Jack & Jill
Head of Schools (£60k) at Chalk

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Job Title
Head of Schools
Salary
£60,000 (flexible)
Company Description
Chalk is a mission-driven Scottish edtech company, backed by the Scottish Government’s CivTech programme and philanthropic awards, building inclusion tools like Chalk Access to support learners with additional needs across Scotland.
Job Description
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.
Location
Scotland, UK (Remote)
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.
Reasons to use Rodeo
I’m in my final year doing Economics and I don’t know whether to apply for grad schemes now or do a masters first. What do you think?
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Also worth knowing: most autumn 2026 applications are open now. Timing matters more than you think.
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Graduate Consultant — 2026 Scheme
Why you're a good match
StrongYour economics background and your summer at a regional bank line up with what PwC looks for on the consulting scheme. Applications close in four weeks.
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Why you're a good match
You’ve got the grades and the economics background, and your bank internship is exactly the experience this scheme looks for. Apply soon — deadlines close within the month.
Experience fit
Your summer at the bank plus your econometrics coursework map directly to the day-one responsibilities on this scheme — client modelling, market briefings, and deal support.
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No noise. No "maybe this fits." Just roles with a clear explanation of why they're right — and where to focus when applying.
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.
The ideal candidate
- 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.
Who are Jack & Jill?
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.


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Your very own career expert that helps elevate your application to the next level.
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.
How does this work?
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 it's a match and the company wants to meet you, they'll make the intro. In the meantime, if you'd like, Jack will send you excellent alternatives.
We never post fake jobs
This isn't a trick. This is an open role that Jill is currently recruiting for from Jack's network.
Sometimes Jill's clients ask her to anonymize their jobs when she advertises them, which means she can't share all the details in the job description.
We appreciate this can make them look a bit suspect, but there isn't much we can do about it.
Give Jack a spin! You could land this role. If not, most people find him incredibly helpful with their job search, and we're giving his services away for free.
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