Sales Representative - Milwaukee

Imagine someone gave you these three things: the opportunity to change the future of education, the autonomy to manage and grow your own territory, and all the necessary tools to be successful. If a job that combines all three of those things interests you, you may be a fit for our Sales Representative role here at Top Hat!

As a Sales Rep, you will be assigned a territory of colleges and universities where you’ll have the autonomy to develop professional relationships with professors, demonstrate the value of our platform and products, and convert them into clients. You will add value by working with professors to enhance their teaching methods and help bring the educational experience into the future. To do this, you will show how our products help both students and professors engage in the classroom experience and how they enable better learning outcomes. In essence, you will be making education better for students: one professor, one classroom, and one school at a time.

This in-territory sales representative position requires approximately 40%-50% of your time to be spent on campus annually. During the sales seasons (approximately mid-January through May and mid-August through mid-December), you may spend up to 75% of your time on campus.

Due to travel requirements, we are only considering local candidates in the Greater Milwaukee area. You will be responsible for travelling to campuses within your territory (Illinois, Wisconsin and St. Louis, MO) to prospect professors.

What You’ll Do:

• You will find, create, facilitate, and close new business opportunities in your assigned accounts

• Represent and sell the full suite of Top Hat and approved partner products and services, including Top Hat’s digital textbook content and SaaS platform

• Effectively position & message Top Hat’s value proposition to professors or department leaders, using a mixture of inside and outside sales techniques

• You will work closely with Customer Success Managers and internal product and marketing partners to ensure a great customer experience for professors and to maximize revenue growth

Who You Are:

• You are highly motivated, achievement-oriented, and excited to join a team driving change in higher education!

• You have 1+ years of experience in a sales role. Experience selling to professors in person on campus is highly preferred

• This role requires 40-50% (up to 75%) of your time travelling to campuses for in-person sales. A valid Driver’s License is required

• You have the sales skills, including the ability to identify, drive, and close large/complex deals, prospect effectively, and run the full sales cycle (including cold calling, demos, discovery, solution presentation, negotiation and closing)

• You are ambitious and have the drive to succeed

• You have experience working in a metrics-driven environment and remain positive when facing common objections

• You have a strong ability to interpret and apply feedback/coaching quickly

Why team members love working at Top Hat:

• A noble mission that creates meaningful, fulfilling work

• A team that cares deeply for customers and for each other

• Flexible, remote first work environment

• Professional learning and development for all role levels

• An awesome and welcoming Toronto HQ

• Competitive health benefits that start on day one

• A management team focused on performance, growth, engagement and connection

• Our winning strategy and market potential

• Innovative PTO policy with lots of time and space for self-care

• Passionate customers that believe in us—and what we do

• A chance to work with new tech like generative AI—and see the customer impact

Inclusion Statement:

Inclusion at Top Hat goes beyond compliance; it’s how we build better teams and better technology. Our Equal Opportunity Employment policy helps ensure a workplace where people of all backgrounds are respected and empowered, regardless of culture, national or ethnic origin, race, color, gender, gender identity, sexual orientation, age, disability, veteran status, religion, family status, or any other characteristic protected by applicable laws.

Accessibility Statement:

We want every candidate to have an equitable experience. If you require assistance or a reasonable accommodation due to a disability during the application or recruiting process, please reach out to us at [email protected]. By fostering an inclusive and supportive environment, we unlock collaboration, innovation, and personal growth across our global Top Hat community.

AI in Hiring:

To help streamline our hiring process, we may use AI-powered tools for tasks such as application screening, resume review, or response assessment. These technologies support our recruiters by improving efficiency, but human judgment remains central. Final hiring decisions are always made by people.