A hairdresser has rather better things to do than admire a software engineer’s handiwork. There are customers to attend to, appointments to remember, and a business to run. When Anthony Smith began developing the software that became Insightly, he went and sat beside stylists to watch them use it. He made changes, returned, and watched again. Four versions and roughly six months of work went into that early process. The chair beside the customer was a useful place to discover whether an idea deserved to leave the house.
Smith was working with four small businesses in Perth: an operator of three hairdressing salons, a consulting firm, landscapers, and a mobile plumbing business. He helped move their operations to cloud applications, including Google Apps and QuickBooks Online. Each had customers. Each lacked a customer relationship management system that suited its work. Existing products, in his view, asked too much of people whose working day happened largely away from a screen. A plumber’s office, after all, can involve a considerable amount of plumbing.
That practical mismatch supplied the opening for Insightly, which Smith founded in 2009. It also supplied a test he would keep applying as the company grew: software had to earn its place in someone else’s day. The eventual company served a worldwide audience and attracted venture investment, but its first constituency was small enough for its developer to sit down beside it. Before there was a market to capture, there were four businesses to understand.
An education far from the office
Smith’s route into business software began in Hamilton, New Zealand. His father was an engineer. At about fourteen, he moved with his family to Perth, where he continued his education and studied computer science and information systems at university. He also travelled through Southeast Asia. The career that followed took him well beyond the familiar geography of a desk, a monitor, and the nearest coffee machine.
From 1999 to around 2004, he worked in the technology arm of a global consultancy, building software for mining operations. Assignments brought remote locations, small aircraft, and memorable people. He later called it “a great global education.” His work addressed the business of extracting and refining ore, where software had to help an operation function. There was little room for an elegant interface that failed to answer the operational question behind it.
A couple of years at IBM’s Australian consulting operation added another kind of experience: working with large mining companies and senior executives. Independent consulting followed. He then teamed up with another consultant to develop a system for a major mining company, spending about eighteen months on the work. He subsequently sold his share and used the proceeds to bootstrap Insightly. His first backer was, in effect, an earlier chapter of his own working life.
Perth, on California time
Google’s emerging application marketplace gave Smith a route beyond those first customers. Insightly connected to the tools small companies were already using, particularly email. Arriving around the marketplace’s launch put a modest operation in front of a much larger audience. The distribution opportunity mattered because Smith could build useful software in Perth without first building a sales organisation around the world.
The inexpensive tools behind the business were equally revealing. He used Google Consumer Surveys, Zendesk, 99designs, oDesk, and Amazon Web Services. Design, support, computing capacity, and some coding could be obtained without assembling an entire company in advance. Early customers supplied suggestions and requests. An application could be small in headcount while depending on a surprisingly busy network of people and services.
Growth arrived with a less glamorous perk: American business hours. Smith described working from nine at night until six in the morning as enquiries, bugs, and support requests filled his inbox. The product was initially free. Its popularity brought venture investors into the conversation, and he made trips to the United States to meet them. Emergence Capital appealed to him because its team understood CRM. Investment also meant moving closer to Google and to investors who preferred their board meetings without a flight to Australia.
In his account of the move in January 2012, the financial housekeeping was strikingly hurried. He signed investment papers, opened a US bank account, and received a $3 million transfer. The first employee joined about six days later. The bank account and the employer arrived almost together. It is a pleasingly untidy detail in a business whose purpose was to help other people get organised.
Why customers offered to pay
The next question was how to turn useful free software into a business. Smith and his investors discussed a paid plan that began at about $12.95 per user per month. At first, the distinction centred on a higher level of support. The small development team was still occupied with bugs and customer feedback, so an elaborate collection of exclusive features was hardly waiting in the wings.
Some customers had already depended on Insightly for months. They wanted to pay for the software that helped run their businesses. That detail gives the usual freemium story a human dimension: customers can value the reassurance of a supported service as well as an additional button. Smith recalled an initial annual revenue run rate of roughly $900,000, with the million-dollar mark passed in the following year.
The product also widened its doorway. For its first two and a quarter years, becoming an Insightly user required using Google Apps. Later, connections to Microsoft Office 365 helped reach another group of businesses. Smith had found a productive place to begin, but a company built around customers’ working habits had reason to follow those habits beyond one software suite.
A higher level of support gave customers a reason to pay.
The customer who grows up
Capital followed the expansion: a $10 million Series B and a $25 million Series C. Smith’s ambition was broad, extending CRM to businesses around the world. The customer base also started to change. Companies that had joined when they were small wanted capabilities for larger operations. He described using Insightly inside his own growing organisation, alongside conversations with customers, to discover what needed improvement.
His worry was quite specific. Having put effort into acquiring and serving a customer, he wanted the product to remain useful as that customer grew. This is a less theatrical problem than finding the next new market, though it can be just as consequential. Success produces new requirements. A system that fits a young company can become constricting when teams, processes, and responsibilities multiply.
By 2021, Smith was writing about the balance involved: understand customers’ plans, invest in the company’s ability to serve them, and resist reshaping the whole business around one enticing large account. His advice left room for both ambition and refusal. A founder can listen attentively and still decide that a requested feature would pull the company too far from its purpose.
“I didn’t really want them to outgrow the product.”
Anthony Smith · 2017
A familiar screen is a design decision
Smith’s later thinking about usability returned to the early salon visits. In 2023, he described deliberately borrowing interface conventions from Gmail and Microsoft Office. Familiar layouts give people somewhere to start. A new application has enough to explain without also making every screen feel like an unfamiliar country.
He treated usability as several concrete obligations: pages should load quickly, workflows should be configurable, dashboards should make information understandable, and integrations should be manageable without elaborate coding. The interesting part is the specificity. A company can print “easy to use” on almost anything. Page speed and the ability to configure a pipeline give that promise something against which it can be judged.
His role was still close enough to the product for customers to see him presenting it. In an AppConnect webinar, he appeared with Joanna Falcone, then vice president of central operations at Better Earth Solar, discussing connections between business applications. The pairing brought a developer’s view and an operator’s view into the same conversation. For software meant to coordinate work, that seems a sensible seating arrangement.
The founder with a mud map
There is another Smith in the public writing: a reader willing to seek ideas outside his own product. His 2020 book recommendations included Scott Berkun’s The Year Without Pants, John Doerr’s Measure What Matters, Youngme Moon’s Different, and Mikkel Svane’s Startupland. Remote work, objectives, differentiation, and another founder’s journey all had a place on the shelf. He also recommended The House That Race Built, an essay collection edited by Wahneema Lubiano, for a wider perspective on society and leadership.
He has been willing to learn within the company, too. While recruiting a permanent marketing leader, he served as interim chief marketing officer. Writing about the experience in 2022, he said it renewed his appreciation for the discipline. A software founder temporarily occupying the marketing chair is a reminder that running a company involves work well beyond the part one originally knew how to do.
By May 2024, Smith had a distinctly Australian metaphor for product planning: the mud map. He wanted an informal guide that could accommodate changes, rather than distant feature dates that customers might hear as contractual commitments. The metaphor suits the career. A mining consultant had become a developer for four small businesses, then a venture-backed chief executive. The direction mattered; the route had repeatedly changed.
In July 2024, Insightly combined with Unbounce, bringing customer management and landing-page software into the same organisation. Smith’s tenure as CEO ended that month. The combined business described a distributed workforce of more than 200 people across Europe and North America. His public LinkedIn profile now places him in Perth, the city where the original customer conversations began.
Looking back, the most revealing detail may still be that chair beside the stylist. It gave a software engineer a view of the moment when his work met somebody else’s work. That is a modest place to start a company. It is also a demanding one: the customer is close enough to show you exactly where you have made things difficult.