Life At Classy: San Diego’s Top Tech Companies

Life At Classy: San Diego’s Top Tech Companies

By Jill Felska

Our “Life At” series – brought to you by Fresh Brewed Tech and Want To Work There – gives a behind-the-scenes look at the cultures of different companies across San Diego.

When people talk about the best places to work in San Diego, it’s almost inevitable that someone will bring up Classy. And for good reason. When it comes to attracting top talent, many employees are now drawn to work with purpose, not just a paycheck. This is especially true for the millennial generation and is a large part of what makes Classy such a desirable place to work.

While Classy started as a simple bar crawl held to raise money for the American Cancer Society, the company has now evolved into a social enterprise that creates world-class online and mobile fundraising software for nonprofits.

The growing SaaS company’s mission? To mobilize and empower the world for good.

Having just reached $1 billion dollars in donations through its platform, I would say the company is indeed doing just that. And, it’s a focus that continues to attract and retain exceptional employees.

That said, the company’s mission isn’t the only thing that appeals to its growing workforce. After spending some time with founder and CEO Scot Chisholm and his team, something else became clear – a focus on transparency and employee empowerment has also been a bedrock for the company’s culture.

Through all of Classy’s highs and lows, leadership has prioritized the continued flow of communication and has made sure that employees always feel comfortable sharing feedback. This atmosphere of psychological safety didn’t create itself – it’s something they were intentional about as the company has grown and plans to keep fostering in the future.

But you don’t have to take my word for it. Here’s what current Classy employees had to say about working at the technology company.

What attracted you to Classy?

“I had the great pleasure in my early Silicon Valley days of working with Yelp through it’s fast growth years and past the IPO. It was a great company, an amazing culture, and a heck of a rocket ship ride. Since then, I have worked with a couple of startups and I was always seeking that rocket ship company that checks all the boxes again. It was a hard find, but I eventually found Classy. I know that I am in the right place at the right time with an amazing company that is going to do big things, all while making a difference in the world.” – Shianne Sampson, Head of Sales Development

“The mission, which is ‘Mobilize & Empower the World for Good.’ I truly believe we do that daily. I work in finance, so no matter what company I’m at I’ll be buried in financial models and living in Excel spreadsheets. I’m motivated when I’m passionate about the mission my work supports, and I found that at Classy.” – Jake Holslag, Senior Financial Analyst

“Over six years ago, I started off getting to know the Classy team while working at the Starbucks down the block from the old office location. Every morning, I would greet and serve many of Classy’s founding and early team members. I grew familiar with the company, their mission, and thought, ‘Wow, wouldn’t it be great to be a part of that family one day?’ Fast forward to 2014, when I was looking for a career change. That was when Scot and Todd approached me with the idea of joining them to help grow and build out a world-class customer care team. I took a leap of faith and joined the Classy team. This decision really changed my life forever. I am working with the most amazing people, and feel pride in the team that we have built. Most of all, I feel like I have a purpose, a reason to stand for something.” – Ed Trujillo, Customer Care Manager

“I started my journey with Classy as a customer and maintained a friendship with my salesperson. On some of my most challenging days in the nonprofit world, I’d reach out to him because he was always upbeat and positive, and I was in awe that he loved walking into his job every day. It was then that I started to get a glimpse into the kind of special that existed at Classy. He encouraged me to apply for a position at the company, and after I received the job offer, I flew from NYC to San Diego to find out if all the hype was real. In my mind, there was no way that the picture I had painted  for myself would align with reality; I was wrong. Everyone I met was incredible, and loved the work they were doing. There was an equal passion for their work life as there was for their personal life. THAT was missing in my life in NYC. Here it is almost three years to the date after I first interviewed for Classy, and I have no regrets about taking that leap. I actually wish I had taken it sooner.” – Barrett Frankel, Manager, Customer Success Management Team

What do you love most about working at the company?

“Classy is incredibly fun, hectic, intense, satisfying, uplifting, and challenging. It hits a number of ‘needs’ a modern professional has – an opportunity for career growth, a truly unique chance to build an actual world-changing product, and an amazing group of individuals that are truly a joy to get to work alongside.” – Tim Gumto, Senior Product Manager

“I’m inspired every day at Classy. It’s not just the work – it’s the people, our clients, and the Classy vision, mission, and core values. I am in awe at the talent that fills the Classy community, the thirst for more, and their drive and desire to be better. It is a community filled with achievers who also just happen to really enjoy being around one another.” – Barrett Frankel

“I have been here for seven years now and I am still constantly learning. The team of people that I am lucky to call coworkers are some of the most passionate, hardworking, authentic humans, and they keep me on my toes. As the company has evolved, so have we. This has forced me to continue to grow and learn new skills and take on new challenges. Working with others that are so dedicated to the company mission, I always feel like the bar is being raised. At the end of the day, I also love that we are still the same company that we were seven years ago with the same group of passionate people.” – Tori Callahan, Lead Marketing Associate

How would you describe the office vibe?

“The vibe is fresh, often times electric with movement and thought. As a member of the LGBT community I feel like I can be my true self at work without judgment or worry. The office is bright, well caffeinated, and usually has a friendly dog or two roaming around looking for a pet behind the ears.” – Ed Trujillo

“Everyone is passionate about helping nonprofits with the work they do to better the world. This passion forms a camaraderie across teams, and there is constant collaboration and innovation at work.” – Sarah Yee, Technical Support Engineer II

“Hardworking, but balanced. In the past year, Classy has really hit a stride with allowing employees to have a more relaxed work environment. Many employees work remote one day a week or have the freedom to be flexible with their schedule. There is an understanding that as long as you get the work done, and do a great job, you can dictate your own schedule. I think that work environment breeds a mutual trust between staff and leadership that creates a really healthy culture.” – Tori Callahan

“The vibe is like piping-hot kettle corn. Things are always popping, and somehow salty and sweet come together to create something delicious. We move at a blazing pace and challenges continually pop up. Regardless of role, folks are quick to help each other so we can deliver an awesome experience for our customers.” – Chris Gast, Director, Customer Experience and Care

How would you describe the company’s leadership style?

“Transparent and empowering. I’ve never worked anywhere where we are such an open book around strategy, changes, and financials. We truly believe in taking employees along in the journey. Leadership is also very empowering. I am given opportunities daily to challenge myself and my team. I’ve learned a ton and continue to do so.” Dina Rulli, VP, People Operations

“A mixture of positive encouragement, constructive coaching, and crazy fun that gets us over a high bar they set on behalf of customers.” – Chris Gast

“Largely non-prescriptive, empowering, and nurturing of individuals and ideas.” – David Fu, Senior Engineering Manager

“I am a coach. My leadership style is to help my care agents learn more about what their strengths are and how to maximize them, while also lending those strengths to the team’s success. My agents are people first. I care about them before numbers. If they know their value, the numbers and metrics will usually fall into place. I trust them to bring their best every day, and they trust in me to do the same.” – Ed Trujillo

What’s your favorite perk or benefit?

“Paid volunteer time off is really cool and people take advantage of it. It’s amazing to see the impact coworkers are having on our community through this company benefit.” – Jake Holslag

“Definitely the flexible schedule and ability to work from home when needed. Although I have a very people-facing job, I am an introvert at my core, so the alone time to focus and be productive is really valuable.” – Dina Rulli

“Vacation days and half-day Fridays. Classy has really doubled down on giving employees sufficient time off during the year which promotes a more balanced lifestyle. I really appreciate that. Half-day Fridays are a great opportunity to spend time with family or friends.” – Tori Callahan

“The view of the ballpark and water never ceases to amaze me. Catered lunches and kombucha on tap are pretty great too.” – Sarah Yee

What do you like most about living and working in San Diego?

“There is a true appreciation for life here. I came from an environment where life could seemingly only be appreciated after you had worked yourself to the brink, climbed the proverbial ladder far enough, and achieved even more. In San Diego, there is still a spirit of striving for greatness, but not at the cost of casting other important aspects of life aside.” – Barrett Frankel

“I’m a San Diego native and am one of the lucky few to have spent most of my life in such a special place. Having a job in the tech sector helping nonprofits is just icing on the ‘America’s Finest City’ cake.” – Chris Gast

“I spend my weekends outside in the beautiful San Diego area. It’s robust enough here to be able to challenge myself to do something new every weekend. I also, thanks to Classy, have been volunteering and getting involved in the community more than I ever have. Me and my family just did a giant marshmallow fight with the kids at The Seany Foundation, and it was one of the most memorable days of my life.” – Shianne Sampson

What do you think the company will look like a year from now?

“We’re even bigger and better. One of our core values is ‘always be learning,’ and when I think about the future, I see us living this value and continuing to learn from our successes and failures, and having become an even stronger company resulting in bigger impact for our nonprofit partners.” – Dina Rulli

“There are so many directions we can take our mission. Individual charitable giving in the US last year was over $260 billion, while only 9% of that giving is done online today. I see that online percentage going up drastically, and Classy will be here to help service that transition in a big way.” – Jake Holslag

“A year from now, I hope we continue to double down on being customer-centric – keeping the voice of the customer top-of-mind and a priority when it comes to iterating on our product and fixing bugs that are inevitable within software development.” Sarah Yee

“I think Classy is at a key turning point and there will be a lot of exciting changes in the year to come. It’s hard to know exactly what those changes will be right now. I think we’ll see a lot of new exciting products and potentially an updated long term vision for the company.” – Page Piccinini, Senior Data Scientist


Interested in joining the Classy team? The company is growing quickly and plans to hire full-time, part-time, contract/freelance, and hourly team members over the next year. You can be on the lookout for roles in marketing & communications, engineering, sales, operations, HR, design, product management, customer support, and data.

Visit the company’s career page to learn more.

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Jill Felska

Jill Felska

Jill Felska helps founders create intentional company culture. Her company, Want to Work There, is focused on providing action steps that leaders can take to positively impact the employee experience, ultimately ensuring they can hire, engage, and retain the right team.

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