Have you ever wondered what it takes to be a Director of Customer Success (CS)?
We challenged three CS leaders with an interactive scenario where they are dropped in as the new Director of CS at a fast-scaling SaaS company. Watch them discuss how they'd face each task, share their thought process and answer questions from the audience as we go.
They cover how to: become a truly customer-centric company, ensure your presence at the executive table, and navigate the challenges of a business reorganisation.
Christian Jakenfelds
Senior Account Executive
Forecastable
Christian is a customer success and revenue leader with a flair for community-led growth. He currently serves as Senior Account Executive at Forecastable and Go-To-Network Evangelist at Commsor, helping companies drive revenue through trusted networks over traditional outreach. Previously, he spent nearly three years at Planhat, where he earned Top 25 CS Thought Leader recognition and played a key role in product-led research and GTM. Christian began his career at Tessian, rising from CSE to Customer Operations Manager while leading major U.S. accounts and building internal CS tooling. He brings a unique blend of operational depth, storytelling, and strategic thinking.
Dean Colegate
Head of Customer Success & Operations
Websure
Dean is a customer success leader with over 10 years of experience scaling post-sales functions across SaaS, AI, and fintech. He currently heads Customer Success and Operations at Websure, overseeing onboarding, professional services, and support. Previously, he led the global CS function at Ada Health, building out a best-practice framework for enterprise clients across healthtech and AI. Dean has held multiple interim leadership roles at high-growth startups, where he’s consistently delivered on retention, change management, and CS tooling at scale.
Jonathan Schradi
Director of Customer Success
Klaviyo
Jonathan is a commercially focused Customer Success leader with over 15 years of experience in customer-facing roles across SaaS, eCommerce, and retail tech. Currently Director of Customer Success at Klaviyo, he previously led global enterprise CS at Scandit and served as VP of Customer Success at Attraqt, where he scaled post-sales functions and drove measurable growth. Known for building high-performing teams and aligning customer value with business impact, Jonathan blends strategic thinking with hands-on execution.
Emilie Dubau
Head of Learning Consulting
Academy to Innovate HR
Emilie is a global customer success leader with over 12 years of experience building high-performing teams across SaaS, EdTech, and digital services. She currently heads Customer Success at AIHR, where she leads the strategy and team behind learning consulting and retention. Previously, Emilie spent nearly eight years at Sana Commerce, serving as VP of Customer Success and overseeing a global team of 30+ across six regions. Her background includes senior roles at DoubleDutch and agency-side digital project management, blending operational rigor with a passion for customer-centric leadership at scale.
