The Staying Power Blog

We write about our own experience scaling a professional services firm. Learn from our successes and failures. 

How to Stop Complaining and Just Figure It Out with David Cristello

Posted by Ben Isley on Jun 4, 2020 3:34:57 PM

In this episode, we're joined by David Cristello, founder and CEO of Jetpack Workflow, a SaaS application built to help accounting firm owners manage deadlines without letting client work fall through the cracks.

This includes payroll schedules, bookkeeping schedules and CFO/advisory schedules and the ability for the owner to have full visibility and manage the team through the cloud-based app.

Entrepreneurial Mindset

In his early 20s, David came across the belief that the most important factor in building a successful business was identifying a painful problem and pulling together the resources to solve that problem. Could David find a problem painful enough that people would pay to solve?

David set out on a journey to interview industry professionals and identify their problems. He began with B2B; it's very challenging and arbitrary to identify and solve consumer problems.

David found a small business owner who had a few specific problems. After a short call, David took away some important information about the problems with QuickBooks' Point of Sale System. At the time, David didn't know what any of that terminology meant. He took notes and asked how to get in touch with other people dealing with that problem. Every day, he would contact people dealing with QuickBooks and the related issues they discussed via email and phone to gain more information about their specific problems. After getting tons of feedback, he felt that the accounting industry definitely needed help and decided to focus his efforts there.

"The greatest risk in any business isn't if you can build it or not, typically the greatest risk is if anybody will ever buy it. Are you actually doing something useful enough that people will purchase what you're about to sell?"

Many times, David considered the consequences of what would happen if he just dropped it all and got a regular 9-5 marketing job. He realized that his problem-solving entrepreneurial urge would not be satisfied and that he would still spend weekends and evenings trying to build something. He realized if was destined to be in that spot that he needed to quit complaining and get it done.

"If I follow that feedback loop of take action, get results, get feedback, change course if necessary and learn more, and then go back and take more action... if I just keep doing that loop, I have to figure it out eventually. Something is going to have to land if I keep improving. I just believed in that process."

The Journey and Building a Team

He pre-sold the software that would solve the problem. With the proceeds, he hired a software developer to create the product. He quickly realized that he needed much more money to create the software product. This significantly stalled his timeline and cost him money straight out of pocket. It took an additional 2 years to make the first hire and run payroll for the first time.

It's important to understand what you can and should learn vs. what you should hire someone else to do. There are some areas of the business that you're already good at or could learn with minimal effort. There are other areas of the business that aren't worth the investment of time to learn. To solve this, David's first hire was a VP of Engineering, someone who could understand how to architect the software and create a scalable product.


David approached sales with the mindset of listening and understanding the problems of the business owner and making sure that Jetpack Workflow could step in and solve those problems.

"I take the time to listen. I think that's what great salespeople do. They fundamentally want to ask you questions and get to understand what you're going through. They're very empathetic on the front-end of sales, but when it gets to the point where you ask for the deal, they're also not timid."

After doing all the work, understanding the painful problem and showing them the solution, you have to be direct at the close. You're killing your own firm and the client relationship if you don't ask for the sale. If you truly believe in your product and you truly believe you can solve the problem, this becomes easier.

At the end of a sale, it can be wise to ask if there is anything holding the individual back from signing. By asking this question, you can figure out the root objections, additional questions, or schedule another call to review. Getting a "no" is not a bad thing - getting a "no" can be a great thing, as long as you ask "why?". Then you can ask "What are we missing? What other questions do you have?".

Challenges in Scaling a Team

At 10 people, everything become much more difficult for David. As team members are added, the layers of communication grow exponentially. David started to feel that he really couldn't communicate effectively. He had to get more thoughtful, intentional and be really clear about setting expectations.

"I will say, I think we are turning a point where it's starting to get easier because we're putting basic management disciplines into the business. Stronger forecasting, stronger project management, stronger scorecards, stronger accountability. We're saying "no" more to more things. We're recognizing cross-functional contributions to complete projects."

The real challenge is when you have different silos all doing the best they can but in different directions. The organization starts to move very slow. Speed matters.

"To me, speed matters. It's one of our values, default to action. You need to be focused and take action."

Structure to Enhance Communication and Accountability

Jetpack Workflow has a clearly defined purpose. That is to help professionals do their best work. They do that by helping solve painful workflow problems. With both of these defined, everyone understands the larger concepts of where we're going.

Management issues aren't usually urgent but they're likely very important. It can be tough to figure out how to actually resolve higher-level and directional issues with action. When the firm is small, this isn't a major issue. With a larger firm, it can be very difficult to coordinate working together outside of meetings.

Learn more about David and Jetpack Workflow:

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