Chief People Officer at Skillshare

| Remote
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Our team is our most important asset, and Skillshare is looking for the Chief People Officer to lead our people operations and build a high-performance team that lives our values of Curiosity, Community, Transparency, and Impact. Our 150 mission-driven employees take great pride in the very personal impact our platform has on our teachers and students, as we find and fuel the creative spark that is in each of us. We have an exciting path ahead of us as we grow the team, expand rapidly abroad, build new products and services, and explore our options in the capital markets.

What you’ll do day-to-day:

  • Strategize: Act as a strategic partner to the CEO and executive team and provide insightful, innovative thinking and problem solving on critical HR issues and serve as a coach for the members of the management team.
  • Develop: Lead the development and evolution of our team and culture, creating an employee experience, compensation strategy, and learning and development program that keeps our amazing workforce effective, motivated, and engaged.
  • Manage: Build and develop our people operations team in a way that is seen as an example of a company that’s getting it right.
  • Innovate: Help us define the future of work as we evolve our remote-first model, learning from the best practices of other companies but adjusting to fit what works for our team.
  • Grow: Expand our recruiting function and build our employer brand as we look to expand the team by 50% over the next year, with each new hire raising the bar.
  • Coach: Scale our management and leadership training programs to ensure our team is led by managers who have the skills and experience to develop their teams.
  • Lead: Lead the diversity, equity, inclusion, and belonging programs that mean a great deal to our employees and the broader Skillshare community.

Why we’re excited about you:

  • Building high-performing teams: You have a framework for how companies turn good teams into great teams and can refine and extend that model at Skillshare.
  • Scale: Your experience scaling organizations beyond 200 employees and across international markets will ensure we understand where we are going over the next several years
  • Public company experience: You’ve worked in a public company, and ideally taken a company through IPO, and understand some of the unique challenges and opportunities that come with the territory
  • Talent magnet: You know how to bring the best talent to Skillshare, and then set up the culture, opportunity, and compensation to keep them happy, productive, and growing over the long term.
  • Strategic and operational expertise: You will bring experience and insight to the exec and board meetings that go well beyond your day job and people operations. 
  • Inspiring and thoughtful communications: Your ability to craft the right message to the team in both good times and bad will help us stay aligned and focused. 

Why you want this job:

  • Growth: There will never be a dull moment - we have a long list of opportunities and high-class problems to tackle; from evaluating long-term capital direction (IPO? SPAC? Stay private?) to international expansion to new lines of business, you’ll help us develop our strategy and build the team to execute on it.
  • Impact: There aren’t many growth companies with a strong platform, subscription-driven business model, AND a powerful social impact. It’s hard to find a company that is both a positive influence on the world and phenomenal business.
  • Team: You’ll be a key member of an executive team that is more than capable of taking the company to the next stage of growth and beyond. 
  • Community: We have a large and uniquely passionate community of teachers and students -- 15% of our NPS comments contain the word “love”. Our platform changes people at their core.
  • Board and investors: We have one of the most supportive boards around. We are very proud to be backed by OMERS Growth Equity, Union Square Ventures, Amasia, Spero Ventures, and Spark Capital, and their networks have paid big dividends for Skillshare.

About Skillshare:

Skillshare is an online learning community for creatives. We have thousands of inspiring classes for creative and curious people and millions of members who come together to find inspiration and take the next step in their creative journey.

Skillshare is committed to building a diverse team that reflects a variety of backgrounds, perspectives, and skills. We’re proud to be recognized as a top place to work by BuiltinNYC, Crain’s, and Forbes, in addition to being one of the five best places to work for women by Bpeace, and a top-rated workplace for dads by Fatherly. We work to ensure a consistent interview process, fair compensation, and an inclusive work environment for all.

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Technology we use

  • Engineering
  • Product
    • JavascriptLanguages
    • PHPLanguages
    • PythonLanguages
    • SqlLanguages
    • TypescriptLanguages
    • SASSLanguages
    • jQueryLibraries
    • ReactLibraries
    • WebpackLibraries
    • Backbone.jsFrameworks
    • Node.jsFrameworks
    • TensorFlowFrameworks
    • YiiFrameworks
    • MySQLDatabases
    • RedshiftDatabases
    • Google AnalyticsAnalytics
    • MixpanelAnalytics
    • OptimizelyAnalytics
    • IllustratorDesign
    • PhotoshopDesign
    • SketchDesign
    • ZeplinDesign
    • ConfluenceManagement
    • JIRAManagement
    • TrelloManagement

An Insider's view of Skillshare

What are some social events your company does?

Moving fully remote has meant changing our approach to team-bonding. We are keeping the energy up with happy hours, trading Zoom backgrounds, and, recently, our affinity group for women of color hosted company-wide trivia that kicked off with a Rihanna dance break.


Senior Creative Producer

How do you collaborate with other teams in the company?

Cross-team collaboration is frequent and organic at Skillshare; we foster a uniquely friendly atmosphere of openness and shared purpose. Through cross-team threads, project-based meetings, comments on RFC's, pull request reviews, Q&A sessions, and, of course, simple conversations, collaboration commonly happens across a table or across time zones.


Director of Engineering

What are some things you learned at the company?

I was immediately impressed and encouraged by the creative problem solving at Skillshare. Data plays a huge part in learning about our members, determining the most popular classes, and fostering creative community. I was a student within the community long before helping build it. My favorite experience so far has been learning watercolor basics.


Director of Business Intelligence

How do you make yourself accessible to the rest of the team?

As a management team, we strongly believe in making ourselves accessible. This includes: 1:1s with direct reports, skip-level meetings, team-wide meetings, coffees with people across departments, and attending team events. More broadly, we apply the same foundational rule we all learned in kindergarten: treat people the way you want to be treated.



What kinds of technical challenges do you and your team face?

We're in an exciting position - we have a product that we believe in and a community that believes in us. The question we face is: how can we build a platform which works for the Skillshare of today, but will scale to the needs of the Skillshare of the future? It’s not enough to keep up with growth; we must build for where our growth will take us.


Director of Engineering

What are Skillshare Perks + Benefits

Skillshare Benefits Overview

At Skillshare, we strive to create an inclusive culture in which each person is compensated fairly, has robust learning and development opportunities, and feels supported in bringing their whole self to work. We also 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, have an unlimited vacation policy (with a required minimum!), and encourage work-life balance.

Our perks include:

- Health, Dental and Vision coverage
- 401(k)
- Unlimited vacation (with a required minimum!)
- 14 weeks parental leave (gender neutral)
- Paid sabbaticals for tenured employees
- Learning and conference stipends
- $750 stipend for setting yourself up for success at home (think: desk, headphones, plants, ergonomic chair)
- Monthly reimbursement of up to $75 for high-speed internet services
- Stipend for mental health/well-being tools (Headspace, Talkspace, Peloton, etc.)
- Monthly coffee/tea reimbursement of up to $25
- Ongoing manager training with LifeLabs
- Inclusion workshops with Paradigm

Volunteer in local community
Partners with Nonprofits
Friends outside of work
Eat lunch together
Intracompany committees
In addition to our social committee, we have dedicated Diversity & Affinity groups in which team members decide to come together around a shared identity or background.
Daily sync
Open door policy
Team owned deliverables
Team based strategic planning
Group brainstorming sessions
Pair programming
Open office floor plan
Documented equal pay policy
Highly diverse management team
Unconscious bias training
Mean gender pay gap below 10%
Diversity Employee Resource Groups
Hiring Practices that Promote Diversity
Health Insurance & Wellness Benefits
Flexible Spending Account (FSA)
Disability Insurance
Dental Benefits
Vision Benefits
Health Insurance Benefits
Life Insurance
Mental Health Benefits
Retirement & Stock Options Benefits
Company Equity
Read more about how we think about equity compensation here:
Match charitable contributions
Child Care & Parental Leave Benefits
Generous Parental Leave
Skillshare offers 14 paid weeks of paid parental leave to both birth-giving and non-birth-giving parent/s.
Flexible Work Schedule
Remote Work Program
Family Medical Leave
Vacation & Time Off Benefits
Unlimited Vacation Policy
Paid Holidays
Paid Sick Days
Perks & Discounts
Casual Dress
Commuter Benefits
Company Outings
Happy Hours
Home Office Stipend for Remote Employees
Professional Development Benefits
Job Training & Conferences
Skillshare creates professional development opportunities by offering an annual budget to attend external conferences, in addition to ongoing internal learning programming.
Lunch and learns
Promote from within
Customized development tracks

Additional Perks + Benefits

In addition to the above, we also offer a number of perks around flexibility – including the option between a 1-month bonus or sabbatical at your 3-year mark, and the ability to work remotely for up to a month from anywhere in the world when you've been on the team for one year.

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