Technical Support Jobs in Wisconsin

Job Description

Role Overview

We are seeking an experienced, strategic Senior Director to lead our Technical Support organization, covering tickets that reach human agents post our AI tier. This leader will set the operating strategy, develop a strong technical leadership team, and ensure customers receive reliable, high-quality technical resolution while driving operational efficiency and scalability across our support systems. Crucially, this role will lead the evolution and transition of human support agents into a proactive workforce closely aligned with our AI teams, driving pivotal cultural and operational change across the organization.

Key Responsibilities

• Set the strategy and operating model for Technical support, translating company priorities into clear plans, outcomes, and accountabilities.
• Lead and develop a multi-layered organization through managers and directors; build a culture of trust, high performance, inclusion, and continuous learning.
• Own service performance across customer segments and channels, leveraging AI-driven tools and automation alongside human expertise to balance responsiveness, technical quality, proactive customer outcomes, and efficient use of resources.
• Define and evolve the measures that show Technical support’s 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 that support predictable coverage and responsible resource allocation.
• Guide the design and evolution of Technical support offerings, ensuring service commitments are clear, deliverable, and differentiated for the customers they serve.
• Use customer and operational insights to identify systemic product or process issues, influence prioritization, and improve outcomes across the company.
• Communicate performance, risks, investment needs, and opportunities to executive leadership with clear recommendations and options.
• Lead organizational change and continuous improvement, ensuring growth does not compromise employee experience or customer trust.
• Represent the customer and support organization in senior-level discussions, including complex escalations and strategic customer reviews.
• Stay current on support, SaaS, AI integration, and service-delivery practices, applying relevant insights and modern AI tools to enhance the organization’s operational strategy.
• Lead the cultural and operational transition of human support agents into a proactive, AI-aligned workforce, partnering closely with AI teams to reshape workflows and modern service delivery.
• Develop a deep understanding of workforce management and act as a key interlock to align staffing strategies with operational demand.
• Champion knowledge management practices and serve as an interlock across teams to ensure continuous sharing and capture of support insights.
• Evolve the human support workforce from a purely reactive model into a proactive organization, partnering closely with AI development and product teams to drive strategic change, refine human-AI workflows, and optimize service delivery.
  

Candidate Profile

• Extensive leadership experience (15+ years) in technical support, customer support, or service delivery within a high-growth SaaS or enterprise technology company.
• Proven track record as a senior executive leading leaders and scaling massive, complex global organizations through major growth phases and strategic transformations.
• Demonstrated success in setting long-term enterprise vision and translating strategy into high-impact operating plans and measurable business outcomes.
• Strong understanding of support operations, customer experience, capacity planning, service-level management, and performance metrics.
• Experience partnering across Sales, Customer Success, Product, Engineering, and Finance, including with senior executives.
• Deep commercial acumen and executive judgment to balance global customer commitments, premium 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; advanced degree is a plus.
• Strong expertise and proven experience in integrating AI and automation into technical support operations, with a track record of driving cultural change and evolving agent roles toward proactive engagement.
Strategic mindset and track record of evolving support organizations toward proactive service models and co-designing automated workflows with AI product teams.

The US annualized base salary range for this position is $174,000.00-$260,000.00. This position may also be eligible for bonus, benefits, or related incentives. While this range reflects the minimum and maximum value for new hire salaries for the position across all US locations, the offer for the successful candidate for this position will be based on job related capabilities, applicable experience, and other factors such as work location. Please note that the compensation details listed in US role postings reflect the base salary only (or OTE for commissions based roles), and do not include bonus, benefits, or related incentives.

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