Cassandra Cooper in

Cassandra Cooper

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Director at Connect with UP
📍 London Area, United Kingdom

Cassandra is a Director at Connect With UP, specializing in payroll technology and product development. With over 25 years of experience in payroll, finance, and regulated workforce solutions, she focuses on enhancing compliance, automation, and transparency in payroll operations for umbrella companies.

She believes strongly that relationships matter and that technology should make life easier, not more complicated. She values the real people behind the technology and emphasizes a human-centric approach in her professional life, appreciating simplicity and directness over unnecessary complexity.

Unique fact: Early in her career as a Financial Controller, she helped transform a manual auctioneering system into an online platform.

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Experience
30 Years
Current Role
Director
Job Level
Mid-senior
Location
London Area, United Kingdom
Personality Overview

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Communication Style
Decision Approach
Work Preference

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Priorities

Topics Cassandra cares about

Payroll Automation
Her current role and experience are centered on building payroll platforms that use automation to improve efficiency, transparency, and compliance.
HMRC & IR35 Compliance
She has deep expertise in HMRC requirements, IR35, and employment law, specializing in audit-ready systems and risk control for umbrella companies.
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Career

Work history

8-2025
Director
Connect with UP
9-2011 - 9-2025
Director of Operations
Various Umbrella Companies | Payroll Operations, Compliance, Systems & Technology
8-1996 - 8-2011
Group Financial Controller
HBC Vehicle Services Holding and Barnes PLC
In the press

Media appearances

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Education

Cassandra has no verified education history

Social presence
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Behavioral profile

DISC profile (public)

DISC behavioral profile

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