Learning & Development Team Lead (Operations)

📍 This Role is Open to candidates in Canada, the United Kingdom, and non-UK European countries.

We operate 24/7 and follow a rotating roster

Estimated annual compensation: USD $50 000 to $90 000. 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