Sales adviser Jobs in Chicago, IL

About Screencastify

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.

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.

Requirements

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.

Benefits

• Competitive Compensation. We take a data-driven approach to our compensation strategy so all employees are paid competitively and fairly.
• 401(k) & Annual Performance Bonus Opportunity. We want to invest in present you and future you, which is why we offer a 401(k) match + Annual Performance Bonus opportunity.
• Flexible Time Off (FTO) Policy. We recognize that time off to rest and recharge is important. The Flexible Time Off Policy (FTO) is designed for our employees to do just that -- balance work and life while maintaining well-being.
• Parental Leave. Generous paid time off for parents to bond with the newest addition to their family!
• Medical, Dental, & Vision Insurance. We offer comprehensive health benefits, including medical, dental, and vision insurance. Plus, all employees receive a free One Medical membership.
• Divvy Bike Membership. If you’re in Chicago, take advantage of an annual Divvy membership -- on us.

At Screencastify, we foster an inclusive, supportive, fun, and challenging team environment. We value having a team that is made up of a diverse set of backgrounds and respect the healthy expression of diverse opinions. We embrace experimentation and the examination of all kinds of ideas through reasoning and testing. Come join us as we continue to change the world through video.

Screencastify is an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, gender, sexual orientation, national origin, age, genetic information, gender identity, disability, Veteran status or any other characteristic protected by federal, state or local law.