Head of Sales / Sales Manager

About Screencastify

Screencastify is a leading technology company dedicated to improving communication and learning outcomes with video. We have established ourselves as a leader in the K-12 education sector in the United States and we are critical in helping scale a teacher and improve student outcomes. We are also actively expanding into new and exciting markets outside of K-12 including bringing our tested solution into companies and organizations.

The Role

We're looking for a player-coach Head of Sales to own and grow our revenue across K–12, higher education, and corporate markets. This isn't a "manage from the sideline" job — you'll carry your own book of business while leading a small team of 2–3 account executives and managing outside reseller partnerships. You'll report directly to senior leadership and have real influence over go-to-market strategy.

What You'll Do

• Carry an individual quota while coaching and developing a team of 2–3 AEs.
• Manage and grow relationships with outside resellers and channel partners selling into education and corporate accounts.
• Build and run a disciplined, repeatable sales process — from prospecting through close.
• Own pipeline health, forecasting accuracy, and CRM hygiene in Salesforce.
• Collaborate with marketing and product to sharpen our message positioning and ICP.
• Identify new market opportunities and help shape how we go to market.
• Recruit, ramp, and retain great sales talent as the team grows.

What We're Looking For

• 8+ years of B2B sales experience, with at least 2 years leading or mentoring a sales team.
• Proven track record of hitting quota as an individual contributor and as a leader.
• Experience selling into K–12, higher ed, or EdTech strongly preferred; corporate SaaS experience a plus.
• Hands-on Salesforce user — you keep your own data clean and you hold your team to the same standard.
• Comfortable with channel and reseller motions, not just direct sales.
• Proficiency with AI models, specifically including Gemini and Claude. Leverage AI to drive speed, quality and results for your role and team.
• Startup DNA: resourceful, adaptable, low-ego, willing to do whatever it takes.
• Based in Chicago or willing to be in our Fulton Market office (320 N Sangamon St) 3 days/week.

Why Screencastify

• Real ownership and influence from day one — no bureaucracy, no committee decisions.
• A product that genuinely matters to the educators and learners who use it.
• Competitive compensation with performance upside.
• A small, tight-knit team where your work is visible and your impact is real.

Compensation

The expected annual base salary for this role is anticipated to start at $140,000 + commission. Final compensation may vary based on experience and qualifications.