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.