Director of Customer Success

What your day could consist of:

• AI-Enabled Engagement: Champion the adoption of AI tools that surface actionable insights, automate workflows, and enable teams to proactively drive customer value at scale.
• Shape the AI Strategy: Co-develop the long-term vision for how AI is embedded across the customer lifecycle—including segmentation, engagement models, team workflows, and customer insights. Partner with AI and operations teams to pilot, test, and refine new models of customer engagement.
• Design for Scale: Own the evolution of scalable success models—combining human, digital, and AI-led approaches to support customers efficiently across segments, including unmanaged accounts.
• Customer-Led Segmentation: Redefine customer segmentation strategies using AI-informed behaviors, product usage, and lifecycle needs—moving beyond traditional ARR tiers to enable personalized, data-driven engagement.
• Retention & Growth: Define and execute strategies that deliver measurable outcomes across value realization, product adoption, and Net Revenue Retention (NRR), using product usage, health scores, and growth signals to identify both risk and opportunity.
• Cross-Functional Collaboration: Partner with Product, Marketing, and Sales to deliver customer feedback, influence roadmap and go-to-market strategies, and align on success metrics and expansion motions.
• Operational Design: Help shape the future-state Customer Success operating model—defining team structures, processes, and tools that support a digital-first, insight-driven approach to customer engagement.
• Continuous Improvement: Drive operational rigor through forecasting, enablement, performance measurement, and iterative process improvements that scale impact and innovation.

What is needed:

• 8+ years of progressive leadership experience in Customer Success, including direct management of managers and oversight of cross-regional or multi-functional teams within a SaaS or tech-driven environment.
• Proven track record of scaling Customer Success programs across diverse customer segments (SMB, mid-market, enterprise), with measurable impact on adoption, retention, and expansion outcomes.
• Demonstrated success implementing AI and automation capabilities within customer-facing workflows—ideally including tools like predictive health scoring, AI-driven segmentation, or co-pilot-style enablement for customer-facing teams.
• Expertise in customer journey design and lifecycle strategy, with a data-driven approach to personalization, onboarding, engagement, and long-term value realization.
• Strong analytical and strategic mindset, with the ability to translate data and insights into scalable plays, prioritization frameworks, and customer-centric actions.
• Deep experience in operational excellence, including team structure design, process optimization, playbook development, KPI tracking, and performance management.
• Ability to lead and influence cross-functional initiatives—partnering closely with Product, Marketing, Sales, and Operations to advocate for customer needs, drive alignment, and support company-wide growth initiatives.
• Fluency in scalable engagement models, including tech-touch, digital CS, and hybrid models that blend automation with human expertise.
• Exceptional communication and leadership skills, with the ability to inspire and develop talent, foster accountability, and drive a high-performing, customer-obsessed culture.
• Experience with customer success and data tools such as Totango and Looker is a strong plus, particularly in building health models, tracking performance, and delivering actionable insights.
• Bachelor’s degree in Business, Marketing, or a related field is preferred, but not required. Advanced degrees (e.g., MBA) are a plus.
• Location: must live within a commutable distance of Chicago, however, the role is remote flexible.