Customer Success Manager

Who We Are Cloverleaf connects siloed HR data and team collaboration tools to deliver personalized, actionable development at scale. Built on validated assessments like DISC, Enneagram, CliftonStrengths, and 16 Types, plus real-time insights, it strengthens team alignment, communication, and performance for over 30,000 teams worldwide. Cloverleaf is on a mission to unleash people to do their best work. We believe that people should be passionate and engaged with the work that they are doing, starting with our own team. The Role Cloverleaf transforms how teams understand themselves and each other — and customer success is where that impact grows. As a Customer Success Manager, you’ll serve as a strategic partner to HR, Learning & Development, and People leaders , helping them deeply embed Cloverleaf into their most important talent initiatives and business processes. Because this role spans enterprise, mid-market, and coach/partner accounts, we’re seeking someone with 3–5 years of B2B SaaS customer success or account management experience who can own the strategic customer journey focusing on adoption and expansion, and operate with confidence across diverse customer environments. This is far more than a relationship management role. You’ll think like a consultant and approach every account with a land-and-expand mindset ; driving the kind of deep, durable adoption that naturally opens doors to new use cases, new stakeholder groups, and revenue growth. What You'll Do You’ll be the trusted strategic advisor helping customers get maximum value from Cloverleaf — and grow their partnership over time. Own a diverse book of business across enterprise, mid-market, and coach/partner segments, serving as the primary point of contact and trusted advisor throughout the customer lifecycle Build deep, multi-threaded relationships with HR leaders, L&D professionals, People Operations teams, and executive sponsors to understand their business priorities and organizational challenges Act as a strategic consultant who maps Cloverleaf’s capabilities to customers’ existing workflows from onboarding programs and leadership development tracks to manager enablement, performance cycles, and engagement strategies Develop and execute tailored success plans anchored to measurable business outcomes: reduced time-to-productivity, stronger collaboration scores, improved 360 feedback results, and more Drive land-and-expand growth within each account: start with deep adoption in an initial team or use case, then leverage that success to expand into new business units, stakeholder groups, and initiatives Proactively identify expansion opportunities by connecting evolving customer needs to additional Cloverleaf use cases, positioning the platform as an integral part of the customer’s people strategy, not a standalone tool Monitor customer health metrics and usage data to identify risk signals and growth opportunities, using AI-powered tools and data-driven insights to prioritize outreach and deliver timely interventions Lead strategic business reviews and executive check-ins that go beyond usage reporting to demonstrate tangible business impact, surface recommendations, and plant seeds for expansion Collaborate cross-functionally with Implementation Specialists, Support, Sales, and Product to ensure seamless handoffs, resolve issues quickly, and relay customer feedback that shapes the roadmap Track and report on key CS metrics including Net Revenue Retention, logo retention, NPS, adoption milestones, and health scores — using data to drive strategy and demonstrate impact Who You Are You’re consultative, curious, and energized by helping customers succeed. You can zoom out to understand a customer’s business strategy and zoom in to solve the adoption challenge in front of you. You love building relationships, connecting the dots, and making a real difference in how organizations develop their people. You’ll thrive in this role if you: Think and communicate like