Hi, I'm Richard Hickson
Technology leader and founder with 20+ years of hands-on experience across IT, security, and SaaS.
Two decades of building and running real world technology
I started my career in IT in 2004 and have spent over 20 years working across almost every layer of the technology stack. From support desks and infrastructure to senior IT management, CTO roles, and founding my own businesses.
I've worked inside fast growing companies, regulated environments, consultancies, and startups. That experience has given me a deep understanding of what technology needs to do in the real world: be reliable, secure, and usable by the people it is built for.
Today, I split my time between running Helpfully IT, building SaaS products, and providing fractional CTO and technology leadership support. I bring a calm, practical approach shaped by having seen what works, what fails, and why.
Professional Journey
A career spanning support, management, leadership, and founding technology led businesses.
Founder of Helpfully IT, an IT consultancy and fractional CTO practice; Gravelship Ltd, building tools that solve real operational problems; and EndorseHQ, the trust conversion platform.
Providing senior technology leadership across security, IT strategy, platforms, and product delivery for growing businesses and startups.
Over a decade in IT Manager and senior operational roles, responsible for infrastructure, teams, vendors, security, and business continuity.
Started in hands-on support and technician roles, building a strong foundation in real world problem solving and customer facing IT.
What I bring to the table
Technology leadership
Leading technical direction with accountability, clarity, and long term thinking.
IT and security
Designing, running, and securing real world systems that businesses depend on daily.
Product and platforms
Building and improving software products with a focus on usability and operational reality.
Pragmatic delivery
Cutting through noise and choosing solutions that work in practice, not just on paper.
Operational maturity
Building systems, processes, and teams that scale sensibly without unnecessary complexity.
Rapid diagnosis
Walking into a business and identifying friction, waste, and hidden problems, often within hours rather than weeks.
Things I've built and run
Helpfully IT
A managed IT consultancy built on clear advice, strong security, and dependable long term support.
helpfullyit.comCalmTab
A lightweight browser extension designed to reduce distraction and cognitive overload.
calmtab.coCalmRota
A scheduling and rota platform designed for clarity, compliance, and real world use.
calmrota.comClaude Code Usage
An open source tool for tracking and understanding AI API usage and costs.
github.com/richhickson/claudecodeusageEndorseHQ
A testimonial and review collection platform helping businesses build trust and social proof.
endorsehq.comCalmStaff Beta
A staff and HR management platform focused on clarity, structure, and calm day to day operations. Currently in private beta.
calmstaff.comThoughts and ideas
Notes on technology, leadership, building products, and running businesses.
Make decisions quickly. Fail quickly. Learn permanently
Delay often carries more risk than action. Problems do not stay still while you think about them.
19 January 2026Seniority is solving a five hour problem in five minutes
Speed at senior levels rarely comes from talent. It comes from having already failed at the problem once before.
16 January 2026Security problems are usually process problems
You can harden systems all you like. If the process doesn't match how people actually work, security will be bypassed.
15 January 2026AI won't be one tool. It will be many
Every major technology shift follows the same pattern. It starts general, then specialisation wins. AI will be no different.
What people say
Let's connect
If you need experienced, hands-on help with IT, technology leadership, or building and running products, I'm always open to a conversation.