Senior 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.