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Account Executive

Skillshare21 days ago
Remote
Canada, United States
Senior Level

Top Benefits

Medical, dental, and vision coverage
401(k) retirement plan
Unlimited vacation with minimum requirement

About the role

Who you are

  • 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

What the job involves

  • 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
  • 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
  • Duration: November 2025 – January 2026
  • Commitment: 30-40 hours per week. Open to flexible or reduced working hours with corresponding adjusts to compensation structure

Benefits

  • Excellent medical, dental, and vision plans
  • 401k
  • Unlimited vacation (with a required minimum)
  • Up to 14 week gender-neutral parental leave
  • 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

About Skillshare

E-Learning Providers
501-1000

Skillshare is an online learning community with thousands of inspiring classes for creative and curious people, on topics including illustration, design, photography, video, freelancing, and more. On Skillshare, millions of members come together to find inspiration and take the next step in their creative journey.

Are you looking for a holistic learning solution for your entire organization? Learn about Skillshare for Teams: https://teams.skillshare.com/

Want to work at Skillshare? Our collaborative culture goes far beyond our online community. It’s a real part of the humans-first way we work as a team. We believe the work we do makes a difference in the lives of our members, and our mission extends to ensuring our own team members live balanced, fulfilling lives. That means different things for everyone, but it begins with a workplace that embraces modern flexibility, inclusivity and transparency. See our career opportunities: https://jobs.lever.co/skillshare