Our Company

Medicine is evolving faster than ever, and so is the way clinicians learn. At Sketchy, we partner with institutions, health systems, and learners to expand access to high-quality clinical education that prepares clinicians for what’s next.

Our mission is to help clinicians build the readiness and agility needed to deliver better decisions, stronger patient connections, and higher-quality care in a world shaped by AI and precision medicine.

We’re reimagining how clinical reasoning, communication, and other core competencies are developed, empowering every learner to adapt, grow, and lead in the future of healthcare.

Position Summary

Sketchy is building the future of clinical education through storytelling, AI innovation, and immersive learning. As Principal Product Manager, you will own high-impact feature development and turn strategy into measurable outcomes at startup speed. You will report directly to the Director of Product.

You’ll thrive here if you:

• Excel in fast-moving environments where ambiguity turns into opportunity.
  
  
• Are fluent in using AI for both product efficiency and product innovation.
  
  
• Set ambitious goals, track them relentlessly, and pivot fast when data points to a better approach.

In this role, you’ll partner closely with engineers, designers, and content experts to deliver solutions that meet the needs of medical learners and educators, while while shaping how AI enhances the way future clinicians think, learn, and practice.

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!  

Responsibilities:

• Align with the leadership team on product vision and strategy, and own prioritization and execution for your section of the roadmap.
• Lead development of generative AI–driven features that deliver adaptive learning experiences, rich reasoning feedback, and measurable gains in learner performance.
• Translate strategic goals into clear, actionable product requirements and user stories that guide development.
• Work with engineering, design, research, content, marketing, and sales to identify needs, design impactful solutions, and coordinate execution so product initiatives are delivered smoothly and effectively
• Partner with engineering to understand technical trade-offs and constraints, and make informed decisions that balance quality, speed, and impact.
• Lead AI-assisted experimentation and rapid prototyping, using data and real user behavior to iterate quickly, validate value, and reduce time-to-learn for the team.
• Monitor and analyze product performance across the product portfolio, using data-driven insights to optimize existing products and inform future product development. 
• Communicate the product goals, priorities, and releases for the entire product group to internal and external stakeholders. 
• Stay up-to-date on industry trends and emerging technologies, applying relevant knowledge to enhance our product offerings across the group. 
• Champion a build-measure-learn product philosophy across the organization, fostering a culture of thoughtful, iterative, and data-driven product decisions.

What We’re Looking For:

• 8+ years of experience in product management, ideally in fast-moving startup environments or high-growth edtech/healthtech companies.
• Demonstrated success operating in executing product strategies and delivering high-quality products and features to market.across 0 to 1 and 1 to 10 product phases.Experience building or integrating AI-powered features to deliver measurable user impact.
• Skilled at analyzing data to uncover insights, guide decisions, and track measurable outcomes.
• Technically fluent, able to grasp complex engineering concepts and translate them clearly for diverse audiences.
• Strong project management skills, with the ability to juggle multiple priorities and meet tight deadlines in coordination with cross-functional teams.
• Experience using AI tools to improve PM velocity, such as accelerating analysis, ideation, experimentation, or feature generation.
• Exceptional communication and interpersonal skills, with experience working in and leading cross-functional teams. 
• Proactive and adaptable with an entrepreneurial mindset and passion for learning.

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. 

Who you will work closely with

Anne Rynearson- Director of Product
Ben Muller - Chief Content Officer
Vlad Iacob - Director of Engineering

Salary Range

$195,000 to $215,000 annual salary plus a performance-based annual bonus and stock options

Our Perks 

• 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. 
• Annual Company Retreat in Cool Places
• Flexible Time Off 
• 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.