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Customer Success Team Lead (Implementation)

Datarails - Remote - Remote - posted 2026-10-15

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Salary: USD 120,000 - 150,000 / annual

Datarails is an AI-powered FinanceOS company helping finance teams transform their workflows through intelligent automation, AI, and seamless integrations. With ~350 employees globally, the company is building next-generation finance technology. The Customer Success Team Lead (Implementation) manages a team of Implementation CSMs and Datarails resources to deliver high-quality platform implementations that meet and exceed customer expectations. This role oversees the entire implementation lifecycle from initial planning through final deployment, ensuring projects complete on time and within scoped hours. Key responsibilities include: **Team Leadership & Development:** Manage and lead implementation CSMs through hiring, training, and coaching. Conduct weekly 1:1s focused on individual growth and career development. Perform regular performance reviews with constructive feedback. Foster a collaborative, high-performance environment by encouraging knowledge-sharing, best-practice discussions, and team camaraderie through ongoing coaching and open dialogue. **Project Management:** Oversee multiple implementation projects simultaneously, serving as the technical focal point. Manage team project plans, timelines, and scoped hours. Review and approve implementation conclusions (handoff to live) to ensure customer expectations are met. Identify and escalate project risks and issues to CS leadership and cross-functional teams (Sales, Product, R&D). **Customer Engagement:** Serve as the escalation point for customers and team members on complex issues, providing guidance and support on calls. Conduct status meetings with customers and provide detailed project updates. Maintain a small portfolio of 2-4 customers to stay current with product updates. **Cross-Functional Collaboration & Process Improvement:** Collaborate with sales, live team, and product teams to continuously improve the customer journey. Provide feedback to product teams on customer needs and potential enhancements. Contribute to the Product expert group. Give feedback to pre-sales on implementation scoping documents. Continuously improve implementation processes, playbooks, and subprocesses. **Requirements:** - 5+ years of industry experience and/or 1+ years at Datarails, ideally in a customer-facing role; ability to operate independently and work with management to improve organizational operations - History of building and maintaining strong collegial relationships, knowledge-sharing, and mentorship; preference for experience as an onboarding buddy for new hires - Strong communication skills; ability to navigate difficult conversations with ease and raise red flags/ask questions with customers and team members - Strong customer skills; prepared to serve as escalation point and take point on challenging implementations - In-depth understanding of Datarails' products, sales, and processes with demonstrated track record of success in current role - Strong relationships with key internal stakeholders and deep understanding of the company's customer base

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