June 10, 2024

Laying foundations of operational scalability: A Q&A with Assembled’s first support hire

Whitney Rose

Assembled just hit a significant milestone: 100 employees. In honor of the company’s journey from three Stripe alums in 2018 to triple digits in headcount six years later, we’re spotlighting early hires and the unique paths they’ve created for themselves at Assembled. You can find all their stories here.

Jessica Bolber, who goes by JB, has built many of the process that have helped Assembled scale from a team of less than 10 to a team of almost 100. In this interview, she shares how Covid layoffs opened the door for her to join Assembled, what she does to overcome imposter syndrome, and why working at Assembled is type-two fun. Her answers have been edited for clarity and concision.

Q. JB, what were you doing before you joined Assembled?

A. Prior to Assembled, I was working at Intercom on their support team. During Covid, my entire team was laid off. For the first time since graduating college, I had some free time. So, I decided to hop in my car and go on a road trip to spend some time in national parks.

Q. How did you end up at Assembled?

A. It's actually a fun story. I was in Yellowstone at the tail end of my road trip around the country when I got a LinkedIn message from BZ (co-founder Brian Sze). The message basically said, “Hey, we’re hiring for a Support and Ops role at Assembled. It would be the first person in this type of role at the company. We would love to talk to you.”

I was confused how he found me, but I was intrigued. When we finally hopped on a call, he said that Intercom was one of their customers and that they had reached out to ask if anyone affected by layoffs would be a good fit for the Support and Ops role. Multiple people suggested me.

Q. So your first role at Assembled was Support and Ops. What did that look like?

A. At that point, there were only eight folks working at Assembled, not including myself. I was employee number nine. Everyone was doing support and talking to people. We only supported customers via Slack channels. So, it was a little chaotic to make sure every message got a response. I was owning all the communication for support queries that came up.

I was also doing customer onboarding and implementation — building out some of that first scaffolding of how we implemented a customer. I think I was shooting to onboard customers in like 30 days or less. I was doing a decent job, too. But our product wasn’t nearly as expansive then as it is today.

Q. Now you're on the finance team, but you were managing employee onboarding when I started. What are all the things that you did in between your first role and your current role?

A. You actually hit all of them. I started off as Support and Ops. Then I was a Program Manager for the People and Ops team, where I built out and onboarded 100% of the company over about a year. That was happening when we were in a hyper-growth period, so it was a lot of people. Eventually, our growth became more consistent, we hired a focused People Lead, and Finance Operations became the stickier, hairier problem — so I stepped in and have been there ever since.

Q. And this is your first experience in a finance role?

A. Yes, this is my first role in finance. Although, many evolutions of myself ago, when I was producing music festivals, I was doing a lot of budgeting and profit and loss statements. So, while this is my first official finance job, I did have some visibility into that world through a different lens.

Q. What's been the steepest learning curve for you to overcome in any of your roles at Assembled?

A. I think it's becoming an expert in something entirely new. When I stepped in to do employee onboarding, I was reaching out to people on LinkedIn who were in charge of onboarding programs to ask them what works and what doesn't work, getting into the philosophies around onboarding internal teammates or employees. So I think it's just becoming an expert and understanding what your role is and how to do it in the best way possible. With onboarding specifically, I thought a lot about how I wanted people to feel when they joined Assembled.

Q. How do you fight imposter syndrome when you're taking on responsibilities that are completely new to you?

A. I think imposter syndrome is something everyone has. So, honestly, I level set my own brain by reminding myself that nobody actually knows what they're doing. Even somebody that's been in a career forever is still faking it until they make it in some ways. We're all just floating around on this big rock, figuring things out one day at a time. Nobody really knows what they're doing. I remind myself of that all the time. I also remind myself that making mistakes is how you learn and grow.

Q. What has Assembled’s culture of seeing value in unconventional career paths taught you about yourself and your beliefs around what you can accomplish?

A. I think it just proves that you can do anything you set your mind to. I’m really grateful that I've had the opportunity to try different roles here, do new things, flex in ways that I never thought I would. It was by no means easy. It’s hard to go from support to building out an onboarding program to a finance role. But I did it. I’ve put a lot of blood, sweat, and tears into Assembled. Ultimately, I think people have seen that, and they’ve allowed me to put myself in new roles because of it.

Q. Going through all those transitions, how do you stay grounded?

A. I do a lot of yoga and meditating. I’m always trying to sprinkle things that help me progress spiritually, physically, and emotionally into my life. If I’m not on my yoga mat between three, four, or even five times a week, I can feel it in my bones. It’s like I need to get out of my skin suit. And for the days when I do feel off-centered, I try to acknowledge it to myself and to those I’m interacting with. We all have those days, and simply naming it can be helpful. I often think about how Thich Nhat Hanh says that the acknowledgment of suffering alone can bring it some relief.

Q. Who have been your biggest mentors at Assembled?

A. Right now, I would say Vincent (Tzeng, Head of Finance). He's my current boss, and he’s been monumental in my growth. I've always technically had a manager at Assembled, but due to the nature of my work, I often felt like I was on my own island, which made me feel untethered at times. Vincent has been a great mentor and anchor.

I would also say Steph (Wu, Head of People). We worked quite closely when I was doing onboarding stuff while she was getting ramped up here. And then I would say Megha (Narayan, Head of Marketing). She is really good at putting people in check and giving you a dose of reality, but it’s always in a gentle way.

Q. What would you consider the highlight of your career at Assembled so far?

A. Honestly, so many things. It's just really cool to think about how so many of the operational things I've done that have helped scale Assembled from a nine-person company to what it is today. I think at one point I was responsible for onboarding 85% of the entire company to date. That’s pretty freaking cool! Improving our billing operations? Multiplying our ARR from an operational standpoint? That’s major. Being a part of the journey from a seed-stage company to a series B company is something I’ve never done before, but it’s cool to look back and see how my fingerprints are kind of all over the place.

Q. What advice would you offer to anyone who would be interested in joining Assembled?

A. Working at Assembled is type-two fun. You’re going to work really hard. There are going to be hard moments. But you’re going to pour yourself into something, then you’re going to reflect, and then you’re going to be like, wow, look what I just did. So be ready to work hard and feel proud about it.

I think it would also be to make sure you have a life outside of work. Have hobbies and friends and things that fill up your cup. Take care of yourself in ways that don’t have anything to do with work, but that’s more of my own general philosophy!

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