Leadership   //   February 27, 2024  ■  4 min read

Tax season is confusing but employers can help

Tax season is in full swing and the drudgery of making sure you have all of your paperwork and are filling out the forms correctly can be overwhelming.

On top of the usual stress, this year the FTC ruled that TurboTax can no longer advertise itself as “free” and popular financial help platform Mint.com is shutting down. In some instances, employers are stepping in, offering assistance, or even free filing to help employees successfully navigate this year’s tax season.

Column Tax is partnering with money management platform Origin to offer free filing. That means that companies like Barstool Sports, Docusign, Nextdoor, the NBA and Reddit that already use Origin also now have access to free tax filing. Last year, Column Tax processed over $100 million during its first tax season and expects to see it taken advantage of in a much bigger way this year thanks to the partnership with Origin.

“Taxes are a huge component of people’s financial journeys,” said Matthew Watson, founder and CEO of Origin. “It’s a huge event that happens once a year for people, and it’s also often the most significant financial windfall that comes into a consumer’s finances on an annual basis. Not surprisingly, this is something that employees come to their employers about quite regularly.”

“It’s a huge event that happens once a year for people, and it’s also often the most significant financial windfall that comes into a consumer's finances on an annual basis."
Matthew Watson, founder and CEO of Origin.

He said they are expecting hundreds or thousands of people to take advantage of the free filing opportunity, with a positive reaction from people so far this season. “It’s a part of a trend that I think is afoot and I think will accelerate,” says Watson.

An individual taxpayer is estimated to spend 13 hours and $240 just to prepare and file an annual tax return, according to the Taxpayer Advocate Service. If an employer is able to help alleviate that cost in any way, it will have a far-reaching impact. 

“A lot of people, this is the most stressful financial experience of the year,” said Gavin Nachbar, co-founder at Column Tax. 

Origin also offers access to certified financial planners, which is especially helpful when it comes to people who might have questions around their tax filing. And where an employer might not be able to offer free tax filing, having financial advisors available to ask questions is extremely impactful this time of year. Monday.com partners with a reputable advisor who comes to the office on a regular basis to speak on a variety of topics. In February, this person came in to discuss tax filing best practices including going over things like whether you file on your own or through a provider, what to be mindful of when you file and more. 

“We have an entire wellness strategy at Monday … and this one piece that we’ve really leaned into this past year  is financial wellness,” said Mike Lamm, VP of People, Americas at Monday.com. “It’s a key component and is a contributing factor to the other verticals of wellness too. We’ve made investments, mainly on the educational side, so our employees know what it means to be financially well.”

“We know there are stats about how painstaking the process is, especially for people who are just entering the workforce.”
Mike Lamm, VP of People, Americas at Monday.com.

In addition to a presentation from the advisor, employees have the opportunity to set up 30 minute-long 1 to 1 consultations with the advisors, either in-person or virtually. While they aren’t able to file their taxes with this person, they can use that time to ask questions that will point them in the right direction, which is especially helpful if someone has a complex income situation.

“We’ve gotten crazy praise for this,” said Lamm. “We cannot get enough slots for people to sign up for. Whether you’re earlier in your career or not, it’s kind of hard to find who is the right financial advisor for me. Getting 30 minutes with them to ask super personal questions has gotten rave reviews.”

For the February 1 to 1 sessions, they were booked up almost immediately because it’s tax season. When tax season brings 54% of Gen Zers to tears, just having someone available to answer any financial questions can pay off in dividends. 

“We know there are stats about how painstaking the process is, especially for people who are just entering the workforce,” said Lamm. “Taxes are rough. Financial literacy is something that not everyone is thinking about, so our approach is acknowledging that and meeting our employees where they are.”