Head of Sales / Sales Manager

Screencastify is seeking a hands-on, player-coach Head of Sales to own and grow revenue across K–12, higher education, and corporate markets. This Chicago onsite role combines strategic leadership with direct sales accountability, as you steward a small team and manage outside reseller partnerships to influence the go-to-market strategy.

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.

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.

Technologies

• Salesforce
• Gemini
• Claude

Benefits

• Competitive compensation
• 401(k) & Annual Performance Bonus Opportunity
• Flexible Time Off (FTO) Policy
• Parental Leave
• Medical, Dental, & Vision Insurance
• Divvy Bike Membership

About Screencastify

Castify, the company behind Screencastify, is a leading technology firm focused on improving communication and learning outcomes through video. We have established a strong presence in the United States K–12 education market and play a pivotal role in scaling teacher tools to improve student outcomes. The organization is actively expanding into markets outside K–12, bringing our proven solution to businesses and organizations.

The Role

The role requires a player-coach Head of Sales who will own and expand revenue across K–12, higher education, and corporate segments. You will actively manage your own book of business while guiding a small team of 2–3 account executives and overseeing outside reseller partnerships. You will report to senior leadership and have real influence over go-to-market strategy.

Why Screencastify

• Real ownership and influence from day one with lean decision-making.
• A product that genuinely matters to 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 starts at USD 140,000 plus commission. Final compensation may vary based on experience and qualifications.