My First Month at Cledara: Takeaways from Oscar Hackett

We speak to Cledara's Oscar Hackett about his key learnings after his first month at Cledara.
My First Month at Cledara: Takeaways from Oscar Hackett

I have just finished my first month at Cledara and it has been incredibly exciting. I wanted to share a few quick takeaways from it, some of which may strike a chord with people in startups. I think sharing learnings is a great tradition of the startup world. So here we go.

Flat teams are creative teams

The hierarchy will come as we grow and it does serve a purpose but I enjoy working in teams where the hierarchy doesn’t exist, or at least you don’t feel it. That is what we have here at Cledara and I am loving it.

I am part of a daily standup with our extremely experienced COO who has built several fintech companies and a marketing graduate who is 4 months out of university. It is always an open conversation where we all bring ideas to the table and discuss. This allows us to be very creative, experiment and iterate fast.

On top of this, there is an understanding that failure is the only way to success. With this mindset, failures can be seen as stepping stones on the way to victory. This should be true at every company, but it is particularly relevant for startups. Don’t get me wrong, results matter and in sales, they really matter. But to get results we are going to have to try a lot of stuff and a lot of it may not work. This philosophy is clear to me already and one of the reasons that Cledara has achieved so much in such a short space of time and why I have really enjoyed my first month.

The scale of the SaaS problem is huge

I have worked with a lot of SaaS companies and I’ve used a lot of SaaS. And I also used to work at SaaStock, so you could say I have been surrounded by SaaS for a while. I am one of those people that loves the opportunities and powers that SaaS gives companies of all sizes. It gives startups superpowers and saves large companies hours. I think it’s truly transformative.

However, coming from a business development perspective, I never fully appreciated the issue of managing all of this amazing software. And this problem is true for startups and for large companies. Let me explain why.

Firstly, having visibility of SaaS as the company grows is a nightmare. In fact, loads of companies still use excel and try to manage it manually. This doesn’t give you a great overview of what is happening in real time and is a pain to manage. Secondly, the finance team, IT team or whoever is in control of all of this, often actually struggles to have that control and do their job. Different software accounts are owned by different people and paid for on shared company cards. To cancel anything is a struggle, and to manage the process is as well. And finally, the finance admin is also super time-consuming. When my great finance colleagues were chasing me for invoices, I never understood the rush, but now I do. The fact they have to do that manually and then manually reconcile these payments is crazy, but that is what happens. Every month.

This month, my eyes have been opened on all the calls I’ve had with people struggling to manage their SaaS, and it has been a pleasure to help them and give them their time back.

Cold calling needs positivity

I am not an experienced cold caller overall. I did a lot of it when I set up my first company in Russia but there I could just get through any gatekeeper by speaking English. However, cold calling in the UK to potential clients is a different game for me. Especially as at my previous company, email and LinkedIn were our big tools, not the phone.

I don’t want to get into a debate of whether it works or not. It clearly does for some B2B companies, but others have also become unicorns without it. For me, it depends on the product, on the persona, on how good you are and on how effective your other channels are.

I wanted to test it though, and this is what I have been doing. The jury is still out as I only started last week but I need to improve to know if it will fully work. All I have learnt so far is that positivity is the number one thing needed to cold call. I knew that getting rejections and no response was part and parcel of cold calling, as it is part of sales. However, it hits harder on the phone and, after 3 hours of no success and a few mistakes on calls, I felt a tad low but I then remembered a quote from Ant Middleton (great books for sales mindsets actually):

“Failure isn’t making the mistake, it’s allowing the mistake to win”

I hadn’t been successful on those calls but I knew I was improving and I can keep doing so. I wasn’t going to let the lack of success beat me. It is this positive growth mindset that drives me to continue to cold and enjoy the process. Positivity is the root of resilience, and you need buckets of it to be hitting the phones. This will be key for me when hiring in the future.

SaaS affects more people than I thought

I have already discussed some of the many pains faced by having all this great software, but what is even more interesting is how many people it affects. I speak to CFOs, CTOs, COOs, CEOs, Finance Directors, Digital Transformation teams and more.

What does this mean though?

For me, it makes it a company-wide issue, but one that people often don’t know there is a solution for. People have come up with some makeshift ways to make it a slightly smoother process but they don’t realise that there is a better way than reduces overheads and gives back time to spend on value-added tasks. This means that we need to educate the market, we are a new type of tool even within our own space and we need to make this clear.


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