Find INSPIRATION for GROWTH | Trainual Chief of Staff Chelsey Krisay (Podcast 230)

Transcript of a Cameron Herold podcast (Second in Command / Podcast 230) interviewing Chelsey Krisay, Chief of Staff at Trainual. Chelsey recounts her career start at Organized Chaos (operations consulting), joining Trainual as an early employee when the company transitioned from consulting to a product (January 2018), and helping scale Trainual (from 1 to ~90 employees). The episode covers fundraising (convertible notes in 2018, a Series A of $6.75M in late 2019, and a Series B of ~$27M in 2021), Trainual’s product positioning (employee handbook + training platform for SMBs, mobile apps and browser), go-to-market focus (companies of roughly 5–250 employees, franchises), and operational practices around remote work, meeting rhythms, and company culture.
Questions this video answers
February 20, 2023 (per episode metadata).
2016 (joined Chris at Organized Chaos in 2016).
January 2018 (stopped consulting and focused on Trainual).
Series A: $6.75 million (raised around November 2019, per transcript).
Series B: approximately $27 million (raised in 2021).
Chapters
I was so worried about like always.
Getting A's in all of my classes.
Stop being so hard on yourself. Don't be such a perfectionist. It's okay to mess up. I think you learn so much when you mess up and at the same.
Time, there's always going to be things.
That you don't know.
Today is Trainual's Chief of staff, Chelsea Crisset. Trainual is a leading SaaS company that helps businesses automate their onboarding and training by documenting every process, policy and procedure in one simple system. Part of helping Launch Trainual. In 2018, Chelsea was the first employee at Organized Chaos, an operations consulting firm also founded by Chris Ronzio, CEO of Trainual. In her five plus years at Trainual, she's helped grow the team from one to 90 employees and growing they now exceed 10 million in ARR and earn top rankings on notable workplace awards like the Inc. Best Workplaces. Chelsea is a Connect board member for Boys and Girls Club of the Valley in Arizona, enjoys hiking with her rescue dog, enjoys yoga, spin and traveling in her free time. So, Chelsea, welcome to the Second in Command podcast.
Thanks, Cameron.
All right, so a fellow lover of travel, where are your favorite destinations you've been to and where do you want to get to next?
I just took my first trip to Europe in May. I went to Italy for two weeks and we went to, I think we were in like eight different cities, so that was really cool to finally get over there. And I actually just got back from Costa Rica last week. So this year has been a big year for travel.
Awesome. Whereabouts were you in Italy?
We started in Venice. We went to Verona, Lake Como, Milan, Cinque Terre, Florence, Tuscany, Rome, and then back to Venice.
Nice. Got engaged in Venice. Great city.
Did you?
Yeah. That whole Cinque Terre area is amazing too. Where would you tell people if you had to go to one spot in Italy? Where would you point them?
Oh, my gosh. I really liked Venice. I think that, like going to Europe for the first time, that was an incredible city to land in, you know, boat over. That was really cool. And I also really liked Rome. Rome still had the like big city vibe, but so much culture and being able to see the Coliseum and everything, that was really cool to me.
Yeah. For your first European stop to be Italy. And then like you said to literally like, if people haven't been to Venice, they don't understand how confusing it is to come from the airport and have to get in a boat to go to your hotel or your Airbnb. It's like Wait, we're on this river in a boat and you're going, where the hell is it? And you arrive and you're like, what? It's just. It's crazy. Yeah. Well, welcome to the love of travel. I'm glad it's on your list. So telling me a little bit about Organized Chaos and what that company was doing and what you kind of learned in those early days there that you brought with you over to Trainual. And then I'll get you to kind of update us as to what Trainual is too. Sure.
So when I first met Chris, our CEO and founder, I was working at a boutique marketing and PR agency. And I'd been there for about five years. I worked with a ton of clients who did everything from digital marketing to traditional advertising. Websites, planned events, like, you name it, I did it. And I always really liked being a jack of all trades there. I met Chris through the EO Network here in Arizona. He knew the founders of that company and he came to do a presentation for our team on Inbox Zero. So getting your inbox down to zero emails every day all about, like, efficiency, productivity. And I just loved that. I was ready to kind of take my next step. I met with him at a coffee shop to actually just pick his brain about other companies that we're hiring. He started, you know, asking me questions about what do you really like doing? What do you not like doing? And he was like, would you want to come work for me? And I was totally caught off guard. Like, that was never the intention of that meeting. And he told me that he had this operations consulting company because after years and years of having his video production company, he had a lot of people asking for advice on how to scale and make their companies run more efficiently. So I took the leap and started with him as his first employee over there at Organized Chaos. And we would go into businesses and we'd interview every employee. We would evaluate everything they were doing with systems and processes, and anytime when we could include technology and software to make things run better, we would. And in those days, even if there wasn't off the shelf software available, we actually eventually had a dev team and we could create custom software for these businesses to help them operationalize everything. And so we did that. I started with him in 2016 there. Trainual was code that he had bought from some ASU students here in the Phoenix Scottsdale area. Very, very like MVP product. It was nothing great, but it was just an add on for our consulting clients. And like I said, it very MVP version, bare Bones, not what it is today at all. And we started to have a lot of people ask about Trainual because they were hearing about it through word of mouth from consulting. And at the same time, we were just realizing that consulting wasn't allowing us to have the impact on the number of small businesses that we wanted to. We were getting into real nitty gritty stuff where we would be going into businesses. I remember one example where I was helping get a company set up on a new project management system. And I was spending all week there getting all of their stuff documented. And we were like, we just don't want to do this anymore. So I guess it was Like December of 2017, Chris sat our team of four down in the conference room and said, hey, how do you guys feel about going all in on Trainual? And my first thought was like, I know nothing about software, but sounds cool. And so January of 2018, Chris and I stopped consulting work. We still had Lisa and Zach on our team, were still doing their normal day to day to just kind of COVID the bills. And so I became the de facto first, you know, CS person. I was the first salesperson. I remember having a few customers ask like, are you the only person that works here? And I was like, no, no, just I'm like your dedicated rep. Everything that you send, it'll come to me. And we just bootstrapped it for a while. But I guess to answer your question about kind of what I learned from organized chaos and brought over to Trainual, really just having like a get it done mentality and figure it out. And I think that's been one of the biggest challenges for me. There's been so many things that I've never done before. I have no idea how to do it. But you just kind of have to figure it out. And oftentimes Chris was so busy that, you know, I had to ask people in different groups I was in, had to ask people outside of those groups and just figure things out.
I like that you actually mentioned the groups because one of the things I was going to ask about was. So Chris was an EO member, was your former CEO then of the company, the marketing agency, as an EO member as well?
Yep. Correct.
Who is that?
So my sister in law, Alexis Crisset, and then her business partner, Melissa dijonfilippo.
Oh, I know, I know. Melissa.
Yep.
They're both in EO.
Okay, very cool. Yeah, so I've spoken to that EO chapter in Arizona three times over the last 13 or 14 years. So I've Met Melissa. I don't know if I've met your sister, your sister in law yet, but yeah, I definitely met Melissa. It's interesting because you were a prior member of the CEO alliance. And what I like about Chris joining a mastermind group like the Entrepreneurs Organization is we realize we don't have to be the smartest person in the room. We just have to be in the right room. I, we have to surround ourselves with a lot of these other people and continue to learn from them. Does he still participate in those kinds of organizations as well? Is he still a member of, you know, mastermind groups or business groups?
He is not EO specifically anymore, but he is a part of a few others.
Which ones is he in?
He is in YPO and I believe still Startup Arizona he's actively involved in as well.
Okay. Yeah, I know some people in Startup Arizona. Yeah, the YPO is almost the, the big brother to the Entrepreneurs organization. So once you get your revenue level above a certain level and you got a certain number of employee count, then you can kind of graduate into ypo. I've got a bunch of really good friends that are in the YPO chapter there as well. Max Hansen, I don't know Max Hansen from Wisecouts, but he's, he's one of our big partners on the executive recruiting side. We send a lot of clients to them. So, so from, from, from organized chaos. And then you kind of got into Trainual and started to bootstrap Trainual. Have you raised money with Trainual or have you just grown organically? How have you grown that way?
Yep. So I guess it was back in 2018, so the first year that we were really all in on Trainual. We had some convertible notes with just some very early believers, some friends and mentors of Chris's. They invested early on 2019, towards the end of the year, I believe it was November, we raised our Series A. So we raised a 6.75 million Series A and then 2021, a little over a year ago we raised to 27 million.
Serious be round.
All right, so that's a serious chunk of change to bring in. So when you bring in 27 million, how does that change the organization? What changes at that point?
I think the biggest thing, whenever we raised especially I mean Series A most of that, I mean there was a time when we had more credit cards than employees at Trainual. And I mean we were just putting everything on credit cards. And I know Chris has stories about that where like his wife went to get groceries and call them In a panic, like, hey, every single credit card is getting declined. And for some reason I just always trusted that Kris would figure it out. But series A was really just to, you know, cover all of the pay off all of the credit cards and help us hire a few key people. And then with our Series B, that really helped us to make some key hires that we needed and then also really elevate the product. So we started, you know, with a very lean product design and engineering team. And with our Series B, we were really able to grow that. And now we have several different squads that are working on different experiences within the Trainual app.
What lessons do you think you pulled from that bootstrapping time at Trainual that you still carry with you as an organization today? Like, what things do you still do that culturally align with being the scrappy startup?
Sure. So what I was going to say was just the really like, scrappy mentality and figuring out how to get things done without always having to spend a ton of money. I think that has really influenced our culture tremendously. People aren't just quick to make purchases. We're not just buying software because we think that it could help. We're really evaluating things. We're making sure that we're spending our money wisely. We've been really efficient with our spending too. Even looking at marketing and advertising, we're constantly evaluating things. We've become really data focused. I think that's the biggest thing that's carried over. Just making sure that we're spending wisely matters a ton. Because looking back at Covid, looking at the great resignation right now, people are worried about how much money we have left and am I going to get laid off? Like, what if things go bad? What if there is a recession? And being able to tell the team that we are spending really efficiently and that we have Runway to get us through X months or years, I think that's really important.
Yeah, it's comforting for them for sure. So tell us a little bit about Trainual. What's the company do? What's kind of the kind of core of your SaaS product?
Sure. So Trainual is a software that allows you to document all of your processes and procedures in one place. So everything from your org chart to the history of your company to unique processes that are specific to a department or a different function within the company. So think of it as your employee handbook that you traditionally used to get a big paper stack when you started a job. And probably no one ever read those. And now Trainual is just at your Fingertips. We have a mobile app for iOS and Android. You can use the desktop version on your browser. And you're able to train your team so efficiently. So, like, when we have a new hire start, it's amazing because, you know, we do a lot of stuff in person. We still try to do onboarding at the office whenever we can. And then we kind of give people time. We block it off on their calendars, train you all time. And they go through and they learn all about the company. They learn about each department, they learn the history of the company, they can see pictures of past retreats we've gone on. They get like a really good feel for culture, all of that, and just being able to search for things when you need it. It's just at your fingertips. We can have video in there, photos, makes it really easy people to find things they need.
And is Trainual still focused on the core kind of onboarding and the hiring of people? It's really more the onboarding, right, or have you expanded the software into processes across the whole organization forever?
Yep.
So it's for everything. So it's used heavily for onboarding, but we obviously want people to use it for just ongoing training as well. So anytime you update a policy or a procedure, you're able to actually send out a push notification. So, for example, we had a lot of different COVID policies for the office and travel, different things like that in 2020. And anytime that we made an update, we were able to send out an alert that things had changed. Even on our company retreat. This is a great example. We just went to Park City with the team in June. It was the first time we were able to take almost the entire team somewhere in a long time. Everything that people needed to know about the retreat was documented in Trainual. And then if anyone had questions like while they were there or right before it, how to book a flight, how to get reimbursed for something, they could.
Pull it up in their phone or just log online.
So are you now competing against Process street and Suite Process and like companies like that, or are you still in a niche of your own because of the heavy focus around the training and.
Onboarding, I would say we're still like a niche of our own. So I've used Process street for onboarding with a different software company, actually, and it was more of a checklist. So Trainual isn't a checklist. It's somewhere where, like I said, much more your employee handbook. It's where everything lives. And it's kind of a hybrid between Like a big enterprise LMS and Google Docs. So Google Docs, you can't assign things to different roles, you can't track completions, but with Trainual you can do all of that.
That's true. So it really is more the manuals that are needed for different areas of the business and the onboarding and growing of employees. Whereas the process street and suite process are more just here's the checklist to do something. But there's no, there's no training component behind any of their stuff. So you are very different that way.
Yeah.
Okay, got it. Because it's interesting because I keep hearing from a number of our members, they a number of our CEO alliance members that they use Trainual and Chris has been a past speaker at our CEO alliance events. You were a past member at the event. So I'm sure you've had some, you know, ability to infect the ideas for the group already. But I think you're starting to get some brand awareness now as well. So where are you focused in terms of your growth and your sales and marketing growth? What's Trainual focusing around?
Sure.
So still a small business focus. That's always been our passion since Organized Chaos Day is we wanted to help those smaller businesses. We never wanted to get into like enterprise mid market. So we're really targeting companies with five to 250 employees. Anyone who has repeatable processes. So whether you are, you know, hiring or you have a lot of turnover, those are all like perfect situations where Trainual would be helpful for you.
Got it. So that actually might lead into one of my questions as well. Does the fact that you're focusing around the small to small medium sized enterprise and not going into the enterprise level clients, is that allowing you to say no to a lot of the feature and functionality requests that the big organizations have?
Yeah, it's kind of always been like an ongoing battle because there's definitely features where more enterprise customers want those or they're a prerequisite to even sign up. And I think we've really had to draw a line in the sand and say we're not going to do these or we are going to do these. Because for a while we were kind of like, I don't know, what do we do? And we would tell people we'll bring it up with the team. And now it's a lot easier to just say like, you know what, this isn't a good fit for you.
Yeah, it's interesting. I've found that so many software programs and products would be so much More profitable as companies. If they would say no to so many of these requests that are really false objections to just buying the software in the first place. Like if.
Yep.
If it was just like, no, this is the laptop. We can't tweak it, we can't make. It's just, do you want this laptop as exists? We can't make it different. Yeah, you have to learn how to handle those objections or you find the client niche. And I think that's really smart that you're staying there. Are there companies out there that you compete against that are more on the enterprise side or do they start doing it on their own when they get to that level?
I think there, I mean, there are more enterprise like learning management systems that have a lot of features that we're just never going to build. So they're so different from us. But I say 2 to or 5 to 250 employees, but there are use cases where we work with a franchise and maybe they have thousands of employees, but they're at a bunch of different locations. There's different instances where people will grow with us over time.
That's pretty cool because I think franchisors can be a very, very big base because they really do struggle with the training. Yeah, that was interesting. So I, I don't know if you knew, I was the second in command for 1, 800 got junk. So I took them from 14 employees to 3100 employees. And you're right that our 3100 employees, only 248 were at the head office. The other 2, 700 were distributed over 330 cities, but all those cities had 10 to 15 employees. They all struggled with that onboarding. So that's a smart niche for sure.
Yeah.
All right. Talk about the way that you're building stuff because you said that you've got kind of a really good analytics team. What do you outsource as a company?
We don't really outsource anything anymore. We've kind of brought everything in house. We did have, you know, some out or I guess it was really just one outsourced CS rep back in like 2020. And we decided that we wanted to have all of our support reps in house. So everyone's under Trainual. Engineering has always been in house too. We do work with an engineering company in Ukraine, but their employees are full time with Trainual. So we have, I believe, about 15 engineers and QA engineers over there that we work with and designers, but really everything's in house. We have like, you know, hired Some PR firms and stuff every once in a while. But we end up kind of just bringing everything back in house.
PR firms are rough, man. I would always bring PR in house too. So why is that? Why have you decided to go in house with everything? Is it because you've got the money now to be able to do it? Is it control? Is it? You know, what's the thought process behind that?
I think a few different things, but really it's just been a big cultural shift. One, I mean, it's hard. Even with the Ukraine team we work with, it's really hard with the time difference, but we make it work with some really, like early morning calls. We're starting to adjust things more and more to make sure that we can really have those, you know, teams come together. We want that team to be able to join our all hands meetings and be a part of like remote team events that we do online. Because since 2020 we've hired so many remote hires across the country that we're not just doing in person events anymore. Every time we do an in person event, we have an online like virtual event that we plan as well.
So I was going to ask about that. You know, we were running a CEO alliance event. Anyone who's listening to this podcast, the event is over. But In September of 2022, we're running an event on building a world class company culture where we have CEOs from all over coming in to spend two and a half days to talk about how to build a company culture kind of post Covid, right Where two years ago, building a company culture, when all of or most of your employees came to work in an office, that's really changed now. So what has changed for trainual? How have you changed or adapted and do you still have an office? What percent of your employees come into? Are you schizophrenic and have everybody everywhere? Where are you?
Maybe a little bit. So I think it was in probably February of 2020. We were coming up, we were at the end of our lease, we were busting at the seams. We'd grown a ton in 2019 and we were looking for a bigger office. So I let our landlord know, hey, we're starting to look for other offices. And we ended up actually having to move out in the middle of COVID and we put everything into storage, which was super. And we took a risk. We signed another lease that started in, I think September or October of 2020. And during that time, as I, as I just mentioned, we started hiring a lot of people. All across the country. So it was no longer like a requirement that you had to be in the Phoenix Scottsdale area to work at Trainual. We slowly, slowly started going back into the office. We had all of the protocols and sign up sheet and all of the things that are just so much fun to deal with. And for a while it was really slow at the office and we questioned like, was this a horrible idea, signing a new lease? And things have slowly picked up. But you have, you know, the same people that go in and then there's people that really just want to be at home. Maybe they live far, maybe, you know, they're a single parent, it's easier to be home. And then we also have people who are parents and they can't wait to come into the office and get away from their kids. So it's still really split. We will never require everyone to come in. I myself personally, I go in like two or three times a week. I try to always go in for in person meetings, especially like my weekly meeting with Chris and then my direct reports and we are moving into another, newer, bigger office probably the beginning of next year.
Have you signed that lease yet?
Yep.
Okay. There's a really great resource. A partner of our CO alliance, Jonathan Kaiser, runs a big Kaiser real estate group. So I don't know if you've ever worked with him, but he's amazing. To help you negotiate with landlords is really solid.
Yes. And we'll move into. It's just there's been a lot of hiccups with construction because that's life, right?
Yeah.
But hopeful that we'll move in early next year. And it's a nice, it's a much bigger spot than we have now. So whenever we do have the whole team come in, you know, for the holiday party, for example, we always have everyone come in for a week and we wanted a hub where everyone could work out of and we could get the whole team together.
So that's awesome. So what are you doing then in terms of kind of embracing this whole remote hires and this hybrid workforce? What are the things that you've had to change as an organization to adapt?
With the Ukraine team, I think we've always been pretty good at having remote setup. Like obviously we've gotten some different technology at the office to make having calls and video conferences much easier. But I think we've really just more than changing things, we've embraced it because we've been able to find talent from across the country and not just be tied down to only finding talent in the Phoenix area or asking people to move here. So I think it's been more of a good thing than a bad thing. And I really feel like we haven't had to change too, too much. I mean, we've always been really reliant on Slack for communication and we use Asana for project management. And then obviously with Trainual, it seemed like a pretty easy change when we had to make it. Even though we were forced into it, it felt really natural.
Yeah, that's what a lot of companies are finding. They're finding right now that there's a bit of a shift with some of the disconnection that people feel from each other that they didn't feel before COVID because they were at an office using some of the tools. There might have been a few more people that were remote. But are you seeing anything there at all that you're having to manage or help people through with a feeling of disconnection from team or. They're only on the one call a week with the team and then they're really doing work for themselves or with themselves for the rest.
Yeah, I would say we offer so many opportunities to get together with the team, whether it's the, you know, summer retreat that we go on, the holiday party and then we have remote events quarterly. There's also. We have different affinity groups that host events. We just had a big culture celebration for Culture Week, I guess that was last month and we celebrated a lot of different cultures that we have within the company. We always had a remote aspect to that and obviously there's going to be people that just decide not to come to those. And ultimately the one thing we have found is that people who aren't very engaged in those events tend to eventually turn over with the company and they look for something else. But it's kind of the, I guess that you can lead a horse to water, but you can't make it drink scenario. But we do everything. I mean, our people, ops team and Tara specifically, who plans all of our events. She does a phenomenal job. And there's always ways to interact with the team.
We do.
If you've ever heard of the Donut app on Slack, it'll randomly carry you with someone each week. So we do a ton of those. We have our weekly or bi weekly all hands meeting where we get to see everyone's face. We do breakout rooms. We always ask like engaging questions in that meeting. So there's a ton of opportunities to get to chat with your team.
Yeah, I think the you guys are doing the Right stuff there for sure. And the donut app, it's funny. A couple of our co alliance members just brought that up at an event recently and I was kind of laughing because it's when the two people get paired up and they have to go and sit and have coffee or donut together virtually over zoom. But it's great because it is.
It is like we actually had started doing it before COVID So it used to be like an in person thing and I think people would go get lunch or get coffee and now it's sometimes, you know, virtual. If you get paired with someone in the same place as you, people tend to go get lunch together or do something.
So great.
It's funny how it's kind of transitioned.
Our, our, our finance group at one attender got junk. Used to have donuts with dollars and every Tuesday they would bring donuts in and you could go into the finance department and as long as you sat in finance to eat your donut and chatted with someone in finance, you could get a free donut. And that was the donuts with dollars was they would just go in to hang out with because otherwise they're like, we're never going to meet anybody because we're all so shy and introverted. But if they come to us, then that was cool. So it was fun.
Our director of finance, this is just a funny thing, but Drew, every all hands meeting that we have every other week, he always shares a nugget and he'll literally have like pictures of like chicken nuggets on the slide. And it's always funny, but he'll share some like, interesting data findings or whatever. But. So we have nuggets with Drew, but I kind of like donuts with Drew, so I might have to.
Yeah, we'll have to tweak that somehow. So maybe he could use donut holes with Drew or something. Right. Instead of the nuggets. They could be little donut bites or whatever they're called. In the US and Canada, we call them Timbits. So you talked a little bit about some of the changes that happened post series A and post series B. I'm curious what lessons you can teach people who are listening about how to go through the process of working with the venture capital firms and how to work with your people internally and how to, you know, not tell everybody what's happening and only tell the right people and dispel any fears and rumors. Any lessons that you can give us from having gone through two rounds.
Sure. So we ended up having a really good process for this. And I think this has been one of my favorite parts of being at Trainual so far. I was super involved in the Series B fundraising round. We had an Asana board where we kept track of all of our investors and we kind of ranked them after calls. There were a lot of key things that we looked at and we always had a few different people on the calls and each person was kind of looking for different things. So I a lot of times was looking to make sure they were a good cultural fit. What would they add to the team? Do they align with our core values? Are they going to let us run things how we want to, or are they going to be the kind of VC firm that steps in and they want to take over and change how things are done? So we would take a ton of notes during each call. This is kind of a silly thing, but it was super helpful. We would always take a screenshot of Zoom so we could remember who we spoke to. Because when you're talking, I mean, we are talking to a lot of different ones and it was really helpful to have that snapshot. And then we would always kind of regroup after the calls, share our takeaways. We'd keep it all in Asana so everyone that was on the calls would write up pros and cons. Was there anything missing? Were there any red flags? And we kind of just went through the process that way. But I also did a ton of research leading up to any of the calls and I would kind of look through, see if they had similar companies in their portfolio, see how those companies progressed after fundraising and kind of what that looked like. So there were a lot of different things that we were keeping in mind. There were months where it was just call after call after call for weeks and weeks and really making sure that we found the right fit.
Do you remember some of the VCs that are involved in your Series A and your Series B? I'm sure you remember the ones in the B round, but do you remember.
The Series B was with Altos Ventures there in the Bay Area. And then our Series A was split between Math in Chicago and 4,490 in Madison, Wisconsin.
Okay, so those are some of the lessons from out of there. I want to talk. You mentioned some of the different meetings that you run with your one on one meetings that you have a one on one with Chris, and then you have one on one with each of your teams. So I'd like you to walk me through what your one on one kind of structure is. How a one on one meeting works, how maybe how yours works with CEO Chris and then how you run yours with your team. And then I just want to ask about some of your other meeting rhythms that you have as a company, but let's talk about the one on ones first.
Sure. So my meetings with Chris have kind of evolved a lot over the last year or so. So for a couple of years we were talking every single morning at, you know, 7, 8am, first thing in the morning, and we would run through the schedule for the day, we would review his notes from the day before.
And that was actually something a mentor.
Of mine had suggested that was super helpful because it always caught any tasks that weren't getting added to Asana. I could alert him of any, like, red flags, any issues going on, ask any questions. So there weren't bottlenecks for the leadership team because everyone would kind of come to me with like, hey, I need this from Chris, or can you ask Chris this? I was kind of like the gatekeeper for that. Fast forward a little bit. After hearing from so many people at COO alliance that, you know, an EA is so important, I talked to Chris and we ended up hiring an EA for him in October of last year. And Hayden was like a game changer. I mean, she changed so much. It took so much admin work off my plate because I was doing calendar management for Chris, scheduling, and there were days where that can take up your whole entire day. And then I had no time to do any of the strategy or planning work. So bringing her on was huge. And now she does those morning standups and then I just do a weekly meeting with Chris in person at the office and there I just have a discussion board in Asana where I track everything I need to run through with him for a while. You know, we'd go through different things like financials. I'm also a part of all of his one on one boards that he has in Asana. So I know what's going on with all of his direct reports and if there's anything I can do to help move those along.
But really it's always we treat one.
On ones as it's not the manager who runs them, it's the direct report they go through and they're asking questions and what they need help with and that's the same way around them with my direct reports. So Chris's EA reports to me and then our office manager reports to me and it's always their time.
So like, what can I help you with?
We have a Few different questions that send out in Lattice each week. So like what, what roadblocks are you running into? What was the highlight or like win from last week? Where can I help you this week? Where are you? You know, where do you want to step in more? Where do you want to grow those kinds of things?
Interesting. And what's Lattice? Is that as software to run your kind of one on ones or.
Yeah.
So Lattice is for performance management. So it's where we do all of like our company surveys. It's where we track enps. It's where you can keep track of praise and feedback. You can do it either anonymously or public. And we actually have Lattice hooked up to Slack so that when someone gives public praise, it comes through in Slack and the whole team can see it too.
Got it. Yeah, I think it must. I think it's a competitor to 155 and I'm an advisor.
Yeah, similar. Yeah.
So I'm an investor and an advisor in 15 5. I think that's where I've heard a lottas before. I just try to pretend that they don't exist. So what about the rest of your meeting rhythms? What other meetings do you run as an organization that you find are really helpful?
Yep. So in addition to the biweekly company All Hands that I mentioned, we also have a quarterly All Hands meeting. And that's what the whole entire team we run through okrs. We are really transparent with finances.
We have.
It's kind of like our employee of the quarter award. We call it the Wooly award. So like Woolly mammoth have a little trophy at the office too. But it got logistically too complicated mailing that out when we hired remote people.
But we give out money to people that win that.
It's all based on the praise that's collected in Lattice that I just mentioned. So it's not just the leadership team picking people. It's actually based on the whole team who they're nominating.
So the quarterly All Hands is always super fun.
We have a lot of music that's played throughout. Sometimes we even have costume challenges. So dress up as your favorite movie, dress up as your favorite holiday, different things like that with prizes and it kind of keeps the team super engaged.
And then we also do an annual.
Kickoff the week of our holiday party every year.
And that's where Chris kind of sets.
The vision for the year to come. We talk about some of the big wins from the year prior. So that's it for like company wide meetings. And then for the leadership team we have a leadership Team check in every Monday. And that's super helpful. We actually have everyone on the leadership team that's in those meetings. They post a weekly update in Slack on Friday or first thing Monday morning with like the big things they were focused on last week and then what they're focused on the current week.
And if there's something that's bolded, we.
Know that we need to discuss it.
And then once again, we have an.
Asana board where we keep track of discussion topics. So if it's something that we kind of want the whole team to, or the leadership team to weigh in on, we'll discuss those items too.
And then sometimes we have other people.
Join to kind of present on different things or we'll talk about like a board meeting that happened.
Things like, I love that you're actually keeping stuff in the discussion board instead of throwing everything into Slack. I mean, I often find that slack and email get so mismanaged when if you keep it in the discussion board, you show up at that weekly meeting, half of what's in there you don't even need to talk about anymore. Like, that was dumb, that was stupid. I'm not even going to bother. That one solved itself. Is that on purpose that you're doing it that way?
Yeah.
And even if I. If there's a time where I notice.
Something and I'm worried that it might get skipped over, I'll put it in Asana just so we make sure to cover it.
That's great. What about your growth? I mean, you've been there since the early days and it's easy for, you know, an organization to skip over top of people. Another great kind of Arizona Valley entrepreneur is Clayton Mask, who is the founder of infusionsoft.
Yeah, Clay's on our board.
Okay, so. So Clay says that, you know, a mid to senior level leader can only go through two doubles in the size of a company before they get outpaced. So you really have to continue growing your skills. All of a sudden the company's, you know, too big to run it. So what are you and the leadership team doing to grow your skills to stay ahead of the curve?
Sure.
So I feel like over the past.
It'Ll be six years for me working with Chris this November, and I feel like I've grown tremendously. Like he's always given me a ton of autonomy to really make decisions. I've run our annual planning, monthly meetings, quarterly planning, and I mean, that can be intimidating one. So I think him giving me the power to help with those big meetings has helped me grow a ton. Because when you might be the person who feels like, you know, there's times where I'm in a meeting and I feel like, oh, everyone in here is so much smarter. They have so much more experience, like, how am I going to relate to the VP of engineering? But I think we have such a great company culture. I have one on ones with everyone on the leadership team either weekly or bi weekly.
And it's always like, how can I help?
If I have questions about things, I'm able to ask them then. So I feel like I'm just growing that way through Exposure one and also through different groups that I'm in. There's been so many people from COO alliance that I still stay in touch with. I was actually emailing Derek this morning, who was on my COO dream team, and they were always a great sounding board because no matter how unique you feel an issue or a stepping stone is, someone else has been there and.
Done that and there's always someone that.
You can go to for help. But training was great with allowing employees to, you know, spend time during their week for these kind of groups where you learn a ton. And Chris is always challenging me, you know, giving me new projects to work on that are oftentimes like way out of my comfort zone and I would never ask to do them on my own, but he trusts me to do them and sets me up with the resources I need. And yeah, I feel like just every day I'm learning so much new stuff.
Awesome. All right. I want to go back to the kind of 21, 22 year old Chelsea, and she's just starting off working for the marketing and PR agency. What advice would you give yourself back then that you know to be true today but you wish you'd known back?
Oh my gosh, so many things.
I.
One, I've always been, like I said.
A jack of all trades. In college, my major was interdisciplinary studies because I couldn't decide on one thing. So I did business communication and psychology and there were people who questioned it.
And looking back, I'm like, that was.
Absolutely perfect because those are all the things I do to this day.
But I think just not being a.
Perfectionist, I was so worried about always.
Getting A's in all of my classes.
Stop being so hard on yourself. Don't be such a perfectionist. It's okay to mess up. I think you learned so much when you mess up.
And at the same time, there's always.
Going to be things that you don't know that's been the biggest challenge for me at Trainual. And working with Chris, I've been thrown into so many different roles. You know, when I going back to when I met him at the coffee shop, he asked things I didn't want to do and I said, please don't make me do sales and please don't make me do marketing or social media.
I love it.
Guess what? I ended up doing both of those things again.
But there's always people who you can.
Learn from and they can help you grow in those areas and you don't need to be the best at them because eventually the company will grow and you're going to hire someone who's smarter and better than you. Which is a weird feeling because this is another thing that I wish someone would have told me and Chris has had to tell me this. But it's okay to let go of things you can delegate to someone. Someone's going to be smarter or better at doing it, and that's okay. We hired a VP of cx, which was good because I had no experience running a CX team. And we hired a director of finance, which is great because I have no finance background. They took things off my plate, but there's always going to be more that's added on. And it's not a knock to you when you have to hand things over because you're not good at them. And I think that is still where I struggle today, thinking like, oh, if I hand this off, it means that I failed and I'm not good enough. And that's not the case. You need to give things to people who know what they're doing.
I agree. I love it. I've yet to find a second in command who has run out of things to do, so, yep, that's smart. Chelsea Chrisset, the Chief of staff for Trainual. Thanks very much for sharing with us on the Second In Command podcast.
Yeah, thanks for having me. Cameron.
One thing that you learn is how to decipher and tell a narrative from numbers. So before you ever do a commercial or mess with marketing or any of that, you need to be able to understand the fundamentals of the business.
More from Cameron

Flutterwave Former Global Head of Operations Awa Kone | When Growth Outruns Operations (Podcast 611)









