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“Is that today’s most pressing challenges, or yesterday’s? Or tomorrows?”

We look at four of the biggest challenges for founders and senior teams of high growth companies.
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Charlie Greenwood
April 23, 2021
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Since we launched Sports Loft, we have worked closely with the CEOs and leadership teams of some of the most exciting tech companies in our sector. They are fantastic companies with some great stories to tell – but it’s not all a walk in the park. Running (and being part of) a startup is hard. Whilst the romanticised stories of success in silicon valley sound lovely,  the reality is more about the endless  investor meetings, the belief that is required as you hear “no” after “no”, and the constant juggling act of building a great team. Some people thrive under the challenges of startup life (I have endless respect for them) and at Sports Loft we have seen first-hand how  the leadership teams at the different companies deal with the challenges that come their way.

So, for this blog, I thought I’d highlight some of the things that pre-occupy founders and senior teams of high growth tech companies at the intersection of sports and media – and if you are reading this and working at a startup in another sector, it might also be quite a familiar list. The aim of this post is to start to give an inside view of what its really like to be at a fast growing startup and we’ll be launching a series of podcasts on this very topic in the next few weeks. This isn’t meant to be an exhaustive list, so I’ve picked four areas: hiring, getting helpful product feedback, fundraising and the sales process. When I asked our founders what were their most pressing challenges, I got a huge variety of responses – my favourite was “is that today’s most pressing challenges, or yesterday’s? Or tomorrows?”. I thought that was pretty fair. So here goes..


1. Hiring

For almost all of our founders, this was their number one concern. They know that they can’t build a company on their own – they need to build a team around them. In many ways hiring the senior team is the easy bit – they get the vision and they have experience in the market. The harder hires are the next layer – the people who will make it happen but need to be able to articulate what the company is trying to achieve, the people who need to be able to think through problems but also get their hands-dirty and make it work.

When I asked Donny White, CEO at Satisfi, he said “The most difficult aspects of hiring are finding people that will be willing to work with less resources, tell people they are at a company their friends have never heard of, get paid less salary than market rate, have to work more hours, and formulate the culture you want to define your organization. And if you mis-hire, it sets everyone back”.


2. Getting helpful product feedback

We heard this from quite a few of the companies at Sports Loft. They are at the stage where they are growing fast, both from a commercial perspective and from a product perspective – they are adding new features on a constant basis and more people are using the product, so more use-cases are developing. Will Brooke, Chief Growth officer at Slate, said “Focus is so hard when it comes to product – it’s easy to go in a million different directions based on customer feedback”

Tom Kuhr, CMO at Greenfly put it another way – “One of the hardest things for early startups is get honest product validation. How do you get prospective buyers to give you direct feedback, when as buyers we all hold back because its part of negotiation? Does your product or service will solve a major problem for them? How much does that problem actually cost the business each year?  Does your product solve 100% of it, or 55%, or 5%?  The answers to those questions dictate how well your product sell out of the gate.”

From a B2C perspective, there is the same challenge around picking the right features to build, but the context is different – consumer focused products can elicit more feedback (and often more data), but there is often less detail so it needs more interpretation. When I asked Andrew Hall, CEO of Get Metrix, he said “The biggest challenge is wading through the signal to noise to build the right features that move the needle on the business metrics”

3. Fundraising

For founders, fundraising is inevitably top of mind. the thought of “always be raising” seems to be a consistent theme, and the idea that “the best time to raise money is when you are not raising” is pretty true. Fundraising is a huge drain on time and resource, especially for the leadership team, but its also a real challenge to get the narrative right and with lots of moving parts

With a background as a VC and now as CEO, Andrew Hall at Get Metrix said “Fundraising always twice as long as you think it will. You need to work out which investors you focus your time on. We all have a bias to leave the meeting with the positive aspects in your mind. You need to work out which are actually doing the actions to give you confidence”

For Nick Goggans, Founder and CEO at Pumpjack, getting the message right is one of the hardest parts – “What is it that investors are looking for? It changes so much. Some investors want the big picture vision, others want to see the metrics – which metrics? Revenue is great, but we’re talking about early stage companies who might have a handful of clients – so what else? Increased product usage time? Customer referals? Increased sales pipeline?”


4. Sales process

One of the biggest issues forB2B companies in the sports and media sector, is getting in front of their potential customers – the right people within the right organisation. The gatekeepers in the sports and media industry – whether they be consultants, agencies or just factors such as available time and competing projects- can be hard to get around.

Dave Minetti is the SVP of Sales at Tagboard. When I asked him about selling as a startup he said: "The most important part, and the hardest part, is building trust within the market. You’ve got a newer product that many people won’t have heard of and you are trying to disrupt their current workflows. They need to be confident to trust you. This is especially true when selling into extremely well-known entities that maybe don’t move as fast as you’d like. It requires an equal balance of patience and persistence."

For Nick Pinks, CEO at Covatic, timing is all important: “aligning to the client’s timing is tough. Sure, you can get lucky, but how do you know when they are looking for a solution, when the budget process works, when they are open to new ideas.”

For Colin Casey, EVP Partner Development at Fevo, “It’s so important to get to the right decision maker. Who actually has the power to make the decision, but also who will influence them. The decision makers are going to be busy people with a lot on their plate so you’ve got to be really respectful of their time, but so much has changed with COVID and senior leaders seem to realise that and are open to hearing about new ideas.”

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Is that today’s most pressing challenges, or yesterday’s? Or tomorrows?"