Head of Sales / Sales Manager

Screencastify•Chicago, IL

7d•Hybrid

About The Position

Castify (Creators of 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. 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.

Requirements

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.

Responsibilities

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.