Conversation summary
Annie Gilchrist interviews Nick Cheetham about the gap between signing a complex client and getting them live, the cost of a rigid onboarding process, and why he invested in Lissom.
For Nick, the customer relationship is tested almost as soon as the deal is signed. As Currencycloud’s former Chief Revenue Officer, he saw customers who had spent months getting to that point meet a standard onboarding process that did not always fit their business.
The relationship usually survived, but sales and account teams were drawn back in, the customer took longer to go live, and their account of the experience could become ‘fantastic, but…’.
Annie brings the view from compliance product work: teams have real obligations, but manual processes have made customer experience hard to protect.
They discuss what Nick’s airport security comparison reveals about rigorous checks, how richer business data and AI could support a more responsive journey, and why he chose to invest in Lissom. The interview below follows the recording’s sequence, edited for clarity and length.
Edited interview
From signed to live
Annie
We know each other from Currencycloud, and you have supported us since near the beginning. You have also experienced the problem we are trying to solve at Lissom from the sales side. You can put a great deal of work into winning a complex client, but you still have to get them from signed to live. What did you see happen at that point?
Nick
We used to assume a certain amount of fallout in the first year, and often in the first few weeks. There were several reasons, but probably the most significant was the onboarding experience. It is demoralising to put so much work into a relationship and have the very first thing the customer experiences be a bad one.
Annie
How long might the team have worked on a deal before the customer reached onboarding?
Nick
Our average deal cycle was about 90 days. It became particularly disappointing when the go-to-market team was trying to enter a new segment. The customer was excited about doing something different with us.
They knew they were a different kind of business, but then they were given the same questions and requirements as a completely different segment. A process that works for yesterday’s customer does not necessarily work for the next one.
The customer starts to think that what they heard from sales does not hold up once they reach the rest of the company. They feel misunderstood. It is more than friction: it says something about whether you can be flexible and understand their business, or whether you are just ticking boxes.
A versatile approach that understands the segments you are entering, and still works efficiently, is crucial.
We typically did not lose those clients. Instead, a huge amount of go-to-market time went into customer success. The account manager and salesperson were pulled back in, which was costly. When the customer described working with Currencycloud, the answer could be ‘fantastic, but…’. That is disappointing. It should not have to happen.
The encouraging change is that people are paying attention to it, and the technology now allows a more versatile approach.
The compliance and customer experience problem
Annie
I have spent a lot of time working with compliance teams and building financial crime products, so I see the other side as well. Those teams are under pressure to protect the business from risk. They have regulatory obligations, information they need to collect and risks they need to assess.
With the previous generation of tools, it was understandable that completing that checklist became the priority.
The thing that suffered was often customer experience. In most parts of a business, you would treat that as fundamental. Onboarding is the first touch of the product, yet the experience could become secondary.
When so much of the work has to be mediated by people, it is hard to do the compliance work robustly and give the client an excellent journey at the same time.
Nick
I had a lot of sympathy for the compliance team. It was a tough job because they were doing most of it by hand. We saw the same issue in more transactional parts of the business. You could get through 800 decisions in a month, and those were decisions, not necessarily approvals.
But that volume did not tell you what mattered to the customer. Could you give them an answer in a day? Could you do it without going back and forth? Could you do it in one pass and make it simple?
You need a team that really understands and cares about the problem. Now there is also technology that can address it differently. It could make the experience, perhaps, even pleasant.
The airport security comparison
Nick
I think about airport security. We all know why it matters and want to travel safely, but nobody enjoys the awkward parts of getting through it. My experience at Heathrow Terminal 5 is that it can be done much more gracefully. The checks are still there, and I believe in them, but the process is easier to move through.
I will choose that terminal when I can. That is what the onboarding experience should be: keep the safeguards, but do it well.
Annie
It is a useful comparison. There is that sinking feeling when your bag goes down the other track and you see a long queue forming. You want to get on with your journey, but the process has suddenly become the thing holding you up.
Nick
Exactly. It has taken a long time, but technology and the will to change the process are coming together. That is what should happen in onboarding too. Keep people safe, and do it well.
Getting what is needed first time
Annie
Our focus at Lissom is getting everything needed for customer due diligence first time. You see this problem across all kinds of onboarding, but it is especially hard with a complex regulated business and a complex risk assessment. If the customer is legitimate, you want the journey to be as smooth and quick as possible.
If someone poses a real risk, you need to stop them. Finding that balance is difficult.
What excites me is the combination of much richer data about businesses from online sources and the ability to work with vast quantities of written information. That could support a live conversation with the customer without every exchange being mediated by a person.
I think it can change the way these processes are built and how we solve this problem.
Nick
I agree. That is why I invested.
What a difficult journey costs
Annie
How much does it cost a business when onboarding a complex client is done badly? How valuable is it to solve that problem?
Nick
With the big, complex relationships, you have built trust. The customer believes in the change they are making with you and in the team helping them through it. They know compliance can be hard, so they may accept a difficult process even while they complain about it.
But it adds time before they can go live, and it takes something away from the confidence they had in you. For a customer in a new segment, it is especially disappointing.
It can be demoralising for the sales team as well. They are out ahead, trying to open new areas, while the process behind them has not caught up. I would call much of the cost an opportunity cost. The team is dealing with this customer instead of getting on with the next thing.
You are not building the strong reference you expected; the customer’s account of working with you comes with a ‘but’. It is difficult to put a single number on that, but it is grit in the system.
The cost becomes easier to measure as you move towards more transactional business. Some customers decide the process is too hard, see an alternative and walk away. The more transactional the relationship, the less likely a customer may be to put up with that trade-off.
How it plays out depends on the business, but the underlying problem is the same.
As more companies solve it, doing this well will become a competitive advantage. Customers notice an easier process, just as you notice the airport where security works smoothly. You may put up with a difficult journey when you have to, but when you have a choice, it affects where you go.
And onboarding checks are often repeated rather than done only once.
Annie
A complex deal can involve several internal teams and stakeholders who all have to keep an eye on it. How do you account for their time and the distraction from what they could be doing elsewhere?
Nick
It is hard to put a number on it. But for a business that is growing quickly, everything is about removing friction. Growing an extra 10% in a year can have an effect on valuation that is much bigger than 10%. That is why this matters.
Why Nick invested in Lissom
Annie
Why did you decide to invest in the team?
Nick
My career has been in startups and scaleups. Since leaving Visa after the Currencycloud acquisition, I have spent my time advising companies and working as a chair or executive chair. I enjoy being in those businesses, and I have seen what works and what does not.
At an early stage it is not all about the particular thing a company has decided to tackle. You will inevitably learn, change direction and work towards finding what the market needs. I look for a team that can do that. I rarely make angel investments, but I knew you, and I got to know the wider team.
I saw intelligence and drive, ambition without ego, tenacity and fearlessness. You find something new every day on a journey like this. I could see those qualities in you and in the team you were building with Esther. I thought you had the ingredients to build a successful company and do it in an organisationally healthy way.
I also knew the space. I knew this was a problem, and I knew you understood it. That mattered too.
Annie
Founder-problem fit.
Nick
Exactly.