Account Executive (Contract)
Skillshare
Sales & Business Development
Canada · Remote
USD 6k-6,800 / month
Posted on Oct 11, 2025
Skillshare is the leading learning community for creatives. With more than 30,000 expert-led classes in illustration, design, photography, video, marketing, and more, Skillshare empowers anyone, anywhere to learn new skills, share expertise, and unlock their creative potential. Hundreds of thousands of member subscribers around the world come to Skillshare to discover new passions, advance careers, and connect with an inspiring community of teachers and peers.
Skillshare for Teams brings Skillshare’s creativity-first learning to organizations around the world. From creative agencies and marketing departments to HR and people teams, Skillshare for Teams helps companies elevate their workforce with real-world creative and professional skills. Businesses use Skillshare to inspire innovation, boost employee engagement, and foster continuous learning through team-wide access to Skillshare’s premium class library.
We’re looking for a motivated, self-starting Account Executive to join our Skillshare for Teams on a four-month contract during our high-demand holiday season, with the potential to convert into a full-time role in 2026.
In this role, you’ll own the full sales cycle—prospecting, pitching, and closing your own deals—focused on expanding Skillshare for Teams through bulk gift card and team license sales. You’ll have the autonomy to build your own pipeline, drive results, and help more organizations unlock their creative potential. This role reports to Growth, Skillshare for Teams.
What You'll Do
- Lead generation: Proactively source and qualify B2B leads for Skillshare for Teams.
- Outreach & prospecting: Generate new business through cold outreach, and inbound lead follow-up across target personas.
- Asset creation: Develop your own sales collateral and outreach materials to drive engagement and close deals.
- Customer needs: Understand each company’s team-learning or gifting goals and position Skillshare’s creative learning memberships as the ideal solution.
- Product demos: Deliver benefits focused demos that showcase Skillshare’s platform, class library, and team learning features tailored to each client’s goals.
- Deal negotiation: Present pricing options, handle objections, and negotiate corporate deals aligned to seasonal promotions.
- Sales execution: Meet or exceed monthly targets by managing the entire sales cycle independently from prospecting to signed contract.
- CRM & reporting: Be detail oriented and track all outreach and pipeline activity in HubSpot, providing weekly performance updates.
- Collaboration: Collaborate across Marketing, Account Management, and Operations to offer a customer-centric experience from first touch through renewal.
What You'll Need to be Successful
- 2–4 years of experience as a full-cycle Account Executive.
- Excellent communication, organization, and negotiation skills.
- Experience giving product demos.
- Ability to work independently and as part of a team.
- Experienced using HubSpot, Salesforce, or similar CRM tools.
- Experience selling SaaS preferred
- Experience driving SMB sales and managing short sales cycles preferred.
Why You're 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.
- Remote culture: A healthy, productive working environment means different things for different people. We optimize for trust and invest in supporting remote teams and focus on transparent communication to ensure an inclusive, equitable work environment for everyone.
- 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.
- Duration: November 2025 – January 2026
- Type: Independent contractor (1099)
- Commitment: 30-40 hours per week. Open to flexible or reduced working hours with corresponding adjusts to compensation structure.
- Compensation: $6,000-$6,800/month + commission and performance-based bonus (based on a 40-hour/week contract). Compensation is adjusted linearly to hours worked weekly.
Contract Details
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.