Edtech.com's Summary

Skillshare is hiring an Account Executive (Contract) to manage the full sales cycle for Skillshare for Teams, focusing on lead generation, outreach, and closing deals involving bulk gift card and team license sales. The role requires independently building a sales pipeline, delivering product demos, negotiating deals, and collaborating across departments to support client needs during a high-demand holiday season contract.

Highlights

Manage full sales cycle from prospecting to deal closing for Skillshare for Teams.
Generate and qualify B2B leads and conduct outreach through cold calls and inbound follow-up.
Create sales collateral and deliver tailored product demos to address client goals.
Negotiate pricing and contracts aligned with seasonal promotions.
Track all sales activities and pipeline data using HubSpot CRM, providing weekly reports.
Collaborate with Marketing, Account Management, and Operations teams for seamless customer experience.
Requires 2-4 years of experience as a full-cycle Account Executive and experience with product demos.
Familiarity with HubSpot, Salesforce, or similar CRM tools is necessary; SaaS sales and SMB sales experience preferred.
Contract runs November 2025 to January 2026 with 30-40 hours/week commitment and flexible hours.
Compensation ranges from $6,000 to $6,800 per month plus commission and performance bonuses based on a full-time schedule.

Account Executive (Contract) Full Description

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 Skillshareâs 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 Skillshareâs premium class library.

Weâre 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, youâll own the full sales cycleâprospecting, pitching, and closing your own dealsâfocused on expanding Skillshare for Teams through bulk gift card and team license sales. Youâll have the autonomy to build your own pipeline, drive results, and help more organizations unlock their creative potential.

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 companyâs team-learning or gifting goals and position Skillshareâs creative learning memberships as the ideal solution.
Product demos: Deliver benefits focused demos that showcase Skillshareâs platform, class library, and team learning features tailored to each clientâs 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

2â4 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: Weâre doing work that matters â 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.

Contract Details

Duration: November 2025 â 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.

About Skillshare:

Skillshare is an online learning community whose mission is to connect curious, lifelong learners everywhere â 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.

Original Job Description

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 companyâs team-learning or gifting goals and position Skillshareâs creative learning memberships as the ideal solution.
Product demos: Deliver benefits focused demos that showcase Skillshareâs platform, class library, and team learning features tailored to each clientâs 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

2â4 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: Weâre doing work that matters â 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.

Contract Details

Duration: November 2025 â 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.

About Skillshare:

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