I’m honored to introduce Laina Crosby, a Product Manager at Toast. Full disclosure, Laina & I used to work together once upon a time. While Laina works at Toast, she is not Toast. Toast is not Laina. She is a person far beyond her professional identity. Lest we forget.
Laina is the rarest of people and allow me to explain. She was born in the warm blanket of sunshine that is Long Beach, CA. She studied, got good grades, and went north to attend the University of California at Berkeley. Perhaps you’ve heard of it. She wasn’t so excited about the prospect of careers like consulting or other cubicle-like work so she kept searching until she found a local AdTech startup across the Bay in San Francisco called AdRoll. Motivated by the mission, people, and buzz of the venture capital infused environment she jumped into a career at growing technology companies.
Over 5+ years at AdRoll she transitioned from roles in Operations to Account Management, traveled to Dublin where she served as a company Ambassador growing AdRoll’s European presence, and then finally transitioned into Revenue Operations to help further operationalize their GTM team. That’s some serious flexibility in one sentence right there. Then, she began to explore what was next.
Laina had always wanted to go to business school and was drawn to schools in the Boston metro area. She loved her trips to Boston to visit friends from college and the people she met along the way. Even though her parents told her they weren’t coming to visit in the winter if she headed East, she took the plunge and headed to the Tuck School of Business at Dartmouth. Close enough. After finishing up at Tuck after a previous summer internship, she joined Nike full time in Portland. Then they let everyone work remotely. So naturally she got on a plane and returned to the California sunshine she was so accustomed to. Wait, producer in my earpiece. Excuse me, she did what? She went back where?!?
A California kid made Boston her new home. You love to see it.
While working as a Digital Product Manager at Nike Laina relocated to the South End. She loved the neighborhood feel of the community. It felt homey to her. There was enough hustle & bustle but not too much. And the seasons. Oh, the seasons. It felt to her like there was constant change. Something new coming all the time. Indeed. She likes frequenting restaurants like Kava Neo-Taverna or grabbing coffee before a stroll at Greystone. And of course, like any true local, Laina enjoys the occasional pilgrimage to Fenway Park.
As Nike ushered their workforce back to HQ in Portland, Laina wanted to stay in Boston and went looking for a local employer. She interviewed at a few different Boston tech companies seeking a company with a big central presence. Enter Toast. When she interviewed there it brought her back to that buzz & mission she experienced at AdRoll – helping small businesses thrive alongside an energized, thoughtful & intelligent team through software.
Toast serves a very unique industry. Laina’s brother is in the restaurant industry so she understood some of the intricacies. When serving restaurants it’s very difficult (more like impossible) to have a one size fits all solution. Or to translate into startup speak: the wide variety of restaurant needs present an interesting problem set that provide numerous opportunities which can only be solved through technology.
I’m told Toast has a lot of bread puns internally. Their internal knowledge portal is called “The Pantry”. Co-workers’ babies are called “croutons”. Moving around internally is “doughbility”. That’s cultural commitment to the bread, people.
As a Product Manager, Laina is on the front lines of some of those challenges the company is tackling. They approach big, complicated problems every day centered around questions like “how do you build a multivariate solution that works for a massive industry with a wide scope of need?”. There are different types of restaurants, sizes of restaurant, and service models. There are shifting trends in the industry such as how employees get paid. Lesser known is that the restaurant industry is a highly regulated one and there are a lot of compliance standards that restaurant operators need to uphold.
And the company has grown really fast. Which presents even more challenges! The crouton is becoming a loaf before our very eyes. I’m sorry..
A few insights from Laina’s 8 months at the company:
Her manager put together a new list of people she needed to meet every 30 days as part of her onboarding. It started with her primary points of contact, then moved onto teammates a little farther out and so on in order to help do her job effectively. If your manager hasn’t done that for you as part of a recent onboarding, get familiar with the org chart and try it yourself!
Like any other new hire, she wanted to come in and have a big impact. But at a company of Toast’s size that is more likely to hurt than help. Laina relayed the critical insight that you have to dial your onboarding velocity & approach appropriately based upon the product size & complexity. She took time to deeply understand the problems her new team was facing as her primary objective. Then she dove into making a list of the highest priority problems before running in guns blazing and making changes. We’ve all met the hammers who see everything as a nail. Being a swiss army knife is a serious skill!
Laina also has the unique insight of onboarding at a new company with a new team in a remote world. Building internal relationships in a remote world ain’t easy, for anyone. She relayed that in office visits have helped but overall coordination to meet coworkers and build relationships is something she’s still working on. This new reality is going to take time..for all of us. Most can relate!
Last, I asked Laina where she sees herself headed in her career. Because I was the interviewer. Ask me that question and the nervous laughter starts as I look for the exits.. She relayed that it has shifted greatly. She was originally convinced she wanted to be a COO and made her way into Product because she could learn to bridge those gaps between engineering, sales, marketing & back to help drive the product vision. Over time she’s become more attracted to Strategy, an extension of her Product chops. Getting a good sense of customer needs, challenges, and the requirements needed to drive expansion all continue to appeal to her growth.
I have no doubt Laina will go on to do great things. Keep an eye on her career! And if you happen to reach out she loves talking restaurant tech, is obsessed with her dog Murphy, and can be seen running the Charles in warmer climates. Thank you for the time Laina, you’re a stah!