Executive Assistant

Executive Assistant to Team & CEO (Remote – UK Hours)

Location: Remote (must be available during UK business hours)
Contract Type: Full-time
Experience Required: 3+ years
Application Limit: Please apply only if you meet all criteria.
Deadline: Applications will be reviewed on a rolling basis.

About Chatterbox

Chatterbox is an award-winning, fast-growing social enterprise that builds technology to accelerate access to meaningful work for marginalised people — including refugees and others who face systemic employment barriers. We believe talent is equally distributed, but opportunity is not. Our platform has been featured in The Economist, BBC, and TechCrunch, and backed by mission-aligned investors.

We are now looking for an exceptionally competent and detail-obsessed Executive Assistant to support our CEO and operations team at the highest level of precision and discretion.

What You’ll Be Doing

Calendar & Scheduling:
• Own and manage the CEO’s calendar with military precision
• Schedule internal and external meetings across time zones
• Proactively anticipate scheduling conflicts and solve them before they arise
Help Desk Support (Freshdesk):
• Respond to help desk tickets at fixed times each working day
• Provide rapid-response support for urgent user needs as they come up
Research & Analysis:
• Conduct desk research to support strategic decisions (e.g., competitor analysis, funding research)
• Synthesize information into clear, concise summaries
Financial Support:
• Maintain and update cash flow spreadsheets
• Assist with cash flow forecasting and reconciliations
• Gather supporting documentation for financial audits and reporting
Operational Assistance:
• Support on backend tech tasks (e.g., updating user data, workflows, or support portals)
• Help manage internal documentation and workflow automations (e.g., in Google Workspace or Slack)

You Must Have:
• 3+ years of professional experience in an Executive Assistant, Chief of Staff, or high-level administrative role
• Demonstrated experience working in a tech startup or high-paced digital environment
• Fluency in Google Workspace, Slack, Excel, and Freshdesk
• Proven ability to handle financial forecasting and reconciliations confidently
• Meticulous attention to detail, and a record of executing instructions flawlessly without needing follow-ups
• Flawless written English and a high standard of professional communication
• Ability to work autonomously and stay available during UK business hours
• Minimum of one and preferably up to three professional references

Bonus – But Important:

We strongly encourage applicants who have a personal connection to Chatterbox’s mission to apply. This may include (but isn’t limited to):
• Having lived experience as a refugee, migrant, mother, or over 50
• Having faced systemic barriers to employment
• Having worked on refugee, migration, or social justice issues in a professional capacity

What Success Looks Like

You will be the CEO’s right hand, trusted to get things done without being chased. You’ll provide high-leverage support that enables the CEO and wider team to focus on strategy, growth, and impact. You’ll bring a calm, consistent presence to a fast-moving, mission-driven startup that’s working to change lives.

To Apply:
Please submit a CV and a cover note (please do not use AI to write this) that highlights how you meet every essential requirement listed above.