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Head of Schools at Chalk

Are you a former Head Teacher or Depute Head in Scotland looking for a new way to impact the education system? Chalk is seeking a Head of Schools to bridge the gap between classroom reality and innovative edtech. Backed by the Scottish Government's CivTech programme, you'll lead CPD, represent the company at national conferences, and shape the roadmap for inclusion tools used across the country. Enjoy the flexibility of a remote role and the influence of a domain expert, helping schools support learners with additional needs at scale—all without the weight of the school calendar.

What's the next step?

Chalk

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Location

Remote (United Kingdom)

Compensation

£60k (flexible)

Company

Chalk

Role overview

Join Chalk as our in-house education specialist, bridging the gap between school reality and product development. You will lead CPD training for school staff, represent Chalk at national conferences, and guide the roadmap for Chalk Access. This role is perfect for a school leader looking to impact Scottish education at scale.

Chalk Learning was founded by a former teacher. We’re building Chalk Access, the tool that helps teachers use evidence to support pupils with SEND (special educational needs and disabilities). We’re contracted by the Scottish Government through the CivTech programme, and we recently won the Renaissance Philanthropy Tools Competition. We are on track to significantly impact education in the UK and internationally over the next 5 years.

What you will do

  • Design and deliver high-quality CPD, training sessions, and onboarding programmes for teachers and senior school leaders across Scotland.
  • Act as the primary voice of the school system within the product team, translating classroom realities into actionable roadmap features.
  • Serve as the public face of Chalk at major education conferences and events, building relationships with local authorities and school heads.

Who this is a fit for

  • Significant experience in senior leadership within the Scottish schooling system, specifically as a former Head Teacher or Depute Head Teacher.
  • Fluent understanding of the Scottish curriculum frameworks, local authority operations, and inclusion tools like CIRCLE or the Autism Toolbox.
  • Exceptional communicator capable of delivering engaging training to adults and translating complex educational needs into technical product requirements.

Why this role is remarkable

  • Shape the future of Scottish education by influencing a product used by schools nationwide to support pupils with additional needs.
  • Work at the intersection of technology and pedagogy in a high-impact, mission-driven startup backed by the Scottish Government (CivTech).
  • Maintain your connection to the classroom and school leadership without the administrative weight or rigid schedule of a traditional school calendar.

How Jack & Jill work together

Jack
I get to know what you’re great at, then find roles you’d never find yourself.
Jill
I recruit from Jack’s network and make the intro when I spot a great match.
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Jack gets to know what you're great at and what you want next, then searches 15 million jobs daily and helps you discover roles at companies like this.

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What happens next?

Jack’s an AI agent for job searching and career coaching. He works for you.

Jill is the AI recruiter working for the company. She recruits from Jack’s network.

If your profile’s a match and Chalk wants to meet, Jill will make the intro. In the meantime, Jack will send you excellent alternatives.

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