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 implementation is where that impact begins. As the Technical Implementation Specialist, you’ll guide customers through a smooth, supportive onboarding journey, helping HR, Talent Development, and business leaders understand what’s possible and translating technical concepts into clear, confident next steps.

Because this is our first dedicated Implementation Specialist, we’re seeking someone with 3+ years of full-time technical implementation experience who has led customer onboardings end-to-end and can operate confidently without an existing playbook.

You’ll support environment setup, light integrations, and clean data preparation using CSV/Excel, partnering with Product and Engineering as needed. Equal parts relationship-builder and technical guide, you’ll make complex ideas feel simple, build trust quickly, and set customers up for early wins and long-term success.

This role is scoped for a mid-level technical specialist and does not require coding or custom integration development.

What You'll Do

You’ll be the trusted partner and strategic driver helping customers reach value fast and feel confident every step of the way.

• Lead onboarding projects from kickoff to go-live with proactive communication, clear expectations, and steady momentum
• Translate customer goals into actionable configurations, workflows, and next steps, making technical concepts simple and accessible for non-technical users
• Prepare, map, and validate customer data using CSV/Excel to ensure clean, accurate imports
• Support light integrations and collaborate with Engineering when deeper technical needs arise
• Leverage workflow automation and AI-enabled tools to streamline onboarding and scale what works
• Build trusted relationships with HR, Talent Development, and business leader stakeholders, listening deeply and serving as a consultative guide
• Partner closely with Customer Success Managers to maintain momentum, drive early adoption, and set customers up for long-term success
• Collaborate with Product, Support, and Sales to share insights, resolve issues, and refine implementation playbooks
• Track key onboarding metrics such as time-to-first-value and adoption milestones, using data to drive continuous improvement
• Contribute to clear internal documentation, templates, and enablement resources that elevate the onboarding experience

Who You Are

You’re curious, structured, and energized by helping customers solve problems. You can zoom out to understand business outcomes and zoom in to troubleshoot technical details. You love clarity, clean processes, and making people’s lives easier.

You’ll thrive in this role if you:

• Can context-switch gracefully between customer calls, data tasks, and technical troubleshooting
• Are naturally consultative and ask thoughtful questions that uncover customer needs
• Enjoy using technology and AI tools to simplify work and make processes more efficient
• Stay calm and adaptable when plans shift (they will!), and know how to keep projects on track
• Love creating order out of chaos: templates, playbooks, workflows, automation
• Work well across teams and communicate clearly with both technical and non-technical audiences

What You Bring

Required

• 3+ years of full-time experience in SaaS implementation or onboarding
• Proven ability to lead customer implementations end-to-end with minimal ramp-up
• Strong project management and stakeholder communication skills
• Ability to translate technical concepts into clear, accessible guidance for non-technical users
• Comfort preparing and validating customer data using CSV/Excel
• Familiarity with workflow automation tools like Zapier, Make, or Workato
• Experience using or learning AI tools such as ChatGPT, Anthropic, and/or Perplexity — with real examples of how you’ve used them to improve your work
• Comfort with common tools in the Customer Success tech stack (Salesforce, HubSpot, Slack, Notion, ClientSuccess, Vitally)
• Strong troubleshooting skills across customer environments, data, and configuration

Preferred

• Experience with BI and reporting tools (Omni, Tableau, Looker, Power BI, Metabase)
• Familiarity with REST APIs and JSON formats
• Awareness of SSO concepts (SAML, OIDC) and ability to collaborate with Engineering on customer setup
• Experience in HR tech, learning tech, or performance enablement environments
• Bachelor’s degree in business, communication, management, information systems, or a related field

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 4% match with immediate vesting
• Truly values-driven team (ask us about it!)

Cloverleaf is committed to pay transparency and equitable compensation practices. The expected salary range for this role is $60,000 to $97,000. 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.