About Skillshare
Skillshare is an online learning community whose mission is to connect curious, lifelong learners everywhere – and, in so doing, build a more creative, more generous, and more prosperous world. Today, our community has grown to millions of members who come to Skillshare to learn creative and entrepreneurial skills, network with peers, and even teach a class themselves. We are backed by OMERS Growth Equity, Union Square Ventures, Spark Capital, Amasia, Spero Ventures, and Burda Principal Investments. Skillshare is committed to building a diverse team that reflects a variety of backgrounds, perspectives, and skills. We work to ensure a consistent interview process, and inclusive work environment for all.
The Role
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. 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.
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.
What You’ll Do
- 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.
Why We’re Excited About 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.
Why You are Excited About Us
- 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.
- Flexibility: We believe that doing your best work means living a full life. That means different things for everyone, so we optimize for trust, invest to support remote teams, offer home office stipends and co-working spaces in multiple cities, have an unlimited vacation policy (with a required minimum!), and encourage work-life balance.
- 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.
- Benefits: We believe that doing your best work means living a full life. We support our team with unlimited PTO, gender-neutral parental leave, anniversary sabbaticals, and healthy stipends for creativity, learning, and personal wellness.
If you're ready to take on strategic design leadership and make a lasting impact, we’d love to hear from you.
At Skillshare, we believe creativity thrives in an inclusive environment. We’re excited to meet candidates from all backgrounds and experiences. 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.
