Account Executive, Midwest

KickUp
Cincinnati, OH

KickUp is looking for an Account Executive to join a team that is reimagining how school districts grow their most valuable asset: their people.

KickUp is on a mission to help every educator thrive throughout their career. Our platform helps educational leaders capture data about teacher growth and use it to drive better outcomes for students. We’re a growing team building a product used by tens of thousands of educators.

Every sales success means more educators getting a say in what growth looks like in their role; every investment we make in our educators, in turn contributes to better student outcomes.

Why you should join KickUp

  • Impactful Product: Our product is a robust, data-rich professional growth platform. We are proud to maintain an exceptional customer NPS above 90 and are establishing ourselves as an emerging leader in the K12 professional growth software market. You will have the opportunity to sell an excellent product that is constantly improving.
  • Growth Opportunities: We’ve proven product-market fit and still have significant growth ahead. Joining at this stage offers substantial opportunities for professional growth and a meaningful impact.
  • Collaborative Team: Our team is humble, sharp, and user-focused with a unique blend of mission-driven and business-smart qualities. We care about the work and are committed to each others’ success.
  • Remote Flexibility: We are a remote-first organization with high flexibility. We offer an extended holiday break, summer Fridays, and “Focus Fridays” – a day with limited Slack and meetings throughout the year. On a semi-annual basis, we gather for team on-sites.

About the role

On your first day, you should show up ready to:

  • Navigate a complex B2B software sale, with multiple stakeholders, where the end user is not always the decision-maker.
  • Know and execute on the full sales process, from discovery calls, demoing, overcoming objections, contracting, all the way to closing.
  • Talk with Professional Learning, Human Resources, Teaching & Learning and Technology leaders in school districts about educator growth!

What you’ll learn more about after you’re hired:

  • The unique features of the platform we’ve built, the results we’re seeing, and our robust CSM model that supports implementation.
  • How our sales process has worked and how to replicate its successes.
  • Our philosophies around educator growth and the impact of actionable data.

With your first week, you will:

  • Introduce yourself on Slack to your new coworkers!
  • Meet with folks from different departments to get a better understanding of the user journey.
  • Try out our platform, take a look at key use cases, and read through and watch customer testimonials, call recordings, and case studies.

With your first month, you will:

  • Join sales calls and begin taking and setting up those calls yourself!
  • Begin moving deals along the sales cycle and building your pipeline.
  • Use the sales and client success team’s wealth of knowledge around current best practices, common themes and narratives, and info about existing customers and impact cases to leverage on your calls.
  • Be able to effectively communicate value propositions and know how to best position KickUp based on needs analysis.

With your first three months, you will:

  • Attend conferences to network with school district leaders and build your book of business.
  • Work closely with marketing to hone any region-, product-, or persona-specific campaigns you’d like to run in your territory.
  • Track close rates and pattern match to help with projections and pipeline management.
  • Share techniques and best practices with other members of the sales team.
  • Share your insights with the product team to help us better serve our users.

With your first year, you will:

  • Close multiple sales and share wins with the whole team!
  • Meet and exceed individual and team sales goals.
  • Cultivate long-standing relationships with districts in your region.
  • Know our CRM (Hubspot) like the back of your hand and use it to forecast pipeline and communicate revenue performance.
  • Have an eye towards market trends and identify opportunities for growth in years to come, with a focus on refining existing sales processes and building out a pipeline during the “off-season”.

About you

We’re looking for someone who:

  • Has a minimum of 2 years of experience in sales, with at least 1 year specifically in the K-12 EdTech sector.
  • Is motivated by driving revenue growth
  • Is hungry to grow and learn -- is open to feedback and seeks to continuously improve
  • Is a natural at building relationships
  • Is persistent and meticulous in follow-through
  • Is comfortable with ambiguity
  • Demonstrates a sense of ownership and pride in both personal and company performance
  • Has a team player attitude and contributes by working effectively with individuals of diverse backgrounds

Position Details

  • This is a remote, full-time position that can be performed anywhere within the midwest US territory.
  • Some travel is expected relating to conferences, in-person events, and meetings in your region.
  • Candidates must be legally eligible to work in the United States.
  • This position involves both base and variable compensation. Base compensation for this position ranges between $80,000- $115,000 with On-Target-Earnings ranging between $115,000 - $170,000 and no cap on commissions.

Benefits

We are a remote-first company, and we offer a range of perks, including:

  • Stock options in our growing company
  • 401(K) plan with employer matching
  • Universal paid parental leave
  • A variety of medical, dental, and vision insurance options
  • An annual stipend for professional learning
  • Flexible PTO policy, extended holiday break, summer Fridays, and “Focus Fridays” – a day with limited Slack and meetings throughout the year

We are building products that help every educator thrive. To do so, we need a team that includes diverse perspectives and a shared willingness to challenge ourselves to improve every day. We recognize that underrepresented groups may be less likely to apply to a role if they don’t meet 100% of the listed qualifications. We encourage you to apply if you meet a majority of the qualifications and are passionate about our mission.

Posted 2026-04-24

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