Jessie Zaylía's Mobile App twrk Provides a Better Job Matching Option

Hi, Jessie! Please share a brief introduction about yourself and your business:

Hi, I'm Jessie. Growing up, one thing I swore I would never be was an entrepreneur because my father was one; when his business went under, we lost everything. So, I chose a stable career as an attorney, but it has been deeply unfulfilling. Luckily, I developed a fair amount of transferable skills after having been a managing partner at a large California firm. When I tried to find a different career using job-matching sites, the job-matching algorithms consistently suggested attorney positions and more attorney positions. It was incredibly frustrating. I just wanted to talk to the "job-search Gods" and say, "STOP SENDING ME ATTORNEY JOBS! Use my transferable skills to find ANYTHING else!" So, I created twrk, a mobile app where jobs come to you. You can talk to twrk, and our AI engine will listen. twrk send you jobs in a single screen; swipe left to reject and right to automatically apply with a customized resume and cover letter. twrk learns along with your swiping patterns. We've taken your customized application process from 2 hours to 2 seconds without sacrificing the job seeker's control.

What was your background prior to starting your own business?

I have been a lawyer for 13 years. I'm good at it, but we're talking 80-hour work weeks. Aside from helping people through pro bono work, my favorite part about being a lawyer has nothing to do with lawyering at all. Rather, I love managing teams, running operations, and driving large projects, which a lot of lawyers don't get to do.

What made you take the leap to start your own business?

Pure frustration led me to start twrk. I wanted a better job-matching product, and the world needed one, too.

Take us back to when you first launched your business; what was your marketing strategy to get the word out and did it go as planned?

We have our pre-launch plan for the app, but the exciting go-to-market strategy is our actual launch, which is planned for spring 2025. I got this idea after reading The Cold Start Problem, and we're keeping it semi-stealth for now.

What is the biggest challenge you have encountered along the way so far and what have you learned from it?

Fundraising is always a challenge. Our Friends & Family round went very well. After that, it has been difficult to get a warm intro to Angel investors because we're in the process of building and don't yet have a validated MVP (but we're very close). So, we've had to run extremely lean and have had to get scrappy/creative to make the current funding last through the pre-launch phase.

What accomplishment are the most proud of to date in your business?

I'm very proud of how well the Friends & Family round went. We raised over $100K. I had to overcome significant limiting beliefs that "I have no connections" or that it's "bad" to ask friends & family to invest. Turns out, I just had to put myself out there. They saw the business plan, and I'd done the math regarding the total addressable market. I have an amazing circle of people around me, including investors, co-founders, and non-investor friends and family. It's a team/community endeavor.

What's next for your business? What can we expect to see over the next few years?

We are filing a patent application and finalizing our MVP. You can expect to see us host several "this ain't your grandma's career fair" career fairs across the U.S. over the next few years.

What is your top productivity tip? 

I use Motion to help keep my tasks in order, and it has been helpful for our team, too.

On the flip side, how do you avoid burnout?

I am so passionate about what I'm doing, and it drives me. I live, breathe, and dream my business. Being a lawyer has led to burnout; developing a business that I believe in has reinvigorated my life.

What is your approach to work-life balance / integration?

I am probably the worst person to ask about this. It's an area where I need to improve, or so I've been told. Having said that, my many rescue dogs as well as my partner in life help to keep me grounded, and they bring me joy every single day.

What is one thing you wish you had known when you started your Entreprenista journey?

I'm really lucky that I joined Entreprenista toward the very beginning of my journey as the CEO of twrk. While having a great product or service is crucial, the relationships you cultivate can open doors, provide support, and offer valuable insights that can significantly accelerate your growth.

When hiring, what is your go-to interview question?

"Tell me about yourself." This is a great interview prompt precisely because it is so open-ended. You can see how comfortable and confident the interviewee is and how long they talk about themselves. You can tell how creative or uncreative they are and whether they can think on their feet.

If you've raised capital for your business already, what are some of your best tips or lessons learned?

Do the BORING STUFF because, often, that is what moves the needle forward. So, get comfortable with math. Research, math, and paperwork are so incredibly important. You have to have your ducks in a row if you want to be taken seriously by investors at any stage.

Do you have a co-founder? If so, how did you find the right one for you and what are your best partnership tips?

I have two co-founders. One is my best friend of 30 years, so that was a no-brainer. She is an HR guru, so she has a lot of domain expertise in the future-of-work space. Our technical co-founder, Shaun, came to us as a total coincidence. We were connected for years on Facebook, but we only had one connection in common — a person with whom I waited tables decades ago. Shaun posted that he had been laid off. He specialized in AI, machine learning, and quantum computing, so I reached out. This all happened at the very beginning of twrk's existence, so the timing was incredible.

What's the one app on your phone you absolutely cannot live without and why?

Happy Cow. I love Happy Cow so much. This is a personal app for me and has nothing to do with our business, but my life would be worse without it. I am the only vegan on our team, and it's great to know that, when I travel anywhere in the country or the world, I can pull up Happy Cow to find nearby vegan (or vegan-friendly) eateries. As for business apps, I'd probably have to go with Slack.

What is your favorite business tool or solution and why?

Canva is my absolute favorite tool. I have created so many things through Canva throughout the years, including twrk's logos, pitch decks, and business canvases.

What advice do you have for aspiring Entreprenistas?

Not everyone should fundraise. Fundraising is for businesses that have a goal of an exit by way of acquisition or IPO in 5-7 years after launch. If you are building a 10+ year business for yourself, however, then focus on scaling in different ways.

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