Rachael Pfenning, VP of Ops at Sprout, orchestrates all of these efforts with 360-degree oversight of the day-to-day operations of the company. She has managed various teams over her tenure, built out hiring and training across the organization and worked closely with Justyn (Sprout’s CEO and Co-Founder) to build the foundation for what the sales, success, marketing, finance and support teams are today. Name: Rachael Pfenning Department: Operations Started at Sprout: August 23, 2010
You’ve been at Sprout since almost the beginning. Can you tell me what you were doing before as well as how you got to Sprout?
I worked in a variety of operational roles in entrepreneurial environments prior to going to business school at UCLA Anderson. Right before joining Sprout, I was working for a technology company in San Francisco that was focused on social products, and I saw that social was an area that everyone was trying to figure out. In the summer of 2010, I was in Chicago, visiting my now-husband, and a business school classmate of mine connected me to Lightbank (Sprout’s original investors). I interviewed with the founders of their different portfolio companies, and Justyn really stood out to me. He seemed uniquely sharp, down to earth and witty, and I knew he was someone I could get behind. At the time, Sprout had six employees—four co-founders and two engineers—and he needed a right hand: someone with a business mindset who was scrappy and could help him build out the business. And Sprout was exactly what I was looking for: a fun, young startup with a business that made sense. A month later, I moved to Chicago.
As VP of Operations, you oversee a diverse team. What’s your charge, and what does a typical day look like for you?
Currently, I am responsible for customer support, finance, product education, HR, talent acquisition, general office ops, and I’m the catch-all for everything in between. The founders and I also work together on any company-wide policies or anything that affects the group at large. A big part of my job is to keep a pulse on our business and help connect dots with others across the company. There is absolutely no typical day. A lot of what I do is very behind the scenes and not particularly glamorous. The cool thing is that the job has evolved: Every six months, I seem to be doing something different for the organization based on Sprout’s ever-evolving needs. Aaron (CTO and Co-Founder) once described me as an incubator. I have grown and managed various teams at Sprout, helping develop our talent and business processes across all organizational levels. Teams would start with me before they were even teams. I would work with Justyn on creating the foundation of a team and managing its day-to-day operations before we brought in experts to build out those functions further. This continues today but on a much smaller scale.
The organization has grown tremendously since you started. What are some of the most significant changes you’ve seen? What has surprised you?
I would bucket the changes into three categories: product, team and customer base.
Product: In 2011, we launched a new version of Sprout: S2, which is a multi-user environment. That was an enormous undertaking that set the foundation for us to be able to scale at the rate we have over the past four years. Also, seeing how fast we can push out new features under our recent restructure into a squad model has been a huge change for the organization. Team: Seeing new teams form and evolve has been a significant change. For example, a year ago, the Success team didn’t really exist, and now they have 14 people, build real relationships with our customers and have a significant impact on our revenue. As a side note, when I started there, I’m not sure how many employees were married, but nobody had babies. Now everyone’s getting married and having kids! Going through those life changes has been a significant change and an awesome thing to experience together too. Customer base: When we first launched S1, we had a lot of success with small and medium businesses (SMBs). Watching the customer base grow upstream to include an impressive list of enterprise and agency customers has been incredible. The fact that we can provide a solution that works for smaller businesses and can scale all the way up to enterprise customers has been key to our success.
How do you preserve culture in a quickly growing organization?
The culture has remained eerily similar to what it was in the beginning. Our people really define what our culture is, and we hire people who can get behind our mission and be insanely loyal to it. From there, we work to be as transparent as possible, from Justyn on down. Our founders are a very humble, behind-the-scenes group of people, and a lot of our culture trickles down from them too. They still work crazy hours and are constantly looking for new ways to keep employees happy, motivated and energized. We never stop thinking and working to improve things for people at Sprout. The four of them have also consistently been 100% committed to building great software, and it shows. People are proud to work to build, market, sell and support our product. This is a huge tie-in to our culture in my opinion. We also like to promote people internally into management roles, which helps preserve culture. While you learn a lot about managing through experience, this year we began offering management training. We wanted to give people the resources they needed to become better leaders and managers, which in turns improves the work experience for other team members.
You and Aaron lead a session about Sprout for every new hire. What is the most important thing you want new employees to know?
Giving new employees a high-level understanding of all the departments and teams we have, along with their respective functions, can help them see where they fit into the puzzle. We want them to feel a strong sense of purpose and see themselves as part of the bigger picture. It’s also important to us to keep the flattest organization possible. I want new hires to know that they can come talk to us. We’re normal, approachable people who genuinely care and want to hear how to make Sprout better. I also lead this session so I selfishly get an opportunity to meet all of our new talent personally.
Outside of the office, where are you most likely found?
Hanging with Wally, Brady and Socks. Wally’s my husband, Brady’s my 1.5-year-old, and Socks is my beloved pit bull. We like to be outside as much as possible, so you’ll often catch us walking around or at the park, even during the Chicago winters.
What are your hobbies?
What I like to call myself—what I’d really like to be in my next life—is the VP of Arts & Crafts. I like doing anything crafty. I make a lot of my own Christmas decorations and things like that. I also like anything outdoors, like playing tennis, skiing, paddleboarding or skateboarding. Pickup soccer is one of my favorite things, so hopefully, I’ll be able to jump back on it as my kids get older. Or I’ll just play with them!
What’s your favorite place in Chicago?
The lake. I realized when I first moved here that people go to the beach but don’t actually go in the water. I don’t get that—I’m one of the weirdos that actually goes in.
Do you have a favorite beer?
I rely strictly on Pete (Director of Web and Mobile Engineering and Co-Founder) and Aaron to tell me what beers to drink. They’re true beer connoisseurs, and they know what I like. I am a big fan of beer in general and have been missing my IPAs and Belgian beers currently while I am baking baby No. 2.
Any final words of wisdom?
The beauty of working at Sprout is that you carve your own path. This organization doesn’t have thousands of layers and jobs; many people have naturally evolved into their roles. I’m a perfect example of that. I didn’t start out doing the same thing I do today. As the business grew, Justyn played to my strengths, and I stayed nimble and added value wherever I could.
