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Investment Adviser Association
Justin Kapahi
Marc Gilman
Vanessa Valerie Tay
Workplace by OS33
Written by Vanessa Valerie Tay
on September 27, 2018

Meet Shana Toscano, Senior Controller at Workplace by OS33. Shana’s responsibilities include accounting, budgeting, financial reporting, analysis, and keeping our CEO and Co-Founder, David Matalon, aware of the company’s financials.

“A large part of my work is about improving processes and getting all the information required to help David make good business decisions, which in turn helps keep things running as the company navigates any obstacles that we may encounter along the way,” said Shana.

Shana Toscano BW


It would be remiss not to point out that Shana also happens to be the warmest, kindest, and most supportive person that anyone could ask for in a colleague. She is always approachable and is very likely to be the first friendly face to greet you at a company social. At the office, Shana always finds time to catch up with colleagues, and puts in the effort to get to know everyone. Her genuine and unpretentious demeanor is a welcome ray of light even in the greyest and most brutal of New York winters.

Prior to joining OS33, Shana had not even thought of leaving her previous role at Axispoint. She was part of a great team and enjoyed working with her mentor.

“My mentor was the one who taught me everything, and I wouldn’t be here as a Senior Controller if not for the time he had invested in me,” said Shana. 

Then, OS33 found her.

“I remember researching David (Matalon) and Jacob (Kazakevich) as much as I could online, and I recall being very impressed with them, what they built, and when they built it. I was very intrigued and amazed that they had developed a software solution that was so forward-thinking and ahead of its time,” said Shana. “I felt that it was a great opportunity for me to join the company before it became huge!”

“As I’ve gained experience, I’ve become more conservative when it comes to life-altering decisions, but I felt a jolt of energy and excitement whenever I thought about OS33, so I decided to take a leap of faith!” said Shana.

Today, after two years on the job, Shana is still very much aligned with the company’s mission and enjoying her work here.

“We’re a lean team, and I know that one of the reasons why David hired me was because I adapt well and very quickly to different people and environments. I have a problem-solving attitude and I care a lot about what I do. If something is associated with me, perfection is what I’m striving for,” said Shana.

She adds, “At times, it’s like having 10 children running in different directions, and I have to decide which direction to go towards first. It’s very difficult, but it has taught me to expect the unexpected – every day, every week, and every month!”

As a self-proclaimed workaholic before her children came along, Shana, who is now a mother to two adorable children, enjoys the flexible work hours at OS33. 

“Being able to work from home and manage my own time has been really helpful. It allows me to focus and get my work done well without compromising on quality time with my children. Part of the Workplace solution is about enabling freedom without compromise, and I think that is very much reflected in our work culture,” said Shana.

There’s never a dull moment at a fast-growing company like OS33. Shana describes the past two years of her career as a “rollercoaster ride” that has kept her on her toes.

“As a perfectionist who would usually go out of the way to meet every single deadline in the fastest and best possible way, I’ve had to learn to feel comfortable saying “no” in a graceful way, as well as to manage expectations,” said Shana. 

“All the challenges, anticipated or otherwise, have served as building blocks for who I am as a professional. I’ve learned so much in the past two years, and I’m looking forward to expanding my skills even further,” Shana added.

If OS33 sounds like a company you would like to work at, check out our Careers page for open positions!

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