Ky Nichol and the trouble with everything going to plan

Ky Nichol had spent years helping with preparations for the London Olympics when he was asked whether he would have a front-row seat. It was a reasonable question for someone involved in getting the place ready. His answer was rather less grand than the occasion: “I’ll be early in line for tickets and hope I get some.”

There is something pleasing about the gap between those two positions. You can help an enormous organisation prepare for an immovable date and still find yourself hoping to join the queue. The plan contains venues, transport, budgets and reporting lines. Somewhere outside its carefully drawn edges stands a person who would quite like to see the sport.

Nichol’s professional life has repeatedly taken him to those edges. He worked around space programmes, then the preparations for major events, then the complicated operations of large companies. Today he is the co-founder and CEO of Cutover, which makes software for coordinating people and automated tasks. His recurring subject is what happens when everybody’s separate plans have to become one event.

Earth had a spreadsheet problem

Before enterprise software, there was the space industry. Nichol’s undergraduate work with NASA involved mathematical models of impact craters for the Shuttle Programme. Later, at the consultancy Pcubed, he led engagement with the European Space Agency on the International Space Station. These were different assignments, linked by the exacting business of making complicated undertakings work.

His account of the ESA engagement includes reviewing human-spaceflight operations and helping establish programme management for the European elements of the station. The work encompassed preparations involving the ATV spacecraft and the Columbus module. His role sat in the organisation of the programme, where technical ambitions must become responsibilities, sequences and decisions.

Space operations gave him an example of people and machines cooperating closely. Enterprise consulting exposed him to an awkward contrast: sophisticated organisations still coordinating critical work through scattered spreadsheets, calls and emails. His career brought him into government, telecommunications and financial services, alongside the major-event work. Different clients could share an inconveniently familiar operating habit.

A spreadsheet has many virtues. It accepts almost anything you put into it, which is also how it acquires rather more responsibility than its maker intended. A list of tasks can look reassuringly complete while leaving the relationship between them to a conversation somebody vaguely remembers having.

The trouble starts between the venues

In his major sporting events work at Pcubed, Nichol dealt with the Athens Games, the football World Cup in Germany and preparations for London 2012. He argued for agreeing responsibilities early and keeping project teams together until there was a sufficiently detailed shared plan. Boundaries could conceal missing work: a venue might be accounted for while its connection to the surrounding infrastructure remained somebody else’s problem.

His guidance also included establishing an early baseline and planning for organisational change. A major event needs different kinds of people at different stages. Its deadline provides an unusually blunt answer to the suggestion that everyone might simply take another month.

Those observations help explain his later company. A technically accomplished team can finish its own assignment and still leave the overall operation exposed. The difficult part is seeing the dependencies early enough to act on them. The stadium and the road must agree about where they meet.

The ticket remark adds a small corrective to all this programme language. Planning an event and experiencing it are separate activities. Nichol could spend years concerned with the former while the latter still depended on an ordinary transaction. Even a programme manager occasionally has to wait his turn.

A small team meets a very large bank

Cutover’s beginnings were modest enough to be measured in lunches. Co-founder Craig Gregory recalls joining the team in 2014, working multiple jobs through lunchtimes and weekends until there was a first proof of concept. Nichol led a group small enough for Gregory to describe it through the familiar two-pizza measure of team size.

That account gives the company’s early work a useful physical scale. Before enterprise adoption and funding rounds, there were people fitting development around the rest of their working lives. Gregory describes wearing several hats, spending much of his time on technology and operations. The organisation was itself a collection of overlapping responsibilities.

The Barclays Accelerator, powered by Techstars, provided a setting in which the prototype could meet a bank’s actual problems. Cutover joined the 2015 London cohort. A contemporaneous account put the time from concept to first contract at 66 days. Nichol described the acceleration with evident satisfaction: “We’ve made three years of progress in three months.”

A later account identified that milestone as a 12-month software evaluation agreement, followed a year later by a global framework agreement. Barclays was a potential customer when the team entered the programme. Becoming one required the software to survive contact with a large institution’s technology, procurement and information-security requirements.

Nichol also supplied a memorable explanation of the problem: imagine coordinating seven performances of Swan Lake around the world through spreadsheets, phone calls and emails. The dancers have enough to do already. His point was that timing and coordination become a separate job when many participants must act together.

The minutes before the market opens

The company found a particular audience in financial services, where complex technology work carries business consequences. Its early team had not designed it exclusively for banks. Banks nevertheless supplied plenty of complicated, regulated operations in which coordination mattered. A customer could help reveal a product’s market as well as test its features.

By November 2019, Cutover announced a $17 million Series A led by Index Ventures. The announcement described adoption across more than 14 global financial-services companies and work supporting operational readiness for technology IPOs. There was also cloud migration, bank restructuring and recovery preparation. The list makes clear how much activity sits behind apparently singular business events.

An IPO offers a useful example. The public sees a company arrive on the market. Behind that moment sit systems, trading capacity, governance and a sequence of preparations. Cutover’s work concerned the orchestration around those events. The ceremony might last a few minutes; the dependencies have been making demands for considerably longer.

Participation in the 2018 FinTech Innovation Lab New York helped the London-based company expand its American operations. The route matters to Nichol’s story because it extended a practical idea into another financial-services market. The company’s growth depended on finding organisations that recognised the problem from their own working lives.

Money to make the invisible visible

In March 2021, Cutover announced a $35 million Series B led by Eldridge, with existing investors including Index Ventures, Sussex Place Ventures and Contour Ventures. The company said revenues had doubled and its workforce had almost tripled during 2020. Those were company-reported measures of a particular period, when distributed work had increased the demands on coordination.

The financing was intended to support product development, engineering and customer capabilities. It also represented a change in Nichol’s responsibilities: the founder of the small prototype team was now running a business with investors, an expanding workforce and customers using the platform for critical operations. Making coordination software entails a fair amount of coordination.

His writing had already made clear that automation alone would leave important work unfinished. In a 2020 article, he argued for connecting specialist tools through an overarching orchestration layer, with culture and responsibility treated as part of the undertaking. Buying another tool would not, by itself, settle who should use it or how it should fit.

That is a relatively patient argument for a software executive to make. It asks customers to think about working practices as well as technology. The aspiration is visibility across the operation: enough shared understanding to carry out change and enough of a record to learn from what happened.

The prototype arrives. Judgement follows.

AI has given Nichol’s longstanding interest in human and machine collaboration a new set of participants. In an April 2026 discussion with Cutover CTO Kieran Gutteridge, he welcomed how quickly coding agents could turn an idea into a working artefact. He saw a substantial opportunity to get ideas into working form.

He also described different levels of consequence, from small experiments to enterprise systems. Fast prototyping made room for learning; more consequential software required testing, observability, security and the ability to reverse a change. Gutteridge’s responses brought the conversation back to engineering experience. Their exchange allowed enthusiasm and caution to occupy the same room.

“If you’re not shipping, it’s a failure of imagination.”

Ky Nichol / April 2026

By September, Nichol was writing about connecting customers’ approved AI models to Cutover through its open-source MCP server. The subject extends the company’s original concern: new capabilities need a way to participate in existing work. An agent that can act still has to encounter responsibilities, permissions and dependencies.

The connection across his career is an interpretation, but a useful one. Space programmes, Olympic preparations, bank operations and AI-assisted work all make demands on coordination. Nichol has kept returning to the moment when an individual contribution must fit into a larger sequence. The tools change. Somebody still needs to know what happens next.

Perhaps that is why the Olympic ticket answer stays with you. After the frameworks, preparations and reporting, there is an actual event people want to experience. The point of all that organisation is to get them there. Preferably with the road connected, the systems working and a little time left to enjoy the occasion.