Head of Learning and Development at Extern (W17)
$100K - $115K  •  
Professional Experience Anytime, Anywhere.
US / Remote (US)
Full-time
US citizen/visa only
6+ years
About Extern

Extern wants to help anyone, starting with students, launch their career by getting access to professional experiences in the era of generative AI. To achieve this mission, we pioneered a new form of professional experience called the remote "Externship" that scales the management of top performing GenZers on real company projects.

Our platform recruits cohorts of students from around the globe to tackle strategic & analytical problems across customer discovery, market insights, R&D, analytics, and product strategy. Training and guidance is provided by subject matter experts, and our automated system and support team removes the resource drain on employees and HR so that externs receive the assistance they need.

Extern launched Remote Externships in 2019 and has helped thousands of students from underserved backgrounds gain professional experience from Fortune 1000s such as PwC, Home Depot, Meta, HSBC, HP, Pfizer, Hugo Boss, Beats by Dre, National Geographic, The Nature Conservancy, Greenpeace as well as numerous growth stage companies. Nearly 80% of students are from underrepresented backgrounds, and we see 1 in 2 students land Fortune 1000 jobs within 6 months of completing an externship. Backers include YCombinator, Foundation Capital, Learn Capital, University Ventures, and Launch Fund.

About the role
Skills: Search

About Extern

The age of higher education is ending. Employers no longer hire based on degrees — they hire based on skills and experience. But in today’s market, getting real experience is nearly impossible. Internships are disappearing, entry-level jobs demand years of experience, and AI is reshaping the workforce faster than universities can keep up.

At Extern, we’re building the world’s first subscription to professional experience where learning never stops and every experience moves you forward. Through Externships — hands-on remote projects in AI, product strategy, data, finance, and more — students and career switchers learn by doing while working with top companies. 

Our platform makes real-world experience accessible to anyone, anywhere by providing companies with a less burdensome way to engage young talent than high touch internships programs. At Extern, we are helping college students and early career professionals not just land an internship or job, but continuously upskill and stay ahead in their careers through real-world experience.

Our Impact

  • Strong Growth: Over 35,000 learners gained real-world experience last year (300% YoY growth). Our new B2C subscription model launched in late 2024 and is already driving fast adoption and strong unit economics.
  • Top-Tier Externship Partners: PwC, Home Depot, Beats by Dre (Apple), HP, Expedia, Epic Games, Unity, Macquarie, Pfizer, and National Geographic trust Extern to connect them with emerging talent.
  • Career Outcomes That Matter: 70% of externs land internships or jobs within six months.
  • Strong Backers: We’re funded by Y Combinator, Jason Calacanis, Foundation Capital, Learn Capital, and University Ventures — who all believe in our vision to replace outdated education models with continuous, experience-based learning.

If you’re excited about shaping the future of education and work—and want to drive growth at startup speed — read on.

The Role

You will own Learning Design as a product: define inventory strategy, set clear content standards, architect a modular externship framework, and run rapid, data-driven experiments, to lift user engagement and program-completion rates. You’ll lead a high-impact team of content specialists and learning designers, ensuring every externship is anchored in evidence-based instructional design, clear objectives, authentic assessment, and cognitive-load best practices, while running fast, data-informed experiments to boost completion rates and unlock early “wow” moments for every learner.

By embedding smart feedback loops and iterating quickly, you’ll ensure each experience delivers portfolio-worthy outcomes and real-world skill development. You’ll work shoulder-to-shoulder with Product, Engineering, and Growth to translate insights into shippable improvements that make learning stick. This role is ideal for someone who thrives in a scrappy, high-speed environment, and is energized by building systems that drive equity, access, and mission-driven impact..

What You’ll Do

1. Set Portfolio & Content Strategy

  • Develop a data-informed externship inventory roadmap that maps market demand, employer signals, and learner personas to quarterly activation / completion targets.
  • Define the modular architecture (templates, rubrics, reflection rituals) and success metrics that underpin the roadmap.
  • Identify and sequence the highest-impact externship improvements to accelerate early activation and raise overall project-completion rates.

2. Accelerate Production with AI & Automation

  • Build and maintain LLM prompt libraries and agent workflows that cut externship development time while delivering scalable, judgment-centric feedback.
  • Establish QA guardrails and dashboards for human-in-the-loop oversight, tracking accuracy, learner satisfaction, and engagement.
  • Transition successful prototypes from sandbox to production, documenting best practices for repeatable use across the portfolio.

3. Drive Continuous Experimentation & Improvement

  • Design and run weekly A/B or multivariate tests—on pacing, engagement, guidance, recognition, and feedback.
  • Analyse results and roll winning variants into the modular framework, updating templates and standards to drive sustained gains.
  • Publish experiment learnings and maintain a living backlog of hypotheses to ensure a steady optimisation cadence aligned with company KPIs.

4. Lead the Learning-Design Organization

  • Hire, coach, and develop a high-performing LD team; set OKRs and foster a culture of rapid, data-driven shipping.
  • Own LD operations in Notion—roadmaps, sprint boards, documentation—promoting transparency and tight alignment with Product, Engineering, and Growth.
  • Uphold a Deliverable Quality Index (DQI) through regular quality audits, learner-feedback loops, and stakeholder reviews.

Success in This Role Looks Like

  • Boosting Activation & Engagement: Optimize early-stage externship experiences so that new learners reach key “wow” moments faster, driving measurable lifts in activation, weekly engagement, and overall program-completion rates—while maintaining a friction-free, learner-first UX.
  • Scaling Externship Inventory & Demand: Implement a modular content strategy and AI-accelerated production pipeline that rapidly expands our portfolio of externships across high-demand disciplines—unlocking new market segments and sustaining growth in qualified user sign-ups**.**
  • Delivering a Signature Work Experience: Embed feedback, reflection rituals, and portfolio-ready deliverables that set Extern apart, deepening perceived value and pushing retention and renewal rates to new highs.

What We’re Looking For

Must-Have

  • 6+ years designing and shipping modular, outcomes-focused learning programs, with experience in consumer products.
  • Demonstrated success applying learning-science principles to drive activation and sustained engagement in digital learning products
  • Proven track record in lifting activation and sustaining engagement through data-driven experimentation, A/B testing, and rapid iteration.
  • Experience building or integrating LLM-powered content workflows.
  • Strategic thinking, entrepreneurial mindset and bias to action—able to move fast and deliver in an early-stage, resource-constrained environment.

Nice-to-Have

  • Hands-on experience with product analytics (e.g, MIxpanel, Amplitude) turning metrics into actionable roadmaps and backlog priorities.
  • Demonstrated ability to build and lead high-performing, distributed teams while running agile sprints and documentation in Notion.
  • Proven skill translating market demand and employer signals into a growth-oriented externship roadmap.
  • Background in learning science, pedagogy, cognitive psychology, product or instructional-systems design.

Why Join Extern?

This isn’t just another job—it’s an opportunity to redefine the way people build careers. If you’re a data-driven, growth-obsessed product leader who thrives on fast iteration, bold ideas, and real impact, this is your chance to build something that will change millions of lives.

Ready to help shape the future of experiential learning? Let’s build the new standard for lifelong career acceleration—together.

  • Mission-Driven Impact: Help thousands of students and career switchers access the real-world experience they need to succeed.
  • High-Growth Startup: Join a high-growth B2C startup in a breakout phase, backed by a nimble, focused team of ~30 full-time employees.
  • Product-Led Growth Focus: Build organic, self-sustaining acquisition loops instead of just “buying” users.
  • Ownership & Autonomy: Work in a high-ownership environment where decisions are made quickly, and you can see the impact of your work in real time.
  • World-Class Team & Backing: Join a mission-driven team, guided by investors like Y Combinator, Foundation Capital, and more.

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