Director of Product & Design, Skillshare
Online learning community for creatives
Be an early applicant
Online learning community for creatives
501-1000 employees
Be an early applicant
501-1000 employees
Company mission
To build a platform that gives everyone the opportunity to be creative.
Role
Who you are
- If you bring deep experience in SaaS strategy for 2 sided marketplaces, pricing and packaging, and scaling product teams — while still being willing to get into the weeds to drive user delight — this role is for you
- You have 7+ years of product leadership experience in SaaS, with proven impact in pricing/packaging, growth strategy, and user engagement
- You’ve led cross-functional product and design teams, balancing strategic direction with hands-on support
- You’re experienced in shaping both product strategy and design systems, with a strong eye for quality and detail
- You thrive on mentoring and scaling talent, empowering others to do their best work
- You’re a data-informed decision-maker, equally comfortable with research insights, user testing, and performance metrics
- You’re a strong communicator who can influence across functions and levels, from execs to ICs
- You balance visionary thinking with tactical execution, knowing when to zoom out and when to dig in
- Bonus points for experience in ed tech, marketplaces, or content discovery, though not required
- If you're ready to take on strategic design leadership and make a lasting impact, we’d love to hear from you
- If you’re passionate about what we do but don’t check every single box, we’d still love to hear from you — curiosity and growth matter most to us
What the job involves
- At Skillshare, we’re building a global community of curious, lifelong learners — and we’re looking for a Director of Product & Design to drive the next chapter of our platform’s growth
- As our Director of Product & Design, you’ll set the vision for our product strategy and design direction, while also managing the teams that bring those ideas to life
- You’ll be responsible for shaping the future of Skillshare’s experiences for students and teachers, ensuring that what we build today ladders up to what’s next for our business
- You’ll also manage a talented product team, helping them grow while elevating product & design quality across the org
- Define Product & Product Design Strategy: Lead the development of a cohesive product vision that balances user needs with business priorities, including pricing, packaging, activation, engagement, and retention strategies
- Drive High-Impact Execution: Oversee delivery of critical initiatives, from platform evolution to SaaS growth levers, ensuring quality, speed, and alignment with company goals
- Manage & Grow Teams: Lead and mentor product managers and designers, creating a culture of collaboration, accountability, and continuous improvement
- Shape Product & Design Direction: Guide the product & design strategy for our core experiences, elevating usability, accessibility, and craft across the platform
- Collaborate Cross-Functionally: Partner with engineering, content, data ,finance, and marketing leaders to align roadmaps, optimize impact, and ensure cohesive end-to-end experiences
- Stay Hands-On When Needed: Jump into the details — whether refining requirements, reviewing flows, or supporting a design sprint — to keep momentum moving
- Look Around Corners: Anticipate emerging opportunities and risks, helping the company prioritize and prepare for what’s ahead
- Our team: We have a passionate, creative, and innovative team that is a lot of fun to work with
- Our mission: We’re doing work that matters – connecting lifelong learners around the world and empowering them to pursue their creativity
- Impact: Your designs will directly shape the experience of millions of students and teachers on Skillshare
- Your growth: You’ll have opportunities to take ownership, collaborate across disciplines, and expand your design expertise
Our take
Skillshare operates an online learning platform where members can access a range of creativity-focussed classes and courses. Targeting skills such as illustration, design, photography and video editing, the company allows individuals and teams to build and improve their skills whether for professional development or just for fun.
On the other side, Skillshare empowers professional creatives to share their skills, tips and tricks to earn money and build their communities. Top earners on the platform make upwards of $100,000 a year, as well as gaining access to a broad range of people who may be interested in their freelance services.
With more than 30,000 classes active on the platform, and over 10 million registered learners, Skillshare has proven its value and carved a strong foothold in the e-learning market. Moving forwards, it plans to continue enhancing its offering - recent additions include Badges, Class Certificates, and Learning Paths - as it further broadens its reach.
Freddie
Company Specialist at Welcome to the Jungle
Insights
Company
Funding (last 2 of 9 rounds)
Nov 2022
$78.4m
SERIES E
Apr 2022
$5m
LATE VC
Total funding: $200.2m
Company benefits
- Excellent medical, dental, and vision plans
- Unlimited vacation (with a required minimum)
- Paid sabbaticals for tenured employees (every three years, starting at your 3-year anniversary)
- Learning and creativity stipend
- Wellness stipend
- Stipend for setting yourself up for success at home (think: desk, headphones, ergonomic chair)
- Monthly internet reimbursement
- Support for utilizing coworking spaces, including a partnership with Industrious
- Ongoing Emotional Fitness workshops with Coa
Company HQ
Flatiron District, New York, NY
Leadership
Malcolm Ong
(Co-founder)Co-founded Skillshare in 2010 with Michael Karnjanaprakorn, who has since left the company. Currently Co-founder and CPO at Terminal 3. In the past, worked as Senior VP of Product at South China Morning Post.
Matt Cooper
(CEO, not founder)Member of the Board Of Directors at YunoJuno. Former Advisor and Board Observer at PowerToFly, SVP of Corporate Development at ScribbleLive, and CEO of Visually.
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