How Check’s Culture of Ownership Empowers its Employees

Check’s commitment to a culture of ownership is more than just lip service. Three key members of the team share how they see this value in action every day.

Written by Eva Roethler
Published on Oct. 21, 2022
How Check’s Culture of Ownership Empowers its Employees
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A culture of ownership may seem like a nebulous and abstract organizational value.

Without action, a culture of ownership is a platitude. It’s a core value displayed on an office wall collecting dust. Paired with action, a culture of ownership is a real competitive advantage. Colleagues become aligned on organizational outcomes, and do their best work because they care more.

The actions that promote this culture must occur on a daily basis in order to make their mark in the minds of the members of an organization: How invested are they in the collective success of the group? What are they willing to do to support the organizational goals?

Of course, everyone wants credit for the wins. The real test of ownership comes with fumbles — and failures.

“Ownership and transparency are warm and fuzzy values. It’s not until things are not going well that those values have an opportunity to shine through,” said Cassondra Garcia, program manager at Check

In her roles at previous companies, Garcia would often expect a tense atmosphere during retrospective meetings, with each participant focused on rationalizing actions and shifting accountability. So she came to her first retrospective at the payroll-as-a-service provider prepared for friction, and left the meeting pleasantly surprised. 

“I had never seen so many people rush to throw their hands up and claim accountability for something that did not work out. That’s when I was really able to buy into the values. Our culture makes it easy to celebrate your wins and learn from your losses,” said Garcia

I had never seen so many people rush to throw their hands up and claim accountability for something that did not work out. 


This culture of ownership at Check didn’t just magically materialize. It is propped up by a number of carefully considered tools including clear documentation, honest communication, regular feedback, transparent compensation bands and even weekly financial reports. Every employee has a full view of the business, which allows ambitious employees to thrive. 

“What makes Check really special is that we have a lot of grassroots initiatives. Nobody at Check waits for somebody to tell them that something needs to be done,” said Senior People Operations Manager Kelly Ballou.

David Sokolow is one such poster child of this culture of ownership and ambition.

Nine months ago, Sokolow, then a product manager, and a few colleagues noticed a different type of customer cropping up. “We had seen a few different technology platforms looking to run their own payroll using our API,” he said. Typically, Check’s customers are focused on building payroll products with the intention of selling payroll as a service, but these platforms pay thousands of workers and operate as technology companies. They wanted to embed payroll in their apps so workers could have a single place to view their pay and so they could scale their internal operations, which were growing rapidly. Building on top of Check directly was a natural fit for them.

At the time, this wasn’t a function the company was focused on. The team openly wondered if it should even be within the scope of their services. Sokolow and a few colleagues decided to investigate further, and realized there were some meaningful benefits, particularly with the rise of gig work and talent marketplaces. 

That was in November. 

By December, Sokolow had been given the title of general manager of Check for Staffing Platforms and Talent Marketplaces, a new division launched in response to his proposal. Check put together a small team, which has already tripled in size. 

Built In connected with Garcia, Sokolow and Ballou for more insight into what a culture of ownership looks like in action at Check. 

Photo of the Check team working together on their laptops.


David, did anyone tell you to start working on the proposal for your new business line? What was the process like at the beginning?

General Manager David Sokolow: There was an open question about this idea. I had a conversation with one of our sales leads and we realized it looked like a great opportunity. I remember saying we should build it out as a business and it wasn’t a yes-or-no question, it was more, “Let’s figure this out.” We have a culture that is receptive to pitching ideas, we know they can come from anywhere. 

I started a document to summarize the opportunity and sent weekly updates when we learned something new. A month and a half later we met with executive leadership to evaluate everything we’d shared and we decided after that period that we wanted to invest in staffing platforms and talent marketplaces as a net-new segment for us.



What are some examples of the infrastructure that supports this culture of ownership? 

Senior People Operations Manager Kelly Ballou: One of my primary objectives, from day one, was building out competency rubrics. This was in response to employee feedback that they wanted clarity, accountability and greater consistency of expectations within their teams so they could take ownership of their own growth and development. Now, we’ve got rubrics in place for 95 percent of employees.

In addition to helping with employee development, rubrics are a tool for managers to calibrate expectations and feedback during the hiring process and during performance reviews. We have twice-yearly reviews and we’re working to develop a culture of year-round, real-time feedback. We want to have enough opportunities throughout the year to reward performance so we can ensure employees have concrete points of recognition to help them on their development journey. 


Meeting People Where They Are

Ballou appreciates that Check has employees fill out guides to their working styles when onboarding. These publicly available guides cover everything from preferred feedback methods, communication styles and how the employee likes to schedule focus time or meetings.


Transparency is crucial to building a culture of ownership, because people need to understand what it is they’re accountable for. Tell us how you see transparency manifest at Check. 

Engagement Manager Cassondra Garcia: We think of information sharing in a very bidirectional way. The focus is on sharing clear and relevant information that includes enough context for readers to understand the message. “What is the purpose of my update?” “Can others act on this information?” Those questions are always in the back of our minds.

Ballou: Knowledge sharing is a universal key competency across our teams. We look for people who are able to communicate clearly and simplify complex concepts. The transparency at Check is also more proactive than I’ve seen in other organizations. Any time we have a board meeting, the CEO sends out the meeting agenda, talking points and data that will be reviewed in a public Slack channel. That transparency is valuable because you know the threats and opportunities facing the business and you can take ownership of decisions within that context.

We’re also really transparent with our compensation philosophy, and publish updated compensation bands in Q1 every year. Everybody at the company can find these in our shared Google Drive and see what any level on any team at the company could be paid. These bands work hand in hand with our competency rubrics so people know what’s available to them and how to get there. 

Sokolow: Our finance leads send out our company cash balance every week, including any major expenses we incur. It’s helped earn a lot of trust that we’re managing everything right and the company is in a stable position. It also gives people the opportunity to ask questions. It’s created a culture of shared accountability and shared responsibility. 

This supports one of our values: to earn trust. The best way to earn trust is to maintain transparency and get comfortable delivering bad news. We recently started doing highlights and lowlights at our weekly all-hands meeting. Before, the all-hands was very celebratory, but adding lowlights helped get everyone more comfortable sharing bad news in a way that helps us improve.

The best way to earn trust is to maintain transparency and get comfortable delivering bad news in a way that helps us improve.”

How do people respond when getting bad news? 

Sokolow: It’s very friendly and constructive. We have a nice, courteous culture here at Check. We had a retro recently where we lost a customer we’d been pursuing for a long time. We were walking through what we could have done better, the stakeholders we could have gotten buy-in from and how we could have been more conservative with estimates. I remember the sales rep who was leading the retro saying, “This is much friendlier than it has been at any of my past companies.” 

Tell us how you see accountability in action at Check.

Ballou: We can all look up the quarterly goals for each team across the company. For example: on the people team, if our goal is to raise retention rates and lower turnover, people could look specifically at those numbers against the plan and hold us accountable to it. 

It can be easy to have tunnel vision about your role, but these company-wide goals help keep us focused on driving the whole business forward. 

It can be easy to have tunnel vision about your role, but these company-wide goals help keep us focused on driving the whole business forward.


Sokolow: Our goals drive accountability within our team. It’s helped with the speed of the initiative — each week I would think, “Oh wait, what did I promise we were going to do last week?” I’m sending this email to the entire company. I want to make sure I’m actually making progress. That culture of documentation and cadence of updates helps drive accountability.

Garcia: The immediate needs of our partners and customers also drive accountability at Check.  We have been successful in swiftly changing course and creating new roles and teams to meet their evolving needs. One example is my transition into a new role focused on early-stage partners. Without direct accountability to improve partner experience, we wouldn’t have challenged the status quo.

What is unique about Check’s culture of ownership?

Ballou: It’s a culture where people feel comfortable coming forward with ideas, with the confidence that they will be given fair reception and full consideration. People here are looking for opportunities to build something of their own within this business. That goes for cultural initiatives as well as business initiatives. They take ownership of our DEIB goals and our wellness initiatives. We’ve had people start 30-day plank or step challenges out of the blue, with no prompting. We also have regular hackathons, which aren’t limited to engineering — everyone is invited to participate, and we hack problems across the business. We’re not siloed, we’re all looking for ways to contribute. 

There are a lot of companies that pay lip service and say, “You can come in and build something here.” It’s been rare in my experience to actually see that in practice. This is not a company where you’re told you can do something, then get shut down halfway through. The default position of our leadership team is trust. If you’re passionate about something and make a reasonable case for it, they are behind you 100 percent. 


Responses have been edited for length and clarity. Images provided by Check.

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