Chief Services Officer

Chicago, Illinois

Direct Hire

Salary Range: $300,000 - $325,000

Benefits: +Equity Hybrid - usually 2-3 days onsite in Chicago

The Chief Services Officer (CSO) leads a global post-sales organization responsible for delivering customer outcomes across customer success, professional services, and support functions. This role is accountable for driving retention, expansion, and services delivery at scale, while leveraging AI and automation to improve efficiency, insight generation, and customer experience.
The CSO will play a critical role in embedding AI-driven capabilities across the customer lifecycle, enabling more predictive, proactive, and personalized engagement across global markets.
 
Executive Responsibilities
Global Customer Lifecycle & Growth

  • Own the end-to-end customer journey, including onboarding, adoption, renewal, and expansion
  • Drive global Net Revenue Retention (NRR) and customer lifetime value
  • Use data and AI-driven insights to identify churn risk, improve adoption, and uncover expansion opportunities

 
AI-Enabled Services Transformation

  • Lead the integration of AI across customer-facing functions, including:
    • Predictive customer success (health scoring, risk detection)
    • AI-enabled support (automation, chat assistants, agent copilots)
    • Digital onboarding and self-service capabilities
  • Partner with Product and Engineering to embed AI into the customer experience
  • Reduce cost-to-serve while improving service quality and responsiveness

 
Global Services Delivery & Operations

  • Build and scale a global delivery model across multiple regions, including onshore and offshore hubs
  • Standardize processes, tools, and operating playbooks while enabling regional flexibility
  • Optimize a hybrid delivery model combining high-touch and tech-enabled engagement
  • Improve operational consistency across globally distributed teams

 
Revenue & Commercial Ownership

  • Own or strongly influence services P&L, renewals, and expansion revenue
  • Partner closely with Sales to drive upsell and cross-sell strategies
  • Improve forecasting accuracy and visibility into customer and revenue pipelines
  • Ensure alignment between commercial expectations and delivery capability

 
Customer Insights, Experience & Compliance

  • Elevate the voice of the customer through analytics and structured feedback loops
  • Improve customer satisfaction (NPS, CSAT) and overall experience across regions
  • Ensure compliance with global data privacy standards and responsible AI usage

 
Leadership, Talent & Culture

  • Build and lead a high-performing, globally distributed organization
  • Develop strong data-driven and AI-literate capabilities across teams
  • Foster a culture of accountability, innovation, and customer-centric execution

 
Qualifications & Experience

  • 15+ years of experience in SaaS, customer success, services, or post-sales leadership roles
  • Proven track record of scaling global post-sales or services organizations
  • Experience using data, analytics, or AI to improve customer outcomes and operational performance
  • Strong understanding of SaaS metrics, recurring revenue models, and enterprise customers
  • Experience working across global, multi-region organizations

 
Leadership Profile

  • Thinks like a global general manager of the customer base
  • Uses AI as a force multiplier for scale and efficiency
  • Balances automation with high-quality human engagement
  • Drives scalable, data-informed growth across regions and teams

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