Learning & Development Team Lead (Operations)

Why Clipboard Exists:

We exist to lift as many people up the socioeconomic ladder as possible. We dramatically improve lives by letting professionals turn extra time and ambition into career growth and financial opportunity. We achieve this with our app-based marketplace that connects workplaces and professionals, allowing professionals to book on-demand shifts and workplaces to access on-demand talent.

About Clipboard:

Clipboard is a fast-growing Series C marketplace. We are a leader in our Long Term Care vertical and are expanding into several others (Dental Offices, Schools, etc). 
We are a YC Top Company with a global, remote team of 700+ people. We have been profitable since 2022, and fill millions of shifts annually at partner workplaces across the US, where tens of thousands of professionals work with us every year.
We are looking for your help to keep growing so we can serve more professionals and workplaces.
To learn more about us, take a look at our website here.

This Role is Open to candidates in South America, The Caribbean and Africa.

We operate 24/7 and follow a rotating roster

Estimated annual compensation: From $25 000 USD annually. Each candidate’s compensation offer within this range will be based on multiple factors including, but not limited to, relevant education, qualifications, certifications, experience, and geographic location. 

About the Role:

Worker Operations is the team that owns end-to-end operations and support for the supply-side (the workers) of our marketplace. We are over 270 team members who serve the 60,000+ (and growing) active professionals on our marketplace. 

We’re hiring a Learning & Development Lead to turn core values into real behavior quickly, consistently, and at scale. You’ll lead a team that builds coaching and training programs to elevate performance in a fast-paced, frontline environment. As a solution software company, the vast majority of the time, the first person a customer speaks with via phone or chat is a support associate. Your work will shape how they show up and ensure those first impressions reflect our values.

Your Team Will Teach:

Empathy as default
Judgment as instinct
Excellence as baseline

What You & Your Team Will Own:

• Build onboarding, upskilling, and coaching programs that make our values measurable and repeatable starting with Worker Support and expanding to leadership.
• Develop agents and managers to deliver world-class service rooted in empathy, curiosity, and critical thinking.
• Operationalize speed, ownership, and feedback into everyday team behavior.
• Design coaching systems that drive real-time improvement and reinforce excellence.
• Build feedback loops that surface gaps early, test solutions fast, and measure impact with precision.
• Raise the bar for how people show up, not just what they know.

What You Bring:

• Several years in L&D, enablement, or adjacent fields, including 2+ years managing a team
• Proven track record of programs that cut ramp time, improve outcomes, or shift day-to-day performance
• Clear, decision-grade written communication
• A portfolio of systems or programs you’ve built, led, and improved based on feedback
• Comfort operating in fast-paced, high-autonomy environments with strong feedback loops
• A mindset grounded in data, first-hand observation, and real-world behavior change not theory

Bonus: Experience with customer support or contact center teams

This Role Is Not for You If You:

• Think training is about information, not performance
• Avoid hard conversations about underperformance
• Prefer secondhand insights over real customer interactions
• Wait for direction instead of finding and owning problems

What We Offer:

Competitive compensation
100% remote work
Unlimited vacation