Commission Edtech Sales Jobs in Wisconsin (NOW HIRING)

Job Type: Full Time Employee

Job Location: Remote (Employee must be based in the Midwest US)

About ChalkTalk

At ChalkTalk, we believe that education is human. It's more than scores and statistics. Be part of a team that's transforming education and achieving up to 6x improvement in student learning outcomes.

ChalkTalk uses student assessments to generate digital courseware for every day in the course schedule. Every modular ChalkTalk lesson comes with teaching materials for the teacher; small group work and computer-adaptive practice for students; and progress reports for administrators. ChalkTalk is delivering improvement in student learning outcomes up to 6x, as measured by third-party test scores. It is currently used to power high school literacy and numeracy instruction district-wide at some of the largest US districts - including 7 of the largest 100. ChalkTalk currently has 16 employees.

Responsibilities

• Sell digital curriculum and instruction deals.
• Own the full sales cycle: prospect, cold call, demo, and close new district partnerships.
• Outbound focus: cold calls, cold emails, and cold drop-ins.
• Develop and execute territory strategy to drive adoption.
• Contribute to and improve outbound processes and sales playbooks.
• Represent ChalkTalk at conferences, trade shows, and regional events.
• Travel 25% of the time to meet district leaders and attend events.
• This is an outside sales position focused on district-level partnerships across the midwest.

You will enjoy this role if you:

• Are excited about the challenge and reward of breaking into a new territory or selling a new product.
• Have strong self-motivation and can set goals, execute independently, and make an impact with limited oversight.
• Excel in a fast-paced, dynamic environment and take ownership in ambiguity.
• Are a problem solver who thinks critically and self-solves rather than waiting for direction.
• Get excited about uncapped commissions and consistently exceeding quota

Qualifications

• Minimum of 5+ years of B2B SaaS sales
• Must have cold calling and/or cold drop-in experience within the last 2 years and comfort with full-cycle outbound sales.
• Understanding of the K-12 education landscape from personal interest or past experience
• Prior experience in a fast-paced startup environment (150 employees or less).
• Resilient, persistent, and self-motivated in an outbound sales environment.
• Big Plus, but not required: experience selling into K-12 districts, ideally within Curriculum & Instruction (C&I).

Why work at ChalkTalk?

• Mission: You want to help provide the best education possible to everyone on the planet.
• Impact: In just 15 weeks, districts that bought ChalkTalk saw their students experience 2–6X MORE GROWTH ON OFFICIAL STATE TESTS compared to their peers who received 52 weeks of traditional classroom instruction. Big impact with vulnerable student populations.
• Awards:
  • 2020: Top 10 finalist out of 700+ companies at ASU+GSV Cup.
  • 2021: Winner of FETC’s Best in EdTech alongside Microsoft & Lego.
  • 2022: Winner of EdTech Week’s EdTech Cup in NYC.
  • 2023: “North America EdTech 200” by HolonIQ.
  • 2024: “The World’s Top EdTech Companies” by TIME Magazine & Statista
  • 2025: “The World’s Top EdTech Companies” by TIME Magazine & Statista
• Competitive Compensation: Competitive salary, commission and equity offers
• Benefits: Health, dental, life, disability and vision insurance.