Daniel Zarick and the art of changing your mind

Daniel Zarick keeps a page on his personal website called “Failed Projects.” It is an unusual thing for a chief executive to leave near the front door. Visitors expecting a tidy parade of accomplishments get the abandoned tools, the promising prototypes, and the products that attracted attention without becoming the businesses he had hoped for. The page makes a useful introduction to the co-founder of Arrows. He has spent years building software, and he has also spent years learning how much a working product can leave unresolved.

Consider The Shakedown, a phone game he made with Benedict Fritz, now his Arrows co-founder. Friends could steal one another’s points by shaking their phones. It was an answer to the wonderfully absurd app Yo, and it reached about 15,000 downloads before fading. You can imagine the difficulty of looking dignified while defending your score. Zarick includes it among his disappointments, but the description retains affection. His archive allows a project to be enjoyable, instructive, and commercially underwhelming at the same time.

Four days a week, packing notebooks

Before there was a sales platform, there were Field Notes orders. While attending Columbia College Chicago, Zarick worked at Coudal Partners, the design company behind the notebooks. He had discovered the job through a website he checked in his school’s design lab. Four days a week, he packed orders for a company whose work he admired. There is something pleasingly concrete about this beginning: a future software founder helping send paper out into the world.

The office also put him near another model of company building. The people at 37signals rented desk space from Coudal, and he got to know Jason Fried and some employees. Along with Wildbit, these businesses helped form his idea of what independence could look like. Design, useful products, and a business supported by its customers made a persuasive combination. His later ambitions for a studio with several products under one roof had roots in those encounters.

Then Twilio hired him. Zarick left college early and became employee 23; he was the company’s second product manager. Jeff Lawson gave the college student an opening into a very different kind of software business. The notebook-packing years and the early Twilio years supplied two competing pictures of success. Neither would remain an instruction manual forever.

A job that should need you less

At Twilio, Zarick concentrated on internal tools. The work was close to the daily frustrations of colleagues: helping support staff diagnose problems with calls, giving sales and marketing teams useful reporting, and making information easier to share. In May 2012 he wrote about an organizational danger that has survived several generations of software fashion. When important knowledge lives with one person, everybody else becomes dependent on that person’s availability.

He described runbooks, training, and tools as ways to spread that knowledge. The ambition was to let people solve routine problems without needing the same colleague every time. “Build the tools which allow them to get the job done without you,” he wrote. It is a quietly demanding standard for a product manager. A successful project might reduce the number of questions arriving at your desk rather than increase the number of people who admire your expertise.

The idea gives his later work a longer history than the latest AI vocabulary suggests. Making useful judgment available to other people was already on his mind. The technology would change; the question of who could get work done, and what stood in their way, had arrived early.

“Build the tools which allow them to get the job done without you.”Daniel Zarick, 2012

The designer who wanted fewer computers

After leaving Twilio, he worked independently through his studio, No Small Things. His portfolio includes work for ngrok, Jewelbots, RunKit, and other software companies. The projects crossed the usual boundaries between design and programming. In his writing, he argued that an interface cannot be fully understood from a drawing alone. Timing, movement, and the placement of a button acquire their real meaning when someone can use them.

For one client’s iPad app, he designed custom controls and then wrote the code to make them work. He wanted the finished interaction to carry the care of the original design. A detail that looked small on a task list could require half a day of attention. That willingness to follow the work into implementation explains more than a job title does.

Yet his 2017 description of a dream setup was strikingly modest: fewer tools, less software, fewer computers and phones, perhaps a cabin to visit. Then came the practical concession that a lightweight MacBook Pro with good battery life would do. Here was someone who made a living building digital things and could still recognize the appeal of putting them down. His preferred tools were simple; his relationship with technology had room for irritation.

Eighty versions of one small square

Zarick’s account of creativity is similarly unceremonious. He has described ideas as pieces that keep tumbling together as he researches, experiments, and makes prototypes. A solution can appear while walking, at the dog park, or over a beer with a friend. Occasionally it even appears at the computer, which is considerate of it.

One client’s iOS app icon took more than 80 variations before the right version emerged. His point was that he could not have identified the answer before seeing it. Making the attempts was part of finding it. That is a useful corrective to the founder biography in which every early instinct mysteriously anticipates the eventual business.

A small 2015 assignment illustrates the other side of that patience. Ian Ownbey contacted him about OneShot, an app developed with Jason Goldman for highlighting and sharing screenshots of text. Zarick fitted a week of design work between other commitments. He was already someone who shared screenshots, and the interaction problems interested him. A familiar behavior, a specific inconvenience, and a short stretch of focused work were enough to make a worthwhile project.

Getting a customer to the useful part

Long before Arrows’ current sales software, Zarick was writing about onboarding. His advice for a new product was unusually hands-on: keep the product simple, talk to people, and help them use it. A young company does not yet know precisely what customers value or where they get stuck. Polishing a universal welcome tour before learning those things puts the sequence backward.

For a more established product, he wanted onboarding to reach the moment when someone understood how the software would help them. Checklists, demo data, videos, and phone calls were possible methods. The essential work was discovering what clicked. Completing a set of tasks could look like progress while leaving the customer unconvinced.

His skepticism about passive analytics followed a related line. Pageviews and event counts could make an explanation feel solid without revealing why someone acted. For his own writing, replies, client inquiries, and newsletter sign-ups meant more than traffic alone. In product work, he urged people to talk to the customers who stayed. These essays show an interest in observable outcomes accompanied by a distrust of convenient stories about what numbers mean.

The dashboard that lost its job

Arrows grew from explorations with Fritz into a company focused on customer success teams in 2020. The early product helped companies and their customers coordinate onboarding. But the team’s research kept bringing them back to familiar workarounds: Google Sheets, Trello boards, and custom CRM reports. Customers needed a shared place to see what they were expected to do. Internally, they already had somewhere to manage customer data.

In early 2022, a planning discussion exposed the mismatch. The team could devote another development cycle to improving its dashboard, or concentrate on the customer-facing checklist. The dashboard would still need more work afterward. They chose a third possibility: remove it and let HubSpot handle the internal functions. Roughly a third of the product went away.

A dashboard is a reassuring possession for a software company. It looks like a place where work happens. Removing one requires accepting that the customer’s existing place may be better. Arrows entered the HubSpot App Marketplace in April 2022. The decision narrowed what the company needed to build and made its relationship to the customer’s workflow easier to explain.

Independence gets a different definition

The financing decision had already required another revision. Zarick initially wanted Arrows to be self-funded. On June 21, 2021, the company announced a $2.75 million seed round from Gradient Ventures and 47 angel investors. Understanding the market and what customers wanted had changed the founders’ assessment of the resources they needed.

In March 2023, Arrows announced a strategic partnership and investment from HubSpot Ventures, with Gradient leading the new financing. By 2024, Zarick was spending considerable effort on the surrounding community: useful how-to content, relationships with agencies, and conversations with HubSpot’s customer-facing employees. The integration needed people who understood where it fit. Distribution was another part of the product’s practical life.

The plan changes again

By October 2026, Arrows describes a different product on its website: software that builds a gameplan for each sales opportunity and prepares work from a team’s playbook. The examples include follow-ups, pre-call preparation, and CRM updates. The company presents this as a way to keep the ordinary work around a deal moving while representatives handle conversations and judgment.

Zarick’s recent public posts also describe rebuilding the business around agents and archiving the classic onboarding app in the HubSpot Marketplace. The platform commitment that defined the earlier company is now part of its history. In a launch demonstration, he shows software noticing a pricing conversation that needs attention and preparing material for a prospect evaluating a competitor. These are product claims and demonstrations, rather than proof that every customer gets the same result.

The sequence gives his old advice about company building some bite. He once wanted a particular kind of bootstrapped success. Later, a particular ecosystem became the focus. Both approaches helped him decide what to do at the time. Neither exempted the company from learning something new. It takes work to build conviction; it takes a different kind of work to notice when circumstances have moved.

Leave the old attempts on the shelf

There is a playful streak running through the record, from the phone-shaking game to an essay defending “Frivolous Experimentation.” Zarick argued that small, apparently unimportant projects can lead to useful discoveries. A person need not begin with a grand claim about changing the world to make something worth trying. That is an agreeable permission slip for anyone staring at a half-finished side project.

Friends call him DZ. His website points visitors toward his work, his writing, and a guide to Formula 1. The interests do not need to resolve into a single professional identity. What connects the career is a willingness to stay close to the thing being made and the people expected to use it. The next decision will have its own conditions. Meanwhile, the old experiments remain available for inspection, including the one that asked friends to shake their phones and steal points. Some lessons deserve a leaderboard.

“Encouraging playfulness, both for yourself and in those around you, might solve more important problems than you expect.”Daniel Zarick, Frivolous Experimentation