Jack & Jill logo

IT Support Engineer (Internal) at Dwelly

Jack & Jill
Department:Technical Support
Type:REMOTE
Region:UK
Location:United Kingdom
Experience:Entry Level
Skills:
IT SUPPORTMACOSWINDOWSLINUXMICROSOFT 365ENTRA IDGOOGLE WORKSPACESLACKVPNNETWORKINGSCRIPTINGAI
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Job Description

Posted on: August 22, 2026

This is a job that Jill, our AI Recruiter, is recruiting for on behalf of one of our customers.

She will pick the best candidates from Jack's network.

The next step is to speak to Jack.

Job Title

IT Support Engineer (Internal)

Salary

Not Disclosed

Company Description

Dwelly is a $170M Series B AI-enabled property management platform backed by EQT Growth, General Catalyst, and Trinity Capital. The company is disrupting the UK’s antiquated rental market by acquiring traditional estate agencies and integrating them into a tech-enabled digital platform to radically improve the experience for landlords and tenants.

Job Description

You will own internal IT operations and technical support at a fast-scaling startup. This role focuses on employee lifecycle management, MSP coordination, and the technical integration of acquired agencies. You will automate repetitive tasks using AI and scripting while ensuring a seamless, high-empathy support experience for a distributed team across Europe.

Location

Remote

Why this role is remarkable

  • Direct impact on a high-growth "roll-up" strategy, managing the technical transition of legacy agencies into a modern, AI-powered ecosystem.
  • Backed by $170M Series B funding from top-tier investors like EQT Growth and General Catalyst, providing immense stability and scale.
  • Culture of extreme ownership and automation where you are encouraged to script away manual tasks and leverage AI tools for operational excellence.

What You Will Do

  • Manage the full employee lifecycle, from device provisioning and account setup to offboarding across Microsoft 365, Google Workspace, and Slack.
  • Coordinate with external MSPs and contractors to troubleshoot complex infrastructure issues including VPNs, networking, and remote access systems.
  • Lead technical migrations for acquired agencies, transitioning legacy Windows servers, email domains, and hosting environments into Dwelly’s centralized tech stack.

The ideal candidate

  • Proven experience in internal IT support for macOS, Windows, and Linux environments, with deep knowledge of Microsoft 365 and Entra ID.
  • Technical proficiency in networking fundamentals including DNS, SSL, and VPNs, alongside scripting skills in Bash or PowerShell for process automation.
  • High empathy and strong communication skills, with a patient approach to supporting non-technical staff through complex digital transformations and integrations.

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.

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.

Originally posted on LinkedIn

Apply now

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