Director, Customer Success - Enterprise

Klaviyo•Boston, MA

About The Position

As a strategic leader of the Customer Success organization, our job is to solve for both the customer experience and our employee experience. We do this by creating trust with our customers and our team through humility and open-mindedness, and by giving the team a strong sense of purpose as part of the Customer Success organization. Our job is to empower the team by giving them the clear vision, direction, and support they need to grow and help our customers own their growth. As Director of Enterprise CSMs, you'll lead a team of managers to deliver the Enterprise CSM team's vision: a world-class customer experience. You'll own the growth and development of your team, drive efficiency through improved process and operationalized plans, act as an escalation point for customer and team issues, and lead your team to develop and execute the strategies needed to reach Klaviyo's business goals. You'll report to the Vice President of Customer Success and focus on refining the Enterprise customer experience, collaborating closely with Onboarding, Sales, Finance, Product, and Marketing leaders to build out the upmarket customer engagement model. You'll fully own the Enterprise customer experience post-onboarding, with success measured against retention and cross-sell numbers for the North American Enterprise CSM team. You're highly collaborative and innovative, with a track record of relentless and effective execution. You're results-driven, you ensure data informs every decision, and you're excited to tackle some of Klaviyo's most challenging opportunities for improving the customer experience.

Requirements

10+ years in Customer Success or related GTM leadership, including 5+ years managing people leaders (not just individual contributors), ideally within a SaaS or subscription business.
Proven track record scaling and leading a multi-layered Enterprise CS organization (40+ CSMs across several regional managers), with direct accountability for retention and cross-sell/upsell targets.
Ability to translate executive goals into team-wide plans — setting clear objectives, cascading metrics, and holding managers accountable for execution.
Strong cross-functional operator, able to align Sales, Onboarding, Product, Marketing, and Finance around a shared customer experience, and to shift thinking or gain buy-in in sensitive situations without damaging the relationship.
Data-driven decision-maker who uses account health signals, retention/expansion data, and predictive analytics to guide strategy and resource allocation.
Experience hiring and leading a high-performing team.
Comfortable as an executive-level escalation point, building trusted relationships with economic buyers and champions inside complex enterprise accounts.
Successful balancing humility and directness — building trust through open-mindedness, giving and receiving feedback well, and creating an inclusive team culture by example.
You've already experimented with AI in work or personal projects, and you're excited to dive in and learn fast.
You're hungry to responsibly explore new AI tools and workflows, finding ways to make your work smarter and more efficient.
You use AI tools to accelerate exploration, shorten iteration cycles, and bring sharper ideas to the table.

Responsibilities

Partner with the Vice President of CS to plan and direct a world-class Enterprise CSM function through clear goal setting, objectives, plans of execution, and team metrics, and ensure goals cascade to all CSMs.
Manage a team of ~40–50 Enterprise CSMs (5–7 managers, each with 5–10 CSMs) regionally dispersed across North America.
Collaborate cross-functionally with Sales, Onboarding, CSM, and Technical Solutions Architects to deliver a strong, aligned customer experience and improve customer sentiment.
Keep the customer journey at the center of every decision, identify opportunities to improve and scale the customer experience, and mitigate customer risk at scale with cross-functional partners.
Partner proactively with marketing, sales, finance, and product to achieve shared goals — including in sensitive situations where you need to shift thinking or gain buy-in without damaging the relationship.
Leverage data and objective measures to make key business decisions; review key objectives and success metrics with the Vice President of CS, highlighting wins, risks, and opportunities across your customer base.
Analyze issues and problem-solve in an objective, scalable way; assign accounts and distribute work across the team for optimal coverage and balance.
Act as an escalation point for managers and customers, building strong relationships with economic buyers and champions in key accounts to protect renewals and drive upsell/cross-sell.
Hire and develop managers — coaching on effective 1:1s, team meetings, accountability, stretching top talent, and performance management — while modeling an inclusive culture built on humility, open-mindedness, and high integrity.
Leverage AI (Claude, Gleen, ChatGPT) to strengthen complex account strategies, identify high-impact use cases, and share best practices with the team.
Develop advanced prompt frameworks for complex, multi-step tasks, train the team on prompt strategy and iteration, and use predictive AI signals to inform renewal and expansion strategy.
Transform workflows by putting AI at the center, building smarter systems and ways of working from the ground up.