Technical Implementation Specialist

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Cloverleaf

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HR Tech • Enterprise • SaaS

Cloverleaf is a company focused on building thriving teams through Automated Coaching™. Founded in 2017, Cloverleaf provides a platform that offers personalized coaching insights directly to your email, calendar, and messaging apps. The company emphasizes values such as optimistic persistence, curiosity for growth, and being genuine teammates. Cloverleaf's solutions are designed to help people understand themselves and their teammates, fostering authentic relationships and enhancing team dynamics. The company has experienced significant growth since its inception, aiming to create inclusive cultures that boost productivity and fulfillment at work.

11 - 50 employees

👥 HR Tech

🏢 Enterprise

☁️ SaaS

📋 Description

• 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

🎯 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

🏖️ 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!)