Our Team

We’ve been where you are.

Every advisor in our collective has run the CX function they now advise on, so they understand the daily pressures, tough decisions, and practical realities you face.

Meet Your Advisors

Caitlin Wood

Caitlin Wood

Functional Expertise:
Customer Enablement, Scaled/Digital CS, Adoption Programs


Ask me about: Customer journeys, adoption data, health scores, customer education programs that actually drive results, scaling teams, balancing life as a parent and a high-performing leader.

Ex-Zendesk and Ironclad, Caitlin spent the last 15+ years working in tech in a rage of different roles in the CX space, with a concentration on Customer Education and Scaled CS leadership. With a particular interest in building strategies that series B/C company’s need to scale, she’s optimized existing teams and built functions from the ground up. Putting a strategy in place that actually gets results and authoring team cultures that make people want to keep showing up is what lights her up.

Founder, Advisor
A woman with shoulder-length dark hair and dark eyes smiling, wearing a navy blazer over a white blouse, standing outdoors in an urban setting with modern buildings in the background.

Roshni Sondhi

Functional Expertise:
CX Executive, Customer Success, Professional Services, Support


Ask me about: CX Strategy, Executive-level cross-functional partnership, preparing board narratives, CSM growth paths

With 20 years in SaaS focused on partnering with customers, Roshni leads Customer Experience at Cortex, overseeing Professional Services, Customer Success, Customer Engineering, and Education. Her career spans seven years running Customer Success at Zendesk and three years as VP of Customer Experience at Grafana Labs, after starting out as a Senior CSM at Oracle. At Cortex, she's focused on building a CX org that turns customers into long-term partners as the company scales. Roshni holds a degree in Chemical Engineering from Georgia Tech and is based in Atlanta, where she spends her downtime cooking, traveling, and keeping up with her two kids and goldendoodle.

Advisor
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Advisor

Bill Kelleher

Functional Expertise:
Customer Education, Documentation, AI-Powered Learning & Scaled Support

Ask me about:
Launching Customer Training Programs, Help Center strategy, In-App Guidance, AI Chat Support, Certification Programs

Bill has spent more than 15 years helping organizations build customer experiences across many facets of enablement, giving him a unique perspective on how these functions work together to create a more informed and effective user base. Throughout his career, Bill has built and scaled programs across legal and construction tech, security & compliance, STEM education, retail, and manufacturing. His cross-industry perspective enables him to quickly identify proven strategies, avoid common pitfalls, and adapt best practices to each organization's unique challenges at different stages of growth.

  • "Caitlin reflected back strengths I couldn't see in myself—and gave me the confidence to pursue a leadership role."

    — Former Leadership Advisory Program Member

  • "She helped me transform a collection of individual teams into a high-performing organization that consistently delivered exceptional results."

    — Former Leadership Advisory Program Member

  • "They guided me to build a team that exceeded targets year after year while creating an environment where people loved coming to work."

    — Former Leadership Advisory Program Member