Guy Haddleton and the art of starting again

Guy Haddleton has spent much of his working life selling the idea that the future deserves a better plan. His own career has been less tidy. It has taken him from the New Zealand Army to British business, from enterprise software in Minneapolis to cloud software in San Francisco, and back to arguments about what his home country ought to make, own and keep. There is a certain pleasure in discovering that a founder of planning software has repeatedly chosen to begin again.

The first software venture began in 1990. Guy and Sue Haddleton used a hundred-dollar credit-card withdrawal to get started, then advertised in the Financial Times before their product had been written. The telephone initially remained silent. Nearly fifty orders eventually arrived. It is a splendidly uncomfortable origin for a business concerned with forecasting: the demand turned up ahead of the supply.

That business became Adaytum. In January 2003, Cognos completed its acquisition, paying US$157.1 million in cash and assuming stock options. The deal had been announced at about US$160 million. By then, Adaytum had roughly 300 employees and some 1,500 customers. A small wager had become a substantial organisation with real budgets, real payrolls and customers who could not afford to treat planning as a parlour game.

The useful question is what happened between the wager and the purchase. Haddleton’s story offers several answers: a partner who shared the enterprise, programmers who understood the problem, a willingness to leave familiar ground, and attention to the people expected to execute the plan. The acquisition price catches the eye. The relationships explain much more.

A captain learns to recruit

Before the software came the army. Haddleton served as an officer in the New Zealand Army from 1974 to 1981, finishing with the rank of captain. He subsequently earned an MBA at the University of Otago. His later business record included managing a stationery distributor and running a pan-European satellite-television marketing business. Enterprise software was a destination reached through several other kinds of work.

His military experience included the Special Air Service. Asked in 2002 what he had carried into business, he emphasised small teams, flexibility and recruitment. He located a team’s power in the strength of its people. The point is plain enough to survive without a motivational poster. It also places the responsibility squarely on the person doing the hiring.

He described a product launch brought forward after learning that a competitor was preparing something similar. The team met the accelerated deadline through an exhausting stretch of work. That recollection exposes the cost of moving quickly as well as the attraction. A strategy does not execute itself. Someone has to do the late nights, and a leader’s elegant arrow on a diagram can become somebody else’s very long week.

The army-to-business connection can tempt a writer into dressing every sales meeting as a military operation. Haddleton’s actual emphasis was more practical. Choose capable people. Understand the situation. Have a plan for the unexpected. Those habits travel well because customers, competitors and circumstances are under no obligation to behave as the spreadsheet says they should.

“The power of a team is in the strength of the people.”Guy Haddleton · 2002

The business inside the budget

Adaytum’s business was helping organisations model, construct and analyse plans. Its customers included Toyota, Lockheed Martin, 3M and American Express. This was software for the consequential, largely unglamorous work of deciding what a business intended to do and whether it could afford to do it. No one gets applause for reconciling a forecast. They tend to get noticed when the forecast goes wrong.

Cognos wanted planning to sit alongside its business-intelligence tools. The acquisition brought an enterprise customer base, expertise and channel partners, as well as software. That matters when considering Haddleton’s achievement. Building a product and building a company capable of getting that product into large organisations are related jobs, but each requires its own work.

There is a revealing detail in Adaytum’s corporate biography. Haddleton had led Adaytum Limited, the original spreadsheet-based business, before it was acquired by Adaytum KPS in 1992. He then led the resulting company. Even within the first venture, the history contains a change of vehicle. The familiar company name conceals some of the reconstruction underneath.

Selling could have supplied a satisfying final chapter. It instead left behind a familiar question: had business planning really been solved? For Michael Gould, who had worked with Haddleton at Adaytum, the answer eventually involved rebuilding the technology. For Haddleton, it involved backing a colleague whose judgement he already knew.

Half a million dollars and time to think

Gould worked on the new software in a barn in Yorkshire. In 2008, after about eighteen months of development, he showed Haddleton what he had made. Haddleton put in US$500,000, and the two became equal partners. Gould later credited the money and moral support with allowing a small team to concentrate on a complete product before it had to start selling.

Anaplan made its first sales in 2010. The important interval comes before that sentence. Someone financed the distance between a working idea and a business customers could buy from. Haddleton’s contribution was partly an ability to recognise the problem, partly a willingness to give the engineering time. Money bought a runway; an established working relationship made it possible to choose the direction.

A cloud-based platform changed how planning software could reach a user. In an early customer’s recollection, there were no servers to install, and the logic felt accessible. The wider proposition was to help different parts of a business work with connected models. Sales, operations and finance could examine related decisions rather than treating their figures as separate little kingdoms.

It is easy to describe a second company as the first company with newer technology. That misses the work involved in returning to a problem. Customers’ expectations change. Distribution changes. The people involved carry experience from the previous attempt, but also have to avoid treating that experience as a complete instruction manual. Familiarity can help a founder recognise an opportunity; it cannot finish the product.

When the founder answers the help desk

Neil Doyle, later a managing director at Bedford Consulting, recalled an early encounter with Anaplan that makes the company’s beginnings feel pleasantly small. He built a model, removed his own workspace-administrator access and locked himself out. Haddleton and Gould helped him get back in. The commercial founder and the technical founder were close enough to a user to rescue him from a self-inflicted mistake.

Doyle remembered that they did so without gloating. This is a modest anecdote, which is why it earns its place. The customer had found a way to trip over the product almost immediately. The response was assistance rather than a lecture. Software promises users control; occasionally the first exercise of that control consists of shutting the door on oneself.

Haddleton also backed Xero early and served on its board. In December 2010, Xero announced that Sam Knowles would replace him, thanking Haddleton for four years of contribution and explaining that Anaplan was taking off in the United States. The change supplies a contemporary glimpse of competing demands. A founder’s time has a capacity limit even when his interests do not.

That departure connects two companies often placed in different conversations: accounting software for smaller businesses and planning software for enterprises. Haddleton had experience of both. In each, the attraction was making financial information more useful to the people running the business. The scale differed. The irritation with cumbersome processes was recognisably related.

Passing the chief executive’s chair

In January 2012, Anaplan announced an US$11.4 million Series B round, taking total funding above US$17.5 million. Haddleton was still CEO. Granite Ventures and Shasta Ventures joined the financing, and their representatives joined a board that also included Gould and Salesforce executive Adrian Kunzle. The circle around the original partnership was getting wider.

Later that year, Frédéric Laluyaux became chief executive. Haddleton moved into the chairman’s role. The transition belongs in the story because the later milestones are often compressed into a single founder’s victory. Anaplan listed on the New York Stock Exchange in October 2018. Haddleton had helped create and lead its early business; subsequent executives and teams carried it through the next stages.

In June 2022, Thoma Bravo completed its acquisition of Anaplan in a transaction valued at approximately US$10.4 billion. Its shares ceased trading. The company had travelled from privately financed development to public ownership and back to private ownership. Those are different chapters, with different people responsible for the decisions in each.

A founder’s contribution need not occupy every chapter to matter. In Haddleton’s case, the early commitment gave an engineering project room to become a commercial proposition. Passing on the chief executive’s chair allowed the company’s leadership to change as the business changed. The story is more interesting with the handover left in.

The next plan has a New Zealand address

His later interests have included solar-energy developer Lodestone Energy and data-storage technology. Lodestone’s 2021 launch joined the idea of electricity generation with the continued agricultural use of land. Exaba, the Hamilton-based storage business he backs, has a different physical foundation: data infrastructure and software. In June 2026, its seed financing was reported at NZ$12 million.

Exaba develops LocalScaler, an object-storage platform aimed at managed service providers. Its pitch concerns the ability to offer storage with greater local control. Haddleton’s involvement gives his current public argument a commercial counterpart. He has been urging New Zealand to use more of its spending to build domestic skills, firms and infrastructure, including energy and digital systems.

These are proposals, with choices and trade-offs attached. A country’s procurement decisions involve much more than enthusiasm for a local supplier. Haddleton’s argument nevertheless follows an identifiable line from his career: expertise grows through doing the work. Buying a finished service and developing the ability to supply it create different opportunities for the people who live there.

The 2023 Flying Kiwi award recognised Guy and Sue together, placing their partnership in New Zealand’s technology hall of fame. Their interests beyond business included an eco-sanctuary in Northland and support for youth organisations. The shared recognition is a useful correction to the solitary-founder photograph. A business story can fit one face on a page while depending on many people outside the frame.

Haddleton’s next chapter is still being written. What remains visible across the completed ones is the willingness to return: to a colleague, to an unsolved planning problem, to New Zealand’s prospects. After the acquisition announcements and the stock-exchange milestone, there is still work he wants done. For someone who helped sell the world better planning software, retirement would apparently be a rather unimaginative forecast.