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 is growing fast, and our customers count on us to help them see value quickly.

As an Implementation Specialist, you’ll serve as a trusted advisor, guiding organizations through onboarding, connecting Cloverleaf to their systems, and aligning every implementation to measurable outcomes.

You’ll partner with HR, Learning, and Talent teams to turn goals into clear milestones like faster time-to-value, higher adoption, and stronger engagement.

You’ll blend consultative partnership with smart, tech-enabled execution, using AI and automation to streamline delivery and scale what works, from automating data prep to simplifying client communications.

You’ll also support pre-sale scoping alongside Sales and Customer Success, managing a balanced portfolio of onboarding projects that deliver consistency, clarity, and impact.

Ultimately, your work will shape how customers experience Cloverleaf: turning insights into action and helping thousands of employees collaborate, communicate, and grow together.

What You'll Do

You’ll be the trusted partner and strategic driver helping customers reach their “aha” moment faster, ensuring onboarding feels both personal and effortless.

• Lead and manage customer onboarding projects from kickoff to go-live, ensuring clarity, alignment, and proactive communication throughout.
• Build trusted relationships with client stakeholders, connecting Cloverleaf’s insights and integrations to their business goals and success metrics.
• Translate customer needs into actionable configurations, workflows, and integrations that accelerate adoption and measurable outcomes.
• Leverage automation tools and AI-enabled processes to streamline delivery and scale best practices without losing the human touch.
• Partner with Customer Success Managers to drive momentum, engagement, and long-term success beyond onboarding.
• Collaborate cross-functionally with Product, Support, and Sales to capture feedback, identify improvement opportunities, and refine implementation playbooks.
• Track and report on key onboarding KPIs, such as time-to-first-value and adoption milestones, to inform data-driven decisions.
• Contribute to internal documentation, automation frameworks, and enablement resources that elevate both the customer and team experience.

Who You Are

You’re a connector, problem-solver, and enabler, equally comfortable discussing business outcomes with HR leaders and refining implementation details with technical teams. You love helping others succeed, and you find joy in making complex processes feel simple and scalable.

You’ll love this role if you:

• Are naturally curious and thrive in consultative partnerships where you can ask great questions and co-create solutions.
• Believe technology and AI can enhance human connection and help teams work smarter.
• Have a bias for action: you don’t wait for perfect information before moving things forward.
• Know how to keep projects on track and stakeholders aligned, even in complex environments.
• Enjoy improving processes, finding ways to automate the repeatable, and elevate the meaningful.
• Thrive in cross-functional collaboration and bring both structure and creativity to your work.

What You Bring

• 3+ years of experience in SaaS implementation, onboarding, or technical project management
• Strong project management and stakeholder communication skills
• Proven ability to align technology implementations to business outcomes
• Familiarity with SaaS integrations (APIs, data imports, workflow automation tools like Zapier or Make)
• Comfort using or learning AI-enabled tools to enhance workflows
• Experience collaborating with Customer Success, Product, and Sales teams

Bonus points for:

• 5+ years total experience, ideally in HR tech, L&D tech, or Performance Enablement tech
• Background working with HR, L&D, or organizational development teams
• Bachelor’s degree in business, communications, management, or information systems, or 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 $57,000 to $92,000. 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.

We know implementation work takes equal parts empathy, curiosity, and precision — and we’re looking for someone who’s done it before and loves doing it well.

If that sounds like you, let’s talk.