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 a strategic partner and can influence stakeholders from end users to C-suite executives
• Are naturally consultative and ask thoughtful questions that uncover what customers actually need to succeed
• Get energized by connecting business problems to platform solutions and articulating the why behind every recommendation
• Stay calm and adaptable when priorities shift (they will!), and know how to keep accounts on track through ambiguity
• Love using data, AI tools, and automation to work smarter and deliver more proactive, personalized outreach at scale
• Work well across teams and communicate clearly whether you're presenting in an executive QBR or collaborating with Product on a feature request

What You Bring
Required

• 3-5 years of experience in Customer Success, Account Management, or a strategic client-facing role within B2B SaaS
• Demonstrated ability to manage and grow a portfolio of accounts with a land-and-expand approach owning renewals, identifying expansion opportunities, and driving revenue growth
• Track record operating as a strategic partner with strong consultative and strategic thinking skills, with the ability to understand a customer's business landscape and influence stakeholders at all levels
• Outstanding written and verbal communication skills, with a confident customer-facing presence in business reviews, executive conversations, and cross-functional sessions
• Ability to interpret and act on customer health data, usage analytics, and AI-driven insights (e.g., predictive churn signals, engagement scoring) to drive proactive account strategies
• Experience guiding customers through organizational change, including stakeholder alignment, user adoption strategies, and embedding new tools into established workflows
  Comfort operating in a fast-paced startup environment where resourcefulness, adaptability, and ownership are essential

Preferred

• Experience in a SaaS startup environment, with familiarity with the pace, ambiguity, and opportunity of high-growth companies
• Background in or deep familiarity with Human Resources, Talent Development, Learning & Development, or Organizational Development
• Experience with behavioral assessments or personality frameworks (e.g., DISC, Enneagram, CliftonStrengths, 16-Types) or coaching methodologies
• Experience with Customer Success Platforms (e.g., Vitally, ClientSuccess, Gainsight, ChurnZero) and CRM tools (Salesforce, HubSpot)
• Exposure to AI applications in customer experience, including predictive analytics, automated engagement tools, or AI copilots
• Experience using data visualization or BI tools (e.g., Looker, Tableau, Sigma, Omni) to communicate customer outcomes and portfolio health

Success in this Role

• Cloverleaf is embedded into customers' core people processes, not treated as an add-on, resulting in deep, durable adoption that naturally creates expansion opportunities.
• Accounts consistently grow over time through a land-and-expand motion: initial deployments expand into new departments, use cases, and stakeholder groups, directly contributing to revenue growth.
• Customers can clearly articulate how Cloverleaf contributes to their business outcomes whether that's improved team performance, stronger leadership pipelines, faster onboarding, or higher engagement scores.
• Net Revenue Retention and logo retention targets are met or exceeded quarter over quarter, with expansion revenue driven by adoption-led growth rather than transactional upsells.
• Customers are engaged advocates who participate in case studies, referrals, and community activities because they see Cloverleaf as a true strategic partner.
• Customer health scores improve across the portfolio, with proactive interventions reducing churn risk before it escalates.
• Cross-functional collaboration is seamless, with clear feedback loops between CS, Product, Sales, and Implementation that improve the overall customer journey and inform product strategy

How We Unleash You to Do Your Best Work

• Flexible PTO and work schedule - with a minimum of 2 full weeks off per year
• Company paid full benefits, including medical, dental, vision, life insurance, and more!
• Recognition rewards and monthly stipend for wellness, technology, pet care, or student loans
• Macbook and home-office set-up stipend
• 401k benefits including a match with immediate vesting
• Truly values-driven team (ask us about it!)

The expected compensation (salary+bonus) range for this role is $70,000 to $110,000. Most new hires start toward the lower to middle end of this range, allowing for meaningful growth within the role as impact and performance increases over time. Final compensation is determined based on factors like experience and skills alignment and where the candidate is leveled within Cloverleaf's framework.

Department Customer Success Role Customer Success Locations Remote Remote status Fully Remote Employment type Full-time