Richard Metcalfe and the Art of Being Small

Richard Metcalfe remembers selling ARKK when the company consisted of three people and very little reassurance. There was no established brand to borrow confidence from. No collection of customer stories to slide across the table. The buyers worked in finance, where taking an unnecessary risk rarely improves anyone’s afternoon. A young supplier needed to offer something beyond a competent demonstration.

He worried about the obvious question: why would a finance director trust a business this small? His eventual answer was to stop treating smallness as an embarrassing secret. Some buyers enjoyed giving a new company its chance. They liked dealing with someone who would answer the phone. There was a human pleasure in backing people early, even when the purchase itself concerned something as apparently unromantic as reporting software.

That recollection supplies a useful entrance to Metcalfe’s career. ARKK’s founder and former chief executive built a business around the exacting world of financial compliance. Yet his recurring subject is people: the customer deciding whether to trust him, the employee deciding whether to approach him, the fellow entrepreneur who knows which question to ask. The software had rules. The conversations required practice.

A very small company, a very specific list

ARKK was founded in 2009. A year later, Metcalfe faced a much more immediate concern than the eventual size of the business. In his account of October 2010, the company had moved into its third office, on London’s Throgmorton Street, and had five staff developing or testing the software. He needed a customer that month to keep things going.

Working alphabetically through an unqualified contact list had produced frustration. He changed the task. He researched 20 names, put them into a spreadsheet and imported them into Zoho. Eighteen answered his calls. Three became serious prospects. One meeting, at the Lloyd’s building, produced the timely order. His celebration for the team was chocolate mousse.

It is an unusually serviceable founding anecdote: a smaller list, better information, a deadline and dessert. The lesson he drew was to identify customers worth winning and share that ambition across the company. The detail that stays with you is the mousse. Corporate history usually orders champagne; a young business has other priorities.

The numbers behind the quiet work

By May 2019, ARKK was selling into a substantially different position. Mobeus invested £5 million of growth capital. The company then reported more than 800 clients in 20 countries, including a quarter of the FTSE 350 and ten of the UK’s twenty largest accounting firms. Those were substantial references for a founder who remembered having none.

ARKK had recently launched for:sight, a platform intended to reduce the burden of reporting processes and give finance teams more time for other work. Its commercial setting helped explain the opportunity. Authorities wanted reporting in digital form; companies still needed dependable ways to prepare it. The work could be tedious while the consequences of errors remained serious.

The money was earmarked for sales, marketing and product development. Bob Henry joined the board, while Amit Hindocha led the investment for Mobeus. By February 2021, a further £2.2 million brought the investor’s total commitment to £7.2 million. The sums mark a different scale of responsibility from the early prospect list: there were now investors’ expectations to manage alongside customers’ deadlines.

Capital came with homework

Metcalfe’s own writing about investment was less celebratory than the subject sometimes invites. In June 2021, he set out the questions a founder should answer before spending the money: what the next milestone required, where the return would come from, which skills were missing, and whether the cash could support the plan. A funding announcement, in this account, came with homework.

He also addressed dilution. Additional capital had to create enough value to justify the ownership surrendered to obtain it. At ARKK, he described investment tied to developing and launching a SaaS platform, with a defined return timetable and hiring to cover gaps in capability. This was the founder looking past the bank balance to the obligations attached to it.

That is a revealing complement to his sales stories. Winning the order solved one problem and created work that had to be delivered. Raising investment expanded the possibilities and the accountabilities together. His interest repeatedly returns to what happens after the agreeable conversation, when somebody must carry out the promise.

The CEO has left the corner office

Inside the growing company, another kind of distance troubled him. In September 2019, Metcalfe wrote about hearing that someone did not know how to approach him because he was the CEO. He had a corner office, useful for confidential conversations. It also supplied a threshold that colleagues could hesitate to cross.

His response was to spend part of the day in communal space near the kitchen. With his laptop there, he could meet people as they fetched coffee. He accepted that this would interrupt the conventional version of getting work done. The interruptions were the point. They created chances to hear what people needed without requiring them to arrange an audience.

He had already made the kitchen a small test of leadership. In a 2018 essay, he described wiping down a messy surface while making tea. It took about half a minute. He connected the habit to accepting responsibility and remembered delivering hundreds of free newspapers in cold weather when he was younger. The argument was pleasantly inconvenient for anyone hoping that seniority conferred immunity from crumbs.

A year later, his lunch sessions included personal goals and plans for vision boards, assembled from pictures in the manner of school projects. He wanted colleagues to know more about one another’s aspirations than a Monday exchange about the weekend could reveal. It is a recognisable thread in his management writing: making room for the person who happens to hold the job.

“Ten opportunities to get to know my people better.”Richard Metcalfe, on working near the office kitchen, 2019

A founder’s education, with a family review

Metcalfe’s enthusiasm for Entrepreneurs’ Organization was sufficiently visible at home to attract a review from his eight-year-old son. At a family party, the child impersonated him as someone whose principal occupation was messing around in EO. The episode prompted a 2015 reckoning with how much time the organisation consumed and what it returned.

The return included a regular four-hour forum with eight fellow entrepreneurs. He valued the custom of sharing experience rather than delivering instructions. People could hear what another owner had lived through and reach their own conclusions. He also described passing useful books to colleagues and arranging opportunities for his team to learn from the wider circle.

In a later account of networking, he recalled how the New York chapter helped during the business’s US expansion. An accountant, a recruitment consultant and an apartment were sorted in one afternoon. The anecdote brings the value of a network down to a sensible unit of measurement: the things you would otherwise spend days trying to organise in an unfamiliar city.

His account of community also stressed staying in contact and helping people without waiting for a transaction. That matters to the shape of his later work. Long before selling coaching, he was describing learning as something exchanged between business owners. He went on to serve as president of EO UK; the network was part of his professional education as well as his calendar.

The founder changes seats

Laurence Kiddle succeeded Metcalfe as ARKK’s CEO on 1 January 2022. Kiddle had advised the board since December 2020 and brought experience from Deloitte and Thomson Reuters. Metcalfe publicly welcomed the appointment and praised the incoming leader’s knowledge. The announcement marked a clear change in who was running the company he had founded.

His next work included helping other leadership teams. In 2023, he described chairing his first board meeting and strategic planning day as Sapio Research’s first chairman, working with CEO Andrew White and COO Jessica Bunce. The setting had changed from building his own reporting business to working alongside people building theirs.

His present founder sales coaching concentrates on early B2B selling: choosing the right customers, explaining value, handling objections, progressing deals and discussing price. The ambition is practical. A founder who can build the product still has to discover whether anyone will pay for it, who makes that decision and what will cause it to happen now.

Permission to ask the awkward question

In recent posts, Metcalfe distinguishes a pleasant meeting from a qualified opportunity. A prospect can admire the vision and enjoy the conversation without having the budget, authority or urgency to buy. He urges founders to ask about the decision process and the consequences of leaving a problem unsolved. Politeness can be expensive when it occupies a forecast.

He also advises acknowledging a sales conversation that is going badly, rather than speeding up the presentation. Asking whether the message is landing gives the buyer room to explain the obstacle. It is consistent with his recollection of selling as a small supplier: a useful conversation depends on admitting the circumstances actually in front of you.

The 2026 GeekSessions conference in Faro put him among a gathering of developers and technology practitioners. His scheduled workshop drew on his path from software architecture into selling, with ten sales basics for technical founders. Alongside talks about AI and software, his subject was the old difficulty of persuading another person to make a decision.

The distance between Throgmorton Street and that workshop is measured in years, customers and accumulated practice. The early order needed a carefully chosen list; a larger company needed accessible leadership; expansion needed people willing to help. Metcalfe now works with founders facing their own version of those problems. Somewhere among the dashboards and demonstrations sits the person who might say yes. He has spent a career learning how to talk to them.