Howard Spector and the career hiding in the paperwork

Howard Spector went looking for a tool to keep track of his working hours and came away with a different career. He had returned to graduate school, completed a degree, and begun the long practical training that followed. Then the record keeping got his attention. California required detailed accounts of the time. Spector had worked in technology. He could see a job for software.

The resulting product, TrackYourHours, let people record their experience online and generate the required forms. A small administrative nuisance had become a business. Soon another question followed: what would he use to run his own practice? He examined the available products, found little that suited him, and began thinking about building again. His intended destination was becoming rather crowded with companies.

SimplePractice began in 2012. Spector became its co-founder and CEO, bringing the habits of a prospective customer into the work of making a product. The attraction of his story lies in that awkward overlap. He had gone back to school to change his working life. The skills from his previous life promptly found something useful to do.

A calendar before a company

A software company can sound inevitable once it has a name, employees, and customers. The beginning is usually less tidy. Spector described an idea that took time to settle: a person sitting in an office, checking a phone before the next appointment. Thinking about that ordinary moment helped him work out the calendar and the mobile experience. There was someone specific to design for, even before there was much to sell.

He teamed up with a former colleague on the technical side and spent roughly a year and a half developing the product before its July 2013 launch. That interval matters. The familiar invitation to follow an instinct tends to omit the months during which the instinct needs menus, screens, and functioning code. An idea may arrive suddenly. Software retains its own opinions about deadlines.

The first sales also involved less glamour than the word founder sometimes suggests. Spector would gather the marketing materials and head to local professional chapter meetings. Curt Widhalm remembered those visits years later. The person running the company had also been the person showing up to explain why anyone should try it.

That detail supplies a useful scale for the origin. Before there was an audience large enough to discuss in round numbers, there were rooms of people who needed convincing. He knew the work they did and the practical irritations around it. Familiarity gave him somewhere to begin the conversation; it did not relieve him of having to turn up.

The useful inheritance of an earlier job

Spector brought more than enthusiasm to those rooms. His technology background included managing complex projects and holding executive roles at startups. TrackYourHours had already taught him how to create a product, maintain it, and build relationships around it. He later sold that business to concentrate on SimplePractice. The second venture could draw on trust earned by the first.

He has described those relationships as an important part of the early growth. People knew the previous product and what he had done with it. That is a less theatrical form of advantage than arriving with a startling pitch. A useful tool can spend years making introductions on its maker's behalf.

There is a particular kind of career advice hidden here. Experience does not have to disappear when someone changes direction. Spector's technical work became more useful when it met a problem he understood from the inside. His education and his previous employment could occupy the same sentence, even though neither had originally been chosen for that purpose.

The blog that needed a better job

By the end of 2014, Spector thought SimplePractice was fulfilling only part of its purpose. The product was developing, but the business advice he wanted to offer customers had fallen behind. The blog contained webinar links and product announcements; it had gone quiet since September. He decided in December to remake it.

In January 2015, he explained the change publicly. People running their own practices were entrepreneurs, he argued, even when they did not describe themselves that way. They still had to make decisions about pricing, websites, marketing, and referrals. The company could share its own experiments and mistakes in ways customers could use.

It was a revealing admission. A founder who sold organizational software had noticed an unattended corner of his own organization. The correction made the company's ambition more concrete. Helping someone operate a business involved explaining choices as well as supplying buttons. The proposed blog would make room for what the team was learning while doing the work.

It also changed the relationship implied by the writing. Product updates tell customers what a company has shipped. An account of a pricing decision or a marketing failure lets them consider how the company thinks. For independent owners making similar decisions alone, that kind of detail can be useful company.

“Everyone, regardless of title.”

Howard Spector, on who should receive customer support training

Who gets to answer the customer?

Spector's view of customer support was similarly direct. In 2020, he argued that every new employee should receive support training and that everyone should regularly help with incoming inquiries. A title would not provide an exemption. The reasoning was commercial and practical: the business depended on its customers, and everybody's work ultimately served them.

Consider what that asks of a company. The people making decisions must encounter the consequences in something close to everyday language. A customer explaining a difficulty can be considerably more precise than a presentation about customer focus. Putting that conversation within reach of different departments changes who gets to know what.

Spector had already been discussing the value of time, automation, and delegation in conversations about entrepreneurship. Those subjects are particularly pointed for people whose businesses depend on their available hours. An owner can learn to price an appointment while continuing to spend an afternoon on a task that a tool could handle. The arithmetic becomes personal very quickly.

His interest extended to employees finding suitable work inside the company. He spoke about people moving into different responsibilities as their abilities became clearer. An organization, in that account, needed continuing adjustment. The same patience applied to improving a product could be brought to deciding where a colleague might contribute.

A title ends. The work carries on.

The CEO chapter did end. By May 2022, Spector was SimplePractice's former chief executive. He had tendered his resignation from the founder advisor role at EngageSmart, effective July 5. The role had changed, and that date marked the end of his advisory chapter there.

His subsequent appointments brought him back to familiar business problems from different seats. On December 4, 2024, Heard announced that he was joining its board of directors. Heard builds financial management software for independent practitioners. Its announcement placed Spector's experience alongside a straightforward need: helping people succeed as business owners.

Then, on February 10, 2025, Jane announced him as strategic advisor and executive partner. The company makes software for booking, scheduling, billing, and other administrative work. Spector said he wanted to help it grow in the United States. This time, he would work alongside an existing founding team, Ali Taylor and Trevor Johnston.

The introduction came from Andrew Riesen, Heard's co-founder and CEO. Spector thanked him publicly when announcing the Jane relationship. It is a pleasingly practical connection in a career full of arguments for relationships: the board appointment and the advisory role were linked by a person who knew whom to introduce.

In explaining the move, Spector emphasized the founders' attention to people and workplace culture. His stated interest was recognizable from the earlier company: a collaborative organization, purposeful work, and sustained attention to customers. The tools and titles had changed. The business questions remained close to the ones that had first caught his attention.

Leave room for the next decision

Spector holds a bachelor's degree from the University of Southern California and earned his master's at Pacifica Graduate Institute in 2004. His interests extend to design, the arts, and the environment. Books have also figured in his account of leadership, including James Joyce's A Portrait of the Artist as a Young Man and Yvon Chouinard's Let My People Go Surfing. It is a reading list with room for both an inner life and a working company.

In a 2018 conversation about finding a calling, the many jobs along his route were part of the story. Looking backward makes those changes easier to arrange. Living through them requires deciding before the pattern is visible. There is something reassuring about a founder whose professional history allows for that untidiness.

He has offered a compact rule for entrepreneurship: stay connected to the work and accept that “there are no shortcuts.” His own record gives the second half some substance. There were forms to understand, a product to develop, meetings to attend, a blog to repair, and customers whose questions needed answers.

The memorable turn came when he treated an inconvenience as something worth his sustained attention. He could have finished the record keeping and carried on. Instead, he made a tool. Then he found another problem nearby. A change of career had left him with an unexpectedly durable occupation: noticing what made other people's working day harder, and finding a way to help.