Director of Product

Sketchy; United States; Remote; USD 225,000 - 250,000; Full time

Job summary

A leading company in educational technology, Sketchy, is searching for a Director of Product. This role involves driving product strategy, managing cross-functional teams, and enhancing learner experiences through innovative solutions. Ideal candidates have extensive experience in product management and a strong understanding of edtech needs. This position offers a remote-first work environment with competitive salary and benefits.

Benefits

Flexible Time Off

Equity

401(k) Matching

Team Events

Annual Work Anniversary Stipend

Wifi & Phone Reimbursement

Disability Insurance

Qualifications

• Minimum 8 years of experience in product management roles.
• 2 years managing PMs or designers preferred.
• Strong knowledge in education technology required.

Responsibilities

• Drive product direction with a team of PMs, designers, and analysts.
• Manage roadmap planning aligned to strategic objectives.
• Ensure execution of product innovation and user research.

Skills

Product Management

Team Leadership

Educational Technology

Strategic Planning

User Research

Education

8+ years in product roles

Job description

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At Sketchy, we’re transforming how students learn by turning complex topics into unforgettable visual journeys. Our mission? To help students master challenging material, achieve higher scores, and bring their knowledge to life through interactive cases. Through a combination of art, science, and cutting-edge technology, we enable students to learn, retain, and practice—effortlessly. The short version? We’re here to make better clinicians.

Position Summary

Sketchy is building the future of clinical education through storytelling, AI, and immersive learning. As Director of Product, you’ll take ownership of our cross-functional product squads and help transform strategic ideas into market-shaping execution, reporting directly to the CEO.

This is a role for a doer and a connector, someone who sees around corners, operates with rigor, and translates vision into results. You’ll be responsible for driving our most critical initiatives forward, managing a team of PMs, designers, and a product analyst, and ensuring that our roadmap stays tightly aligned with learner and educator needs.

We’re looking for someone who brings structure, creates momentum, and fosters accountability without slowing the team down. Experience collaborating with content teams is a plus, especially in aligning curriculum and product strategy to deliver a cohesive learner experience. Ideal candidates will have a deep knowledge of education technology and a strong instinct for how products can meet the emotional, cognitive, and practical needs of medical learners and educators alike.

Sketchy is hiring remote employees in these select US states: California, Colorado, Florida, Illinois, Massachusetts, Michigan, New Jersey, New York, Pennsylvania, Texas, Utah, and Washington! Don’t see your state? No worries! Sketchy is always on the lookout for the best talent out there—wherever there is!

Responsibilities

• Management and delivery leadership for our squads, with direct oversight of PMs, Designers, Research and Product Analytics.
• Roadmap planning facilitation aligned to our 2-week sprint cycles—ensuring teams are focused on the highest-leverage work.
• Execution of innovation bets identified by the C-team and advisory council—owning the translation from idea to tactical delivery.
• Product development—working closely with research, content, marketing, and sales to deeply understand what learners and educators are struggling with, and designing solutions that are delightful, and effective.
• Metrics ownership of product health and the connection to business outcomes—including engagement, satisfaction, conversion, and retention across the learner and educator lifecycle.
• Team coaching and operational rhythm building, instilling the processes and feedback loops that support consistent execution and continuous improvement.
• User research strategy and execution—driving qualitative research that generates actionable insights
• Establishing rapid prototyping practices that enable squads to quickly validate ideas, shorten feedback loops, and reduce time to insight—especially for AI-driven experiences.

What We’re Looking For

• 8+ years in product roles, with at least 2 years managing PMs or designers
• A strong foundation in edtech or medical education, with direct exposure to learner and educator workflows, motivations, and pain points
• Excellent judgment in making tradeoffs between speed, scope, and user impact
• An AI-first mindset with a deep curiosity on how to push the boundaries with technology
• Experience working in squad-based orgs with fast decision cycles and cross-functional accountability
• Experience collaborating with content teams is a plus
• You are equally fluent with strategic abstraction and operational detail
• You thrive in a lean executive structure, balancing strategic inputs with executional ownership.
• You lead with clarity, accountability, and trust, creating the conditions for teams to operate with focus and autonomy.
• You think operationally, balancing ambition with realism and ensuring initiatives are scoped to ship and learn quickly.
• You understand the learner’s world—and the educator’s—and you know how to build products that respect their time, intelligence, and goals.
• You thrive in a flat, nimble structure—collaborating directly with the CEO and C-team to turn strategy into execution.

If you don’t have 100% of the bullets listed above, that’s okay! We know there are no perfect applicants. If you are passionate about making a meaningful difference, we want to hear from you! Learn more about Sketchy’s culture at sketchy.com/careers.

Salary Range

$225,000-$250,000 plus bonus and equity

• Remote First - Make a difference from wherever you want to work.
• Flexible Time Off - We work smarter, not harder. No accruals, just real work-life balance.
• Equity - From day one, you’ll have a stake in our future growth.
• 401(k) - We support your financial future with up to 5% matching.
• Team Events - Get to know the team with virtual events, monthly outings, company retreats, and more.
• Annual Work Anniversary Stipend
• Monthly Wifi & Phone Reimbursement
• Short Term & Long Term Disability

Sketchy Group LLC is an Equal Opportunity Employer. All applicants will receive consideration without discrimination on the basis of race, religion, color, sex, age, sexual orientation, marital status, national origin, disability, or any other basis prohibited by applicable law.

Seniority level

• Seniority level

  Director

Employment type

• Employment type

  Full-time

Job function

• Job function

  Product Management and Marketing

• Industries

  Higher Education, E-Learning Providers, and Education

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