Technical Implementation Specialist

Cloverleaf • Cincinnati, OH

72d • $60,000 - $97,000

About The Position

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.

Requirements

• 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

Nice To Haves

• 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

Responsibilities

• 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

Benefits

• 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!)

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Number of Employees: 11-50 employees