Edtech.com's Summary

Sketchy is hiring a Director of Product. This role involves taking charge of cross-functional product squads, transforming strategic ideas into execution, and managing a team to ensure alignment with learner and educator needs. The director will drive critical initiatives, foster accountability, and enhance the product experience for medical learners and educators.

Highlights

Leadership of product squads with direct oversight of PMs, Designers, Research, and Product Analytics.
Facilitating roadmap planning aligned to 2-week sprint cycles.
Executing innovative ideas and ensuring tactical delivery.
Metrics ownership for product health related to business outcomes.
Over 8 years of experience in product roles, with at least 2 years managing PMs or designers.
Experience in edtech or medical education preferred.
Salary range is $225,000-$250,000 annually.
Benefits include remote work flexibility, 100% individual health coverage, equity, and more.

Director of Product Full Description

Director of Product

Our Company

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.

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. Ideal candidates will have a deep knowledge of education technology and a deep 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
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

Our Perks

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.
100% Individual Health Coverage - We got you covered!
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.

The pay range for this role is:

225,000 - 250,000 USD per year (Remote (United States))

Original Job Description

Director of Product

Our Company

Position Summary

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
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.

Salary Range

$225,000-$250,000

Our Perks

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.
100% Individual Health Coverage - We got you covered!
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

The pay range for this role is:

225,000 - 250,000 USD per year (Remote (United States))

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