In this episode of OnBase, host Chris Moody sits down with Craig Chiofalo to explore what it truly takes to build and lead a world-class support engineering organization. Craig pulls back the curtain on the operational strategies and tech stack powering Demandbase’s award-winning team—including how tools like Salesforce Einstein and SupportLogic are transforming their approach to proactive support. He also shares lessons on hiring for excellence, scaling impact without ballooning headcount, and why deep, daily collaboration across product, engineering, and customer success is the cornerstone of lasting success.

Key takeaways

Right Team, Right Tech: Hiring the right talent, enabling them with strong onboarding and internal tools, and layering in AI-driven technologies can drive exponential impact without scaling the team linearly.
Cross-Functional Collaboration Is Everything: Craig attributes much of the team’s success to deep integration with product, engineering, and customer success—teams that work together daily to elevate the customer experience.
Award-Winning Process Maturity: From rewritten job descriptions to internal training certifications and advanced sentiment monitoring, Craig’s team has refined its approach year after year to earn industry recognition.
Operationalized AI: AI tools like SupportLogic and Salesforce Einstein are leveraged not just for efficiency, but for better sentiment analysis, proactive support, and smarter data insights.

Measure What Matters: In addition to SLAs, Craig’s team emphasizes customer satisfaction and effort scores—tracking detailed metrics while staying focused on proactive issue resolution.

Quotes

On Team Excellence
“This team is phenomenal—not just individually, but in how they collaborate. That synergy is the catalyst behind everything we’ve achieved.”

On Leveraging AI Thoughtfully
“AI should be seen as an assistant. It's like a dishwasher—you still load it and unload it, but it saves time and effort on repetitive tasks.”

(04:00): How Craig rewrote job descriptions and created testing processes to hire and retain top-tier talent.
(09:00): A deep dive into Salesforce Service Cloud, SupportLogic, and the internal troubleshooting app that dramatically reduces time to resolution.
(14:00): How the team uses data and proactive alerts to prevent fires before they happen.

(18:00): Craig’s thoughtful breakdown of AI as a productivity enhancer, not a replacement.

Tech Recommendations

Salesforce Service Cloud + Einstein: A central support platform now enhanced with AI capabilities for smarter case handling.

SupportLogic: Real-time sentiment analysis and escalation prediction across customer interactions.

Resource Recommendations

Newsletter:

MIT Technology Review – AI-focused and practical
Harvard Business Review – Daily updates on leadership and strategy

McKinsey – Insightful newsletters with AI-related content

Shout-outs

Umberto Milletti, Chief R&D Officer at Demandbase
Angelle Stromeyer, RVP Customer Success at Demandbase

Erika Setla, Sr. Director, CX Strategy & Ops at Demandbase

About the Guest

Craig Chiofalo is a customer-focused leader with over 20 years of experience directing customer support, service, and success teams across SMB to enterprise clients. Currently Vice President of Support Engineering at Demandbase, Craig leads a Stevie Award–winning team recognized for delivering outstanding customer service. He brings a proven track record of building high-performing, collaborative teams that exceed goals, with a leadership style rooted in fairness, energy, and a deep passion for technology.

Craig has held key roles at IBM, Silverpop, CallRail, Calendly, and Salsify, often joining during critical growth phases to scale operations, implement smart automation, and drive cross-functional alignment. His expertise spans platforms like Salesforce, Zendesk, Jira, Confluence, and SQL—always with a hands-on, data-informed approach to delivering exceptional customer outcomes.

Ep. 520 | Beyond the Ticket: Building Award-Winning Support at Demandbase