Maja + Erica Pearson: Vacation Fund

This has been an exciting week for Holistic! If you haven’t yet heard, we have a fellow joining us from Balkans. Maja Jovicic is in Chicago as part of professional exchange program, World Chicago. Maja (pronounced MA-YA), has become a part of the Holistic family and her work with Holistic will consist of various projects including the interview with Erica Pearson from Vacation Fund which you are about to read. You can follow Maja along in her personal blog to hear all about her experience with World Chicago, Holistic, and Chicago in general!

Part of the Holistic family. Left to right: Tom Alexander, myself (Elda Baez), Valeska Anleu, Maja Jovicic, Bryce Huguenin.

Part of the Holistic family. Left to right: Tom Alexander, myself (Elda Baez), Valeska Anleu, Maja Jovicic, Bryce Huguenin.

Erica Pearson is the Co-Founder and CEO of Vacation Fund. Vacation Fund is an employer-matched vacation saving platform that incentivizes employees to put money aside and take meaningful vacations every year. It allows employees to direct a portion of their paycheck into a separate Vacation Fund Account, and allows the company to match a portion of the contribution. This make employees’ dream trips more financially attainable, and helps companies better attract and retain happy, healthy, productive talent.

Erica Pearson — Co-Founder & CEO of Vacation Fund

Erica Pearson — Co-Founder & CEO of Vacation Fund


How does Vacation Fund work? Is it app-based, or do you go to companies in person?

Vacation Fund is sold as a B2B SaaS product and service. It is a web-based application available for use on desktop, tablet, and mobile devices. The Vacation Fund Program involves coordination with the company’s payroll provider to get up and running.

What was the inspiration/motivation that started Vacation Fund?

I grew up in a family that did not spend money on “stuff”. My father only wanted to spend money on “experiences”. We lived on a budget, but we managed to go on 3 trips a year as a family. By the time I turned 22, I had visited over 40 countries.

Initially, I just wanted to help people save for their travel goals, allowing them to live their lives to the fullest. As we started asking people what prevents them from going on vacation, some people said they can’t afford to travel as much as they’d like, and others said they hesitate to ask for time off of work. They said they feel guilty asking for time off, or they aren’t sure how much time off is actually acceptable. Around that time, C-Suite executives at companies started to ask if they could contribute to their employees’ Vacation Fund to encourage them to use their vacation days and give them a benefit they would actually value and take advantage of. Pivoting from a B2C fintech product to a B2B SaaS company is what really set things in motion.

Vacation Fund has a pretty cool team! How did you guys find each other?

Early on in this crazy startup journey, I came across a wickedly talented full-stack developer at a tech social that shared my passion for creating something valuable out of nothing. He had a full-time job, but was excited enough about what I was trying to create that he actually wanted to help me find someone that would be qualified to join Vacation Fund as a technical co-founder. Fast-forward two months of writing my job postings and evaluating potential candidates, he sent me a text saying that he was thinking about how many people this platform will help, and that perhaps he should be the one to build it. Today, I can proudly say that he is my friend and co-founder.

Our highly skilled front-end developer (Bryan) also bravely maintained Vacation Fund’s presence in Toronto while Abhi and I moved to Chicago for a few months to hit the ground running in our company’s second office. We found him through AngelList.

Everybody loves a good vacation, and you’ve traveled a lot. Do you think vacationing is a good way to experience diverse cultures?

Yes, absolutely! I think in today’s knowledge-based economy, it’s really important for people to get out of their everyday routines and experience something new. I think when people start to travel, eat new food, experience other cultures, and get a chance to interact with people that speak a different language or live a very different lifestyle, it helps people put things into perspective. Thinking differently and developing empathy are two of the beautiful outcomes of traveling to new places.

Vacation Fund is based in Toronto – do you work with some companies in the U.S. as well?

Yes! Since expanding to Chicago, we had an opportunity to figure out how our processes work for our American client companies vs. our Canadian client companies. There are a lot of American client companies anywhere between 100 and 5,000 employees in discussion about starting to offer Vacation Fund to their employees, but most of the companies in our Techstars cohort also said they wanted to start offering this to their employees that need a bit of a push sometimes to take a vacation. An ambitious, growing startup team is an easy place to work hard until you burn out.

When it comes to establishing yourself with new client companies or in new markets, what would you consider your biggest challenge?

We’re learning very quickly that the companies with between 100 and 1,000 employees seem to be our most eager clients, but the larger the company, the slower the sales cycle. Smaller companies can go from inbound inquiry to onboarding within a month. Larger companies need to consider the return on investment that they can expect based on making a financial commitment towards employees’ vacations, and increasing employee satisfaction, productivity and retention as a result.

Employee engagement is a burning issue nowadays. Do you believe Vacation Fund is a contributor to the solution?

It’s funny because it sounds controversial, but we truly believe that employee engagement increases when employees are given a financial incentive from the employer to take time away from the office. One of my advisors actually called Vacation Fund “a regularly scheduled oil change for your employees”. We believe that people are at their best in terms of satisfaction, productivity, motivation, and gratitude towards their employer when they have time dedicated to being away from the office, to get out of their routines and experience something new. At Vacation Fund, we are working to help our client companies maximize their employee engagement by aligning employer and employee desires.

Bonus question: What do you think about Chicago? Best thing about the city?

We love Chicago. Culturally, it feels very much like Toronto. We’ve really enjoyed starting the company in Toronto and working to maintain a presence in Chicago. I know these may be cliche tourist answers, but the Chicago River and deep dish pizza always make me smile.

Screen Shot 2018-10-19 at 9.31.42 AM.png

To learn more about Vacation Fund check out their new video!