Account Executive - Chicago

Account Executive - Chicago

Location: Chicago, Illinois

Type: Full-time

Salary: $75,000 - $95,000 OTE Dependent on experience

About Us:

At Zen, we're changing how schools find the staff needed for kids to thrive. There is a severe shortage of teachers and the support staff needed to support all children, accelerated by the pandemic. Millions of students experience understaffed classrooms and specialist programs. Schools looking to fill these roles with traditional agencies spend billions of dollars in high agency markups, which further hampers budgets and leads to more problems down the line.

That's why we've developed an alternative solution. Our online platform provides schools instant access to hundreds of fully vetted teachers and support staff. Since our inception in 2017, we've saved schools over $30 million globally, reinvesting that money back into school budgets and increasing teachers' pay.

The Opportunity:

Join an ed-tech startup that's reshaping education. This is your chance to be at the forefront of change, where innovation meets impact. We're not just selling a product – we're transforming the way schools operate, filling classrooms with the staff needed for kids to thrive and saving the education system millions of dollars along the way.

You'll engage directly with school and district leaders, diagnose their staffing challenges, and show how Zen's platform can save time, money, and stress while ensuring every classroom is staffed with qualified educators.

As Zen continues its rapid expansion across North America, this position offers significant room for growth, both in impact and career trajectory.

What You'll Be Doing:

Based in the Chicago office, you'll own the full sales cycle - from initial outreach and discovery to demo, negotiation, and close - with school and district leaders across the U.S.

- Prospect, qualify, and manage your own pipeline of charter schools and districts.

- Conduct discovery conversations to understand district pain points and position Zen's solution effectively.

- Lead demos and guide schools through the evaluation and onboarding process.

- Collaborate with school success and account management teams to ensure a seamless handoff post-sale.

- Maintain accurate and up-to-date CRM records and report on pipeline metrics.

- Make consistent outbound outreach to key decision-makers (typically 40+ calls per day during active prospecting periods).

- Attend and represent Zen Educate at U.S. conferences, events, and school meetings.

- Embrace the dynamic nature of startup life, where no two weeks are the same, and a willingness to dive in and get the job done is essential.

Who We Are Looking For:

- You have 1–4 years of full-cycle sales experience, ideally in SaaS, EdTech, or staffing.

- You are skilled at both building pipeline and closing deals, and comfortable running discovery, demos, and negotiations end-to-end

- You are a passionate and motivated team player who thrives in a collaborative environment where your contributions are valued

- You have a growth mindset and are dedicated to refining your craft as a sales professional.

- Experience in education, either as an educator or selling to K-12, is a huge plus

What's In It For You?

Work that you want to talk about

Competitive salary

Ownership in the company

18 days PTO (15 Flexible, 3 over Christmas) + 9 stat holidays

Fun-loving, tight-knit team solving a problem that makes a difference

Hybrid - currently 2 days/week in-office but this is subject to change

Diversity and Inclusion:

At Zen, we strive to build a culture of equity and inclusion, where everyone is respected, valued and appreciated for their unique traits, experiences and perspectives. We are committed to creating a safe, inclusive and equitable environment where our team can thrive, regardless of age, ethnicity, race, gender identity, sexual orientation, socio-economic status, disability, religion or beliefs. We value our differences and believe that practices of Diversity, Equity and Inclusion help us create a fairer, more compassionate environment for all.

We welcome applicants with diverse backgrounds and different experiences and perspectives — just like the staff who teach through Zen and the children at the schools we work with. We believe in hiring the best people from the widest pool and creating an inclusive culture where people's voices are heard and all our team can look forward to coming to work.

We are committed to building a team that reflects the diversity of our community and promoting an equitable and inclusive environment for all. We seek out diverse opinions, beliefs, and experiences because they collectively make us stronger; we've had former teachers, pilots, fundraisers, engineers, lawyers, marketers, social media experts and more join our team.