Tough at the Top

Running a business or being in a leadership position can be extremely tough. The challenges that come across your desk aren’t the easy ones and rarely the quick ones. They are often complex and take time to work through. There are always multiple challenges at any one time. You may or may not have anyone you can turn to for advice. Therefore, in my experience, it can be ‘Tough at the Top’.

Throughout our journeys, we must look back at our choices and decisions. It’s important to reflect and improve on the negatives and build on the positives. We must pat ourselves on the back from time to time for all that we’ve achieved; I encourage everyone to take a deeper look at the challenges that have been overcome and share the experience gained.

Bringing me to the topic of this blog, below, I share some of the experiences I had in my first year as a first-time CEO.

Journey to ‘The Top.’

Firstly, let me explain how I started my journey and found myself in the seat of the CEO at Inbay.

  • Colt International – 1997/1999 – 2 years
    • Assistant PC Administrator
    • Network Administrator
    • Senior Network Administrator
  • Nexus Software UK Ltd – 1999/2007 – 8 years
    • Senior Network Administration and Webmaster
  • Taylor Made Computer Solutions – 2007/2015 – 8 years
    • Business Solutions Specialist
    • Software Development Manager
    • Technical Services Delivery Manager
    • Head of Account Management
  • Autotask / Datto – 2015/2019 – 4 years
    • Solution Consultant / Solutions Consultant Team Lead
    • Director of Global Product Management
    • Director of Sales Engineering and Partner Success, International
  • Inbay – 2019/Present – 3 years
    • CEO

As you can see, I have worked in 4 businesses before joining Inbay, with an average tenure of 5.5 years. Within each company, I was allowed to learn and progress.

Looking back at my first job with Colt, I was in the right place at the right time and had the right attitude. When I joined Colt, they were about to migrate their business from using a Unix-based system/network to Microsoft NT 4. So they sent me to all the relevant Microsoft courses and allowed me to help implement 25+ servers in two different countries. Fantastic experience that I will never forget.

Similar could be said for my time at Taylor Made. Few people know that I joined Taylor Made as a Senior Engineer. However, after four weeks in the role, I realised, and they realised, that I wasn’t at the same level as the other two Senior Engineers in the business. I hadn’t had the exposure to the vast number of systems that an MSP supports. However, I did have the right ‘can do’ attitude and had experience with Microsoft SharePoint, which opened the opportunity as a Business Solution’s Specialist, consulting in SharePoint and Project Server.

I could probably write an entirely separate article on my time at Taylor Made, how I managed to change between roles and the challenges I faced. But for now, to keep this post shorter, I will say the eight years gave me a tremendous rounded experience of working at a manager level in a £10 million turner MSP.

Having said that, Autotask gave me my first Director level experience, working within the Product Management team. Having worked at an MSP and consulted with over 50+ MSPs during my time as a Solution Consultant, it was unequivocally a positive next step. Datto then acquired Autotask, allowing me to head up the Sales Engineering and Partner Success functions, which were thoroughly enjoyable positions in a brilliant company.

I loved working for Datto! The company has excellent products and exceptional values and is undoubtedly the largest company I have had the pleasure of being a part of. I have many highlights from my time there, which include running a QA session with Austin McChord, CEO and founder of Datto, at their annual DattoCon conference and implementing changes in the Sales Engineering team to empower the Sales reps further. But perhaps that’s another article?

I spoke with Sanjay Singh, Chief Revenue Office at Datto, about my next opportunity with them. Heading up Sales Enablement worldwide sounded like a perfect next step for me, which could have led to further opportunities, but then came Inbay.

Certainly not an everyday experience having somebody ask you to run a business! I suddenly had the opportunity to try to do things my way. Take all the best bits from the various leaders I have worked with and try to be the best I can be. This opportunity and the fact the business was failing were very appealing to me. It was a tough decision that I have reflected on several times since.

1st Year Challenges

I often refer to ‘challenges’ and never to ‘problems’. I do this because I feel the word ‘challenges’ leads to a more positive mindset than using the word ‘problems’. I often remind myself that challenges can be fun and always overcome.

The New Boy

Having left a very secure job with many growth opportunities, I quickly realised I was once again ‘the new boy’. But this time, everyone was looking at me with anticipation and uncertainty. Some people worried, some people wanted changes and some with high expectations. Of course, I did expect this, but I didn’t appreciate that I was completely unknown by the company, the staff, and even the owner. The owner, John Prenn, did interview me, but how much do you really get to learn about someone through an interview process?

The challenge was simple. I was unknown to the company and most of our customers.

Responding to the challenge was very simple, one word, TIME. I had to be available for people, get to know people, be open and listen, and allow enough time for people to get to know me. In my first six months with Inbay, I travelled to our Technical Operations Centre in Sri Lanka every month. I spent three weeks in our London office, then at least one week in Sri Lanka. It’s fair to say by the end of the six months, I was exhausted, but we had achieved a lot as a business, and I was no longer the unknown CEO. I started gaining some trust; this brings me to the next challenge.


Building trust in a relationship takes time. You can’t just tell people to trust you, and you definitely can’t make people trust you. It’s how you are with people and the actions you take that allow you to build trust. For example, when I first walked into Inbay, there was a lack of ‘trust’ within the business between UK-based staff and staff in Sri Lanka. There was a ‘them and us’ type of attitude. The UK team, from my perspective, was previously perceived as the leadership team and the staff in Sri Lanka as… ‘just the staff’. I might be speaking out of turn, but that’s how it felt on many occasions.

I spoke to many clients during my first six months, pretty much all of them. The general feeling I had from them was that the services were ‘okay’, but there had been issues which could lead to a lack of trust.

There was also uncertainty for the business owner about what had been happening. I won’t expand on this statement now but know; that when I say there was a lack of trust from everywhere, I’m not exaggerating.

The challenge was clear, a lack of trust from everywhere!

I decided to break down this challenge. We needed to build trust internally and externally. I initially focused on the internal trust issues. We started with the basics, setting company values, with ‘trust’ being one of them. We spoke about our values during our monthly staff meetings, which we call our All Hands Meeting. We then created a vision for the business along with a mission statement.

Vision Statement. – “To establish Inbay as the leading solutions provider in the Information Technology channel, maintaining our core company values while we grow.”

Mission Statement – “To equip small to medium-sized Managed Service Providers globally with the best-outsourced services, allowing them to succeed.”

We then visualised the journey we needed to go on as a business and as individuals to succeed.

Our expedition to the Summit of Everest, as we call it.

By setting the above and constantly communicating them, along with everything I did to overcome the ‘new boy’ challenge, I eventually overcame the trust challenge internally. However, it did take longer to vanquish the trust issues in the industry.


I’m a firm believer in having the right tools for the job. This probably has to do with my childhood hobby of building radio-controlled planes. You can’t cut a piece of balsa wood with a chainsaw; actually, you can, but it will make a mess! When it comes to running a business, the same principles apply. You need the right resources in place to succeed. Don’t think of resources as just people; think much broader.

When I started at Inbay, it was clear that we didn’t have the right tools to help us support our mission and vision statements. There were also team members in the wrong positions. There were also several new positions needed in the company. Our Technical Operations Centre in Sri Lanka was running out of an ancient building with leaks, no air-conditioning and security concerns. How could I expect people to be their best in this environment?

The challenge was an abuse of the right resources across the board.

I started tackling this challenge by creating a leadership team who would meet every Monday morning for an hour. There were several thoughts behind this, outside of regular management duties. The focus, to help with communication, the management team would be responsible for letting their teams know what was happening within the business. We still did our monthly All Hands meeting, but this was a way to provide indirect updates throughout the month. It also allowed the management team to voice the challenges that they are having and helped me and others build trust with one another.

It was easy to find a better office. We managed to secure twice the floor space in a brand-new building just two streets away at the same cost. The building needed to be fitted with partitions, ceilings, floors, and furniture. Allowing us to apply our branding, which included our Everest journey and company values. The management team kept staff up to date with what was happening and soon had everyone looking forward to the new facilities.

As part of the office move, we provided everyone with new equipment, a considerable investment at the time but one that was needed and appreciated. We then worked on every team member’s development plans and career pathways. Again, we wanted to provide career progression and improve staff retention.

The global pandemic

Eight months into the role as CEO, we truly started to make headway with the challenges listed above. However, several other complex challenges continued to be worked on. And then! The global pandemic.

I’m sure many of you can instantly relate to the challenges COVID bought upon us. I won’t go into all the obvious ones. Instead, I’ll talk about a few less obvious ones that impacted Inbay and our staff.

We run a 24/7 365 operation. We staff multiple shift patterns to allow us to provide the services that our customers (MSPs) rely on to support their customers (end clients). We can’t turn the lights off at 17:00 and worry about it the next day. We must stay operational. I’ll pause here and add that at the time, we had staff in four different countries:

  • United Kingdom
  •  Sri Lanka
  • America
  • Demark

We also provide services across the globe. So we had to closely monitor the impact of COVID in all of the countries we had staff and the counties we had customers in; this continues today.

The challenge was managing the impact of COVID whilst keeping the lights on.

The first thing I said to our management team was that it’s time to over-communicate. We must work through this as a team and ensure our staff and their families are safe while trying to keep as close to ‘business-as-usual’ as possible. We initially had daily meetings to discuss challenges as they unfolded and decide on the best cause of action.

People always come first. I may be stating the obvious, but we wouldn’t have a great business if we didn’t have great people. Therefore, and please don’t take this the wrong way, we couldn’t afford for someone to get COVID and impact the technical operation centre. One person could have quickly taken out the entire operation. So we instantly decided to enable staff to work from home which meant we had to provide extra equipment, laptops, monitors, internet bandwidth etc.

When the vaccine was made available to the UK, there was a considerable delay before it was available in Sri Lanka. Naturally, then, much of the team was hesitant to take the vaccine. Of course, you can’t force people to do something they are unsure about, but you can help answer questions about any uncertainties. I recall asking the nurse who gave me my COVID jab if she would be happy to take a picture as I wanted to share it with my staff.

What I would do differently

We learn from our own experiences and others. Of course, I would do things differently if I were in the same position again. But, I do feel I did everything I could with the challenges we faced at the time.

I would have more confidence and make faster moves. I would address personnel challenges quicker, get people settled, and get people in the right seats. I would do more with ‘resources’ and get external advice from people with more experience than myself.

I would also bring the business strategy in quicker. However, you need to understand a business before implementing a strategy.

If you would like to keep up with my journey or just connect, please add me on LinkedIn here and be sure to follow Inbay here for the latest updates.

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