Jason Westland and the plan that needed rebuilding

Jason Westland had spent years getting projects over the line. Then he built a business whose first product could barely keep its customers. The software was slow. Bugs were plentiful. People arrived, tried it, and left. For someone selling a better way to manage work, this was an awkward demonstration.

ProjectManager.com began in 2008. Its first version took nine months to produce, and Westland’s later verdict was blunt: “it failed miserably.” He had put proceeds from earlier businesses into the venture, mortgaged his house, and taken on credit-card debt. His mother had mortgaged her house too. Behind the tidy promise of an online project plan sat a distinctly untidy family exposure.

That makes the next part of his career more interesting than a funding announcement. Before ProjectManager could help other people see whether their work was on track, Westland had to get his own product working well enough for people to stay.

A telephone call at the wrong moment

The idea took shape at MORGO, an invitation-only gathering of entrepreneurs in New Zealand. It was 2008, and the financial crisis was unsettling the economics of his existing downloadable-software business. Sales had fallen by about a third. A conference full of software founders offered an unusual place to consider what to do next.

Westland saw a possibility in subscriptions. Customers could use software online and stop paying when they no longer needed it. The attraction for the customer created a problem for the founder: revenue would arrive gradually, while the expense of building the product arrived promptly. The bank account, regrettably, had no interest in the elegance of the model.

He wanted an online project-management business with a capable Gantt chart and a name that needed little explanation. During the conference, he called the owner of projectmanager.com. The business began with a familiar managerial irritation, a shift in how software was bought, and a telephone call.

Before the browser, the people

Westland’s professional education had already included large organizations and complicated work. He studied at the University of Otago, earning a Bachelor of Commerce with majors in Information Science and Economics. In his account of his first job after university, he was 22 and responsible for a project involving 25 people. A small team can contain quite enough opportunities for surprise.

His early work included a nationwide IT deployment for a bank. The first server installation failed, he later recalled. Yet he enjoyed leading teams and working against difficult deadlines. People, suppliers, equipment and customers were part of the attraction: the project manager had to bring them together, rather than merely admire a schedule.

He went on to work on British Rail’s Strategy Implementation Programme. Method123 and MPMM brought his experience into tools and methodologies for other managers. His book, The Project Management Life Cycle, organized the work into initiation, planning, execution and closure. The interest in making complicated work usable preceded the subscription business.

The release that earned its name

By December 2009, Westland said, there were fewer than 100 customers in the system and churn was approaching 100 percent. There is a particular cruelty to that combination. You can keep finding people willing to try the product while almost nobody gives you a reason to believe they will remain.

January 2010 brought what the team called its Gold release. Westland’s explanation of the turnaround was practical: the feature set had been right, but the quality had fallen short. Once that changed, retention rose beyond 12 months. Average users per account jumped to five. Within two months, he said, NASA had signed up for IT projects; the United Nations also became a customer.

He dated profitability to January 2011, about a year after the release. In his telling, the marketing had not suddenly changed at the moment customers began staying. The product had. It is an unusually useful detail in a founder’s story, because it gives the improvement an identifiable cause instead of assigning everything to determination.

A classroom with a business attached

Westland had another asset: he could teach the people he hoped would become customers. Project management produces an inexhaustible supply of questions. How do you plan a project? What belongs in a budget? What should happen when the dates slip? A useful answer can travel farther than an advertisement.

In December 2012, he described a marketing approach built around free resources and professional communities. Templates, articles and social channels gave managers reasons to visit before they were ready to buy software. The commercial connection was straightforward. Someone who trusted the advice might eventually try the tool.

The operation was small. Recalling the period before the 2014 expansion, he described two full-time developers, a tester, a support person and himself, with marketing largely his responsibility. Later, the company expanded its content team and acquired a LinkedIn group. Its mobile app carried educational material alongside software access. Some people came for the lessons and never used the product.

That last detail is revealing. Free help has to remain useful to people who never become customers. Otherwise, the classroom starts to feel like a sales meeting with unusually long opening remarks.

“I simply built a community of people who were interested in project management.”

Jason Westland, 2016

The argument inside a Gantt chart

The product’s position depended on a specific kind of work. Westland described project software as a triangle: task lists across the broad base, formal project management in the middle, and project-and-portfolio management above. His chosen ground was the middle, where a deadline requires a plan and the relationships between tasks matter.

A Gantt chart makes those relationships visible over time. Move one activity and connected activities may need to move too. In Westland’s account, supporting a large, linked plan inside a browser was an important technical challenge. The point was to let people work with a schedule, rather than simply look at one.

His positioning explains why the story keeps returning to visibility. A project plan is useful when the people doing the work can update it and the person responsible can understand the consequences. A beautifully organized document that has ceased to describe reality has a limited career as a management tool.

The customers had already crossed the ocean

By June 2014, the company reported about 15,000 users globally and another 150,000 users of its mobile app. Around 80 percent of its user base was in the United States. The business still had its headquarters in Auckland. Its customers had made the international move before the organization supporting them had caught up.

A reported $3.5 million Series A, led by Zeus Management, was intended to expand American sales and marketing and develop the enterprise platform. A board was being assembled with Guy Haddleton, co-founder of Anaplan; Herb Hunt, a former IBM executive and Wynyard director; and Graham Shaw, a Xero director.

The figures belong to that moment in 2014. They describe a founder making an operational decision: customers were abroad, so more of the business needed to be there too. Money could fund the people and presence that an internationally accessible website could not provide by itself.

Austin, with reasons attached

Choosing an American city gave Westland a chance to be specific about his preferences. Seattle had weather he disliked and put him close to Microsoft. New York did not feel right for the stage of the company. Silicon Valley brought expensive competition for staff and, in his view, too much attention to the next possible stock-option windfall.

Austin appealed through its people, its startup culture and the ability to recruit for a growing business. Westland was thinking about compensation, incentives and the experience of the people he needed. The geographical decision was also a staffing decision.

By May 2016, he described marketing and customer-support colleagues in Austin, with development continuing in New Zealand. He reported 16,052 paying users, carefully clarifying that these were users rather than customer organizations. He also wanted the platform to serve a broader range of people doing project work. Manufacturing was already among the examples he mentioned.

The marker and the listening problem

Westland likes a whiteboard. He has described getting up with a marker as a way to generate ideas and widen a discussion, while admitting it can lengthen meetings. It is a recognizable occupational hazard: the meeting is almost over, and someone has discovered a fresh stretch of white space.

His account of moving to America includes a less flattering admission. He hired marketers and initially thought he knew better than they did. Their performance helped change his mind. He came to see the value of giving capable people room to use their expertise. A founder who built the original marketing operation could still become an obstacle to its next version.

His published advice also makes room for the team. Alongside deadlines, budgets and requirements, he lists customer satisfaction and a happy team as project goals. The list gives the work a human measure. A schedule may show completion; the people involved decide whether they would willingly do it again.

Back to the scattered spreadsheet

Today, Westland identifies as the founder of 8Dflow, based on Australia’s Sunshine Coast. ProjectManager’s current leadership page names Stephanie Ray as CEO. The distinction matters: his history with the company is a founder’s history, while his present public work has another name and a more specific audience.

8Dflow is developing software for small and mid-sized manufacturers managing quality issues. Its starting problem is scattered follow-up: spreadsheets, emails, documents and evidence that live in different places. The proposed workspace brings issues, responsibilities, actions and closure into a shared record. The company describes the product as in development.

The setting has changed from project schedules to factory quality work, but the recurring interest is easy to recognize. Somebody must know what happened, who owns the next action and whether the work is finished. Westland’s career has repeatedly returned to that ordinary, troublesome question.

In 2010, his own business needed an answer. It arrived through a better release, followed by customers who stayed. There is something fitting about a project-management founder having to revise the plan. Even the person selling the chart has to do the work.