Episode 13: Checking in

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 So, you know how I basically start every episode of this podcast by telling you that it's a very special episode? Well, guess what, y'all? This is a special episode. Shocker, I know. This episode is special because, well, I'm kind of the guest. So I'm bringing on my friend Kelli to interview me about my journey in operations and what I'm working on now.

I've known Kelli for seven or eight years at this point and have been lucky enough to work with her at two different companies, including my current role at Tech Ladies. She's my Opsy BFF, or as a previous guest, Dianna Moore, called another guest, Lauren Walker Reader, in an earlier episode of this very podcast, Kelli is my partner in Shine. So she's been my right hand, my thought partner, my confidant, my cheerleader, and I like to think I've been the same to her over the years. So I think she's the perfect ops pro to come on and dig into things with me so that you can get a little bit more insight into Opsy and this person who's been chatting at you for twelve episodes so far. So welcome.

Kelli Hi, everybody. Great to be here.

Caro Yeah, thanks for coming on to chat with me, Kelli. It's like so weird to be on the other side because like you're interviewing me. So it was a different dynamic to prepare for this episode.

Kelli Yeah, for sure. And I'm a huge podcast listener, but this is the first time I'm ever actually on a podcast. So yeah, I feel like I'm in another dimension right now.

Caro Yeah, I think I don't know anyone who listens to as many podcasts as you do. You're definitely up there. I feel like in like the top 2% of podcast listeners, like you've always got a podcast playing in the background no matter what you're doing.

Kelli Yep, everybody hit me up for recs.

Caro So yeah, thanks for coming in and chatting. I guess like I should stop trying to lead this and I should like let you lead the dance, right?

Kelli Yep, exactly, exactly. I'm gonna take it over from you here. So yeah, I'd love to start out by having youshare about your history, especially because I know that, while I feel like none of us have a traditional career path anymore, I feel like yours has been especially non-traditional. So yeah, could you tell us about your early days and especially kind of about the turning points in your career as you moved from one step to the next?

Caro Yeah, so I was definitely not planning to be an operations person or really to work in tech either. I studied interdisciplinary arts in school, and I was definitely someone who barely graduated high school. I went to art school because that was what I was really passionate about.

And I think looking back, I had a series of jobs that I think were operations, but I wouldn't have thought of them that way. And I wouldn't have described myself as an ops person or that as like my ultimate career path. It was just something I did to kind of survive and pay the bills and make it pay my way through school.

And so, yeah, when I graduated college with an interdisciplinary arts degree, it's like, "What do you do with that?" Well, you teach, and you lean back on technical skills. And so I had taught myself to code as like a preteen. And that was one of the ways that I, you know, was able to support myself was working kind of on these like scrappy freelance design and development projects. And so I ended up doing a lot of that and teaching development and being a teaching artist, which is like a whole other thing. And then I went back to my alma mater, actually. When I'd been in college, I'd been an orientation leader, which is basically what I know now as event ops, or like event logistics, whatever you want to call it. And so it was managing these large scale orientations for a large college where you had hundreds and hundreds of people coming everyday, twenty days a summer, and you had to worry about things like space rentals and tablecloth rentals and tablecloth cleaning and staffing and AV and catering and all of that. And so now I look back on that. I'm like,obviously that was an op jobs, and it was maybe one of the first jobs I really ever loved. I loved putting all those pieces together and making sure everything ran smoothly.

And so shortly after graduation, when I was still kind of scrapping together this, like, living, my old boss - I had done that job for about three years and ultimately like ran the other, or managed the other, orientation leaders and ran the program - She was like,"Hey, we're taking this online for students who can't make it in person. And so you have the technical skills.

You know the program really well. How about you come build this online education program?"And so I went back and did that. And that was kind of my first like, again, not tech - It was in higher education - but a little bit more getting my foot into that door. And that was ultimately the job that really prepared me for my first job in tech, which was at a company called Skillcrush, where I met you. In fact, you were one of the people who hired me, and you were definitely the one who onboarded me. So you've been there ever since, I think, I guess literally like, my first day in tech. You were there welcoming me with open arms.

Kelli For sure, for sure. Well, yeah, I'd love to hear a little bit more about making that jump from, yeah, kind of like you said, like event ops, kind of into more like operations in the tech industry. What made you decide to make that leap? And what was it like to kind of move over to a new space?

Caro Yeah, it was definitely challenging. I wasn't really prepared for startup life. And so I would say like the first six to even twelve months, it was a little like shaky. I wasn't sure I was going to like make it. And I think me and my CEO at the time had to like find our footing, right? Like I was just really used to the pace of higher education. So I guess to give a little more context, the job I was doing at Skillcrush was technically called Class Manager, which I guess now I would describe as like education ops or class ops. Or like really it was delivering the product that we were selling.

Kelli Program ops?

Caro Yeah. Skillcrush is an online bootcamp, one of the largest, and it's specifically for women and underrepresented groups in tech. So a really high population of People of Color, of women, of people with chronic diseases,like people who are traditionally not included and who aren't really considered when you think about likekind of an in-person bootcamp that's asking you to give up your life and restructure your day and your commitments and stuff. And so really trying to make tech a more accessible place for people to learn digital skills and be able to break into the industry and ultimately hopefully have a higher salary and more flexibility in their lives.

So the team that I was hired to kind of manage was the class team, as we called it. It was really a team of designers and developers who worked part-time for Skillcrush as instructors and teaching assistants. It was like managing kind of the customer support piece of our students, so making sure their questions got answered and ultimately making sure that our staff felt trained and prepared and that they could support our students really well, that students felt like they were having a great experience and that our curriculum is like up to date. And so we kind of managed everything from like online office hours via Zoom to like the Slack community for the students to like answering questions via email.

There's a lot of customer support in there and just a lot of logistics. Like how do you deliver certificates of completion? How do you separate up office hours to make sure that like, you know, an instructor isn't wasting their time and sitting on an empty call but also that they're not overwhelmed. Like there was just a lot of little things that you know…

I was there for years and so saw a lot of different problems and saw that industry of online education and tech education especially really change. But I've been coming from higher education where the cycles were different. It was a semester. And so it was like, okay, we realize this doesn't work. Let's Improve this for next time. We'd do that. Like we would figure this out in the summer. And then we would like fix it for January before like the winter session started. And at Skillcrush we started a cohort every month. And so it was like, oh… You know, you have a busy week leading up to enrollment, then you have a busy first week, and then you have like a week to like make those changes before the next cohort's coming in. And so I just wasn't used to that cycle. And I think that that was like the hardest adjustment for me.

Kelli Move fast!

Caro And now I love that. It's one of the things I love about tech, but at the time I just felt like kind of a failure and like I wasn't cut out for that job.

Kelli Yeah, which is ironic because… Yeah, I felt the same way when I started at Skillcrush. I was like, oh, we're going to go this fast. But I feel like I see that as such a skill for you nowadays. That you move forward thoughtfully but quickly. And that's so important, especially in the tech industry.

Well, digging in a little bit more there at Skillcrush, I mean, you were there for a long time, six years. That's a lifetime in the tech industry. What were the big projects or initiatives that you worked on there that you're most proud of or maybe that taught you the most?

Caro Yeah. So I think over my time there, my role really changed, obviously, to kind of like a head of ops, to a director of ops. And by the time I left, I was running kind of two teams. I was still running kind of that class operations teams, but I had a right-hand - Shout out Christy, who's in Opsy and who really ran the day-to-day of that team and took over a lot of those class operations. And then we had a more like company ops team,which you know you were my right hand on. And we kind of handled everything from like people ops to some finance stuff to, you know, just like company operations, right? Like how do you operate more effectively as a company? And so I did a lot of interesting things in the course of that time. And a lot of justlike working really closely with what was then like a management team of like me, our head of product engineering and our CEO and then like a head of sales and marketing. And so I got to see so much about like how a company runs and how particularly like a bootstrap company who's really focused on cash flow and profitability and also like wanting to live up to their values of being like a good place to work and build a great company. I think I just learned so much about how to make decisions through that lens and to weigh those priorities that can compete sometimes.

One of the things I really liked about Skillcrush that I think I like about ops in general and then I think a lot of other ops people will relate to is this special projects lens of: Here's a thing that needs to be done; We don't really have a full-time person to do it; No one's dedicated to this; Let's find the ops person who can figure it out. Those are the projects that I think, looking back on, were some of the most challenging and also some of the most interesting. Two specifically come to mind and one I don't think is something that anyone would call interesting or exciting, but it's health insurance.

I don't know if you remember when we went through this whole rigamarole, but, for various reasons we had been paying people stipends instead of health insurance. We had a health insurance stipend that was in theory… could be used for health insurance. We were a small team. We were spread across a bunch of different states. I feel like such an old lady when I say this, but, back in our day, there weren't these modern payroll providers.There weren't all these PEOs that existed. In fact, Gusto existed, but we couldn't even use it because it didn't exist in all the states that we had employees in. We had our hands tied into these really legacy systems that were not meant to be used the way that we were using them. I spent a lot of time. We'd hire a new employee and we'd be like, what state are they in? Cross your fingers and hope it was a state we were already registered in. Otherwise, I'd go down a rabbit hole of like, "Okay, the Illinois Department of Revenue,the Illinois Department of Workers Comp". Registering us and having to remember to deregister. It was a whole different world.

I think insurance was the perfect example of that because we really wanted to offer health insurance and move away from these stipends for various reasons. Definitely the right move, definitely something we needed to do, but a hard process especially because no one at the company had bought health insurance for a remote distributed team across several states before. We barely knew how health insurance worked in general. Actually, I was probably one of the funniest people to take on this project because I had never… Skillcrush was the first... I'd never had health insurance before I joined Skillcrush, got a stipend, and went through the US marketplace to buy healthcare. I didn't know the difference between coinsurance and copay, much less how to go about this process. I really just had to approach it with like, "Okay. I'm going to go to a broker. I'm going to ask a bunch of dumb questions, and I'm going to preface it as like, 'I have no idea what I'm doing and I'm going to need you to explain this to me.'" Like I have no idea. Like I'm a 23 year old responsible for - I wasn't actually 20, I think I was like mid 20s - but I'm like a mid-20 something who has no idea how insurance works and is now responsible for getting insurance for a company of 25 people, youknow? And so that's what we did. And there was just so much like paperwork and so much, "Okay, you sign here and you do this."And I look back at also how many forms we accepted via Google forms.

Kelli Security!

Caro Yeah. Like, that was not secure. How much stuff... Like, yeah, right. Like again, this was 2015, youknow? We probably knew better, but like didn't have a better solution. So but I think to not continue thistangent longer than I need to. I think the thing I really learned there was like, how to approach a problem that you have no idea how to approach, right? Like I think about it visually as like, someone put something in front of you, like this big mound of a problem, and you just kind of like take laps around it, and you're like,where's the entry point here? Like where do I even start? And I think those are some of the most intimidating problems for me that sometimes I still find myself like moving from day to day on my to-do list because I don't know how to start. But I think that that was like a really good lesson. And like, you just have to start,right? Like you just have to get in there and ask a bunch of questions and not be afraid to look like an idiot and figure things out as you go.

And you know, at the end, I think one of the benefits that I had no idea of what I was doing is that I approached it that way with the team, right? Like I didn't expect... We had a pretty young team, and I didn't expect them to know things that I didn't know,right? And so I was able to... We had like a bunch of town halls. We like, as a team, we talked about why we were making this move, why it was good for them, why it was good for us. Like we picked out the plans together and then I really like explained, this is what a co-pay is. This is what a deductible is. This is how you can make a decision that's right for you and your family. And I think that that was something that like really fit with our values and really benefited the team. And I think the times that we were able to do that, I'm really proud of, even though it was a... On the surface it was a very unsexy problem of getting health insurance for a team. I think it was a good experience of like, yeah, you can figure stuff out. You just gotta ask for help and try and figure things out as you go. And over the years, I led that process a couple more times, and then you took it over and we learned a lot in the process and, by the end of it, it became pretty easy, right? Like it was like a routine thing. And so I think that that was probably one of the projects I'm most proud of.

And our transparent salary tiers. We really wanted to standardize some pay. We got to a point where the company was making more money, and we wanted to bring on new employees at a competitive wage. We wanted to pay people fairly when they came in, but then we also had these like employees who had been with us who are underpaid now based on the market because it was what we could afford to pay them. And we wanted to find a way to bring them up sustainably while also hiring the new talent that we needed and to just like pay fairly and in accordance with our values. And so I devised like a transparent pay system, rolled thatout to the team and then over the course of a couple of years also iterated on it as we grew and as we figured out what worked and what didn't work and kind of what the problems with that were. And it wasn't perfect.

But I think it was really transparent, and it was really straightforward and it removed a lot of ambiguity in salaries that I think is particularly important when we think about things like pay gaps, you know, and wage gaps between different groups in tech. And so, Skillcrush was a small little team, but it was like, if I could do that for a small little team, that's like an impact I'm proud of.

Kelli 16:00 Yeah. Well,I feel like these projects have really hit on your superpowers. You know, I feel like the insurance project, you know, that kind of idea of like, you know, figure it out and also bringing people in while you're figuring those things out. What would you say you learned most about when you did the transparent salary tiers? What was kind of your takeaway looking back on that?

Caro I think I probably have a couple big ones, but I think really the specific actionable one for me was that we had a lot of part-time employees, and it was important to us that they were classified as employees because that's what they were. They weren't contractors. And so that was like a whole other project that I did where we reclassified everyone as part-time employees. We standardized their pay, their hourly rates, and we offered health insurance. And that was like, really important to us. We really wanted to be able to offer that we felt like it was in line with our values and what we believed in as a company, but also it was important and valuable from a recruiting standpoint. We had all these designers and developers whose hourly rate for instruction is not the same as it is when they're freelancing. We could be a really great anchor client for them, but the pay was not going to be the same. Thiswas another way we could be like, "We can give you health insurance. We can give you health insurance that you don't have access to as a freelancer, especially if you don't have a partner who you can access it through."

We did that. I think it was one of those things, you've got to, you know, know the rules to break the rules. I think I didn't quite realize the impacts of that decision in terms of salary. So, for example, like for better or for worse, I would argue it's for worse... And I'm speaking very much about the U.S. benefit system is like… Health insurance is what incentivizes people to go full time. And so we had all these part timers who we've created a system for where like, if they worked twenty to thirty hours a week for us as a part time employee, and they already got health insurance, it was really hard to incentivize them to like take on an extra ten hours a week. And like it made a lot more sense salary-wise... like for us to have them on salary, right? And for them to be full-time committed employees that like, in a time where things get busy, like we all've just got to like rally and like get it together. But if you're a part time employee, you could be like, "No, I hit thirty hours, and I don't have the availability to go over." You know, which is totally fair. You're a part time employee, right? You know? And so the business really needed to convert some of these part time employees to full-time employees to scale up as we were growing. We didn't want to hire twenty part-timers when we could have ten full-timers, but we created a system where they weren't necessarily incentivized to do so because we had been giving them health insurance. That was like a problem that I... I think I don't know that I would do it any differently because I still want to give people health insurance. But I think it was something that we didn't necessarily think about.

And I think the first system, like the first set - we called them salary tiers - and the first set of salary tiers that we released just didn't have enough nuance for growth either. And so I think it was about like trying to make it fair and reduce negotiation to like almost none for new employees and to make it really clear like how much room for growth you had in terms of salary and how you could get there. But I think I was a little naive in terms of how black and white we can make it. And I think looking back, I'm like, you can't make a system that is completely objective and that is totally black and white, but what you can do is you can make it as black and white as possible. You can reduce the subjectivity as much as possible, but there's always going to be 5%. And to some degree, you need that 5% to be a successful business. There are some situations that you just can't account for even in what ended up being like a 35-page set of salary tiers, right? Like we tried to cover everything, but, to a certain degree, there's got to be some management discretion. And I think that's a whole other conversation around like, at the end of the day, you have to trust the leadership even if you don't always agree with their decisions. You have to trust that like, you know, you believe in their values or you agree with them and that like, we're all gonna make the best decision that we can and move on. And so I think that that was a real learning for me is that sometimes you can't have the perfect scenario, like it doesn't exist and you just have to like do the very best that you can and accept that.

Kelli Yeah, yeah. I feel like that's another Caro superpower, like iterate and then also be okay with it not being perfect because nothing is ever perfect.

So yeah, I wanted to take you onto your next step in your career. So yeah, you were talking about moving on. So how did you move on from Skillcrush? What was your next step?

Caro 20:29 Yeah. So I had been at Skillcrush by the time I left for six years, and I think I spent a fair amount of time before I left thinking about leaving. And it was really hard because I loved my job in a lot of ways and it continued to remain interesting. And I had a really great team and I also didn't take for granted the fact that I was on an all women executive team. And so of just really great leaders who were very valuable as aligned, who I could talk very transparently with and like be a full, like I could bring my full self to work.

You know, I think that's become kind of a cliche statement, but I like really felt that way. And I was fully remote and a time where like remote was becoming more common, but this was was still pre-pandemic before it really hit widespread adoption and so I just felt like I had resigned myself to like, "Okay, I need to move on at some point, but like when I do, I'm going to have to give up something that's important to me." And it just felt like I was going to have to make a compromise. Like it wasn't going to be a mission that I cared about as much or a team that I loved as much or it wasn't going to be remote or like, you know, those kinds of things. And I think something I realize now is that's not the case.

But I think a big part of my motivation to move on other than I just like, I still had projects that were interesting to me, but I think other people will hopefully relate to this too. It's like to a certain degree, the core business problems don't change, right? Your product, your positioning, your customer doesn't change. Andafter six years, I was just ready for a new problem, right? I was ready for a new customer set, a new industry to learn about, just something just like new. Also, I was just really worried that I was going to be someone who people would look at my resume and be like, "Oh, she only knows how to do ops at Skillcrush." I was really worried about that. I think with some hindsight, I don't think that was as important or that big of a concern, but I was very concerned with it at the time. But I was resistant to leave Skillcrush.

I started consulting just to get my feet wet and do other projects and learn more about companies and to build that experience that way. And so I did that for a while. And that's actually how I found Tech Ladies. I will always remember this. Allison, the founder of Tech Ladies, had posted like a part-time... I think it was like a job board manager, events manager. It was some little part-time job. And I'd followed her on Twitter. We kinda knew each other but had never really talked. And so I applied. And I remember before the interview being like, "I am not going to do this job. Why did I do this? This is not where I see my career path going." But then we ended up chatting for what was supposed to be a 15-minute interview, and we chatted for an hour and just really vibed. We were just like, "Yes, we are aligned in the type of businesses that we want to build andthe type of mission that we're aligned on."

I ended up starting as a consultant, and my hours grew over time. Within a couple of months, it was like Tech Ladies didn't have any full-time employees at the time. It was just Allison and then a handful of part-timers,including myself. It became clear that it was a good fit. Allison had, unbeknownst to me at the time, she'd been thinking about making an operations hire. And so I think she'd been thinking more like director-level and then having worked with me and she was like, Okay, I see the value in hiring a more like, you know,senior, even more senior, like executive-level person. And so, so yeah, like, eventually I just took the plunge. It was hard to leave Skillcrush and like say goodbye to that great team, some of whom I had, like you, I'd worked with for like six years, you know. But ultimately, it was, it was the right move.

You know, I joined as employee number one at Tech Ladies. So I was VP of Ops. And then last fall, Allison kind of took a step back from the business, and I took on the general manager role which is like what I Wanted to do. I think, you know, for a long time now, I've known that I ultimately wanted to be like, if not a founder, then like a CEO or like I wanted to run a business and was like ready for that challenge. And so this presented a really great opportunity to do that with a business that I really love and care about and already knew pretty well, you know, I'd been involved with it for two years. It wasn't like coming in as like the new boss who doesn't know anything about the business, you know, like I had like worked in the business a lot and in some ways have done almost every job at the company. So it was a very unique opportunity to have my first like GM/CEO kind of role.

Kelli Yeah, well speaking of all the jobs at the company, what do you actually do as GM? I mean, what is a general manager and what does that look like in particular at Tech Ladies for you?

Caro Yeah, it's an interesting role because I think it changes quite a bit. I mean but I guess you could say the same for operations. I do feel like it's an operations role and even more so when you put an ops person like me in it. But I think a lot of times a general manager is someone who runs a business unit or like a line of business for a larger company. So sometimes a company may be so big that they have the CEO, but there's like a line of business that's important enough and really kind of runs as its own business within a business. And so that is typically, I think, what a general manager is. And so they still kind of report up to a CEO, but they like are kind of a mini CEO. And so that's kind of how I function at Tech Ladies, even though we are a very small business. We have a team of six, I think we're at, full-time employees and about as many part-timers. So I run kind of... I don't know. I run the business, whatever that means day to day. And that changes. So I guess like...

So Tech Ladies, we're the largest community of women in tech, and we primarily focus on supporting women in the industry, whether that be women in technical roles or women in non-technical roles in tech. That's avery... We have a very broad definition of that. You know, if someone feels like they're a Tech Lady and they belong with us, regardless of their gender identity or their exact job role or company, like we want them to come and get support and be part of our community. And so the way that we serve them is through this like very robust free community. And then we have a smaller, more intimate paid community called Founding Membership, as well as a Leadership Accelerator for women who are trying to upscale. And our goal there is to really narrow that leadership gap... It's something ridiculous - 30% of executive roles go to women. And I Think we're still less than 9% of CEO roles. And so really trying to help women level up in that way.

And then a really big part of our business is hiring services. And so it's helping women find opportunities at really great companies and helping great tech companies hire great talent. And so we do that through a job board, a candidate database, and a whole bunch of employer branding opportunities events, things like that. And so we kind of play matchmaker, slash recruiter, slash cheerleader in that way. And I really focused on hiring services when I was before I stepped into the GM role, both as a contractor and a VP of ops. And so that's like the biggest part of our business. And so I still do a lot there. And my background in hiring and recruiting and HR or like people ops, I think, really is a strength and an asset and allows me to know the business in a really much more intimate way. But yeah, so I still, you know, so I manage our team, I kind of set priorities. I look at where the market's going and try to stay ahead of it. It's kind of like hard, I guess, like any ops job. It's like a hard job to define because I think it changes week to week, especially because we are a small team and I still do a fair amount of what we called earlier special projects.

Kelli Actually, I'd love to get you to share a little bit. You know anybody who reads the news nowadays knows that hiring in the tech industry has been super interesting lately. Yeah, how do you handle that as the GM of a company who, like you said... You know, one of the biggest things Tech Ladies offers is hiring services. So, you know, what kind of interesting cases or trends have you seen or been seeing? And then what are your thoughts on what's going on right now?

Caro 28:23 I mean, it's a really rough market, I think for everyone involved, especially just because it's so uncertain and no one knows what things are going to look like in three months, six months, a year. And so it's been really rough. We've been trying to like pivot and stay lean, but also, you know, spend a lot of time thinking about how can we help our partners. How can we help all these women in tech who've just been laid off, right? Like every week you hear another... like about another massive layoff at a company we've all heard of. And our Head of Sales yesterday told me... She's like, "I just can't go on LinkedIn anymore. It's like not doing me any good." And I think in a lot of ways, we would all probably benefit from some regulation in that way because I do think a lot of it is a much needed market correction based on what we now see as overhiring in 2020 and 2021. But that doesn't make it easier when you're the manager having to lay off a team or when you're being laid off. And so something we're seeing a lot is... I think really the layoffs are coming from these bigger companies, from the FAANG companies andthe next tier down. I think I'm seeing it on a much smaller scale, with small to medium sized or even in the couple hundreds. It's the companies under a thousand, I'm seeing less layoffs. But I think what we're seeing there is just hiring freezes and people scaling back their hiring plans. They're just not planning to hire as much as they were before. I think something that we're really trying to to focus on is like, "Don't give up on DEI just because you're not hiring a dozen roles." A lot of the companies that we work with are still planning to hire a couple roles and inevitably you're going to have to backfill people on your team. And so I think it's just about how do we adapt our services and our offerings to meet them where they're at in the market so that they can still hire great women on their team because we just know that it takes time, right? You can't slap a job posting on, whether it be Tech Ladies or another job board, and just hope for a diverse pipeline. You have to build your awareness in that space. You have to prove yourself. That you're going to be a good place for these people who have maybe been burned before in the industry to work. That takes some time. When you just stop all efforts, you're going to have to start over. I think you and I have seen too that it's so much harder for bigger companies to catch up. It's so much easier to build an inclusive culture when you're five team members than to convince that first Black engineer, that first woman engineer to join that team than when it's 100. I'm really passionate about helping those smaller companies, but we work with companies of all sizes.

I think as a GM, I'm always trying to figure out, "How do we grow? How do we stay profitable?" We offer really high touch hiring services. We're not just a job board. We have to be profitable, we have to pay our bills, but also wanting to support these really small companies that have a much more limited budget. And I think that that's kind of one of those core business problems that I am really motivated to solve, especially as someone who has spent her career at quote unquote smaller businesses and really loves working at those types of like, not only small companies, but like bootstrap companies, early stage companies. I find that really interesting, and I want more Tech Ladies to be able to participate in those opportunities.

Kelli 31:43 I mean, you spoke a lot about special projects. And now, related to what you just shared... Well, about hiring and in the tech industry, there's one special project that I would love for you to brag about.

Caro Should have known this was coming!

Kelli Yep. Yep. You know, that's me, ever the cheerleader. But I think this is especially interesting for everybody to hear because, you know, from an ops point of view, you know. How you solved a business problem and also how it turned out to be a big win for you personally. So tell us about this project, which I think you know what I'm hinting about here.

Caro 32:19 Yeah, you're hinting so big, but I know exactly what you're talking about. So yeah. So when I… Shortly after I started at Tech Ladies, like in the first year, we just had more and more hiring partners coming to us asking about what they often refer to as a resume book or a talent pool and wanting to be able to reach out to Tech Ladies directly. So I think a job board... There's a reason a job board is just one part of our hiring services. It's not a full strategy. You can't just throw up jobs on a job board and hope for a qualified, diverse talent pool. So how can we help our partners do that? And so we realized, we had all these great Tech Ladies in our community but not all of them were searching the job board. Not all of them were looking at it regularly. And so we had a lot of partners who were like, "I know you have these Tech Ladies. Like we've talked about it. Like we have the stats, like these Tech Ladies that we're looking for exist in your community,but they're not applying at the same rates on the job board." Because job boards... Like job boards aren't fun.

Like I think ours is really cute. It has gifs and unicorns, but like it's still a job board. You're not going to be,like, spending your free time there. Like if you can avoid it, you know, a job board is where you go and when, you like, have to like... you need to be applying for jobs, you know? And so we were like, there's so many Tech Ladies out there who are interested in new opportunities and who would totally like be down to hear about them and potentially make a change but who don't want to be looking at a job board every day.

And so what we devised was this need for what we now call the candidate database. So this, what is now a very robust tool, started out very much as an MVP. This was before I was full time even, I think. Yeah, I was working very part-time for Tech Ladies on the side. I built it out with the help of our Head of Hiring Services, Wendy, who's just a very experienced recruiter and career coach and really knows the candidate side in particular very well. And so we really devised this MVP, which was essentially an Airtable, if you're familiar with... I mean, I know you're familiar, Kelli, because we've been down that rabbit hole together. So it's a kind of this no-code tool Airtable. We like devised a system where Tech Ladies who met certain criteria that we knew our partners were looking for, could apply to be part of the Candidate Database. We'd review their application. We'd work with them to make sure their profile was really up to date and had all the kind of information that hiring managers are looking for. So everything from, you know, not only their LinkedIn and their resume, but like what their current job is, what they're looking for in their next job. Are they looking to be at an early stage or mid stage company? Are they only wanting to work in fintech? Do they need visa sponsorship? Like, are they willing to relocate? Like we got all of that in one place and then we needed to find a way to like display it, right? And so the MVP was literally like an Airtable embedded into like a Webflow page with like a login, like a password-protected login that we changed regularly. Like probably not regularly enough. But it was enough to validate this as a real product, right?

And like, it really was a game changer for the business and now we've built out a much more robust, like,actual like app for our hiring partners who can go in and they can say, you know, "I'm looking for an engineer with more than five years of experience who is in the New York City area or in Austin or, you know, open to relocation remote", whatever. And they can browse through a really qualified pool of candidates who also happen to be women and happen to be like 45% People of Color and just have a really great experience. That's super relevant for these roles. And so everyone in there is someone who is actively looking for open to changing jobs in the next six months. And so I think it was a big unlock for our partners, and it was a big unlock for our business and allowed us to grow like a hundred percent quarter over quarter, like six quarters in a row. And so building that with no code tools, like made that possible, right? Like we wouldn't have been able to do that if I had to pay an engineer 10 or15 K to test this idea because we're just too small of a business to take that kind of of risk. And so, you know, it is one of the things along with just like, the luck of, like some... really being able to bring on some really great team members that took us into like a seven-figure business.

And, so through that work, Zapier, the popular no-code automation tool, had a... They decided to start hosting an annual no-code day because apparently anyone can just like make it like key lime pie day or like pinata day or whatever. So they registered No-Code Day, and, as part of that last year, they had a contest for no-codeprojects. And so I submitted the Candidate Database because I was really proud of it. And also just like both as, like, a tool but even more so... Just, like, the impact it had on our business. And I think it just really proved the value of bootstrapping and MVPs and like using no-code to like validate. And I was lucky enough to win. So I yeah... I won their first ever no-code contest, got a great prize, and had some other opportunities to just like work with them more closely and be more involved in that space. And so it was a great win forTech Ladies and for me personally, for sure.

Kelli 37:17 Yeah. I feel like this is another Caro superpower, putting yourself out there. You know just... if you want something, build it and then share about it. And yeah, I feel like the universe came back and gave you the reward you deserved here. And of course, you know, for Tech Ladies, it was huge as well.

Caro Well, you're always my biggest cheerleader, Kelli. So thank you for that.

Kelli There are many reasons to be. And actually, I would love to hype you up again. Like I was, well, saying, you're always the one putting yourself out there and building things. So I would love to hear about what led you to create Opsy, where we are talking today. What brought you to make this community for all of us?

Caro Yeah. So Opsy is a community and podcast for operations people working in tech, primarily like mid to senior ones. It was just something I wanted to exist. And after years of complaining about how it didn't exist,it just kind of became a like a "put-up or shut-up" moment. And so I started it in the fall of 2020. Oh no, 2021, I think. And yeah, I think like I had always been the only or the most senior ops person on a team. And I think there's a lot of imposter syndrome that can come with that role because you are walking around these big problems and trying to figure out how to approach it and feeling like the way that you're doing things isn't the right way to do things. And so I spend a lot of time and effort trying to build what I call my ops Voltron, which is just a bunch of smart ops friends who have different specialties and experiences than me that I can reach out to for support when I need it and that I can support in return. And I think that that's been a great way for me to learn and like network and, you know, just like make some cool friends who... many of who have now been on this podcast.

But it just like it was very inefficient, right? Like it was a lot of me sending like cold DMs and like awkward Twitter messages and LinkedIn messages and stuff and like chatting to people during Zoom webinars and sending cold emails and stuff. And I was just like, "I'm an ops person. I don't don't like this inefficiency. And this should be easier and not everyone is going to do that and put themselves out there in that way and they shouldn't necessarily have to." And so I wanted to create Opsy to remove that step for people and to like bring all of these great people together to have that space where you could just, you know, ask, "Hey, has anyone done this before?" I think I just kept running into scenarios where I would do like monthly, you know,or quarterly check-ins with friends and they would tell me really proudly about a project they were working on. And I would be like, "It sounds like you killed it. That is so great, but also I did the same thing a year and a half ago, and I wish I had known you were working on that because I would have like given you all my docs. You know, like you could have had a starting point. I could have like helped you and made that easier." And so I think those were the two things I was really trying to solve for. And, luckily, other people seemed to want that too. It definitely took off a little more. I mean, I was definitely hoping for the response that I got. Luckily, yeah, people were into it.

And so the podcast really came less out of desire to have a podcast and more out of the fact that I have always wished... I think because I come from more of a design and development background originally, I was very used to sharing my work, right? Like there's a lot of, I mean, the nature of development is that you put your codein repos, you know, that your team can see and you work on it together and like you blog, you do talks at conferences. And there's just like not that same level of like show your work in the ops community. And I just like, partly because the nature of our work can be really specific, and I think partly because we're behind the scenes people. And so it's like pulling teeth to get an ops person to like do a write-up about something really cool that they did. And so I was like, "Okay but I think I can get them on a podcast and then I can just interview them and learn that way, right?" And not ask them to have to write a blog post or prepare anything. I can just interview them. And then, selfishly, it's just a really fun way to meet new people and to have an excuse to be nosy and ask them all the things I want to ask them about areas of ops that I had never heard of before, don't really know anything about because those are just conversations that I love to have. And so yeah, I think that's how it started. It started there, and now we're here.

Kelli What do you love most about Opsy? Why, when you know, lay in bed at night and you think, "I'm so glad I have this community that I created", what is it that comes to mind first for you?

Caro 41:44 I think it just is having people that you can turn to to ask questions. I think everyone... like the power of community is so important and whether... I think it doesn't have to be Opsy, but I'm like, everyone deserves a community of people that they can turn to, whether that's Tech Ladies, whether that's Opsy, whether that's... you know, we've been partnered with some really great communities like Operations Nation and the BizOps Network and stuff. Because I'm not... I'm like community over competition, you know, and Iwant everyone to be able to find their space on the internet and their like little crew of people who are going to cheer them on and help them be successful. I get that not everyone can have a Kelli, but everyone should have a Kelli, right? The next best thing is a community of people who are going to cheer you on and make you brag about yourself and also say, "Hey, I get it. That sucks when you're facing stuff at work that sucks."

Kelli Yeah. Well, speaking of community and advice, I would love to really keep turning the tables on you here as we're wrapping up and ask you a question I know that you ask your other podcast guests: What advice would you give to somebody who wants to do the kind of work that you do?

Caro 42:54 You know, I ask everyone this question and only having it turned back on me, do I realize how hard it is in the moment. It was actually a friend that emailed me the other day and her like teenage daughter is planning to take a gap year after high school and kind of is more interested in kind of like operations kind of work. And I was thinking like, "What is my advice?" You know, because I think there's obviously some difference between someone who's right out of high school trying to build a career and someone who's, youknow, maybe more mid career or senior or whatever, but I think it's just... to reference yet another Opsy podcast episode with my friend Cristina from the Obama Foundation. She talked about just the power of raising your hand. I think that I come back to that a lot and I think I would maybe spin it even a little bit differently of shooting your shot. It's just taking on the project that's like you don't know how to solve because you're interested in it and because you know it'll have a good impact. I think that that's one of the best ways to learn those things. You learn so much from it. And then also just like quantitatively, it is like such a great thing that you can have on a resume that you can talk about in an interview that you can shareonline that you can really build your credibility with. And so I think whether that's in your day job, whether that's inside projects, like I think something that I don't think people do enough... is like rely on like side projects or volunteer work or hobbies because like those skills are transferable. And like, if an ops person came to me and was like talking about how like, you know, they planned this whole, real example, actually… someone planned this whole like community learning festival and just all the ops in it. And it's like... if I washiring for an ops person, that's a great, that's a great proof point, you know? Even if their previous jobs were only slightly related. And so I think it's like that.

And then I think the second thing is just like, shoot your shot, right? When Zapier posts a no-code contest and you have a project you're proud of, apply for it, right? Don't talk yourself out of it before someone else can talk you out of it. And I think I had one of my very best friends who I was lucky enough to meet on the first day of college and have been stuck with ever since. I think watching him those four years of school together. He applied for everything. He applied for so many fellowships and internships and scholarships, and he was just constantly shooting his shot to a point where I was just like, "What? You're never going to win that." Outwardly, I'd be the supportive best friend and then internally I'd be like, "What? That's such a long shot." But the thing is, is if you take 100 long shots and you get 10 of them, like, that's a great return. Like you had10 great wins, right? And so like applying for the Zapier No-Code Contest was a long shot. Starting Opsy was a long shot. Like before I started Opsy, I started like another little side business that like did not work,you know? And like some things aren't going to work. But you know... if like the universe told you that like you were going to be successful on your fifth shot, you would like love the four failures that came beforehand because you would know that like number five was coming. And so I just like try to like approach life that way. And I get that this is all very general advice, but I think it's the best advice because I don't think with ops... I don't think it's about what certifications you have or necessarily the exact experience. It's just about that willingness to like take on those special projects and figure things out and meet other people and network and share what you're doing. I think that those are the two things that have been really key for me.

Kelli Yeah. Well, speaking of advice, what are you working on this year that you'd like advice on? What are you trying to learn or get better at?

Caro That's a good one. I need two things. One, generally I'm just trying to figure out how to stay ahead. I think especially being in an industry - when we think about the hiring part of Tech Ladies specifically - that market is just changing. So I'm just constantly trying to think about to what degree do we stay the course and to what degree do we test other things, right? Because we tested something new with the Candidate Database and it was a huge win for us, right? And so how do I think about what job seekers are gonna need a year from now and six months from now? And what companies are gonna need to hire great talent in six months or in a year? And what are our community members gonna need to be successful? Cool, we can give them leadership training. We can give them support. What else are they gonna need? And yeah, it's really general. I think... I just like am trying to balance that with the interim and the short term. Yeah, I think it's just on a different scale as GM than I ever had, you know, in like my previous ops roles.

And then I would say very specifically I have been very proud... like I have an email system and it works. And I know exactly how I handle like my inbox and you know, and it just doesn't work anymore. Ithink like the system I've used for like six years, just like I just have too much email, too many individual email inboxes. And I'm just like trying to find an email inbox tool that I like. And my problem is that I have a Mac, but I also have an Android, and so I need... So many of these apps like only work on Mac. And I'm like,"That's fine, but then you have to reverse sync so I can use the Gmail app." I don't know. At this point, I'll take any and all inbox management tools, apps, recommendations. And yeah, I feel like I'm getting... I have too much incoming, and I just like need better organization. So that's something I'm working on right now. Yeah, both of those things.

Kelli Oh man, you're teasing me with that one. You know that I am the tools lover over here.

Caro Oh my god, the tool queen.

Kelli Already given you a thousand suggestions.

Caro I think all of your recommendations came from podcasts too, which was also very on brand. You were like, this podcaster I love loves this one.

Kelli Yeah. 100%. So y'all keep bringing in those tool recs, both for Caro and for me.

So this has been amazing to get to talk to you. And, even though I've been here for a lot of your journey, to get to kind of hear you look back on it and reflect on it and also share so many insights. I know that I have learned so much from you over the years, and I'm so grateful for that.

Caro I got you.

Kelli And so grateful for the Opsy community too and all the amazing people there. So thank you for letting me come and turn the tables on you. This has been a great time, and I hope everybody appreciates everything that Caro is doing for us.

Caro Well, thank you. And thanks everybody for listening and joining us today. Have a great day, week,month, life. And stay Opsy, folks.

Thanks for listening to Opsy. You can find resources and links from this episode in the show notes at opsy.work. And 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!