Role overview

As the first sales hire at Chalkie, you will partner directly with the CEO and Chief of Staff to define and execute our mid-market sales strategy. You will own the full sales cycle, targeting districts and large school groups to establish our presence and build our foundational sales playbook.

Chalkie

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Education

Chalkie is an AI-powered educational technology platform that helps teachers create curriculum-aligned lessons, classroom resources, and teaching materials in minutes. Founded in 2024, the platform uses artificial intelligence to generate standards-aligned learning materials including slides, activities, and worksheets based on subject, education level, and curriculum requirements. Teachers can input a topic and key details such as year group and learning objectives, and the platform creates customized classroom-ready content. Chalkie includes an AI-enabled slide editor allowing teachers to refine and personalize lessons to their specific needs. The company aims to reduce teacher workload and planning time, enabling educators to focus more on classroom teaching and student engagement.

What you will do

Execute full-stack sales cycles targeting mid-market school groups, MATs, and K-12 districts to drive revenue growth.
Represent Chalkie at industry trade shows and manage a mix of inbound leads and proactive outbound prospecting.
Document and refine the company's sales playbook, translating early successes into a scalable, repeatable commercial engine.

Who this is a fit for

Deep domain expertise in the EdTech market with a proven track record of selling successfully into the K-12 sector.
Demonstrated "do-er" mentality with the ability to execute independently without an existing support team or framework.
Exceptional communication skills capable of navigating complex stakeholders within large school groups and Multi-Academy Trusts.

Why this role is remarkable

Step into a high-impact founding role where you will build and define the entire sales function from the ground up.
Work directly alongside the executive team to shape the commercial strategy of a rapidly growing EdTech startup.
Influence the future of education by bringing innovative technology to K-12 districts and Multi-Academy Trusts across the UK.

How Jack & Jill work together

I get to know what you’re great at, then find roles you’d never find yourself.Ok, I'll go first. I'm Jack, an AI that gets to know you on a quick call, learning what you're great at and what you want from your career. Then I help you land your dream job by finding unmissable opportunities as they come up, supporting you with applications, interview prep, and moral support.

I recruit from Jack’s network and make the intro when I spot a great match.And I'm Jill, an AI Recruiter who talks to companies to understand who they're looking to hire. Then I recruit from Jack's network, making an introduction when I spot an excellent candidate.

Founding Salesperson at Chalkie