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 astrategic 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 with3–5 years of B2B SaaS customer success or account management experiencewho 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 aland-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 businessacross 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 relationshipswith HR leaders, L&D professionals, People Operations teams, and executive sponsors to understand their business priorities and organizational challenges
Act as a strategic consultantwho 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 plansanchored to measurable business outcomes: reduced time-to-productivity, stronger collaboration scores, improved 360 feedback results, and more
Drive land-and-expand growthwithin 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 opportunitiesby 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 datato 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-insthat go beyond usage reporting to demonstrate tangible business impact, surface recommendations, and plant seeds for expansion
Collaborate cross-functionallywith 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 metricsincluding 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 thewhy 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 inCustomer Success, Account Management, or a strategic client-facing rolewithin B2B SaaS
Demonstrated ability tomanage and grow a portfolio of accountswith a land-and-expand approach owning renewals, identifying expansion opportunities, and driving revenue growth
Track record operating as a strategic partner with strongconsultative and strategic thinking skills, with the ability to understand a customer’s business landscape and influence stakeholders at all levels
Outstandingwritten and verbal communication skills, with a confident customer-facing presence in business reviews, executive conversations, and cross-functional sessions
Ability to interpret and act oncustomer health data, usage analytics, and AI-driven insights(e.g., predictive churn signals, engagement scoring) to drive proactive account strategies
Experience guiding customers throughorganizational change, including stakeholder alignment, user adoption strategies, and embedding new tools into established workflows
Comfort operating in afast-paced startup environmentwhere resourcefulness, adaptability, and ownership are essential

Preferred

Experience in aSaaS startup environment, with familiarity with the pace, ambiguity, and opportunity of high-growth companies
Background in or deep familiarity withHuman Resources, Talent Development, Learning & Development, or Organizational Development
Experience withbehavioral assessments or personality frameworks(e.g., DISC, Enneagram, CliftonStrengths, 16-Types) or coaching methodologies
Experience withCustomer Success Platforms(e.g., Vitally, ClientSuccess, Gainsight, ChurnZero) and CRM tools (Salesforce, HubSpot)
Exposure toAI applications in customer experience, including predictive analytics, automated engagement tools, or AI copilots
Experience usingdata 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!)

Cloverleaf remote jobs

Customer Success Manager