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.
• Strong operational acumen — able to bring structure