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In a competitive landscape, companies leverage creativity to attract top talent. By prioritizing employee-friendly practices and work options, you can foster a thriving, innovative workplace culture that enhances retention.

When you’re bootstrapped and competing against well-funded rivals, creativity and innovation in your approach are crucial to help make your company a more attractive place to work, especially if your competitors are offering higher salaries.

OnSecurity was bootstrapped for four years before we secured our first external investment. My approach has been to reflect on all aspects of previous roles I’ve had and what it was I disliked about them, creating an environment that was the opposite of this. One of our core values is to be employee-friendly.

As CEOs, we implement this value by focusing on a life–work balance rather than work–life. We feel that our employees perform more effectively if they recognize and prioritize life outside of their work first. We’ve adopted this philosophy at OnSecurity and it has proven effective. Our employee retention rates are exceptionally high, especially compared to the rest of the cyber industry.

Happy employees perform well and contribute to a great workplace environment.

Initially, we were a remote-first company, operating without an office for our first year. I find the ongoing debate about returning to the office puzzling because remote work isn’t a one-size-fits-all solution. Our approach is to be empathetic. We have staff who thrive in the office and others who don’t. For those who work better from home, that’s where they stay.

Most of our technical staff work remotely most days. To be completely transparent, our sales team generally works in the office more frequently, especially during their first year. We believe that they benefit from a more collaborative and cohesive space.

Conscious choices

I believe we’ve successfully achieved our goal of building a truly enjoyable workplace with flexible benefits. We offer generous annual leave; remote, in-office and hybrid working options; as well as ‘work from anywhere’ opportunities.

This means if you want to explore a new country without burning through your holiday, you can work from abroad for a while.


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We also offer flexible working hours. Most people appreciate the assurance that if personal matters come up, the company is here to support them.

Creating this environment wasn’t instantaneous – it took considerable effort and iteration. Here’s a look at the steps we took to establish a flexible working model.

Hire thoughtfully

This involves more than just finding someone who can perform their job well. It’s also about ensuring they’re a great cultural fit. We are meticulous in our hiring process, focusing on both competencies and cultural alignment. When hiring, especially for senior positions, precision is key – think scalpel, not sledgehammer.

Address mis-hires quickly

Though it might sound harsh, this is crucial. Even with the best hiring practices, occasional mis-hires will happen. If someone isn’t a good fit, especially from a cultural perspective, it’s important to address the issue swiftly.

In a startup, a bad hire can be detrimental, so cutting your losses promptly is necessary.

Treat employees like adults

At OnSecurity, this principle is fundamental. Once we have the right people, we trust them to manage their tasks effectively. This means we don’t micromanage or require constant approvals for minor requests. You’re an adult doing valuable work, so how and when you get it done is up to you.

It’s interesting to see new hires from other companies initially needing approval for every single task. Here, we trust you to handle your responsibilities without needing a hall pass.

Clear mission and objectives

Hiring great people is only effective if they understand what to do and why. Your mission should be clear, objectives should be set and measurable and everyone should know how they contribute. While this is challenging and something we continually strive to improve, clarity in these areas is vital.

Leverage technology

For a flexible workplace, effective communication and collaboration tools are essential. We rely heavily on Slack, for example. If someone has a personal appointment, they update their status on Slack. If an employee wants to work from another country, early communication helps us plan accordingly.

Good management requires effective tools to track performance, output and wellbeing. We use various software-as-a-service platforms to manage this, continually refining our approach.

Business benefits

While the advantages of flexible work and remote options for employees are clear, they also bring significant benefits to the business. Some of these are tangible, but many are less obvious.

For instance, high staff retention reduces the costs associated with recruitment and brings long-term expertise and experience. More importantly, maintaining a positive atmosphere and high morale is crucial.

Happy employees perform well and contribute to a great workplace environment. It’s gratifying to hear new team members contrast their previous experiences with their positive impressions of OnSecurity.

Conor O’Neill

Contributor Collective Member

Conor O’Neill is the Founder and CEO of OnSecurity, a leading penetration testing vendor based in the United Kingdom dedicated to delivering high-impact, high-intelligence penetration testing services to businesses of all sizes. Its mission is to simplify the management and delivery of pentesting for its customers, using its platform to help them improve their security posture through expert testing, actionable insights and unparalleled customer service. For more information visit https://www.onsecurity.io/

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