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Canadian Entrepreneurs - Erica Pearson of Vacation Fund

Sep 7, 2019 | 10 minute read | @charlieinthe6

"I grew up in a family that did not spend money on stuff. My father... taught us the value of saving, but also of visiting new places and interacting with people from different cultures."

Discover why Erica Pearson founded Vacation Fund, an employer-matched travel savings program!

1. Hi Erica! What's your background?

Hi Charlie!

If we go way back… I grew up in a family that did not spend money on “stuff”. My father was very selective about how he spent his money, but always emphasized the importance of travel. He taught us the value of saving, but also of visiting new places and interacting with people from different cultures. By the age of 22, I had been to over 40 countries. Our family never stayed in expensive places, but we were grateful for the opportunity to travel.

My background was pretty straightforward up until the day I left RBC. I was a high school student that worked hard, got involved, and played every sport possible, then I went to Queen’s to earn my Bachelor of Commerce degree and play on the Varsity Field Hockey Team, then I got my full-time job at RBC Capital Markets where I had an opportunity to rotate desks every 4 months, until I landed in the CEO Office of Investor & Treasury Services working as an Analyst. From there, I officially resigned from RBC in February 2017 to pursue Vacation Fund.

2. What motivated you to get started with Vacation Fund?

“Don’t start a startup unless you’re so passionate about solving the problem that you CAN’T not do it.”

I remember sitting on the trading floor reading articles on Notable every day about young people starting companies. Those articles inspired me to start doing my homework… looking at all of the “How to Start a Startup” materials and Paul Graham Essays online. And one of the most important lessons I learned early on was “don’t start a startup unless you’re so passionate about solving the problem that you CAN’T not do it."

Based on my upbringing, I was really passionate about helping people save specifically for experiences. I truly believe that experiences like traveling significantly increase people’s happiness and quality of life. I found bucket list platforms that help people plot out the things that they want to accomplish, and I thought “that’s great, but those are expensive trips and people need to start saving for them if they want them to happen”. So the initial intention was to build an automated savings tool, specifically for people’s travel goals.

“I don’t think my boss wants me going on vacation.”

Then, in 2017, after I’d quit and met my co-founder, we started asking people what prevented them from going on vacation. Half of the people said budget, and the other half said “I don’t think my boss wants me going on vacation.” Around that time, I was pitching this to tech CEOs in Toronto who started to ask if they could contribute towards their employees’ Vacation Fund to encourage them to use their time off. This was the demand-based pivot we needed to turn Vacation Fund into an employer-matched vacation saving platform, designed to incentivize employees to put money aside and take meaningful vacations every year.

3. What went into building the initial product?

Before I ever quit my job, I took part-time courses at BrainStation to figure out what it would take to build a platform like this. I took Intro to Web Development to learn the basics of coding, and then I took a User Experience Design class to build the first clickable prototype of Vacation Fund. This is what we used to start asking questions.

Thankfully, when we landed our first B2B client Eighty-Eight Agency in February 2018, I was able to onboard the company with a Vacation Fund branded Typeform survey. I then coordinated with their payroll processes to set up employees’ contributions, and I emailed them once a month (myself) to tell them how much money they had saved towards their next adventure.

"Doing things that don’t scale allowed us to identify what our entire product and service looked like"

This idea of hilarious manual processes and doing things that don’t scale allowed us to identify what our entire product and service looked like in its most manual form, and guided us for what to build in the first version of our web-based application. The first version was completed in August 2018 thanks to my co-founder, our UX designer, and our front-end developer.

4. How have you attracted employees and grown the team in such a hot tech market?

I will speak to our most recent experience on this, as we just hired employee #4! The process looked something like this:

  1. On Friday, October 12th we drafted a job posting for a Project / Relationship Manager, and put it up on AngelList.

  2. We left the posting up for 4-5 days, and watched ~70 applicants express interest.

  3. We unpublished the job, and emailed everyone further explaining what it means to join a startup as person #4, and requesting that if the candidate were still interested in applying, we would like to see a 2 minute video sent to us by Thursday, October 18th describing themselves, their career background, and why they are excited about what Vacation Fund is doing.

  4. We watched the ~25 videos sent back to us by the deadline, and selected 14 candidates to meet in person.

  5. We then conducted 14 in-person interviews, and selected 4 candidates to come in for another meeting in person.

  6. We had two of our advisors conduct a meeting with the 4 final candidates, and got it down to 2.

  7. We made an offer, and our new Project / Relationship Manager joins us full-time as of Monday, November 19th.

I can’t say for sure, but I think regularly sharing (i) our company’s story, (ii) our early successes, and (iii) our participation in Techstars in Chicago really helped peak people’s interest in the company and the role. Almost every candidate that came in for an interview had watched our explainer videos, our demo day pitch, and had searched online for any information they could find on us. I was impressed with how much these candidates knew already about our story and progress. I think it also helps that we are selling a mission and vision that truly aligns with people’s values and priorities today. Our concept and value-proposition is relatively straightforward, and a lot of people are just looking for something that they can be passionate about.

5. How have you attracted customers and grown Vacation Fund?

"We haven’t done any paid marketing or advertising so far"

So far, customers have come to us as a result of networking, warm referrals, and creating awareness on LinkedIn. We haven’t done any paid marketing or advertising so far, but I have been active on social media (LinkedIn specifically), sharing articles that are aligned with what we’re doing.

The employee benefits space has changed a lot since the labour market became so tight, and as the demands of younger generations in the workforce began to significantly impact people’s employment decisions. Vacation Fund is very clearly aligning employer and employee desires, by giving employers an easy way to encourage employees to use their vacation days (making them happier, healthier, more productive, etc.), and giving employees the push that they need to take time off and regularly prioritize new experiences. This is an offering that really resonates with people, especially as disconnecting seems to become increasingly challenging, and stress and burnout are battles people are facing daily.

6. What's your business model?

We charge companies a subscription fee per month depending on the company’s size. In 2019, we will also begin to generate travel affiliate commission as we learn more about people’s travel goals and can show them offers that are aligned with those goals.

7. What do you think has had the biggest impact on your sales since you started?

I think our consistent effort to network with HR professionals and company decision makers is what has most significantly impacted our sales to date. We’re also not afraid to ask questions that may not always produce the answers we’re looking for. There are a lot of companies that could generate a significant amount of value in attracting and retaining talent by offering Vacation Fund, but there are also a lot of companies that are not necessarily within our target market. The more questions we ask, the more quickly we’ve been able to identify what our best customers look like.

8. Have you found any resources or habits particularly helpful or advantageous?

Yes, absolutely. I meditate, I listen to one motivational video in particular every morning, I eat incredibly healthy food, I make time to workout, and I make an effort to disconnect almost every weekend. I also prioritize spending quality time with my boyfriend, my family, and my friends.

I’m very much a believer that there’s no such thing as “one size fits all” in life. There are certain entrepreneurs that can work 12-18 hour days 7 days a week without making time to socialize or cook or workout. When I attempted that lifestyle and gave up my healthy habits during my first 6 weeks of Techstars in Chicago, I learned the hard way that I can’t live like that. When I’m not at my best it negatively impacts not only my personal health and happiness, but also the progress of the company. I can’t emphasize enough how much prioritizing health and wellbeing matters, especially when our company goals are so ambitious and there’s so much important work to be done.

In the coming year, one of my objectives is to make more time for reading. My favourite tech startup-friendly book has been The Hard Thing About Hard Things by Ben Horowitz.

9. Do you have any helpful advice for other aspiring entrepreneurs / wantrepreneurs?

"When you know that you’d never forgive yourself if you didn’t at least try to take an idea and turn it into a company, go for it!"

Entrepreneurship is a very demanding and rewarding lifestyle. Create a vision board for yourself. Figure out what you want your life to look like 5 years from now, and figure out whether or not you can take a couple years to make zero income and start to put the pieces together for what might become a successful company. There are extreme highs and lows involved in starting a company. Talk to the people in your life about wanting to make the transition. When you know that you’d never forgive yourself if you didn’t at least try to take an idea and turn it into a company, go for it! :)

I’m always happy to make time for aspiring entrepreneurs to share the good stuff and the bad stuff. There are many of your own mistakes to make along the way, but you only learn by starting to execute and getting things wrong.

It’s a crazy way to live, but now I can’t really imagine doing anything else.


⚡️Thanks for sharing Erica! ⚡️