The world's most popular classroom video solution.
Chicago, IL

Director of Design (Chicago, IL)

| Chicago
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About the role

We’re seeking a Director of Design to lead the company in exceptional, seamless design through all touch points of our product and brand. You will be the leader in defining and managing how the world interacts with Screencastify, working with our Product Designers, Brand Designers, and Marketing Team to ensure all outputs are consistent, thoughtful, simple, and tell a unified brand story.

In this role, you will play a critical part in how we can push our design strategy forward and make our product vision a reality. You’ll be the design advocate and thought partner for all major business stakeholders, implementing design principles and expectations at the company level. This role is perfect for you if you’re excited to manage and mentor a team of passionate designers while being not afraid to dive into the weeds yourself. You have an eye for pixel perfect designs, industry best practices, and human-centered approach to solving complex problems.

While we we have a preference for this role to be based in Chicago, we are open to remote candidates and encourage you to apply regardless of where you live.

Why is this role special?

You get to have a massive impact. As our first Director of Design, you’ll be instrumental in unifying the design experience at Screencastify. . Your work will be seen and used by millions of people.

Work with an extremely talented team. Our small but mighty team aspires to achieve results similar to companies with many times our headcount.

Work for our users. Above all else, you will be an advocate for our users and will get to know their voices and stories better than most people in the company.

Join us at a magical time. We're bootstrapped, profitable, and support tens of millions of users, which gives us a huge green field to work with. You'll join at the perfect time to shape how we grow from here.

What you'll do
  • Manage a team of cross-functional designers to produce high-quality, cohesive work across all user touch points - including defining clear goals, prioritizing work, and building a collaborative team culture
  • Implement design system and hand-off processes to optimize for efficient development cycles
  • Guide ongoing design work and uphold a high quality standard for user experience
  • Own Screencastify’s visual identity, voice, and brand look and feel
  • Partner with Product and Go To Market teams to deliver conversion driving designs and hit Quarterly OKRs
  • Mentor and grow design team to create a culture of thoughtful feedback, collaboration, and excellence
  • Work collaboratively with the design team to solve complex product and UI problems, contributing hands-on design work when needed
  • Own overall user experience, identifying points of friction and opportunities to create an amazing user experience
  • Build user personas and library of research insights


You're perfect for this role if you have...
  • 8+ years experience in Product Design; 4+ years of experience managing product designers
  • Experience building and implementing design systems across product and engineering teams
  • Strong proficiency in design software, such as Sketch and Figma
  • Ability to solve complex problems and advocate for design decisions to major stakeholders
  • Experience leading design brainstorms, ideation sessions, and user research
  • Excellent visual communication and leadership skills, excited to create an inclusive and collaborative design environment
  • Ability to empathize with users and are passionate about testing and iterating to ship data driven solutions to hit company-wide metrics
  • Experience in an agile, fast-paced environment, prioritizing hard tradeoffs between functionality and design
  • A portfolio of representative work demonstrating above skills


  • Competitive compensation. We take a data-driven approach to our compensation strategy so all employees are paid competitively and equitably.
  • 401k plan. We want to invest in the present you and future you, which is why we offer a generous 401k match with our 401k plan.
  • Minimum vacation policy. We recognize the importance of taking personal time off and require our employees to take at least 15 vacation days per year. You’re also encouraged to take additional paid time off, as needed.
  • Flexible work policy. Gone are the days of being in an office from 9-5, Monday through Friday. We recognize there are better ways to measure productivity than counting the number of hours you’re in the office and that sometimes the office isn’t the best place to be productive.
  • Parental leave. Generous paid time off for parents to bond with the newest addition to their family!
  • Medical, dental, and vision insurance. We cover 100% of employee medical premiums and 50% of employee dental & vision premiums. Plus, all employees receive a free One Medical membership.
  • Professional development. Each department has a professional development budget and employees are encouraged to take workshops, attend webinars, join associations, and anything else that could help grow their careers. Did we also mention employees get free access to Udemy for Business?
  • Divvy bike membership. If you’re in Chicago, take advantage of an annual Divvy membership -- on us.
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Where we are

We are a remote first company, but we do have a (completely optional) office space in the thriving Fulton Market neighborhood of Chicago.

Technology we use

  • Engineering
  • Product
  • Sales & Marketing
    • C++Languages
    • JavascriptLanguages
    • PythonLanguages
    • RxJsLibraries
    • NgRxLibraries
    • Node.jsFrameworks
    • Google Cloud DatastoreDatabases
    • Google AnalyticsAnalytics
    • WordpressCMS
    • HubSpotCRM

What are Screencastify Perks + Benefits

Friends outside of work
Daily sync
Open door policy
Team owned deliverables
Team based strategic planning
Pair programming
Documented equal pay policy
Unconscious bias training
Diversity manifesto
Mean gender pay gap below 10%
Hiring Practices that Promote Diversity
Health Insurance & Wellness Benefits
Dental Benefits
Vision Benefits
Health Insurance Benefits
We cover 100% of employee medical premiums and 50% of employee dental & vision premiums.
Mental Health Benefits
Our medical insurance includes coverage for mental health services and we also have an EAP (employee assistance program).
Retirement & Stock Options Benefits
401(K) Matching
We match 100% of contributions, up to 4% of an employee's annual gross pay.
Company Equity
Performance Bonus
Match charitable contributions
Child Care & Parental Leave Benefits
Generous Parental Leave
Flexible Work Schedule
Gone are the days of being in an office from 9-5, Monday through Friday. We recognize there are better ways to measure productivity than counting the number of hours you’re in the office.
Remote Work Program
Vacation & Time Off Benefits
Unlimited Vacation Policy
Generous PTO
At Screencastify, we've implemented a minimum vacation policy. All employees must take at least 15 days of PTO per year.
Paid Holidays
Perks & Discounts
Casual Dress
Commuter Benefits
Company Outings
Most recently, the Screencastify Squad went kayaking!
Happy Hours
Home Office Stipend for Remote Employees
Professional Development Benefits
Job Training & Conferences
We have a Udemy for business membership and each department has a professional development budget for employees.
Promote from within
Online course subscriptions available
Customized development tracks
Paid industry certifications

An Insider's view of Screencastify

How would you describe the company’s work-life balance?

Screencastify truly believes in “work hard, play hard.” As a mom of 3, I am able to balance it all and not feel so overwhelmed that I can’t do it. Having a good work-life balance helps to reduce stress and prevent burnout. It’s refreshing to work for a company that truly cares for its employees' well-being, both on a mental and physical level.


Customer Success Manager

What projects are you most excited about?

We just launched the alpha version of a browser-based video editor. Not only was the backend tech a major breakthrough - I really feel that it's the simplest, most convenient tool of its kind. The editor alone can take this company to new heights.


Software Engineer

How do you empower your team to be more creative?

At Screencastify, we often talk about how to create the conditions for our employees to thrive. Empowering our team to be more creative starts will trusting them to create the conditions they need to do their best work, and supporting them as a whole person...not just an employee.



How do you collaborate with other teams in the company?

Making outreach videos with my peers on the Sales team to make more personable customer connections - after all, we're not robots!


Success Manager

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