Senior Director, Customer Success

About Customer.io Hi, my name is John S, CRO at Customer.io , and I am looking to hire a Senior Director, Customer Success. Over 7,500 companies — from scrappy startups to global brands — use our platform to send billions of emails, push notifications, in-app messages, and SMS every day. Customer.io powers automated communication that people actually want to receive. We help teams send smarter, more relevant messages using real-time behavioral data. We're looking for a Senior Director to lead our Customer Success organization. Reporting to the Chief Revenue Officer, you'll be responsible for driving adoption, delivering value, and ensuring customer retention — through a combination of scaled digital programs, high-touch enterprise engagement, and AI-powered systems that help our team work smarter. This is not a purely operational role. You'll be expected to build and run the CS function from the inside out — designing systems, coaching managers, and owning executive relationships with our most strategic customers. You'll also serve as a key voice in the CRO leadership team, contributing to decisions that shape how Customer.io grows. What we value Empathy for customers and teammates. We meet people where they are, listen deeply, and act with care. Clarity and transparency. We communicate openly — whether with customers or colleagues — so expectations are clear and trust is built. Bias for action. We move quickly, experiment often, and adapt when things change. Operational excellence. We bring structure and rigor to how we work, without overcomplicating or slowing down progress. Collaboration over silos. We partner across CS, Technical Support, Account Management, Product, and Sales to deliver a seamless customer journey. Curiosity and adaptability. We embrace new technology, including AI, and see change as an opportunity to get better. Inclusive leadership. We value diverse perspectives, encourage debate, and create space where every team member can grow and thrive. What you'll do Own NRR, retention, and onboarding outcomes across the Customer Success organization — setting the metrics, managing to them, and holding the team accountable. Build and scale CS through AI, automation, and systems thinking — designing programs that serve more customers efficiently without simply adding headcount. Own relationships with our largest, most strategic accounts — leading executive QBRs, onsite meetings, and C-level conversations that connect product capabilities to clear business outcomes. Step in directly when needed to stabilize or expand key accounts, navigating complex organizations and aligning multiple stakeholders. Design and evolve engagement models across customer segments — from one-to-many digital programs for SMB and mid-market to high-touch enterprise partnerships. Hire, coach, and develop CS managers and ICs into a high-performing, customer-obsessed team. Partner with Sales, Product, Engineering, and Marketing to close feedback loops and ensure customers are getting continuous value from our platform. What we're looking for 10+ years in Customer Success or related customer-facing roles, with at least 5 years in senior leadership (Director/Senior Director). Proven track record driving NRR, retention, and adoption outcomes at a B2B SaaS company, ideally supporting both mid-market and enterprise customers. Hands-on experience with AI and automation in a CS context — not just an awareness of the tools, but a builder's instinct for how to apply them. Strong executive presence; equally comfortable in internal strategy conversations with the CRO and in C-level customer meetings. Demonstrated ability to scale CS programs — from digital, one-to-many engagement to tailored executive business reviews. Experience managing and expanding strategic customer accounts, including driving adoption, deepening executive relationships, identifying growth opportunities, and delivering measurable business outcomes. S ... (truncated, view full listing at source)