Learning and Development Lead

Job Position: Learning & Development Lead

Work Arrangement: Remote (LATAM and EA based preferred)

Job Type: Full-time, Independent Contractor

Work Schedule: Monday to Friday 40 hours per week-9:00 am to 5:00 pm EST business hours

About Pearl Talent

Pearl connects the top 1% of global talent with high-growth startups across the US and EU. We've bootstrapped our company to millions in revenue and are adding ~$400K in new annualized revenue each month. Our clients—backed by top-tier VC firms like Sequoia, a16z, Founders Fund, and Y Combinator—are building the future across industries like fintech, SaaS, healthcare, and legaltech.

Founded by a 3x entrepreneur from the Philippines, Pearl is deeply committed to creating economic mobility for world-class international talent. We believe that while opportunity isn't equally distributed, ambition is—and we're here to bridge that gap.

Why Work with Us?

At Pearl, you'll be joining a team on a mission: to give brilliant global operators the opportunity to earn more, grow faster, and work with the world's best founders. We offer a fully remote environment, regular team retreats, and a high-performance culture rooted in transparency, ownership, and constant learning.

You'll work directly with top-tier talent and fast-scaling companies while shaping the way operational excellence is built, scaled, and delivered at global startups.

Hear why we exist, what we believe in, and who we're building for: Watch here

Role Overview

We're hiring a Learning & Development Lead to coach and level up the 100+ operators we've placed across high-growth startups. You'll design scalable learning systems, lead personalized and group coaching programs, and integrate AI-driven tools into our workflows to improve productivity. You'll collaborate closely with account managers and client success teams to track performance and deliver impact across legal, financial, SaaS, and healthcare roles.

This is a high-ownership role for someone who's obsessed with capability building, scalable systems, and using technology to drive real-world results.

Your Impact

Your work will directly influence how effective and indispensable our talent is to clients. Through strategic coaching, AI integrations, and ongoing upskilling, you'll improve efficiency, client satisfaction, and long-term retention. You'll also be a key player in shaping how we measure talent performance and deliver learning at scale.

Purpose of Your Role

To ensure that Pearl's placed talent continues to perform at the highest level—while designing scalable, AI-augmented learning programs that allow us to grow without compromising quality. You'll empower talent to be more strategic, more productive, and more valuable to the startups they support.

Key Metrics You Own

• Average monthly rating of 8/10 or higher from talent on coaching sessions
• 70%+ of talent actively using AI tools in their daily workflows
• Quarterly development reports delivered with insights and recommendations
• Documented improvements in client feedback on talent performance
• All training and documentation delivered on time and to standard

Key Responsibilities
Coaching & Capability Building

• Design and lead coaching initiatives: 1:1 coaching, group sessions, async materials
• Customize learning content based on vertical (SaaS, legal, healthcare, finance)
• Collaborate with account managers to address individual or team performance gaps
• Track and report coaching effectiveness using qualitative and quantitative KPIs

AI Enablement

• Build AI toolkits, workflow automations, and tutorials for use across client accounts
• Train talent on integrating AI into their workstreams for productivity and output gains
• Support internal rollout of AI automation in hiring, onboarding, and client ops

Learning Systems & Documentation

• Develop modular, scalable learning paths for different roles and industries
• Create a knowledge base of best practices, SOPs, and performance standards
• Partner with internal teams to improve onboarding and continuous learning systems

Internal Enablement & Support

• Support recruitment teams in assessing coachability and growth potential during hiring
• Partner with success managers to ensure ongoing development aligns with client goals
• Contribute to a performance feedback loop that improves how we measure, coach, and grow our people

Requirements

Must-Haves

• Proven experience in a Learning & Development, Coaching, or Training leadership role
• Exceptional communication skills, with the ability to coach across experience levels
• Strong systems thinker—you can build scalable programs that deliver consistency at scale
• Familiarity with AI tools (e.g., ChatGPT, Notion AI, Zapier, etc.) and interest in workflow automation
• Experience working with or supporting global teams in a remote-first environment
• Organized, self-directed, and able to manage multiple priorities simultaneously

Nice-to-Haves

• Previous experience supporting teams in legal, finance, healthcare, or SaaS environments
• Experience designing asynchronous learning systems or microlearning content
• Background in performance coaching, behavior change, or adult learning theory

Benefits

• Potential for profit share based on performance
• Fully remote, forever
• Annual team retreat
• Unlimited PTO

Our Recruitment Process

1. Application
2. Screening
3. Skills Assessment
4. Topgrading Interview
5. Final Interview
6. Job Offer
7. Onboarding

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