Building and Scaling Customer Success Teams: A Startup’s Playbook | The Pair Program Ep53

In this episode, we sit down with Romaine Buck, VP of Customer Success at Articulate, and Toni Ann Careccio, Chief Customer Officer at PortPro, to explore the evolving role of Customer Success (CS) in startups and beyond. Both Romaine and Toni bring a wealth of experience in building and scaling CS teams that drive real value for customers and businesses alike.

They discuss:

• The impact of Customer Success: How CS helps companies uncover the “why” behind customer needs
• Key differences between customer success and customer service teams, and why this newer discipline has become essential in tech
• The role that CS teams play, including managing renewals, upselling, and building strong customer relationships
• Fostering a culture of continuous learning and adaptability within CS teams
• Where Romaine and Toni see this field heading for startups and beyond

If you’re scaling a startup, leading a CS team, or just curious about how Customer Success drives business impact, this episode is packed with actionable insights and strategies.

About Romaine Buck: Romaine is the VP of Customer Success at Articulate - an e-learning software company for creating workplace training. Before Articulate, Romaine was the Director of CS at Sprout Social and led CS for the central region of LinkedIn’s Sales Solutions product. Romaine transitioned into Customer Success after a sales career at LinkedIn and Monster.com. Prior to saas, Romaine also had careers in property management and journalism.

About Toni Ann Careccio: Toni is the Chief Customer Officer and Board Member at PortPro, a technology company with deep expertise in the global drayage industry. She has built an expert team of drayage and customer success experts to ensure that PortPro’s clients are taken care of from the minute they join the company by carefully listening to their needs and addressing their concerns. Before her role at PortPro, Toni worked as an Associate at Edison Partners where she was responsible for sourcing and evaluating investment opportunities in the Enterprise Solutions sector. Prior to this she co-founded and served as Chief Operating Officer for Axle Technologies, a robust ELD and Fleet Management Solution for trucking companies in the US and Mexico.