37 min read

Episode 14: Paving your own career path in ops

The community builder who paved her own career path to the COO seat.
Episode 14: Paving your own career path in ops

One of the reasons Opsy exists is to help operations pros build their networks and grow thir careers. And this month's guest is an expert at both!

A true community builder in every sense of the term, she's built up both an impressive network and a great skillset over the course of career. And she's done so in a really intentional, strategic way that I know we can lean a lot from.

If you're considering a new role, contemplating whether senior leadership is right for you, or even thinking about a less linear 'next step,' then this is the episode for you!

About Our Guest

Our guest is Nicole Vasquez, who has spent her career 'hopping lily pads' to build a fulfilling career in operations.

Nicole spent the early years of career strategically growing her operational skills across functions, before starting her entrepreneurship journey as the owner of two brick and mortar coworking spaces in Chicago.

Her first foray into tech was co-founding Deskpass, a platform for flexible coworking. She recently left her role as Chief People Officer there to start a new chapter—COO of Refresh Miami, southern Florida's oldest and largest organization supporting the local tech ecosystem.

About this Episode

In this episode, we chat about:

  • How Nicole ended up founding a high-growth tech startup and why she ultimately left to work at a nonprofit
  • What Nicole did to prepare for her first 60 days in the COO seat—and what she'd do differently, if she could do it again
  • How to use reflection, your community, and even some self-assessments to figure out your next role
  • Why more People Ops pros should consider the COO role—and why more businesses should consider putting them in that role!
  • And why 'hopping between lily pads' is better than climbing the corporate ladder

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Show Notes

Stay in Touch


Welcome to Opsy, a podcast for people doing opsy work in tech. I'm your host, Caro Griffin. Every month I dig into what Opsy work really is by talking to an operations pro who has something really cool to teach us—in a traditional part of ops like HR or finance, or a newer specialty like no-code ops or marketing ops. Thanks for listening!

Caro Griffin 00:27
Today, I'm here with Nicole Vasquez—entrepreneur, community builder, former Chief People Officer and now COO. Nicole is probably best known as the co-founder of Deskpass, a popular product for finding flexible co-working spaces all over the world. But she recently stepped back from her full time role there as Chief People Officer and into a new role as COO of Refresh Miami, I was lucky enough to cross paths with Nicole a decade ago when we both lived in Chicago, back when she was running her own physical co working spaces, and was just one of those people that you see everywhere, because she knows everyone, and just really embodies that community builder persona that I so admire.

I've really enjoyed following the twists and turns of Nicole's careers, because she's one of those people who makes career moves that I wouldn't necessarily expect watching from the outside, but totally makes sense afterwards. I think she really stays true to herself and what she's looking for, and where she can have the most impact. And I think, like a lot of us, it took her a while to realize that she had secretly been an operations pro the whole time. So, suffice to say, I'm excited for this episode, because I know Nicole has so much advice and perspective to share, settle in for a good one.

Welcome, Nicole! Thanks for joining us today.

Nicole 01:33
Thanks for having me! I'm thrilled.

Caro 01:36
Yes, so excited to chat, not only because I get a chance to catch up with you, which is always nice. But because I just feel like a lot of people will relate to your story and, kind of, the twists and turns that your career has taken. So, you know, let's start where we always do at the beginning. Can you tell us a little bit about your career journey so far?

Nicole 01:52
Well, you said it first by saying that [there were] twists and turns. I always say the disclaimer, that I think [a] career is like choosing your own adventure. And that doors appear in the video game of life when you've achieved a certain set of skills or experiences, or your gut is just saying it's time to move on. I've always been an advocate for the frog jumping on different lilypads when the time is right.

So, with that, I'll go very quickly and say that in my early career, I was employed in a variety of business operational roles that basically gave me insight into every aspect of running a business: sales and marketing, business and administration. Actually, the one part that I didn't do was finance. That's still my like, “what is it that?”

Caro 02:31
The achilles heel, or the thing where you're like, “No,” the thing that like makes you sad…

Nicole 02:36
Yes, but there are numbers people for that, right?

Caro 02:40
I appreciate that you're not a numbers person, because that's my thing. That’s where I'm like, yes. When the people person isn't a numbers person, I get to do the numbers. So, you know, peanut butter and jelly butter.

Nicole 02:50
Exactly. And that's okay. And I see that. Know your strengths and don't obsess over your weaknesses, right?

I was employed until the age of 29 in different business operations roles. And for me, you know, like the lilypads of life, I would go to the next [role]. And it wasn't always the exact same industry, it was that I took those skills and said, "Okay, I want to apply this to a different job.” And then, at 29, I quit my job and started my first coworking space in Chicago. And that's where I think I really charted the rest of my path, because I fell in love with coworking and community building and bringing people together.

So, very quickly, I started a coworking space in Chicago, which was successful. Then I had a second one. And I ended up starting and selling both of those in Chicago. But then I was approached by a friend of mine to start Deskpass, which is a global network of coworking spaces, and I worked on that and scaled up with my team for six years.

Just recently, in November of 2022, I had a proud mama moment where I looked at my company, Deskpass. And I said, the company is doing fantastic. The team is amazing. They operate like a well oiled machine. But they're humans, right? So I don't like calling them a machine. But they're a fantastic team. And I had this moment where I was like, if I was to transition out now, it would be okay. They would all be in a good spot.

And I was starting to feel like I was ready for the next challenge. Which brings me to now being the COO of Refresh Miami, which is Miami's oldest and largest organization supporting the technology and startup ecosystem here in Miami. So, after almost a decade of being an entrepreneur, I am now an employee, a proud employee because I brought my skills and experience to an organization that I love and is mission driven.

I'm bringing that startup mentality that moves fast and makes a difference mentally and the organization's like, whoa, whoa, we haven't moved this fast in years. But they love it and they're amazing people and you know, I think it's great.

Even a year ago, I would have never thought I'd be employed again. But my heart said it and I had that proud mom moment where I said, ‘it's okay to move on from a great company that you helped to build.’

Caro 04:52
Yeah, totally. I relate to that. And I'm sure other people do, too. Six years is a long time, especially in tech, even when it is your baby, even when it is something you've built from the ground up, you know. At the end of the day, you could look for new challenges and new problems to solve, but it's still the same core business.

Nicole 05:07

Caro 05:07
You know, sometimes, we're just ready for something new.

While preparing for this episode, first of all, I didn't realize we have the same alma mater. I totally missed that!

Nicole 05:16

Caro 05:16
We both went to Columbia [College Chicago]. And then I also didn't realize too like, you know, you've worked in government, you've started your own brick and mortar businesses, you worked in tech, and now you're at a nonprofit. I mean, I love that because I do feel like you've really just followed… I guess I just love that analogy of like, leaping between lily pads, that's such a cool little analogy.

Nicole 05:37
Yeah, it wasn't in a true line, it was a lateral move. I'm gonna make a sports reference, my husband's not gonna believe it… But like, I think I'm pretty sure in football, there's a way that you could throw the ball like laterally.

Caro 05:49
I'm not the one to ask, but I love this.

Nicole 05:52
I was like that. [With every move] I’m moving forward, but it's kind of like a tangential move. So, it's like a diagonal, and it helps you to zigzag. I've leveraged where I was to go to something else. Instead of going straight to the next, you know, big promotion in that exact line of work, I was like, let me change a little bit, get a little bit more senior level, but do something slightly different. And I like that. It works for me.

Look, I'm a proud generalist, right? I love knowing a lot about a lot of different things. At its core, I do operations, but I like different things.

And I have a friend who's an amazing expert in this one very specific thing. And she has done all like the exact straight line career and that's worked for her. So, I always like to say, you know, follow a little bit of your personality with your past experiences with what you want to be doing next and go for it, manifest that. It sounds a little Tony Robbins, but it's okay.

Caro 06:50
No, it's great. Because I think there are established paths for that kind of traditional climbing up the ladder, going from manager to assistant director to director to you know, VP, whatever. But I think, so often, we get laser focused on those [rungs]. Like, we’re climbing that ladder and realizing, wait, is this actually what I want? Am I interested in this? Am I excited by this? And so I always really appreciate talking to people who have followed, you know, the lily pads, no matter where those are.

Let's dive into Deskpass a little bit. It sounds like it was your first real startup, or tech company, per se, but you had been around tech for a while. Obviously, you've been a longtime entrepreneur, but I'm sure that your coworking spaces that you were spending all your time in were full of tech people, too. So, you know, tell us a little bit about why you made the jump to co-founder of a startup when Sam approached you with the opportunity.

Nicole 07:40
It's interesting that you bring up always being around tech. You're right, as an entrepreneur of a brick and mortar place, I was always going to events and you meet all these tech people and you're in tech and every business these days is run on tech.

My first coworking space actually, I was trying to be revolutionary and have it where you could book shifts. That's why it was called The Shift. I was like, ‘We're gonna leverage tech to be able to book your working sessions.’ And then I was like, ‘Oh, people just want to come in all day. Let's get rid of the scheduling aspect.’

I mean, look, I think my thing that I say is, it's the human component of business. Even though I'm individually a very tech savvy person, I'm a quick learner… as an individual entrepreneur of a business, and,I mean, for almost two years, I was the only employee of my very first business, so I had to do [everything]. I was the IT [person] for a physical space. And I also created our website using, you know, a Squarespace or Wix or something like that. You have to dive into tech on your own as an entrepreneur. And, of course, once you get to a certain size, you need to have more evolved and mature technology and processes in place.

But, ultimately, what I loved, is that when my business partner Sam approached me, he owned a design company, he was a technologist. So he was like, I have the technology, I can easily create the technology, I need the people side. And he's like, ‘you have a brick and mortar coworking space. You're amazing at operations, you're amazing at community building, let's partner up. It was peanut butter and jelly, like you said earlier, right? I had the human side of the business, and he was the technology side. So, that was what was most appealing.

In my days at Deskpass, for those six years, I oversaw our customer service team, building out our network of coworking spaces—meaning literally one by one inviting coworking spaces, getting them onboarded until we had a larger team that was able to help out with that, and all the internal employee [stuff]... I don't have a HR background.

I mean, HR is very technical. And I always say this, I mean no discredit or anything to HR, because their work is so hard, but what I mean is like… I had to learn HR and I think that there's a little bit of an aspect of, when you are people operations person, you inherently understand some aspects of HR obviously, not all the accredited stuff because it's very hard and takes a lot of work.

But I think company culture, running a company… if you are an inherent people ops person, you can learn that quickly. So, I mean, I was our HR director, I was our People Operations. So I was always the human aspect of the business and the voice of Deskpass whether to our customers, our partners, our service providers. So yeah, the voice I guess. Not that I have a great voice but, you know…

Caro 10:14
I think everyone listening will disagree. We can all cheer on Nicole and tell her she has a great voice, right? Literally on the podcast right now. [Laughs]

Nicole 10:21
[Laughs] Shall I sing now?

Caro: 10:24
Maybe at the end. Maybe we like ‘sing out,’ you know. Are you ready to warm up your voice?

No, I mean, I feel like what you're speaking to, of wearing all of these hats, is such the ops role, such a generalist role. Like you said, you know, every entrepreneur has to be a generalist, especially in the beginning, when you don't have the funds or the resources for a team to be the on site IT to do all that.

It sounds like you were really uniquely positioned for Deskpass because you knew what coworking space people wanted, you knew what people who just wanted to cowork wanted, and so it's a very cool lilypad hop. I'm really going to beat that anology to death because I really like it.

Nicole 10:58
This reminds me—there was a woman that [wrote] a LinkedIn post where she said, ‘I love seeing co-founders that are Chief People Operations, because I hardly ever see that. Co-founders are usually CEO, COO, CTO, or CFO, right?

Caro 11:15
Yeah, never Chief People Officer.

Nicole 11:16
Exactly. It didn't hit me just because I wasn't in the traditional HR realm. I didn't come from that background, but she had. And I think she said something like, ‘the companies that I see that are the most successful are people who have cofounders that care about the people versus just the numbers or the operations of the business.’

That always stuck with me, because for me, in my background, people is the number one thing. I'm not saying that someone who comes from a technical background doesn't put people first. It’s just that in my businesses, we were always based on accommodating people, gathering people, community building. And so, for me, I just can't imagine a company that doesn't put the human component first. But… that's just my own background.

Caro 11:57
Yeah, no, I mean, I totally agree. I’ll have to put this in the shownotes but I recently read a really interesting article that we kind of cross-posted on Opsy, with the author's support. She's the COO, I forget her name. So, apologies! Again, I'll put it in the notes. But she's the COO of Whereby, which is a video conferencing tool. Her background is people operations and I think, also went to law school. And so she has a law degree, she has, you know, different skills, kind of like you, and she was really making this case for why more people ops people should be the Chief Operations Officer, and why they should be…. I think, in your case, you know, at Deskpass, you weren't the CEO, but you were still a co-founder, you were in the C-suite, you like had a real big seat, you know, at that table, right?

Nicole 12:43

Caro 12:43
And I think that's normally something that we don't see. And so, regardless of whether it's a CEO or a COO, like the importance of that, I hope is something that we as an industry can, really wrap our brains around.

Nicole 12:53
Yeah. And it should be noted that I had three male business partners, and they are all incredible humans, I mean, big advocates of women. I always joke that two of my business partners had kids before I had a kid and they were the Mr. Moms, on the calls with their kids running in. And it was awesome. I mean, they were the ones juggling and saying, ‘I can't make this meeting. I'm sorry, our nanny is sick today.’ For me, that was a huge eye opener. That was just one big thing.

But, I mean, going back to being the only woman in leadership, and as a co-founder, there were so many times that they were like, ‘Wow, thank you for bringing that perspective as the human aspect of the business.’ But then I think also [being a female] plays a role in that, right? I mean sometimes we have very different ways of thinking. And so I thought that was a very nice mix. And obviously, I felt the same way. A lot of times they brought perspectives to the table that I hadn't, of course, considered. And so I thought that was really great to have that as a founding team.

Caro 13:48
Yeah, totally. And like, again, just speaking to why that diversity is so important. When you don't have [different voices] in the conversation, so many things can get overlooked, right?

In addition to being co-founder at Deskpass, like you said, you were the Chief People Officer for a long time. What were your favorite parts about it? And what was most challenging?

Nicole 14:06
It's interesting, because when we first started Deskpass… If anybody knows the app ClassPass, it was ClassPass for coworking. So, when we started Deskpass we were B2C, direct to consumer. I was actually the Chief Community Officer. I was brought on board to bring on our co-working spaces as partners, and then also our members, the users of the app, because these were individuals who were signing up for themselves. That was a whole different ballgame, right?

It was bringing those people, who were just similar to the people in a coworking space, where they wanted to meet other people, they wanted to network, they were growing their business. That was [the job] for a few years and so I managed the community and that was generally you know, general community building practices.

When we switched to B2B, we were a business to business product. Our members changed quickly. These were employees of a corporation, of an enterprise. And to be honest, they didn't care to collaborate with other people. They didn't care to network. They weren't there [for that]. This was a benefit that their company provided them.

That’s when I transitioned to Chief People Officer, because when we were no longer direct to consumer, we didn't really need the member community. So, I changed hats from Chief Community Officer and I had to change all the things we were doing. I mean, I was managing our interactions with our members, we were building out this online portal for them… Then we switched to business, and we had to be honest and say, ‘You know what, they don't need this.’ We were going to keep our online portal for the business members, and they weren't going to use it. So, we didn't do that.

I quickly switched over to Chief People Officer, and look, let's be honest, my team was 20 employees, Chief People Officer is usually a role for a larger company, 50 plus employees. It was kinda like this hybrid role of HR director meets Head of Customer Service, meets a little bit of operations, meets project manager. So, in a sense, the [part of the] Chief People Officer role that I didn't really get into was a lot of people analytics, which is what I really wanted to do once we got to a certain level, and then very technical HR. Because again, I'm not classically trained in HR, that's really hard. There's so much, you know, information and accreditation, and I wasn't going to try to pretend to be that HR, because that stuff needs to be taken seriously. I did a lot of company culture, any communication with our customer service…

What I loved about chief people officer was, again, just the human component and making sure that, internally, our employees, were… I don’t want to say the word happy, maybe engaged, satisfied, mission driven, determined, and supported, I think is the biggest thing.

So, internally, it was making sure employees were supported, and then externally, making sure that we were truly being a partner to our partners.

I mean, we have more than 1500, almost 2000 coworking spaces that we partner with around the world, and making sure that we have a mutually beneficial relationship with them, not a take relationship. So, that was the other part of the role.

My Chief People Operations role really evolved. And, even when I left, you know, it was still not a true Chief People Operations role in the sense of a company that would be double our size.

Caro 17:07
Yeah, no, that totally makes sense. You adapted to the size of your company, really made the role your own and also like, did what your company needed at various times. That is a lot of operations. Like my role, you know, even if my title doesn't change, a lot of times I feel like my role changes every six months. The business changes and who we've hired and what the business needs, are different. So, I think that makes a lot of sense. And it's nice to acknowledge that because sometimes it feels like no one else is admitting but we're all kind of doing it.

I would love to chat a little bit about Deskpass as a team because you were fully remote, right?

Nicole 17:42
I mean, a lot of people were remote. I mean, you've been a digital nomad for so many years, right? Before the pandemic. I mean, the joke is like, ‘we were remote before it was cool, right? Before you were forced to be a remote majority.’

I've been a remote worker for almost a decade. Deskpass has been remote since the inception, it’s a global team. We have teammates… literally, we had one in Australia, and one in California, and then everything in between. Being a remote team is hard, but when you've been doing it for a long time, it's almost second nature.

At its core Deskpass is a hybrid work solution. We give people and companies the ability to choose where they get their work done by giving them access to workspaces. So, we were using our product. We were the exact people who needed a product like ours.

For me, it's about empowering people to make those choices and giving them the support, they need to be able to make those choices. For example, giving them a stipend to book coworking spaces near their home so they can be closer to their kids’ school, or so that they don't have to have a one hour commute. There's also remote team policies that we put in place, like, look, you can go and travel for two weeks, but if you're going to have your hours significantly different, that's something to discuss with your manager in advance. Or, if you're going to be in a very remote place where you're not going to have internet... Yeah, that's something to discuss. But ultimately, if you want to go to Germany for two weeks, then that's that's fine, right?

And also, you know, little remote work policy things like how we didn't require people to sync their Google Calendar with their Slack to show if they were in a meeting, but we showed them how to do it if they wanted to. And the majority of our employees did it because they knew that way, when they're in a meeting and they see that Slack message come in, they're not worried like, ‘oh no, this person is gonna think I'm ignoring them, right?’They'll see that I'm in a meeting.’ Of course, you're familiar with asynchronous communication.

I wrote our entire employee handbook by hand, instead of taking it from somewhere else, and kind of customizing it, and the reason is that I wanted to document almost what we were already doing but then put it in to writing because we already had such great team practices.

Now we have a handbook that explains the remote policies FAQs. Sometimes a new employee would come on and be like, ‘So you say that our schedules are flexible. What if I have a doctor's appointment? Should I tell my manager?’

And it was like, ‘No. If it's only an hour, it's okay. You don't have to tell anyone. We advise you to put it on your calendar so nobody tries to reach out to you or schedule something during that time. But you don't have to share that with us. And we trust that you'll make up that hour when you're able to write and ultimately, you still deliver on the things you have to get done.’

Now, if you're going to be offline for six hours in the middle of a workday, then yeah, please let your manager know. And if it affects any projects that you're working on, please just let [your manager] know. But we trust that you can coordinate that with your team.

It's almost like very basic honesty and communication. It's almost like in a healthy relationship, you can communicate things easily with your partner, and it doesn't have to be hard. If you have good communication, then things work well. And that's how it is.

Caro 20:57
Yeah. Sometimes it feels like we're trying to overthink these very basic, common sense things. But also, you know, as someone who's also scaled a business, you get that that the more people you add, the more you realize, “Oh, I feel like that's common sense but maybe it’s not…”

Nicole 21:09
Yeah. You have to document it.

Caro 21:10
That's for sure. But I liked that you started with what you already had, right? I feel like so many people approach company values and an employee handbook in the same way where it’s aspirational.

Nicole 21:20
Yes! What we should be doing.

Caro 21:22
Yeah, what we should be doing or what we think we believe. And it's like, no, let's start with what we actually have, what we're actually doing and who we are. And then, if writing that causes us to take a hard look at ourselves [laughs] and we decide that's not where we want to be, then we can pivot.

So, I love that, and also the fact that you, to circle back to something you said a couple minutes ago, about stopping the community dashboard.

That was like a big part of your role and you were loving it. You didn’t glaze over it, but you went past it, and I'm like.. ‘Wow, now that that's something that like, when it is your baby, and I imagine something that you cared about as a community builder, it's hard to walk away from that and be like, ‘This isn't what the business needs anymore.’

And so I'd love to hear a little bit more about that. And I imagine COVID had a really significant impact on Deskpass in the beginning, and now. And so I’d love to hear kind of how you've tackled those pivots.

Nicole 22:14
It's interesting that you bring up stopping the dashboard because that was not my idea. That was actually my business partner's idea. We were in a meeting because what was happening is, when as we pivoted to b2b, I was still so in this community [mindset]. I went on this project of, ‘How do I provide community for enterprise employees?’ I was busting my hump doing that and I was unable to take my head and look up.

We were in a leadership meeting and I was like, ‘You know what, I'm really struggling. Here's the plan I have in place.’ My business partner was like, ‘Maybe we don't need the dashboard. Maybe we don't need this community. What if people don't want this? Why do we still need it?’ And he said in a very nice way. It was just a business strategy, a point that he made. And I just immediately knew that he was right. I said, ‘You are absolutely right. It’s not needed.’

That's a beautiful thing, to have those hard decisions, but coming from a place of trust, and also what's best for the business. So, that was interesting. And another reason I was okay with removing that is because we can support those company employees in a different way. Instead of me building an online portal, where our individual consumer members could collaborate with each other, now, enterprise employees just wanted to know very quickly how to use the product, who else on their team is using it. So, instead, we built out educational resources, because that was the community support that those clients needed. It was very different than the other group.

I think during COVID, looking back… I mean, look, COVID was terrifying. We were still B2C. When COVID hit, we shut down the entire business. We paused all of the reservations because we didn't have the health and safety requirements built out to support and communicate what spaces were doing, and for members to ask what was going to happen when they arrived at a space.

Thankfully, as tech companies go, we had just raised our first seed round a few months before that. As a team, we said, we're going to pause all operations, we're going to hunker down, we're going to rapidly change our platform to accommodate for health and safety requirements. And, about halfway through COVID, that's when we decided to pivot to B2B because we said, ‘Companies are gonna come back, but it's going to be different.’ We bet on the future of work.

Oh, I'm sorry. No, we've pivoted right before COVID.

But anyways, we hunkered down and we said, ‘Let's put people’s safety first.’ And our members really appreciated that. We did not have a lot of churn during COVID. A lot of members just said, ‘We'll hang in there.’

We rolled out a pause, but a lot of members chose to pause [instead of cancelling] and said, ‘Look, we want to support you in the future based on the way that you handled it.’ And that was really meaningful to us.

Caro 24:54
Yeah, that's amazing. I feel like Deskpass has really become kind of a leader in that hybrid workspace because, as you said, companies came back. That was great forethought, being like, ‘They're gonna come back. People are gonna want more flexibility.’

People often think of remote work as working from home, but I think you and I are a great testament to [different definitions]. I'm recording this podcast at home and and then I'm gonna go work at a cafe. I go to a different cafe every day, or a coworking space. I know you're always bouncing around coworking spaces. So, I like that variety. And I know you do too, and that flexibility. It's great that you built that out on that enterprise scale for employees, especially those who haven't worked remotely before.

Nicole 25:31
Exactly. Covid was the largest global work from home experiment. And what did we see? There was not one industry that went down in flames because everybody worked remote, not one, right? Overall, the remote work experiment was successful. And it was successful in showing that companies could still reach their end goals, employees could still be productive, without being in this one singular location.

Now, don't get me wrong, I do not believe in a one size fits all approach. I do not think all employees should be remote five days a week. I do not think all companies need to have three days a week in the office. There is no one size fits all approach. The one thing I will say is that every company should figure out what's best for their company, based on their employees, their industry, what type of work they do, where their employees live. I mean, look, if you're a marketing agency, there's a lot of in-person collaboration, ideation whiteboarding, that is a magical thing that happens in person. So, they're probably going to be meeting in person more than, let's say, an accounting firm, where a lot of that work can be done independently. Maybe they instead meet on a monthly basis together for company culture building, but not necessarily for team collaboration things.

So, what I love about remote work, and what I love about this hybrid work that has emerged as the preferred solution for so many companies is that they're figuring out what works best for them based on their employee needs, as well as the work that they do. And I think, for me, that would be my recommendation going forward.

If I was the Head of HR at a company, or a lot of times, they even have a VP of Real Estate, I would just start to look and say, ‘What is going to work best for us individually?' And then based on that, what are the ways I can support these employees?’ Is it a stipend for a coworking space? Is it bringing in a benefit, like Deskpass, where you can manage different stipends based on department or even based on employee? Is it scaling down that big company office and opening smaller locations throughout the suburbs, or in different neighborhoods? Maybe it's completely getting rid of the company office, and instead twice a year using that money towards a twice annual retreat for employees. You know, it's a beautiful new direction and I'm excited to see, in 5 or 10 years, how we're gonna look back and be like, ‘Wow, work has significantly changed.’ I'm excited to see what that looks like.

Caro 27:53
Yeah, absolutely. And I think you know, what you're speaking to is the ability to be like, ‘Okay, let's take a step back.’ It's similar to what you had to do with the Community dashboard, right? You needed someone to say, ‘Hey, maybe this isn't a problem that needs to be solved, right? Or like, maybe we need to let go of the fact that we think this is the way we've always done things.’

The right person in that role is going to do what you did and be like, ‘Oh, you know what, you're right. I'm not gonna hold on to this, just because we've always done it this way, or because I think that it's really important.’ Because I think there are people out there who are like, ‘No, we've always done it this way. We've always worked in person, we're always gonna do it that way.’

That openness to trying, you know, the half a dozen options that you just listed off the top of your head. There are opportunities out there to really think about the best thing for the business and the employees and improve both the bottom line and the employee experience. So I'm with you, I'm excited to see what work looks like in five years, because it's already changed so much in the last five years.

To take kind of a step in a different direction. I want to make sure we have time to talk about your new, exciting role at Refresh Miami.

You talked about how you stepped back, you looked at Deskpass, you had that proud mom moment, and were ready to move on. How did you go about looking for a new role? You had been an entrepreneur for years! Tell us a little bit about that process.

Nicole 29:08
It's interesting, because it was not an overnight decision, right? I didn't wake up one day and say, ‘I want to transition away from my own company.’ Not at all. I listened to, it's cheesy, my heart, my gut, and my gut was saying, ‘I'm ready for the next challenge.’

I was looking within the industry and thinking, ‘Do I want to still want to work in hybrid work?’ I've been in the hybrid work and remote work industries for almost 10 years. And I had this feeling that, even though I could talk about it in my sleep… There are parts of me that I enjoy, which is obviously the community building aspect, supporting entrepreneurs, being an aggregator of information and disseminating that information.

And learning! Learning was a huge part. I think Deskpass was hitting a point as as a company grew where I was no longer needed [to learn in the same way]. Things were moving very quickly, but it was more about implementing processes then learning and rapidly evolving for my role specifically. As the company grew in my role, I was gonna start rolling out like data analytics, or people analytics. I was gonna start rolling out just a lot more big company processes. I realized that I love the scale up. I love the learning process. And because of my experience, I wanted to bring that to somewhere else.

So I started thinking about that. But it was funny because I don't think I actually knew that at the forefront. I just started having these feelings inside based on the work that I was doing, I liked it, but I wasn't thrilled by it. And I just had this feeling. But then what I realized is, when I looked at my teammates… I mean, before I went on maternity leave, I had hired two new people, and upskilled an existing employee, and I remember even right before I went on maternity, I kind of had this… it was almost like you're in a movie and you turn around, and just kind of like slowly nod. You're like, ‘This is good.

Caro 30:58
No, I know exactly what you mean.

Nicole 31:00
And then I went on maternity leave. During maternity leave, there was this existential moment of like, ‘Who am I? I’m miss mom now.’ But when I go back to it, I always knew I wanted to continue in a career. But then I got back and I was like, ‘I think the person I am has evolved.’ And it was time. Maybe it was also that I wanted to just continue to help other people on a very granular level.

But with that, it was a long way of saying, I had those feelings for a few months, and I just listened to them. And I started to do what I do, which is sit with it, think about it, and just observe and think.

My big thing on the weekends is that I go for a very long walk—three, four hours without a podcast, without anything, without answering my phone. I take it, you know, just in case I break an ankle or something. Who knows. But I don't listen. I just walk and I think.

Caro 31:50
I want to knock on wood… [Cross-talk and laughing] Well, I’m glad you’re taking your phone. That’s a long walk!

Nicole 31:59
[Laughing] It is, yeah.

Caro 32:00
[Laughing] Sorry, I’m just picturing you walking through Brickell with a broken ankle.

Nicole 32:06
And people like, ‘Are you okay??’

Caro 32:06
Sorry, such a derailment…

Nicole 32:08
But I’d be like, [serious voice] ‘I just had to think, you know.’ I'm like, hopping along… ‘I just wanted to be alone to solve this problem!’

But, I mean, ultimately, what I did was I started to ask myself the deep questions. I went back to my top five strengths, the Gallup Clifton Strengths Finder test. Every year, I do this activity where I say, ‘What do I love as a person? And what do I love to do professionally’ And then I see where those overlap.

I recently just did that. It's like, how do you say, Ikigai or it's the Japanese like finding…?

Caro 32:44
Oh, yes. I actually don't know if I'm pronouncing that right, either. But I know you're talking about, yeah.

Nicole 32:50
Yeah, so I did those, and I created an updated profile of who I was. I recognized the underlying themes, because I am a generalist, [were that] I like different things. I love to travel, as you know. I love people, food and culture. I love learning about technology. So, there wasn't one specific industry. But the underlying thing is, I'm an aggregator of information. I'm an information synthesizer. I like getting things done. I like things being organized and efficient. Through this soul searching, I realized that the underlying theme was operations. And that's when I had that light bulb moment go off.

Ironically, at the same time, I was talking to somebody who owned a venture firm, and he asked me to be their COO. So, I started talking with a very good friend of mine, because she's in venture. And at the end of it, she was like, ‘I think you'd be great for the role that you're considering. But I have to tell you, I've always wanted to hire a COO for Refresh. And you are that person that I've always wanted to hire.’

That was serendipity because I wasn't actively looking. But I was talking with people close to me about this soul searching I was doing. I only talked to a few of my best friends, but that's when I realized, oh, my gosh, I really want to go specifically into operations for a business that I care about, that's making a difference. And here I am, I made a big change.

Caro 34:18
I mean, that's the power of a network, right? Of building people around you whose opinions you really trust, who you can rely on to give you those honest answers, but also who know what they're talking about, who are part of your professional network, as well and making them friends.

Nicole 34:32
It was validation too, right? It was validation from people who knew me saying, ‘Yes, you can do that.’ Or, like, ‘Have you thought about this type of thing?’ I didn't know what I was looking for, but those conversations helped me to get a little clearer on that. And that was helpful.

Caro 34:49
No, and I'm totally an external processor. And so talking to the people that I trust, who are friends who have nothing to do with tech or ops, and then there are people I love in tech ops, many of whom have been on this podcast! Asking like, ‘Can I run this by you? What do you think?’ I think those gut checks are really important, at least in my experience. So I'm glad that you got to serendipitously, really, lilypad hop to this role.

So, tell us a little bit more about Refresh Miami. What does the organization do? And what is your day-to-day going to look like?

Nicole 35:21
Refresh Miami is South Florida's oldest and largest organization that supports the technology and startup ecosystem. It was started in 2006, by our founder who was having coffee with a bunch of friends in technology, and they said, ‘Look, we need a organization that supports this industry.’ Their original goal, which it still is today, is to support, connect, grow and educate in the Miami tech ecosystem.

They did that originally through programs and education—events, bringing people together, connecting the dots for people, helping them to grow their careers. Over time, now it's a media organization. We have an entire news organization putting out daily articles about technology and startups. We have our member community, we have events—we're relaunching our events after COVID.

During COVID, they stopped events. So, we're launching our signature events where once a quarter, we bring in a top notch speaker to the Miami ecosystem, and make these events free and accessible to all. And then we have our jobs and hiring. So, those are the four pillars: news, events, members, community and jobs and hiring.

What I love about Refresh is that everybody knows Refresh in Miami tech, because you get the weekly newsletter that has almost 16,000 subscribers. It's like the pulse of Miami tech. So, if you're in tech, or you want to know about it, or you're wanting to be an entrepreneur, or you're in startups, or you just care about this industry, you get the newsletter.

It's a very beloved organization. With that, it's a nonprofit, which is interesting. I've never worked for a nonprofit. I come from a rapid growth technology company. So, that was an interesting change. But it's a beloved organization.

The biggest thing is the founder, the Executive Director, they are huge leaders in the ecosystem here. And the thing is, they have literally other jobs. And so they brought me on to take advantage of all the opportunities that come our way at Refresh, to make things run smoother, and to be able to scale.

I came in to optimize the business, help scale the organization, ultimately having a larger impact in Miami, which results in people finding technology jobs, people getting information they need to advance their career and technology, really just being an aggregator and a supporter. So, what I'll say is, because you asked what I do on a day-to-day basis… I had never come in as a COO to a new organization. It was a blank slate. They were like, ‘Here's what we currently do. Let's optimize it.’

They didn't say, here’s where we’re going. So, what was cool is that the first, maybe 30-45 days, I was just in obsessive heads down, research mode. I was interviewing our members, asking for or collecting feedback from our members, talking with teammates, and I put together an entire 2023 roadmap of where the organization will go from here. And every single pillar, I went through and said, ‘Okay, this is working, this is not working well. Here's my suggestions.’

Ultimately, I put together this entire roadmap with suggestions, went back to the executive director and founder and presented it to them. It was like, here's my findings. And they were like, ‘Yeah, let's do it.’ And now we are, little by little, checking things off the list. That, to me, was deeply satisfying.

And the last little thing I'll say is, in the first few days, I was already getting pulled into calls where… I just wanted, like 45 days to be heads down and do all of this. But what I liked about it is that I'm glad I wasn't operating in a vacuum.

I'm glad that I was doing my research and strategy planning. At the same time, also being involved right away with calls about partnership about all the business operations because it helped me to evolve my perspective. Some of the suggestions I had in the first week were very different from what I had 60 days later, after I understood how the business had operated, and what its pain points were. And now I feel extremely comfortable.

I love that process, that discovery, that aggregation of information, turning it into a strategy. Now we have this plan, and I look at our roadmap multiple times a day to double check that not only are we on track, but that any new initiatives are in line with that. I just kind of made the treasure map and now we're going down that… Yeah, we're doing it, which is crazy and cool.

Caro 39:38
Yeah. I see so much overlap in how you're describing the COO role and my own General Manager role. I just can’t help but think, you're making the role your own again, right? And what the business needs.

Like you said, it’s a nonprofit structure. So, it's a little bit different. There isn't like a CEO, but also like the founder and executive directors, they have day jobs, right? They have other things on their plate. And, so, you're leading strategy and roadmapping. And maybe in a slightly different way than some other COOs would, because that's what the business needs. And that's what you're good at.

That's similar to how I feel, because you know, Tech Ladies was acquired so we're part of a bigger organization. We don't have a CEO who's focused on the business, so that's what I'm doing. We'll have to compare notes later, even more so. But no, that was great. Thanks for walking us through that.

I think sometimes, approaching a new role, especially when it is a step up or in a different industry from your first COO role, can be really intimidating. It's always interesting to hear how people approach it.

Nicole 40:39
Yeah, it's a lot. I think the only thing I would say… What was that movie with Will Ferrell where he's like, giving the speech and then he’s like… ‘What happened? I blacked out.’ He was so in the zone, and he just forgot.

I actually think that was my first 30 days on the job. I literally worked through the holidays. I did not want to take off because I was so loving the heads down time.

The only thing I would say is that in this organization, everybody was part-time, even the executive director. I'm the only full time person. But we have multiple contractors, we have an entire team. It's a big team, but they're all part time in some way. And so I came in and was moving fast. And what I love is that my team, they knew that it was all with good intentions. But I had teammates say that we went from a very casual, a slower moving organization, to operating like a very efficient company. And they all say the same thing. I love it. I'm glad because we're doing great work… but it happened quickly.

I wouldn't say that I didn't involve people on the way, because I absolutely did. The one thing I didn't know is how… I wouldn't say slow but I mean, nonprofit, part-time workers versus high-growth, technology people… so different.

I think I would have asked for more pulse checks along the way. I think that would be my one thing because I was just in go mode. [Laughs] But I remember nobody else was.

Caro 42:12
[Laughing] Especially around the holidays!

Nicole 42:15
[Laughing] Yeah, they were probably like, ‘Get a life, woman!’

Caro 42:16
On brand, Nicole. On brand.

Nicole 42:20
‘Go home! Don’t you have a kid?’

Caro 42:20
You’re like, ‘I am home.’

Nicole 42:21
Yeah, and I’m like, ‘I am home and he is literally on my arm, but I'm still working.’

Caro 42:25
Yeah, on brand. Well, before we wrap up, I always like to ask… I feel like you just gave some great advice for [starting a new COO role], in particular. But is there any other advice that you would like to give to someone who maybe wants to do the work that you do? Who is thinking about a more senior people ops role or maybe transitioning from people ops to a COO role?

Nicole 42:47
It's interesting. There's a specific path you can take to get into operations, right? I'm sure there's lots of blogs and articles, and like even career counselors that can tell you, ‘Okay, this is what you need to do to actually do those things.’ My thing would be, my personal suggestion, because there are so many resources about career paths, I would say, just ask yourself, what is your personality? What do you actually like to do?

For example, when I was thinking of the COO role, I actually started looking online at roles of COO and I started looking at other roles, right—Chief Strategy Officer, investment relations, tangential roles to myself. I started looking at those job descriptions and I started weeding out like, ‘I actually don't like those responsibilities. I really liked those responsibilities.’ Then I went and did all of those self-identity activities to make sure that I was on the right path.

My thing is, whenever I make big decisions, it's all calculated and weighed out. And it's logical, right? You have to make smart decisions. But I think it has to be weighed against a healthy dose of like, ‘Who am I? What do I want to be doing?’ And if that means diving deep on your own using some tools, a few surveys, or asking people that are close to you, people you've worked with… That's how I've always made decisions. There's the strategic, logical piece. You can't not have that aspect. But then the other half is, just, know thyself. Because don't you ultimately want to be doing work that you care about, and you like?

Caro 44:13
Yeah, no. That is a great thread to this whole conversation, right? How to…I don't know, following your heart sounds so cheesy, but like following your passion, or where you're engaged and the things that matter to you.

And so I guess maybe the final question here is, on the flip side, what are you working on this year that you'd like to work on. What should listeners reach out to help you with?

Nicole 44:33
Well, I know you're amazing at this because you won an award from Zapier about automation, which is incredible. Props to that. [Caro laughs]

We are making all the changes [at Refresh]. So that's exciting. But, I think once that's done, when the organization is running very smoothly, that's when I want to make it run even more smoothly. I want to be looking into more automation.

So, once we have the processes smoothed out, I’d love to have an outsider come in and be like, ‘Well this can actually be automated.’ Or, ‘this can be done with better software.’ Because, right now, we need to fix up the car so it runs. But then, maybe at that point, someone says, well, maybe you just need, I don't know…. [Laughs] I don't know why I chose a car.

Caro 44:45
[Laughing] Sports, cars… I think we peaked with the lily pads.

Nicole 44:49
[Laughing] Yeah, all downhill from there.

But I mean, I want someone to come in and be like, maybe you just need a new… I don't know, engine? Or, just get a different car, right? [Laughing]

Caro 45:28
[Laughing] Yeah, totally. I think that analogy works.

It’s great that you're approaching the process first. I think that's the number one mistake people make with automations. They try to automate before they know what they need to automate, right? So, I think you're on the right path. And I'm sure we have lots of no-coders out here when you're ready, who are going to be excited to help you with that. So, Nicole, thanks so much for coming on and chatting with me. This was great!

Nicole 45:50
Thank you, Caro. You're awesome!

Caro 45:52
Back at you! I can't wait to follow your journey at Refresh Miami and all the great stuff that you get up to this year. So, yeah, thanks again for joining. And thanks, everybody, for listening.

Nicole 46:02
Thanks for having me.

Thanks for listening to Opsy. You can find resources and links from this episode in the show notes at opsy.work. While you're there, I hope you'll take a second to join our free community where we share resources and opportunities that help us all level up in our ops careers. Again, that link is opsy.work. Until next time, stay Opsy, friends!

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