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, metrics, and process without sacrificing agility.

A collaborative leader who welcomes debate, challenges assumptions, and thrives in a fast-moving environment.

Why you'll love this role

AI-First Opportunity: Build the next generation of CS from the ground up — with AI and automation as core inputs, not afterthoughts.

Enterprise Impact: Own and deepen relationships with our most strategic customers, influencing outcomes at the highest levels.

Strategic Scope: Shape how Customer Success operates and evolves at a company scaling toward $500M ARR.

Leadership Platform: Join the CRO leadership team and contribute to company-wide priorities, not just CX metrics.

Compensation & Benefits

We believe in transparency. Salary range for this role is $200,000 - $220,000 (or equivalent in local currency) depending on experience and subject to market rate adjustment. In addition, there will be a variable comp target to enrich the overall package.

We know our people are what make us great, and we’re committed to taking great care of them. Our inclusive benefits package supports your well-being and growth, including 100% coverage of medical, dental, vision, mental health, and supplemental insurance premiums for you and your family. We also offer 16 weeks paid parental leave, unlimited PTO, stipends for remote work and wellness, a professional development budget, and more.

See full benefits here →

Our Process

No gotchas, no trick questions - just a clear, human process designed to help both of us make an informed decision.

30-minute video-call with Recruiter

30-minute video-call with Hiring Manager

3 x 30-minute interviews with potential team members (Chief People Officer, CFO, and Chief of Staff - Revenue)

60-minute Case Study + Review Call

All final candidates will be asked to complete a background check and employment verifications as part of our pre-employment process.

Customer.io recognizes the stifling impact of systemic injustice on diverse communities. We commit to using our influence to increase inclusion and equity within the tech industry. We strive to build an inclusive team culture, implement bias-free hiring practices, and develop community partnerships to expand our global impact.

Zoom is the only video conference platform that we use, virtual interviews will be conducted using the video capability (i.e., not via the chat), and offers will be extended in writing on official Customer.io letterhead. Please be vigilant in all of your job search activity, and if you have any questions please contact jobs@customer.io.

Join us!

Check out our careers page for more information about why you should come work with us! We believe in empathy, transparency, responsibility, and, yes, a little awkwardness. If you’re excited by what you read — apply now.