Unstructured

This company earned a 99% Great Place to Work score (even after a layoff!)

In this episode of Culture Uncovered, Jena Dunay sits down with Lindsay Gonzalez to unpack what it looks like to build a fast-growing, remote-first company at the forefront of AI infrastructure.

From transforming messy, unusable data into something AI can actually work with, to building a 99% employee satisfaction culture, Unstructured is solving one of the biggest blockers in AI adoption while scaling a team that genuinely enjoys working together.

They also get into the real side of startup life, from navigating layoffs and rebuilding trust to maintaining a high-performing culture while doubling headcount.

What you’ll learn:

•  What Unstructured does and why data readiness is critical for AI 
•  What a 99% employee satisfaction culture actually looks like 
•  How they maintain connection in a remote-first, fast-growing team 
•  What it takes to succeed in a high-ownership, no-handholding environment 
•  How to stand out as a candidate and get noticed 

Unstructured Highlights:

• Founded: 2022 
• Headquarters: Sacramento, California (remote-first, distributed) 
• Team Size: ~78 full-time + growing rapidly 
• Industry: AI / Data Infrastructure 
• Culture: High-trust, ownership-driven, fast-paced, collaborative, human-first 

Unique Perks & Programs:

•  Remote-first work with flexible setup 
•  Company and team offsites to build connection 
•  Generous parental leave (including adoption and surrogacy) 
•  Strong benefits with increased employer contributions 
•  Home office setup and internet reimbursements 
•  Fun, high-engagement Slack culture (games, challenges, team moments) 
•  Real internal mobility and growth through hands-on work 

To learn more about Unstructured:

• Careers Page (They’re hiring!) 
• LinkedIn Page
• Lindsay's LinkedIn Profile

Transcript

Jena Dunay: Hello friends and welcome back to another episode of Culture Uncovered where we go behind the scenes of cool companies to work for. And today I have the honor and the privilege to be speaking to my friend, Lindsay Gonzalez, who is People Experience and Operations Lead here at Unstructured, a super interesting company, really forward thinking in the AI space. So Lindsay, thank you so much for joining today.

Lindsay Gonzalez: Yeah, absolutely. I'm so excited to be here.

Jena Dunay: Why don't you share a little bit about what Unstructured actually does for those that maybe have never heard of your org before.

Lindsay Gonzalez: Yeah, absolutely. So Unstructured standardizes the pre-processing of unstructured data for agentic AI. I know that's a bit of a mouthful, so I'll go into it a little deeper.

That means what? So there has been a lot of progress in generative AI, but most enterprise systems still really struggle with a basic mismatch, where modern AI models reason fluently, but the data they depend on arrives really fragmented and flattened or stripped of the context long before the inference begins.

So Unstructured transforms real world documents like PDFs and slides, emails, scans, reports into data that enterprises can reliably use in retrieval and search and agentic AI systems. Over the past year, we've expanded beyond document parsing into a full pre-processing layer for generative AI.

The Unstructured platform supports about 68 file types right now and growing, more than 30 enterprise connectors, layout aware transformations that preserve structure, hierarchy, and meaning.

And so how it works is a new auto-orchestration system dynamically selects the optimal processing strategy on a page by page basis. It balances costs, speed, and accuracy without manual tuning. And a new model context protocol server has further embedded Unstructured directly into AI workflows, which kind of enables models and agents to process data using natural language commands.

And the platform is relied on by about 82 percent of the Fortune 1000, and it's deployed across commercial and public sector environments where reliability and compliance really matter.

Jena Dunay: So tell me in a nutshell, what does that mean for the organization?

Lindsay Gonzalez: So it means that where AI systems are becoming operational dependencies instead of the experiments for businesses that they once were, we're in a position where we're making data readiness a solved problem.

Jena Dunay: Yeah, that's cool. That's cool. I like that. That's very succinct and makes sense to my brain, right? So how big is the company? How old is the company? Tell us a little bit about funding. Walk us through some of those basic high level things.

Lindsay Gonzalez: Absolutely. We're currently 78 full-time and 10 part-time hourly employees. We anticipate doubling in size or more over the next year, so we're in a fast growth spurt.

We were founded in 2022, really started hiring in 2023, so we're still pretty new. And we're a Series B, looking for what will become, I think, the next round of funding very soon.

Jena Dunay: Yeah, where are you guys headquartered at?

Lindsay Gonzalez: So technically Sacramento, that's where our CEO is based, but we're a remote first distributed company all across the US with a few international employees, small hubs with workspaces set up in San Francisco and Seattle.

Jena Dunay: Yeah, very cool. Okay, so across the board. So if anybody's listening, they're like, okay, I'm in Florida. Would they still be a good fit potentially if they're the right fit for the role?

Lindsay Gonzalez: Yeah, absolutely. We have employees all over the place.

Jena Dunay: Okay. I love it. I love it. Awesome. So we learned a little bit about how big the organization is. Clearly you're in a growth spurt. Clearly you're in the forefront of this AI movement.

It's funny. I was telling you before we hopped on this call that I was at a conference last week and everything is AI, AI, AI. But I feel like so many people don't know how to actually use it. They're still in experimentation mode.

So it sounds like for you, it's really those organizations that are no longer in experimentation mode. Operationally, we have to be utilizing this to get to that next level in the organization or just the next iteration of the organization. So yeah, that's pretty cool.

Lindsay Gonzalez: Yeah, absolutely. I mean, I think all organizations need to go this route if they want to succeed now.

And so we are solving a problem that really all businesses need, that they have this, I think it's 80 percent of most organizations have data that they can't even utilize for AI. And we're just solving that problem. And it's a really big one.

Jena Dunay: Yeah, it is a really big one. So, tell me a little bit about your journey to Unstructured. How did you come across the organization? What made you want to join?

Lindsay Gonzalez: Yeah, so I started with Unstructured on a fractional contract, part-time. The amount of time I was dedicating to Unstructured ticked up really quickly. Actually, my two-year anniversary will be tomorrow, April 1st.

And I took the role originally because I knew James, our head of operations. We had cross collaborated on fractional client work before I had my daughter. And while I was on parental leave, he took a full-time position with Unstructured.

Taking on work for Unstructured was a natural step following parental leave because we love working together. He needed help and Unstructured had been his favorite client for a long time before he went in-house.

I say a long time, but it's still such a baby company that it wasn't even that long. But that's not really the why of things, right? So if I tell the story of why, I have to zoom out a little bit.

My bread and butter, that is most of my experience as a BizOps leader, was at early stage tech companies, mostly venture backed. And that comes with a lot of turbulence. Working in-house in a leadership role for early stage startups is a lot of fun, but the learning by fire comes with its downside.

I loved it, but you also give up a lot. It's difficult to maintain a good balance when everything is a fire drill and underfunded and you're kind of hand holding a dreamer through the most difficult moments every single day.

So when I started fractional work, it was really so that I could gain more control over what I was working on. And it worked. I started to help founders see the value in constant daily prioritization and focus.

And it helped me redefine that my time is really valuable. I feel like less time given is more valuable output and better outcomes for myself and the businesses.

But then the full-time transition to Unstructured, it was a long, slow conversation because I really love fractional work. But Unstructured has something really special.

The people who work here are incredibly bright. And the CEO, Brian, he's got his head screwed on right. He understands that businesses are like puzzles, that everything is kind of a trade off, and he really knows that he's got great people. I could see that from the moment that I started contracting, that he would keep prioritizing people as we grew.

And so I feel my time is still valued, I'm still respected, and I'm so glad that I took the in-house role. I looked at it as an opportunity to do more of what I love at a really promising company. And that's been true for about a year since I started in-house.

Jena Dunay: Yeah, that's really cool. I love that journey of fractional to full time. I think that just shows, okay, you guys are an earlier stage organization, only a couple years old, right? But have had a lot of growth in the past couple of years.

And then I think specifically for your own journey, for other people to be listening, if you're a job seeker or even just another fellow people leader, the fractional route is an interesting route to take. That is an interesting route to then potentially go full time at an organization.

And so I love that they convinced you enough, which is a big convincing by the way, they convinced you enough that you really liked working with the organization to go full time in-house, which doesn't always happen.

And so I think that's also a testament to the culture. So you mentioned the people and you really enjoyed obviously working with the senior leadership team that you've gotten to respect, obviously the CEO of the organization.

How else would you describe the culture at Unstructured for those that maybe, again, have never heard of your organization and would be curious, like hey, this is a growing company, I might want to be part of this. What would I be a part of?

Lindsay Gonzalez: Yeah, I think hard but fun. And we have some data points on this, right? We run engagement surveys twice a year. We run pulse surveys on an ongoing basis. And we actually just did a Great Places to Work certification where they have a survey of our internal employees and benchmark us against other companies in the industry.

And we got a 99 percent, for an industry benchmark of 57. It's really crazy across the board. All of our results that our employees were happy with XYZ were like 99 percent, I think 98 in a couple places.

But what I'll say is I had the pleasure of sitting down with some of our original, our longest tenured employees about a year ago. And they all had the same thing to say. People work really hard, sometimes too hard, but they're having fun doing it.

I think the company, we don't take ourselves too seriously. We're not trying to be something that we're not. The all hands, they feel really lighthearted and still really silly. There's room for everyone to chime in with jokes. The chat is really funny through those.

All hands every week, our kudos culture is uniquely strong. Both the company-wide channel and the smaller group channels are really active and positive, but they don't feel performative or toxic.

And I would say Brian, our CEO, is surprisingly human, not scary. I kind of mentioned that before. But we all know he's smart. He's not out of reach. So not operating from ego like I think a lot of founders do.

And I think the same can be said across the board for those in leadership roles. It really does trickle down. They're punctual, they're respectful of others' time, but open to changing their mind when it's important and they listen.

And I think that's a really beautiful thing. It gives permission to the rest of the company to speak up and to innovate and to reach across the aisle and say, hey, I've got a great idea. And they're not scared that it's going to be shot down or laughed at.

Jena Dunay: Yeah, that's really cool. So it sounds like a couple things that I'm hearing is one, the data shows that it's a great place to work. That is an unheard of number.

What do you think is the main reason? Is it because of maybe all those things that you talked about coming from the top? What is your perspective on why that is?

Lindsay Gonzalez: I think that people like working with great people. And when you look at our little word graph that you get back in the engagement or this Great Place To Work result, the word People is front and center. It's really big.

And I think that comes back to us over and over again. So when you're part of a team and you actually like showing up to the meetings to be with your team members, I think it makes a huge difference.

But there's also a lot of support for people. We do a lot to help support employees and make sure that in the remote first culture, we can still bring people together. So I think that goes a long way.

Jena Dunay: Yeah, I couldn't agree more. I think that intentionality, especially as you're building a rocket ship, can be hard to sustain.

So I'd actually like to ask you this from a people perspective. How do you maintain that people stay in the forefront as you guys scale and as you grow? And you're going to be hiring, you said doubling in the next year. How are you thinking about keeping the culture what it is while also letting it morph and expand as you guys grow?

Lindsay Gonzalez: I think that is going to be a challenge that we are going to have to take some of what we have done and keep it going and some things are going to need to change.

So I will talk about what we do now. Right now we are remote first. We do company-wide offsites. We have not done one in quite a while, but in lieu of the larger company-wide offsites, we have been doing smaller team offsites and group offsites, trainings and onboardings in person, bringing people together as often as we can.

We have really generous paid parental leave for all employees becoming new parents, whether adoption, surrogacy, fostering. It is flexible. It can be extended beyond the paid period.

We also offer standard benefits like health, dental, vision, life, remote office setup and reimbursements for things like internet contributions.

But this year, where most companies are seeing healthcare costs go up substantially across the board and having to pass some or all of that to employees, we have been able to lock in better plans with lower rates and better contributions for employees and dependents.

So we are really proud of that. And I think that is something that we have had a lot of support on, is getting ahead of an issue and trying to figure out and get support, especially budget, to make sure that we can get ahead of it before it becomes a problem.

And I think that is going to carry into this next phase, just almost knowing there is permission before you need to ask for it to get ahead of a problem.

Jena Dunay: Yeah, which is not always the case at organizations, especially founder-led organizations. And you have been a part of and touched adjacent to a lot of orgs.

I have talked to a lot of people, I have been inside organizations, and this authority thing or providing permission before asking for it is such a big deal to people feeling like they bring value to the workplace and that they are valued also at the same time.

Lindsay Gonzalez: Yeah, and so I think the challenge is going to be how can we keep the red tape away as we grow.

Right now, going to the leadership and saying, hey, I have got better benefits options, it is going to mean a big change for employees, but it is going to be worth it. We can do better in these ways. And guess what, the company is going to save some money.

I would like to take that money we are going to save and pass it to employees with bigger contributions. It was like obviously yes. There was no red tape. There was no pushback. There was absolute support.

And I think the challenge is going to be keeping that true.

Jena Dunay: The other thing that you said that I really love, and I have heard this as a theme for remote first companies, is the offsites. Maybe not always company-wide, but team-wide.

That is becoming more popular, I feel like, where teams will go to an offsite and use that as an opportunity to really build those relationships and get some good work done.

And I do think that those in-person connections really do make a difference. I think I have mentioned this on this podcast before, but my sister worked for a company for two years, never met any of the people in person.

And when she left the organization, I was like, are you sad to be leaving? She said, I do not know anybody. I was not connected to anybody there.

They did a bad job of really connecting people. I will give them some grace, it was around COVID, but they did not do that intentionality that I feel like a lot of organizations know to do and have to do in order to keep that connectivity and make the people the biggest asset in the organization.

So for you, what are some practical things that you have found work for your organization to keep that connectivity going in a remote first culture?

Lindsay Gonzalez: I think there are quite a few things that we do and that we are going to keep trying to do. Aside from bringing people together in person, we try to keep up with some little fun tidbits here and there.

So we have, I did a Slack Advent calendar for 24 days leading up to Christmas. I called it non-denominational, but of course I love Christmas.

Every day we had an obscure fun fact that somebody submitted to me, and only me. I was a little elf and I would post it, and the first person to guess would get a prize in the form of cash, increasing up to, I actually got a pretty big budget for this.

So the amount of winnings went up every day. And I cannot even tell you, some of these Slack threads had over a hundred comments. People got really involved and loved it so much that I have not stopped getting questioned about when the next Slack fun time was coming.

Right now we are in the middle of, well it is day two of our non-denominational Easter egg hunt extravaganza, where I post a picture of somebody’s workspace and everyone tries to guess whose workspace and what the Easter egg is.

So it is just fun. I think even just bringing people into one Slack thread to joke around for 15 minutes at a time makes a big difference.

And then we have in the past done some team trivia events or holiday stuff like dressing up for Halloween. Our head of product and engineering, his name is Chris, he dresses as Father Christophermas and gives out silly prizes around the holidays.

But we have done random coffee. We are going to relaunch something like that in the near future. People got a little tired of it, so I think you need to give people breaks in between these things.

But we do as much as we can to bring people together. And I will say, I mentioned our all hands, they are really funny. 

Jena Dunay: All hands sounds boring but it doesn’t have to be.

Lindsay Gonzalez: It doesn't have to be. It is not just leaders talking at you for a half hour to an hour. Each group brings their people in. They tell you what they are up to. We rotate between product and engineering and field engineering to get updates.

We have news you can use, which is my group’s updates, and some of it is just kind of fun and funny, celebrating things, celebrating people. And the comments are really funny threads.

Jena Dunay: Yeah, so good. I love that. Tell me what professional development looks like.

Obviously, honestly, the whole experience of working at a company your size and in your industry is going to be a professional development opportunity.

But are there any practical ways that you guys are thinking about learning and development or just upskilling your workforce?

Lindsay Gonzalez: So I actually think that most growth opportunities come in the form of innovation at Unstructured. We are really small, we are changing by the day, and it means there is lots of room to dive in and take on something new.

I have seen folks level skip during a performance cycle. I have seen others thrive as a first-time manager. We have people who have changed roles or teams several times.

It is totally adaptable and dynamic. And when I recently asked one of them if he was okay, half jokingly, on this roller coaster that he is on, he told me that he is having a blast and would not have it any other way.

So I think we have leaders and managers who encourage innovation. They want their team members to try out new things. And when they see potential or success signals, they get support. And the same goes for tooling. A year ago, I watched one of our engineers talking about vibe coding at our company-wide all hands, the first time I had ever heard of it. And now everyone is testing out and excelling by adopting the newest tools in AI out there, especially our engineering team.

Our recruiter, she is the best sorcerer I have ever worked with. She is leveling up using tools like Juicebox and Ashby. And I have been using Lattice’s AI features, Notion’s AI features, and agents. It is encouraged, and I really think that those that are excited to learn have all of the opportunity to try out what is new and get a leg up if they want to.

So it is sort of a departure from the old way of thinking about learning and development, where maybe you would give a budget to take a class or get a certification. It is more learning by doing.

That said, we do support if somebody comes to us and says, I think it would really benefit me to take this class and it costs whatever amount. We have been supportive and we have absolutely paid for those things and helped them get there.

Jena Dunay: Yeah, that is awesome. Now we have talked about all these great things about your organization, and no company is perfect. So share with us what you feel like either you have gotten wrong or could be doing better at in the future.

Lindsay Gonzalez: Gosh, of course. Well, you and me, Jena, I love that you called me a friend at the start of this podcast. We definitely are. We met off the back though of what I would really call a prime setback.

So about a year ago around this time, we had to make a difficult decision to reduce force after taking a really hard look at the ways our product and business had changed and would change.

And we determined that we had a number of people in roles that they were not well suited for or did not need any longer. I have seen this before, of course, but this one felt worse. We are small. So saying goodbye to even a handful of people took its toll.

But we tried to maintain transparency throughout the whole process, offering support. And I think having you step in and help those impacted have a soft landing made a huge difference. Not only for those who received the outplacement services, but also for those staying, having reassurance that we are doing our best not to just kick anyone to the curb. And I think it tells employees that they would not be treated poorly if they found themselves in a similar situation.

So we have made mistakes in guessing where our product was going and then it taking a different direction a few different times. But I think that is kind of just the growing pains of any company going through the kind of seed to A to B stage. It is finding product market fit and then finding ways to scale.

And so that is going to happen. And I think we have done our best to power through it and keep people’s attitudes and minds as strong as possible.

Jena Dunay: Yeah, I feel like I am so glad you said that. One, I just loved working with you and your team. And honestly, the fact that you are even bringing this up on this podcast shows a lot about the transparency of the organization. And also coupled with the fact that recently you did the Great Places To Work and there was still a 99 percent satisfaction score.

I think that says a lot about the organization that even in times of hardship, in the past years of rebuilding, I always say that the year after any sort of reduction in force or separation from employees, there is going to be a trust rebuilding. And I think all those things that you talked about, you guys were really proactive about even at the early stage that you were at.

And so I just applaud you for that, one, for trusting us, but then also just for the team members that were, as we call the left behinds, that are still there. How do we make sure that they feel secure? I am grateful that you mentioned that.

And again, what a great, I mean, getting that Great Place To Work signal that was so high is such a testament to the work that you have done in the past year. So congrats on that!

So let us talk a little bit about if somebody is listening to this and they are like wow, this is a really cool place to work, I am interested. I know that they are going to be growing. What types of employees succeed here and who does not succeed here?

Lindsay Gonzalez: Great question. I think that the more self-managed a person is and the more ownership a person takes in their work, the better at Unstructured.

We are kind of too small to have any handholding. And I think that goes for any area of the business.

If you are in a big organization and you are used to somebody kind of telling you what to do and how to get to the next stage and what you are working on, or even in personal growth and development, we are not really that.

We do help managers support their employees and help them grow and develop, but I think the more drive and motivation a person has to figure things out themselves and take initiative, the more successful they will be. And there is the flip side of that too. If you are not comfortable in that kind of environment, then you probably would not be very successful here.

Jena Dunay: Yeah, that makes sense. So what areas, you mentioned doubling in size, tell me what are some of the areas that you all are looking to grow in, maybe hiring wise, certain departments or types of roles in the next 12 to 18 months.

Lindsay Gonzalez: Definitely. We are focused on scaling in three core areas.

The first is engineering, especially backend and infrastructure engineers who can build in Python and have experience with distributed systems, data pipelines, and increasingly AI and machine learning or large language model based applications.

A big part of our roadmap is helping companies transform unstructured data into something usable for AI, so the foundation there matters a lot.

The second is customer facing technical roles, so solutions architects and forward deployed engineers. We land larger enterprise and public sector customers, so we need people who can sit alongside those teams and actually help design and implement and scale real world use cases.

And then the third is go to market, very targeted though. We are not just hiring volume. We are looking for people who understand how to sell or support highly technical products, especially into data infrastructure or AI.

So overall, I would say the theme is highly technical, highly curious, and comfortable operating in a fast moving and kind of ambiguous environment.

Jena Dunay: Yeah, that is really good. I think that anybody would be lucky to be a part of your organization. Just what you guys are building, who you guys are serving, and the opportunity that is in front of you all is very exciting and could be very exciting not even just from a resume building standpoint, but just the opportunity to witness all the ups and downs that come with building a company like you guys are building.

Where can someone go to learn more about your organization, to learn more about what it is like to work there and what opportunities you have available?

Lindsay Gonzalez: So we have all of our openings listed at unstructured.io/careers, but they can also reach out directly to our recruiter Lisa on LinkedIn or via email. I am happy to share that with you after the podcast.

Jena Dunay: Yeah. Tell me, and this is just more for the job seekers that are listening, what do you think really makes somebody stand out in the application process?

Lindsay Gonzalez: We hire for signal over polish. So I would say it is less about having the perfect resume and more about how you think, how you approach problems, how you operate in real scenarios, and especially what you are passionate about.

The people who stand out, they come prepared, they ask thoughtful questions, and they show that they can move quickly on owned outcomes. So we are really looking for drivers, not passengers.

And I will also say we get a really high volume of applications. We have a slim but incredibly mighty recruiting team. If the role and the organization are something that a person is really keen to go for, it definitely does not hurt to reach out directly to the hiring team or the team you are interested in joining, or even find an in with someone in your network.

We have a really generous referral program, so if you are great, our employees are rewarded for bringing you in. So definitely be proactive and reach out.

Jena Dunay: Yeah, I love that. Lindsay, it was so fun to get to talk to you in this context and just to share more about Unstructured and your organization and what it looks like to work there.

So if you are interested in learning more about Unstructured, we are going to have all of those links in the show notes as well. And take what Lindsay said to heart, and if you are interested in one of the roles, reach out to somebody on the team and actually put yourself out there with a nice, concise, very persuasive message as to why you are the perfect person for the job.

So thank you, and we will see you next week on another episode of Culture Uncovered.