Jobs · Sales · Illinois

Head of Sales / Sales Manager

Screencastify · Chicago, IL · 3 wk ago
HybridSales$140k/yrFull-time

About 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.

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.

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