Ep. 230 – Trainual Chief of Staff, Chelsey Krisay

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Our guest today is Trainual’s Chief of Staff, Chelsey Krisay. 

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.

Prior to helping launch Trainual in 2018, Chelsey was the first employee at Organize Chaos, an operations consulting firm also founded by Chris Ronzio, CEO of Trainual. In her five+ years at Trainual, she has helped the team grow from 1-90 employees (and growing), exceed 10M in ARR and earn top rankings on notable workplace awards like Inc Best Workplaces. 

Chelsey is a CONNECT board member for Boys & Girls Club of the Valley – Arizona and enjoys hiking with her rescue dog, yoga, spin and traveling in her free time.

In This Conversation We Discuss:

• What lessons Chelsey learned from a start-up business 
• How Trainual uses their analytics to give them clarity on their growth
• What changes Trainual needed to make in order to adapt to a more remote setup 
• How marketing has helped Trainual spread their message to a wider audience

Resources:

Connect with Chelsey Krisay: LinkedIn 

Trainual – http://trainual.com

Altos Ventures – https://altos.vc/

4490 Ventures – http://4490ventures.com/

Math Venture Partners – https://www.mathventurepartners.com/

Connect with Cameron: Website | LinkedIn

Get Cameron’s latest book “Meetings Suck: Turning One of The Most Loathed Elements of Business into One of the Most Valuable

Get Cameron’s online course – Invest In Your Leaders

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In this episode, we have Trainual’s Chief of Staff, Chelsey Krisay. 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. Prior to helping launch Trainual in 2018, Chelsey was the first employee at Organize Chaos, an operations consulting firm also founded by Chris Ronzio, CEO of Trainual.

In her years spent at Trainual, she has helped grow the team from 1 to 90 employees and growing. They exceed $10 million in ARR and earn top rankings on notable workplace awards like the Inc Best Workplaces. Chelsey is a CONNECT board member for the Boys & Girls Club of the Valley in Arizona. She enjoys hiking with her rescue dog, yoga, spinning, and traveling in her free time. Chelsey, welcome to the show.

Thanks, Cameron.

A fellow lover of travel, where are your favorite destinations you’ve been to? Where do you want to get to next?

I took my first trip to Europe in May 2022. I went to Italy for two weeks. We were in eight different cities so that was cool to finally get over there. I got back from Costa Rica so 2022 has been a big year for travel.

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.

We got engaged in Venice. It’s a great city. That whole Cinque Terre area is amazing too. If you had to go to one spot in Italy, where would you point people?

I liked Venice. Going to Europe for the first time, that was an incredible city to land on and take the boat over. That was cool. I also liked Rome. Rome still had the big city vibe but so much culture. Being able to see the Colosseum and everything was cool to me.

For your first European stop to be Italy. If people haven’t been to Venice, they don’t understand how confusing it is to come from the airport and have to get on a boat to go to your hotel or Airbnb. It’s like, “Wait, we’re on this river in a boat,” and you’re going, “Where is it?” You arrive and you’re like, “What?” It’s crazy. Welcome to the love of travel. I’m glad it’s on your list. Why don’t we start with a little bit about Organize Chaos, what that company was doing, and what you learned in those early days there that you brought with you over to Trainual? I’ll then get you to update us as to what Trainual is too.

When I first met Chris, our CEO and Founder, I was working at a boutique marketing and PR agency. 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, and planned events. You name it, I did it. I always 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. It’s all about efficiency and productivity. I loved that. I was ready to take my next step. I met with him at a coffee shop to pick his brain about other companies that we’re hiring.

He started asking me questions like, “What do you like doing? What do you not like doing? Would you want to come to work for me?” I was caught off guard. That was never the intention of that meeting. He told me that he had this operations consulting company. 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.

I took the leap and started with him as his first employee over there at Organize Chaos. We would go into businesses and interview every employee. We would evaluate everything they were doing with systems and processes. Anytime when we could include technology and software to make things run better, we would. In those days, even if there wasn’t off-the-shelf software available, we eventually had a dev team and we could create custom software for these businesses to help them operationalize everything. 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. It’s a very MVP product. It was nothing great, but it was an add-on for our consulting clients. It was bare bones, not what it is in 2022 at all. We started to have a lot of people ask about Trainual because they were hearing about it through word of mouth from consulting. At the same time, we were realizing that consulting wasn’t allowing us to have an 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. I was spending all week there getting all of their stuff documented and we were like, “We don’t want to do this anymore.”

It was December 2017. Chris sat our team of four down in the conference room and said, “How do you guys feel about going all in on Trainual?” My first thought was like, “I know nothing about software, but it sounds cool.” In January 2018, Chris and I stopped consulting work. We still had Lisa and Zach on our team doing their normal day-to-day to cover the bills. I became the de facto first, CS person. I was the first salesperson. I remember having a few customers ask, “Are you the only person that works here?” I was like, “No. I’m your dedicated rep. Everything that you send will come to me.”

We bootstrapped it for a while. To answer your question about what I learned from Organize Chaos and brought over to Trainual is having a get-it-done mentality and figuring it out. That’s been one of the biggest challenges for me. There have been so many things that I’ve never done before. I have no idea how to do it, but you have to figure it out. Oftentimes, Chris was so busy that I had to ask people in different groups I was in or outside of those groups and figure things out.

I like that you mentioned the groups because it’s one of the things I was going to ask about. Chris was an EO member. Was your former CEO then of the company, the marketing agency, an EO member as well?

Correct.

Who is that?

It’s my sister-in-law, Alexis Krisay, and then her business partner, Melissa DiGianfilippo.

I know Melissa.

They’re both in EO.

I’ve spoken to that EO chapter in Arizona three times over the last several years. I’ve met Melissa. I don’t know if I’ve met your sister-in-law yet. It’s interesting because you were a prior member of the COO Alliance. 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. 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 mastermind groups or business groups?

He is, not EO specifically anymore, but he is part of a few others.

Which one is he in?

He is in YPO and I believe Startup Arizona where he’s actively involved as well.

I know some people in Startup Arizona. The YPO is almost the big brother to the Entrepreneurs’ Organization. Once you get your revenue level above a certain level and you’ve got a certain number of employee count, then you can graduate into YPO. I’ve got a bunch of good friends that are in the YPO chapter there as well. I don’t know if you know Max Hansen from Y Scouts. He’s one of our big partners on the executive recruiting side. We send a lot of clients to them. From Organize Chaos, you got into Trainual and started to bootstrap Trainual. Have you raised money with Trainual or have you grown organically? How have you grown that way?

It was back in 2018. In the first year that we were all in on Trainual, we had some convertible notes with some very early believers. Some friends and mentors of Chris invested early on. 2019, towards the end of the year, I believe it was November, we raised a $6.75 million Series A. In 2021, we raised a $27 million Series B round.

When you bring in $27 million, how does that change the organization? What changes at that point?

There was a time when we had more credit cards than employees at Trainual. We were putting everything on credit cards. Chris has stories about that where his wife went to get groceries and called him in a panic like, “Every single credit card’s getting declined.” For some reason, I always trusted that Chris would figure it out. Series A was to pay off all of the credit cards and help us hire a few key people. Our Series B helped us to make some key hires that we needed and then also elevate the product. We started with a very lean product design and engineering team. With our Series B, we were able to grow that. We have several different squads that are working on different experiences within the Trainual app.

Before I even ask you about Trainual, what lessons do you think you pulled from that bootstrapping time at Trainual that you still carry with you as an organization? What things do you still do that culturally align with being the scrappy startup?

What I was going to say was the scrappy mentality and figuring out how to get things done without always having to spend a ton of money. That has influenced our culture tremendously. People aren’t quick to make purchases. We’re not just buying software because we think that it could help. We’re evaluating things. We’re making sure that we’re spending our money wisely. We’ve been efficient with our spending too.

Even looking at marketing and advertising, we’re constantly evaluating things. We’ve become data-focused now that we’ve grown our data team. That’s the biggest thing that’s carried over, making sure that we’re spending wisely. That matters a ton because looking back at COVID and the Great Resignation, people are worried about like, “How much money we have left? Am I going to get laid off? What if things go bad? What if there’s a recession?” Being able to tell the team that we are spending efficiently and that we have the runway to get us through X months or years is important.

Tell us a little bit about Trainual. What does the company do? What’s the core of your SaaS product?

Trainual is 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. 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.

Business Growth: Trainual allows you to document your business procedures in one place, from your organizational chart, company history, to unique processes in each specific department.

Trainual is 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. When we have a new hire start, it’s amazing because we do a lot of stuff in person. We still try to do onboarding at the office whenever we can. We give people time. We block it off on their calendars’ Trainual time. They go through and learn all about the company.

They learn about each department and the history of the company. They can see pictures of past retreats we’ve gone on. They get a good feel for the culture and all of that. Being able to search for things when you need them is at your fingertips. We can have videos in there or photos to make it easy for people to find things they need.

Is Trainual still focused on the core onboarding and the hiring of people? It was more the onboarding or have you expanded the software into processes across the whole organization forever?

It’s for everything. It’s used heavily for onboarding, but we want people to use it for ongoing training as well. Anytime you update a policy or a procedure, you’re able to send out a push notification. For example, we had a lot of different COVID policies for the office and travel, different things like that in 2020. Anytime that we made an update, we were able to send out an alert that things had changed.

Even on our company retreat, which is a great example. We went to Park City with the team. 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. If anyone had questions while they were there or right before it, how to book a flight, or how to get reimbursed for something, they could pull it up in their phone or log online.

Are you competing against Process Street, SweetProcess, and companies like that or are you still in a niche of your own because of the heavy focus on training and onboarding?

We’re still a niche of our own. I’ve used Process Street for onboarding with a different software company and it was more of a checklist. Trainual isn’t a checklist. It’s much more your employee handbook. It’s where everything lives and it’s a hybrid between a big enterprise LMS and Google Docs. In Google Docs, you can’t assign things to different roles or track completions, but with Trainual, you can do all that.

Business Growth: Trainual is not a checklist. It is more of an employee handbook that serves as a hybrid between big enterprise LMS and Google Docs.

It is more the manuals that are needed for different areas of the business and the onboarding and growing of employees, whereas Process Street and SweetProcess are more like, “Here’s the checklist to do something.” There’s no training component behind any of their stuff so you are very different that way. It’s interesting because I keep hearing from a number of our COO Alliance members that they use Trainual.

Chris has been a past speaker at our COO Alliance events. You were a past member at the event so I’m sure you’ve had some ability to infect the ideas for the group already. You’re starting to get some brand awareness as well. Where are you focused in terms of your growth and your sales and marketing growth? What’s Trainual focusing around?

Still a small business focus. That’s always been our passion since Organize Chaos days. We wanted to help those smaller businesses. We never wanted to get into enterprise mid-market. We’re targeting companies with 5 to 250 employees, anyone who has repeatable processes. Whether you are hiring or you have a lot of turnovers, those are all perfect situations where Trainual would be helpful for you.

That might lead to one of my questions as well. The fact that you’re focusing on small to medium-sized and not going into enterprise-level clients, is that allowing you to say no to a lot of the feature and functionality requests that the big organizations have?

Yes. It’s always been an ongoing battle because there are features that more enterprise customers want or there’s a prerequisite to even sign up. We’ve had to draw a line in the sand and say that we are not going to do these or we are going to do these. For a while, we are like, “I don’t know. What do we do?” We’ll bring it up with the team and it’s a lot easier to say, “This isn’t a good fit for you.”

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 false objections to buying the software in the first place. It’s like, “This is the laptop. We can’t tweak it. Do you want this laptop as exists? We can’t make it different.” You have to learn how to handle those objections or you find the client niche. That’s smart that you’re staying there. Are there companies out there that you compete against that are more on the enterprise side? Do they start doing it on their own when they get to that level?

There are more enterprise learning management systems that have a lot of features that we’re never going to build. They’re so different from us. I say 5 to 250 employees, but there are use cases where we work with a franchise. Maybe they have thousands of employees, but they’re at a bunch of different locations. There are different instances where people will grow with us over time.

Name drop for me. Who are some of the franchisors that you work with?

I’d have to check our website to see exactly who I can share because there are some that have asked us not to list them on the website or anything. I don’t want to screw that one up.

That’s pretty cool because franchisors can be a very big base because they do struggle with training. I don’t know if you knew that I was the second in command for 1-800-GOT-JUNK?. I took 14 employees to 3,100 employees. You’re right. Of our 3,100 employees, only 248 were at the head office. The other 2,700 were distributed over 330 cities. All those cities had 10 to 15 employees. They all struggled with that onboarding. That’s a smart niche for sure. Talk about the way that you’re building stuff. You’ve got a good analytics team. What do you do in-house? What do you outsource as a company?

We don’t outsource anything anymore. We’ve brought everything in-house. It was one outsourced CS rep back in 2020. 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, QA engineers and designers over there that we work with, but everything’s in-house. We have hired some PR firms and stuff every once in a while, but we end up bringing everything back in-house.

PR firms are rough. I would always bring PR in-house too. Why have you decided to go in-house with everything? Is it because you’ve got the money to be able to do it? Is it control? What’s the thought process behind that?

A few different things, but it’s been a big cultural shift. Even with the Ukraine team we work with, it’s hard with the time difference, but we make it work with some early morning calls. We’re starting to adjust things more and more to make sure that we can have those teams come together. We want that team to be able to join our all-hands meetings and be a part of remote team events that we do online. Since 2020, we’ve hired so many remote hires across the country. We’re not just doing in-person events anymore. Every time we do an in-person event, we have an online virtual event that we plan as well.

I was going to ask about that. We were running a COO Alliance event. Anyone who’s reading this show, the event is over, but in September of 2022, we’re running an event on building a world-class company culture where we have COOs from all over coming to spend two and a half days to talk about how to build a company culture post-COVID. Building a company culture in 2020, all or most of your employees came to work in an office. That’s changed now. What has changed for Trainual? How have you changed or adapted? Do you still have an office? What percent of your employees come into one? Are you schizophrenic and have everybody everywhere? Where are you at this?

Maybe a little bit. It was in probably February 2020. We were coming up. We were at the end of our lease. We were bursting at the seams. We’d grown a ton in 2019 and we were looking for a bigger office. I let our landlord know, “We’re starting to look for other offices.” We ended up having to move out in the middle of COVID and put everything into storage, which was super fun. We took a risk. We signed another lease that started in September or October of 2020. During that time, we started hiring a lot of people all across the country. It was no longer a requirement that you had to be in the Phoenix, Scottsdale area to work at Trainual.

We slowly started going back into the office. We had all of the protocols, the signup sheets, and all of the things that are so much fun to deal with. For a while, it was slow at the office. We questioned, “Was this a horrible idea, signing a new lease?” Things have slowly picked up, but you have the same people that go in and then there are people that want to be at home. Maybe they live far. Maybe they’re a single parent and it’s easier to be home.

We also have people who are parents and they can’t wait to come into the office and get away from their kids. It’s still split. We will never require everyone to come in. I go in 2 or 3 times a week. I try to always go in for in-person meetings, especially my weekly meeting with Chris and then my direct reports. We are moving into another newer, bigger office probably at the beginning of 2023.

Have you signed that lease yet?

Yes.

There’s a great resource, a partner of our COO Alliance, Jonathan Kaiser who runs a big Kaiser real estate group. I don’t know if you’ve ever worked with him, but he’s amazing to help you negotiate with landlords. He’s solid.

There’s been a lot of hiccups with construction because that’s life, but we’re hopeful that we’ll move in early 2023. It’s a much bigger spot than we have so whenever we do have the whole team come in for the holiday party, for example, we always have everyone come in for a week. We wanted a hub where everyone could work out and we could get the whole team together.

What are you doing then in terms of embracing these 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, we’ve always been pretty good at having remote setups. We’ve gotten some different technology at the office to make having calls and video conferences much easier. More than changing things, we’ve embraced it because we’ve been able to find talent from across the country and not be just tied down to only finding talent in the Phoenix area or asking people to move here. It’s been more of a good thing than a bad thing. I feel like we haven’t had to change too much. We’ve always been reliant on Slack for communication. We use Asana for project management. With Trainual, it seemed like a pretty easy change when we had to make it. Even though we were forced into it, it felt natural.

That’s what a lot of companies are finding. They’re finding 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 the team? They’re only on one call a week with the team and then they’re doing work for themselves or with themselves for the rest.

We offer so many opportunities to get together with the team, whether it’s the summer retreat that we go on or the holiday party. We have remote events quarterly. Also, we have different affinity groups that host events. We had a big culture celebration for culture week. We celebrated a lot of different cultures that we have within the company. We always had a remote aspect to that. There are going to be people that decide not to come to those. 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.

It’s like a, “You can lead a horse to water but you can’t make it drink,” scenario, but we do everything. Our people ops team, and Tara specifically who plans all of our events, does a phenomenal job. There are always ways to interact with the team. If you’ve ever heard of the Donut app on Slack, it will randomly pair you with someone each week so we do a ton of those. We have our biweekly all-hands meeting where we get to see everyone’s faces. We do breakout rooms. We always ask engaging questions in that meeting. There are a ton of opportunities to get to chat with your team.

You guys are doing the right stuff there for sure. With the Donut app, it’s funny. A couple of our COO Alliance members brought that up at an event and I was laughing. It’s when the two people get paired up and they have to go, sit and have coffee or donut together virtually over Zoom, but it’s great.

We had started doing it before COVID so it used to be an in-person thing. People would go get lunch or get coffee. Now, sometimes it’s virtual. If you get paired with someone in the same place as you, people tend to go get lunch together or do something so it’s funny how it’s transitioned.

Our finance group at 1-800-GOT-JUNK? used to have donuts with dollars. Every Tuesday, they would bring donuts in and you could go into the finance department. As long as you sat in finance to eat your donut and chatted with someone in finance, you could get a free donut. That was the donuts with dollars that they would go in to hang out with. They’re like, “We’re never going to meet anybody because we’re all so shy and introverted. If they come to us, then that was cool.” It was fun.

This is a funny thing, but our Director of Finance, Drew, at every all-hands meeting that we have every other week always shares a nugget and has pictures of chicken nuggets on the slide. It’s always fun, but he’ll share some interesting data findings. We have nuggets with Drew, but I like donuts with Drew so I might have to talk to him about that.

You’ll have to tweak that somehow. Maybe you could have donut holes with Drew or something. Instead of the nuggets, they could be little donut bites or whatever they’re called in the US. In Canada, we call them Timbits. You talked a little bit about some of the changes that happened post-Series A and post-Series B. I’m curious about what lessons you can teach people who are reading on how to go through the process of working with the venture capital firms, how to work with your people internally, how to not tell everybody what’s happening and only tell the right people, and dispel any fears and rumors. Are there any lessons that you can give us from having gone through two rounds?

We ended up having a good process for this and 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 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. Each person was looking for different things.

A lot of times, I 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 VC firm that steps in and they want to take over and change how things are done? We would take a ton of notes during each call. This is a silly thing, but it was super helpful. We would always take a screenshot of Zoom so we could remember whom we spoke to.

We are talking to a lot of different ones and it was helpful to have that snapshot. We would always regroup after the calls and share our takeaways. We’d keep it all in Asana. Everyone that was on the calls would write up the pros and cons. Was there anything missing? Were there any red flags? We went through the process that way.

I also did a ton of research leading up to any of the calls. I would look through, see if they had similar companies and in their portfolio, see how those companies progressed after fundraising, and what that looked like. There were a lot of different things that we were keeping in mind. There were months when it was call after call for weeks and weeks and making sure that we found the right fit.

Do you remember some of the VCs that are involved in your Series A and Series B? I’m sure you remember the ones in the B round.

Series B was with Altos Ventures. They’re in the Bay Area. Our Series A was split between Math Venture Partners in Chicago and 4490 in Madison, Wisconsin.

Was there a Chris that’s a partner with Altos? He’s Canadian.

There might be, but I have not met him.

I can’t remember what his last name is. I got to look him up. It may not be, but I think it is. Those are some of the lessons from there. You mentioned some of the different meetings that you run with the one-on-one meetings with Chris and then each of your teams. I’d like you to walk me through what your one-on-one structure is, how a one-on-one meeting works, maybe how yours works with CEO Chris, and then how you run yours with your team. I want to ask about some of the other meeting rhythms that you have with the company, but let’s talk about the one-on-ones first.

My meetings with Chris have evolved a lot over 2022 or so. For a couple of years, we were talking every 7:00 or 8:00 AM first thing in the morning. We would run through the schedule for the day and review his notes from the day before. That was 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 red flags and issues going on and ask any questions so there weren’t bottlenecks for the leadership team. Everyone would come to me like, “I need this from Chris. Can you ask Chris this?” I was the gatekeeper for that.

Fast forward a little bit, after hearing from so many people at COO Alliance that an EA is so important, I talked to Chris and we ended up hiring an EA for him in October 2021. Hayden was a game-changer. She changed so much. It took so much admin work off my plate. I was doing calendar management for Chris and scheduling. There were days when that can take up your whole day and then I had no time to do any of the strategy or planning work.

Business Growth: Hiring a virtual assistant is a game changer. It can take so much admin work off your plate and do more strategizing and planning for your business.

Bringing her on was huge. She does those morning standups. I do a weekly meeting with Chris in person at the office. I have a discussion board in Asana where I track everything I need to run through with him. For a while, we’d go through different things like financials. I’m also a part of all of his one-on-one boards where he has an 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.

It’s not the manager who runs the one-on-ones. It’s the direct report. They go through asking questions and what they need help with. That’s the same way around them with my direct reports. Chris’ EA and our office manager report to me. It’s always their time. It’s like, “What can I help you with?” We have a few different questions that send out in Lattice each week. “What roadblocks are you running into? What was the highlight or win from last week? Where can I help you this week? Where do you want to step in more? Where do you want to grow?”

What’s Lattice? Is that software to run your one-on-ones?

Yes. Lattice is for performance management. It’s where we do all of our company surveys and track eNPS. It’s where you can keep track of praise and feedback. You can do it either anonymously or publicly. We 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.

It’s a competitor to 15Five where I’m an investor and advisor. That’s where I’ve heard a lot of it before. I try to pretend that they don’t exist. What about the rest of your meeting rhythms? What other meetings do you run as an organization that you find helpful?

In addition to the biweekly company all-hands, we also have a quarterly all-hands meeting and that’s with the whole team. We run through OKRs. We are transparent with finances. It’s like our Employee of the Quarter Award. We call it the Woolly Award like a woolly mammoth. We have a little trophy at the office, too, but it got logistically too complicated mailing that out when we hired remote people. We give out money to people that win that.

It’s all based on the praise that’s collected in Lattice. It’s not just the leadership team picking people. It’s based on the whole team who they’re nominating. The quarterly all-hands is always super fun. We have a lot of music that’s played throughout. Sometimes, we even have costume challenges like dressing up as your favorite movie or favorite holiday. There are different things like that with prizes and it keeps the team super engaged.

We also do an annual kickoff the week of our holiday party every year. That’s where Chris sets the vision for the year to come. We talk about some of the big wins from the year prior. That’s it. It’s like company-wide meetings. For the leadership team, we have a leadership team check-in every Monday and that’s super helpful. We 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 the big things they were focused on last week and then what they’re focused on the current week.

If there’s something that’s bolded, we know that we need to discuss it. We have an Asana board where we keep track of discussion topics. If it’s something that we want the whole team or the leadership team to weigh in on, we’ll discuss those items too. Sometimes we have other people join to present on different things or we’ll talk about a board meeting that happened, things like that.

I love that you’re keeping stuff in the discussion board instead of throwing everything into Slack. I often find that Slack and email get so mismanaged. If you keep it in the discussion board and you show up at that weekly meeting, half of what’s in there, you don’t even need to talk about anymore. That was dumb and stupid. That one solved itself. Is that on purpose that you’re doing it that way?

Yes. If there’s a time when I notice something and I’m worried that it might get skipped over, I’ll put it in Asana so that we make sure to cover it.

What about your growth? You’ve been there since the early days and it’s easy for an organization to skip over the top of people. Another great Arizona Valley entrepreneur is Clate Mask, who is the Founder of Infusionsoft.

Clate is on our board.

Clate says that a mid to senior-level leader can only go through two doubles in the size of a company before they get outpaced so you have to continue growing your skills. All of a sudden, the company’s too big to run it. What are you and the leadership team doing to grow your skills to stay ahead of that curve?

Since working with Chris, I feel like I’ve grown tremendously. He’s always given me a ton of autonomy to make decisions. I’ve run our annual planning, monthly meetings, and quarterly planning. That can be intimidating. Him giving me the power to help with those big meetings has helped me grow a ton. There are times when I’m in a meeting and I feel like, “Everyone in here is so much smarter. They have so much more experience. How am I going to relate to the VP of Engineering?”

We have such a great company culture. I have one-on-ones with everyone on the leadership team, either weekly or biweekly and it’s always like, “How can I help?” If I have questions about things, I’m able to ask them. I feel like I’m growing that way through exposure and also through different groups that I’m in.

There had been so many people from COO Alliance that I still stay in touch with. I was emailing Derek who was on my COO Dream Team. They were always a great sounding board. No matter how unique you feel an issue or a stepping stone is, someone else has been there and done that. There’s always someone that you can go to for help.

Trainual is great with allowing employees to spend time during their week for these kinds of groups where you learn a ton. Chris is always challenging me, giving me new projects to work on that are oftentimes way out of my comfort zone. 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. I feel like every day I’m learning so much new stuff.

I want to go back to the 21 or 22-year-old Chelsey. She just started working for the marketing and PR agency. What advice would you give yourself back then that you know to be true now but you wish you’d known back when you were 21 or 22?

There are so many things. One, I’ve always been a jack of all trades. In college, my major was Interdisciplinary Studies. I couldn’t decide on one thing so I did Business Communication and Psychology. There were people who questioned it. Looking back, that was perfect because those are all the things I still do but not being a perfectionist.

I was so worried about always getting A’s in all of my classes, which my parents never cared about. They would joke that my brother did the alphabet. He’d get an A, B, C, and D. They were like, “Whatever. It’s not the end of the world.” Stop being so hard on yourself. Don’t be such a perfectionist. It’s okay to mess up. You learned so much when you mess up. At the same time, there are 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. 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, marketing, or social media.” I ended up doing both of those things again.

There are always people whom you can learn from and they can help you grow in those areas. You don’t need to be the best at them because eventually, the company will grow and you’re going to hire someone smarter and better than you, which is a weird feeling. This is another thing that I wish someone would’ve told me. Chris has had to tell me this. 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. 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. It’s not a knock to you when you have to hand things over because you’re not good at them. That is still where I struggle thinking like, “If I hand this off, it means that I failed and I’m not good enough.” That’s not the case. You need to give things to people who know what they’re doing.

I’ve yet to find a second in command who has run other things to do. It’s smart. Chelsey Krisay, the Chief of Staff for Trainual, thanks very much for sharing with us on the show.

Thanks for having me, Cameron.

Important Links

• Trainual
• Process Street
• Slack
• Asana
• Donut
• Altos Ventures
• Math Venture Partners
• 4490
• Lattice
• LinkedIn – Chelsey Krisay
• Website – Cameron Herold
• LinkedIn – Cameron Herold
• Meetings Suck: Turning One of The Most Loathed Elements of Business into One of the Most Valuable
• Invest In Your Leaders