operations, and building proactive service models. A bachelor’s degree or equivalent practical experience is required; an advanced degree is a plus. The US annualized base salary range is $174,000–$260,000. The position may also be eligible for bonus, benefits, or related incentives. Zendesk describes its working model as hybrid, combining in-person collaboration at its offices with flexibility to work remotely for part of the week. AI or automated decision systems may be used to screen or evaluate applications. Zendesk is an equal opportunity employer and provides reasonable accommodations for applicants with disabilities and disabled veterans.

Requirements

15 or more years of leadership experience in technical support, customer support, or service delivery within a high-growth SaaS or enterprise technology company.
Proven experience as a senior executive leading leaders and scaling complex global organizations through growth and strategic transformations.
Demonstrated ability to set long-term enterprise vision and translate strategy into operating plans and measurable business outcomes.
Strong understanding of support operations, customer experience, capacity planning, service-level management, and performance metrics.
Experience partnering with Sales, Customer Success, Product, Engineering, and Finance, including senior executives.
Deep commercial acumen and executive judgment in balancing global customer commitments, service quality, workforce dynamics, and multi-million-dollar operating budgets.
Excellent communication, executive presence, and stakeholder-management skills, including the ability to explain trade-offs and recommend a path forward.
Strong people leadership, talent development, and organizational design capabilities.
Ability to lead distributed teams across regions and work effectively across time zones; flexibility may be needed for critical customer or business needs.
Bachelor’s degree or equivalent practical experience.
Strong expertise and proven experience integrating AI and automation into technical support operations, including driving cultural change and evolving agent roles toward proactive engagement.
Strategic mindset and a track record of moving support organizations toward proactive service models and co-designing automated workflows with AI product teams.

Nice To Haves

An advanced degree.

Responsibilities

Set the Technical Support strategy and operating model, translating company priorities into plans, outcomes, and accountabilities.
Lead and develop a multi-layered organization through managers and directors, cultivating trust, high performance, inclusion, and continuous learning.
Own service performance across customer segments and channels, using AI-driven tools, automation, and human expertise to balance responsiveness, resolution quality, proactive outcomes, and resource efficiency.
Define and evolve measures of support value and health, including customer experience, resolution quality, service levels, capacity, and business impact.
Partner with Sales, Customer Success, Product, Engineering, and Finance to align coverage and service commitments with customer needs, commercial strategy, and product priorities.
Establish scalable global capacity planning, forecasting, staffing, and escalation models for predictable coverage and responsible resource allocation.
Guide the design and evolution of Technical Support offerings so service commitments are clear, deliverable, and differentiated.
Use customer and operational insights to identify systemic product or process issues, influence prioritization, and improve company-wide outcomes.
Communicate performance, risks, investment needs, and opportunities to executive leadership with clear recommendations and options.
Lead organizational change and continuous improvement while protecting employee experience and customer trust.
Represent customers and the support organization in senior-level discussions, complex escalations, and strategic customer reviews.
Stay current on support, SaaS, AI integration, and service-delivery practices and apply relevant insights and modern AI tools to operational strategy.
Lead the cultural and operational transition of human support agents into a proactive, AI-aligned workforce in partnership with AI teams.
Develop a deep understanding of workforce management and align staffing strategies with operational demand.
Champion knowledge management and support continuous sharing and capture of support insights across teams.
Partner with AI development and product teams to evolve reactive support into proactive service, co-design automated workflows, and optimize human-AI service delivery.