Sr Director, Customer Success and Outcomes

LeanData helps the world's fastest-growing companies automate, simplify, and accelerate revenue. We're hiring a Senior Director of Customer Success to lead, evolve, and scale our Mid-Market CS organization. Reporting to the Chief Customer Officer, you'll own end-to-end customer success strategy — segmentation, engagement models, and success planning — while playing a central role in shaping the customer experience at scale.

You'll also be at the forefront of how we apply AI: building an agentic CS motion that drives real focus, efficiency, and customer impact. This means reinventing how a high-performing team operates, not just automating what already exists.

In close partnership with Sales, Product, Professional Services, and Support, you'll ensure customers achieve measurable outcomes — directly driving gross and net revenue retention. This is a rare opportunity to build durable foundations for scale at a company that sits at the heart of the modern revenue stack.

Hybrid: Two in-office days per week (Santa Clara)

Responsibilities

Strategic Leadership

• Own the strategy, structure, and results of a 5–7 person CS team — including engagement models, success planning, and a scalable operating model grounded in the customer journey.
• Lead the evolution of CS by leveraging our tech stack and frameworks to free the team for the work that matters most; build leadership depth through mentorship, succession planning, and clear career paths.
• Drive a "CS AI" motion for SMB accounts that maximizes efficiency without sacrificing customer satisfaction.

Execution & Delivery

• Direct execution of playbooks across our Solution Value Framework — covering adoption, risk mitigation, and expansion in complex Salesforce environments.
• Maintain early-warning systems for churn risk, enabling proactive retention at scale.
• Serve as the senior escalation point for high-impact customer issues.
• Drive operational rigor and consistency through Salesforce and CS tooling.

Collaboration & Influence

• Act as the primary voice of the customer, shaping Product roadmap and Engineering priorities from frontline insights.
• Partner with Sales and Account Management on renewals, expansions, and strategic account growth.
• Collaborate with Marketing to generate customer advocacy, references, and case studies.
• Lead executive business reviews and cross-functional planning sessions.

Metrics & Outcomes

• Own and deliver gross revenue retention targets for the Mid-Market CS organization.
• Ensure customers achieve measurable outcomes tied to revenue efficiency, pipeline conversion, and GTM alignment.
• Define, track, and report on adoption, engagement, customer health, time-to-value, and CSAT.

Qualifications

Required

• 8–12 years in Customer Success, Account Management, or post-sales leadership in B2B SaaS.
• 3+ years managing and scaling CS teams, with a track record of developing talent and leaders.
• Demonstrated ownership of GRR and net retention targets.
• Strong operational and analytical mindset; able to translate data into executive strategy.
• Experience supporting mid-market and enterprise customers through complex implementations.
• Relevant degree from a well-regarded college or university, MBA a plus

Preferred

• Experience scaling CS from mid-market to enterprise in a high-growth environment.
• Technical familiarity with Salesforce-native platforms or RevOps/GTM infrastructure.
• Background in RevOps, Sales Ops, Marketing Ops, or revenue intelligence.
• Comfort aligning CS motions with both sales-led and product-led growth models.