How Jetpack Workflow’s Founding Still Informs Its Day to Day

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From the beginning, it’s been all about discovery


It’s mythologized that Isaac Newton was inspired to develop the law of gravity after an apple fell from a tree onto his head. Whether true or fabricated, the notion stuck that the “aha” moment launches a founder into building more. It’s that lightbulb that creates a solution to a problem.

“There’s a lot of pain in the world, which means there’s a lot of opportunity to create amazing products and companies around that pain point,” Jetpack Workflow founder David Cristello said.

That means ditching the notion that solutions fall from the sky.

Jetpack Workflow is a project management tool built for accountants, CPAs, and bookkeepers. But when Cristello set out to create the Pittsburgh-based startup six years ago, he knew nothing about accounting. In fact, before he settled on the industry, he was hellbent on creating a tool for dentistry practices. He spoke to dentists for nearly half a year before turning to his current customer base.

“Dental practices are amazing; they’re wonderful people, but I wanted to talk to a different market because, after four months, I didn’t have that one painful problem to solve for,” Cristello said. So he turned his attention to a different industry: With more than 10,000 accounting businesses in the U.S., Cristello considered the market manageable. “If I could even get 5 percent of that market … it would be enough to run some sort of business.”

But accounting was still worlds away from Cristello’s experience in social work. He was without a friend, relative, or contact to learn from—which was precisely what he hoped for. “Part of the process is to go to complete strangers who have no reason to do business with you other than they feel like you’re going to solve their problem.”

But to find the solution, the immediate goal was to “become passionate about the pain.” Cristello estimated he sent thousands of email inquiries and interviewed almost a hundred accounting professionals over the phone about the most painful parts of their day to day. “I had nothing to sell; I just wanted to learn.”

After months of pure customer research, Cristello unearthed a common pain point from his audience: In the bookkeeping world, companies were desperate for a project management tool to meet their specific needs. “They were facing a checklist problem, which I thought had been solved by 2014,” Cristello said. He showed them tools like Asana, Basecamp, and Trello, none of which met the needs of this market.

With between 1,000 and 5,000 deadlines each year from different projects and clients, none of the out-of-the-box software solutions worked for the firms. They were keeping track of projects through classic bookkeeping or old-school filing systems likely to fall victim to human error.

Using the knowledge amassed over discovery, Cristello started sketching out a solution, pitching it to a dozen accounting firms for pre-purchase. He brought contacts a PDF explaining the project and told them, “If I build something and you hate it, I’ll return the money.”

The pitch worked, and with firms on board and $5,000 in the bank, Cristello’s next task was finding a software developer to build the product. “At the time, it felt like all the money in the world,” he recalled. “I was like, you can definitely build software for five grand.”

Cristello didn’t realize it at the time, but building the product was an entirely new discovery process. “The interview and pre-selling the idea early on was really fun and challenging,” he said, “but the software development was the biggest, hardest, and most expensive challenge so far. There were a million things I did wrong in the whole process.”

Without a background in tech and development, Cristello went into the process blind, hiring a developer without a design in mind. After a year of building, he turned to an entirely different developer to refine the product. “We got the product up and running, eventually, but it wasn’t super pretty,” Cristello said.

Looking back on the development process, Cristello acknowledges that perhaps the missing element was the discovery he’d valued early on. “I wish I had spent more time just talking with product managers and software companies,” he said. ”Just asking questions about how to build a product from scratch.”

Because the final phases of development were self-funded, it was an expensive yet invaluable lesson Cristello still draws from today. “As we grow and create more, there are people in and out of this city that are great mentors to learn from.”

Group photo of the Jetpack Workflow Team. Photo Credit: Jetpack Workflow.

Half a decade later, Jetpack’s growth is still informed by discovery. Cristello’s love of interviewing people prompted him to create the company’s podcast, Growing Your Firm,” as a marketing distribution channel. From the interviews with professionals in the industry came a book, “Double Your Accounting Firm.”

Instead of cramming their reliable software with new customer-requested features, the team dives deeper into the pain points to figure out the core of the issue, building the feature in reverse.

Discovery never stops, and Jetpack plans to accelerate its growth in 2020, adding new hires to a team of 20 and continuing to listen to customers’ feedback to move the business forward.

Emma Diehl
Contributing Writer
Emma is a Pittsburgh-based technology and lifestyle writer, covering everything from machine learning in law enforcement to historic building preservation. Her byline has appeared on XOJane, NPR, Huffington Post, NEXTPittsburgh, and Very Local.