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The Art of Failing Fast & Learning From it in HR

By OpenComp


The venture backed ecosystem is intimately familiar with the importance of “failing fast,” especially in times of economic uncertainty — just so long as you learn from it.

In this conversation, serial HR executive Jessica Marucci shares top lessons from her decade at DigitalOcean as it scaled from 5 to 500 employees, first in the role of finance manager then director of employee experience - as well as what’s she’s doing differently at Catalyst Software in her role of VP of People & Places.

Join us as we discuss:

  • Common HR mistakes during economic shifts
  • Top reasons for employee attrition today
  • How to encouraging employees to vocalize their needs to be productive at work





CAITLIN ALLEN: And then Nancy will just do what we normally do is like, I'll introduce myself, you can say you're there too. And then we'll, that'll be basically the introduction. The venture backed ecosystem is infinitely oops, wrong word. Alright, and I'd forgotten to introduce ourselves. So, hi, everybody, Caitlin Allen here, one of your co hosts

NANCY CONNERY: Nancy Connery, the other co host, co founder of open comp and principal at Connery consulting. Thank you for joining us today.

CAITLIN ALLEN: Yes, thank you. Today we are going to talk about the art of failing fast and learning from it when you're in a human resources or people capacity. The venture backed ecosystem is intimately familiar with that term, the importance of failing fast, especially in times of economic uncertainty, just too long, of course, as we all learn from it. So in this conversation, we are going to talk with serial executive in human resources, Jessica Maroochy, who is who will share with us the top lessons that she's learned from her decade plus at Digital Ocean as it scaled from five to 500 employees, first in the role of finance manager, then director of employee experience. And lastly, we'll dive into what she's doing differently. And the same at catalyst software, in her role of VP of people and places.

JESSICA MARUCCI: Thank you, Caitlin.

CAITLIN ALLEN: Thank you so much for being here. Jessica. We would love to start off with a fun fact about you. What are what's call it one or two things most people don't know about you. Try OpenComp's comp tools.

JESSICA MARUCCI: I would say the first isn't a layup for me. But commonly misconstrued. I am Lebanese I'm 100% Lebanese, which is extremely rare, we did a 23andme with my family, and I'm literally 100% Lebanese, it's the most boring 23andme You've probably ever heard of. And I decided I had to be in tech in high school in order to go to a high school that I wasn't zoned for, and I swore I would never be in front of a computer my whole life. Fast forward to here, I am not necessarily an engineer, which is what I would have been aspiring to be at that point. But I'm still working closely with engineers and tech. And, shockingly, in front of a computer for the rest of my life.

NANCY CONNERY: We'll Yeah, I was gonna say if your days are anything like ours, I think all three of us are in front of a computer all day almost every day.

JESSICA MARUCCI: Exactly. It was just a funny misconception in high school, like what you think you want to do and how you end up here. Obviously, the world transitioning to all in front of a computer has been the big change to

CAITLIN ALLEN: well said. We've already heard a little bit about your background, Jessica. But Nancy and I were were wanting to ask how someone gets promoted from finance manager to Director of employees.

JESSICA MARUCCI: It was so it was a hat that I always wore. Very early on in a startup just like probably everyone that's listening to this might have even had the same experience, you're wearing every single hat that's possible. And it was very easy for me to roll up my sleeves and just do whatever was necessary to be done at the time. I at the founders previous company, I was doing all of their QuickBooks, their AP, their AR, the payroll, the office management, anything that was not tech was just asked Jessica and that transpired and grew and grew as Digital Ocean grow. And when I went on parental leave for my first child, I did some soul searching at that time, too, and came back and we needed a VP of Finance and we hired them. And every time the first of the month came along, I was miserable, doing QuickBooks all day and contacting customers for payments. But every other day of the month, I love my job and what I was doing and had a conversation at South by Southwest with my VP of strategy where he's like, You got to take this hat off, you're gonna get replaced if you don't, because the company's doing very well. And we need a true and real finance person, a CPA, someone with a finance background, not just someone to do the books here and what we really need you to do is take on employee experience exclusively, that's where you thrive. That's where people come to you for that's where you've had the largest improvements and growth in the company. And people feel and enjoy the culture that you've built and been a part of building, take off the finance hat, whatever the manager, he wasn't even my manager. He was just a VP of strategy, having a brunch after like our big party and I went home and cried and I was like they're gonna replace me and he's like, my husband was like, there that doesn't sound like they're gonna replace me. It sounds like if you stay in finance, you're gonna get replaced. They can't replace you on people and you That's what I did, I took off the hat, pass it on to true finance people got to do what I loved and was did very well at 24/7. And I think my career completely changed at that point.

CAITLIN ALLEN: And we are so excited to dive into some of those lessons, you you said in our prep call that you were excited to join catalyst software to do all the things to use your phrase, right that you learned the quote, wrong with this time around, I would venture a guess that if you were there for a decade, you probably did a few things, right. But I'm curious to hear what some of those things are.

JESSICA MARUCCI: I think it's more on being proactive versus reactive. We were as we were growing and building a scale, a company that was just scaling extremely rapidly. We kept running into walls of what people wanted, what people needed, what they didn't have. And I knew coming into catalyst that I wanted to build it before it was asked from us. So perfect examples, being levels, feedback cycles, compensation bands, things that you take for granted, when you're in conglomerate, monster organizations or, or the Googles and Microsoft's of the world. They already have all this stuff planned out. And that's what you're signing up for. Startup life is a different world. And if you don't have the core foundation of giving people what they need to know that they can grow here, they could develop, they can communicate properly, they can get feedback from their manager, they know what they're doing wrong, they know what they're doing, right. And starting that, from the beginning from scratch, was just way easier to handle and support a culture that people want to be a part of. differently. I know it was like a leg for comp too. Sorry, what, Nancy

NANCY CONNERY: I completely agree with you that startup world is a whole different world. It's not for everybody. But if but if it's for you, it's an it's an amazing ride. So sounds like you've had an amazing ride. So congratulations. As the economy has shifted very quickly, in the last few months, you know, what are some common mistakes your team hopes to avoid making? And how are they how are they staying, you know, staying in their lane and staying away from making those actual mistakes? OpenComp's comp tools are the best.

JESSICA MARUCCI: That's a great question. And obviously, something we're learning from and doing right now. I think we all had grand plans for spending and employee experience pieces and events, maybe that were happening and read the room. Does everyone want a trinket or piece of swag. If you're telling them we don't have the money to spend on a new a new software that they have? Probably not. So recognizing what we planned for the beginning of this year, is out the window. The economy has taken a downturn, we have to plan we have to be efficient with our spend, we have to be efficient with what we're planning for. And we have to truly spend on things that are going to give us an ROI. And that ROI is engagement too. I don't want to just do an escape the room virtual event just to do an event and check a box. What do people really want? What do they want to hear from and who do they want to hear from and a term that we just recently did is literally that like canceling whatever event we were going to do that was going to probably have 20% attendance. And we have our ERG, the Latin X group planning all of our events for the month and very simple things like Latinx artists at the beginning of our all hands meetings and be wrong meetings in the background of our organization of our office during the day doing a Latinx one on one or a q&a during one of the lunches with some employees that volunteer to do. So that's what people want to hear and who they want to hear from what they want, how they want to spend their time getting to know their employees versus just doing virtual events to do them.

NANCY CONNERY: Yeah, fascinating. I had a conversation similar but different in that whole vein this morning around, you know, how do we how do we bring lnd internal instead of hiring the external vendors and you know, what is the value and reading the room and just the very messages that you you'd succinctly brought to the top of mind as well.

JESSICA MARUCCI: And unfortunately, those are the things that came up because of the economy and the downturn. It would have been a much more a quarter from now looking back on. Why did our attendance drop or what are we doing the right stuff still? And just because we planned this three months ago, should we still execute on it? Like do people care about the same thing they cared about three months ago today? So keeping things fresh and relevant, I think is really important.

NANCY CONNERY: Yeah. And no, they don't care about the same things. Point blank.

JESSICA MARUCCI: boards don't even care about it according to my entire network like everybody's kinda feeling a lot of whiplash from what the industry is telling us what it's like to be in SAS right now and what the board directions are in preparing to buckle down for the end of the year or beginning of next year. Yeah.

CAITLIN ALLEN: So events, swag, those are both off the table. What are the other things that are top of mind for you? Is retention of their?

JESSICA MARUCCI: Yeah. So that was like number five, I made note to myself, like, retention is huge. And you want to be able to retain especially your top performers and high potential employees who communication and open comms with everybody all the time. So for every organization, that's going to look different for me, I'm doing surveying right now, in addition to, I'm fortunate enough to have a business partner on my team that's actually going out there to talk to employees, and whether it's in a formal state interview setting, or it's just a catch up with employees, just to understand what's going on what's making them tick, why, why are they still here, we're all getting recruiter messages. I know for sure, I would bet every dollar that I have that every single person in my company has gotten a recruiter message in the past two weeks, like they all exists, they're throwing blanket nets out to get as much attraction as possible for what that's going to look like. What's keeping you here, and having those conversations very regularly and what it entails. And don't let it just be a conversation, put some action behind it, you're hearing a theme of what's going on with these people. And, and this is what I care about. Okay, let's turn that into action. And we've set up a couple of goals through the end of this year and the beginning of next year for putting those things in place. And one of the things that has continuously come out is growth internally, and internal mobility. So we actually have a senior pm who used to be in CES. And that was one of our success stories. I have an InfoSec engineer who wants to go in software engineering, supporting them there, I have someone in CS, who wants to be in product, giving them the level of exposure, putting them in the room with product, people on product calls to understand what it's going to look like to make that transition in their career. And hopefully give them the opportunity to do that here. Where if you're limited to headcount, if you're limited to salary, or huge baller raises, you're not limited to giving people the growth that they want in their career today. Yeah, that's,

CAITLIN ALLEN: that's when we've heard from our team to about growth internally wanting. We're in the process of putting together our leveling framework. So I think that'll help for part of that. But wanting training and opportunities for learning and growth are the exact same. And I heard this morning from someone on my team that he was helping a friend over the weekend look for position, that's the same as the one that he has. And he did a deep dive into how compensation has shifted since he was hired last year. And it's it's changed pretty dramatically to that, which was a I knew that conceptually, but it was a very close to the heart moment, shall we say? Comp tools from OpenComp are most loved by customers.

JESSICA MARUCCI: People also care about things differently now post COVID. So I would answer this question completely differently in 2019, than I am now. But specific to compensation. Looking at the full package, I'm getting a lot more people assessing health care and benefits than I ever have before. And there's two levels to it. One level is obviously a post COVID world where people have had to use their health care, and they know what kind of impact that it has on their dollar and what they care about. And then the other side is a targeting more mature employees who are later stage in their career who are factoring in health care for their children, my kid needs braces, and how much is that going to cost me? Or when I'm going for all of these checkups very regularly with multiple children or my spouse who cares about it? Like what is that going to have a second matter? So going upscale on experience usually ties to a bigger factor on comp as a whole looking at the package entirely. And what does the work life balance look like? Everyone talks about it? What does it actually mean in practice that catalyst? And how do we encourage people to shut off at the end of their day or take off regularly to make sure that they don't burn out?

NANCY CONNERY: How do you how do you weave in the work life balance? I mean it I think it's fascinating in this post to COVID world that they're some of the barriers have been broken down. You know, most people work from home now. And how do you really how do you encourage people to shut it off and have that separation?

JESSICA MARUCCI: vocalize it from the top down all the time? is definitely one aspect where my CEO is the first person who he went to Italy and he's shut down, I'm not available. I'm on PTO, I'm with my wife. And that might mean that he went really hard the first a whole month leading up to it, making sure He's tying all ends everyone has what they need, how they're completing where we're going to be, what's the schedule look like this is in my absence, what you're going to need. But then when you take that time off, actually shutting down for PTO in those scenarios, respecting your time during the day, put your childcare pick up on your schedule, I tell people all the time this I'm like, Look at my calendar, you see, I have my drop offs and my pickups, no matter what, like, that's something that I have to do. Did I do it in pre COVID? World? No. But there's a different world now. And just having the flexibility to be able to be home and do my take my lunch break, pick up my son, drop them off, bring him back to my nanny, come back online gives me a nice balance of being the mom that I want to be and being present, even if it's just pick up and drop off, it's still something that matters to my family and is impactful to my children. And setting that from the top down also makes a huge impact. Because people witness it. And I had someone on my team who wasn't putting it on their calendar, and she was like, Oh, is it okay, if I take this from the phone, I kind of like, put it on your calendar, block your time, like do that. That's an important time you have to do it. And if you want to take calls, take calls if you want. But if you don't block your time, it's really important to do mental health Fridays, once a month, we give everybody off. And that's very different than our unlimited PTO. Because it's very different. When the whole company shuts down and you're not missing an email, you're not missing a Slack message it and that truly gives you the opportunity to shut off. And we do that twice a year for a week as well. We just did it in August for the first week of August. And we do it again between Christmas and New Years where catalyst stops. And we will pick back up as soon as we're back altogether and just get give everyone that chance to do what's important for them.

NANCY CONNERY: That's great, what a great way to to respect and pay back to your employees in other ways than just pure compensation. So I commend you and the CEO and various leaders for for the the culture that you have created and instilled during very interesting times. Yeah, yeah. No, it's, it's admirable. Yeah, what is one initiative, you know, goal or piece of advice that you plan to operationalize in the next few months, you know, before the year wraps up,

JESSICA MARUCCI: I think the internal mobility guide, tying to what we've been doing organically is actually going to be a great thing for people to visit and have as a document. So build build out what does it entail to transition from one role to another? What what what needs to be true for this to happen? And how can we support you in what this looks like? So actually putting like, what has gone on organically into a system and process, I think that's going to go a long way. And just continuing to build out a people wiki. Great that we have a five person team great that we're all on Slack very regularly great that you could schedule a meeting with my business partner, myself, or really anyone on the HR team whenever you want. But some people would rather click endpoint and find and just read it over and understand, okay, this is what I need to do. This is where I find this, this is how I operate. This is what's needed of me, and just being able to document and prepare to scale. Because it's wonderful that we're not your average startup. And we have all of these systems in place to make sure that you feel structured and supported and you have your career growth ability. It's another thing to go and read on it and find a whole documentation on what it looks like and what has been done before you and recognize that nothing is in concrete, like we could change, adjust and edit anything as we want moving forward. But giving people the ability to know that they have the chance to grow here and really putting pen to paper on what that looks like I think is huge.

NANCY CONNERY: Yeah. And also educating them in different ways. And you just referenced the different ways that people learn and absorb information. And so the very fact that you honor that is great as well. And what about next year as you think about next year and goals and such.

JESSICA MARUCCI: Next year, I think planning strategically for how we want to bring people together. We recently got together in June, the whole entire company, at an off site in Florida and what happened organically in people just meeting and being in a room or being on a beach with others that they will never have met before. There's just something that builds a momentum and how we're operating for that. And we're planning for what that's going to look like from a physical standpoint and then drawing on that on a team by At basis for what is it going to look like for every team to get together? What are the goals that they need to accomplish? What is coming together in person going to entail? And what's the ROI to the business and what they're setting out to achieve prior to meeting and what they're getting back and how they're reporting and circling, circulating it around? I think that's one of the bigger initiatives for 2023. And then just making sure kind of back to the beginning of our conversation, how are we spending, HR needs a very close tie to finance and making sure we're spending things on spending on the right areas and what people care about the most and making sure they know we're spending it, and we're spending it on them, and we care about them. And that's something that that matters, and how we operate and getting them to, to feel supported. Thank you.

CAITLIN ALLEN: We all got together last week, a couple members of the executive team Jessica in person. And I swear we did more in two days than we've done in two months. It was just all levels of productive. So I'm resonating very deeply with your comments about getting together in person. And it is the new challenge we all get to figure out in this hybrid work environment

JESSICA MARUCCI: approach. Absolutely. And I bet that momentum is carrying on in your meetings now virtually, where it was like, Yes, this is what we talked about, let's get it done. And you know what to do. And it's, it's, it's crazy. But this is the world of where we're gonna live moving forward. So making sure we could plan accommodate for it and, and budget for it the right way. So that we can ensure that people have the face to face time that they need with their teams, and then also be able to be refreshed, recharged at home, to take what they learned in those conversations. And in the non Zoom meeting where you just had like a chat while you're having coffee to learn something about a person and take that into their next into the next role.

CAITLIN ALLEN: This we've touched a lot on effectively, like the art of learning in this conversation. And some of that, I think is mindset. Some of it is skills you develop over time. So I'm curious as a last question, what's one thing you would tell our listeners to remember about how to keep their learning chops up to snuff?

JESSICA MARUCCI: Especially in HR, but probably works in every industry have a network that you rely on. So a group of people that are your peers, that you can rely on for information that you need, or just seeing what they're going through. So I'm in an HR networking group, and it's email, predominantly with a one time meeting, in the morning or in the afternoon, we alternate every single month, we have different topics based on what's hot during that time. And there's just something so refreshing about knowing you're not doing this alone. You don't have to reinvent the wheel, there's a good chance the wheel was already built. Someone already had this, this thread already existed three months ago that someone else was going to vote and everybody chimed in on their experiences. And I find myself reading threads that have nothing to do with me that I have not experienced yet just to learn this is what's offered. This is how other people are operating. This is what they're doing. This is how they reacted to it. And seeing the different ways that people responded as a part. And then I'm like googling their organization. How large is their company that this is what they did. And oh, this is remarkable. And like I'm like on LinkedIn researching, going down rabbit holes in a much better way than going on an Instagram rabbit hole, going on a LinkedIn rabbit hole to figure out what what it what this company did and how they responded to this crisis is the best way to learn and know knowing that you're not alone is huge, especially in people. My former boss at Digital Ocean used to tell me like it's really lonely at the top, you have to have a team you trust and a team you care about like, because you're when you're a leader in HR. Some people never get past you being the HR leader and they're not going to be your friend. They're probably being fake. They might not be as raw as they would if it were a different role or a different department and I take a lot of pride in breaking down that fire barrier as an HR leader where I'm still human, I still know how to fund I could still talk to you about whatever's going on in your world. But who are we talking to as HR leaders and who are we able to go to without offending upsetting, making it about someone at the company? And having a network group or a networking group of your peers is crucial and critical to me? For sure.

CAITLIN ALLEN: You heard it here first and networking community of peers over Instagram rabbit holes.

JESSICA MARUCCI: Yes. That was not scripted, but it's definitely true. I've gone on all kinds of rabbit holes scenarios, but it's really helpful to have your own peers in your or industry.

NANCY CONNERY: I mean, I think of you next time I'm on LinkedIn in about a half an hour here so

CAITLIN ALLEN: Well, Jessica, thank you. This has been wonderful. We appreciate you. You lending us your time.

NANCY CONNERY: Thank you so much.

JESSICA MARUCCI: Thank you. I've enjoyed chatting with you guys. Hopefully I gave a couple of nuggets. It was great.


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