The 4 Stages Of Growing a People Operations Team

Chris Ronzio

(02:08):

Hey everyone, and welcome back to Organize Chaos. I'm your host, Chris Ronzio, and today we have a special group of people here with me. They're actually three of the All-Star, All-Star, All Stars from inside the walls at Trainual. We've got, I'm kind of reading around the circle as I'm looking at you, Sasha Robinson. We've got Marlowe Everett and Chelsey Krisay. Welcome everybody.

Sasha Robinson (02:35):

Woo, woo.

Marlowe Everett (02:35):

Thanks for having us.

Chris Ronzio (02:35):

Thanks for coming on. All right, so to set this conversation up, we decided to have this chat, because we got this listener question that was asking about what I recommended for HR in startups, People Operations, whatever you want to call it. We started having this kind of dialogue around, "Well, what does People Ops or HR look like at different stages of a business?" As I thought back to our experience with Trainual, it went from me being the person doing the HR and hiring and People Ops and everyone reporting to me and then it went into this stage, where we had Chelsey as an operations manager and, handling the operations in the business, and she took some of that off my plate. Then Sasha, you came in as kind of the first People Ops leader in this function. Then as we've grown that team, now we've got Marlowe that's taken on a much bigger role with recruiting and hiring and performance management.

(03:37):

Through each stage of Trainual, each of you and me, I guess, have held the seat in the People Ops, HR seat. I thought it'd be such a cool conversation for us to have just talking through those stages and hopefully everyone that's listening can get a ton out of that. You're all nodding, but I would love you all to introduce yourselves very briefly just to kick this off. Why don't we go in order, if you could just tell yourselves or to tell the listeners when you started with Trainual, what your role has been first within this HR world and then today. Why don't we start with Chelsey, you were here first.

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Introductions

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Chelsey Krisay (04:15):

Sure. I'm Chelsey. I was, as Chris said, the first employee here at Trainual. I've been working alongside Chris for six years now, four of those since we launched back in 2018. I've worn several hats along the way, including Operations Manager/HR/Office Manager, head of CX. I helped build the foundation of our CX and sales team, Chief of Staff, and then more recently Special Operations, where I wear cross-departmentally on a lot of different innovative ideas.

Chris Ronzio (04:46):

Amazing. So many hats. Your closet must be just full of hats that you've worn here. Yeah.

Chelsey Krisay (04:50):

So full.

Chris Ronzio (04:50):

All right, Sasha, how about you?

Sasha Robinson (04:55):

Yeah, so I'm Sasha Robinson. I'm our head of People Ops. I joined as our 15th employee over three years ago. I was our first person in People Operations, so I was very fortunate to have an incredible foundation already from both Chris and Chelsey. I came into a really luxurious situation, but my job then was everything from recruiter to benefits administrator, to events planner, designing our confident performance strategy and trying to stay sane through that process.

(05:25):

Then as the business has matured and we've been able to bring on more folks to the team, including Marlowe, I've been able to focus on different things. Nowadays, I am running a team of three. I am focused on how do we continue to scale our incredible culture, now that we're just about a hundred employees and ensuring that we keep the trains running?

Chris Ronzio (05:48):

The trains running, the trains at Trainual. All right. One of the passengers on the train, Marlowe, you came in, how big was the company when you started?

Marlowe Everett (05:59):

Oh wow. I was employee number 40 in November, of 2020. Things have changed quite a bit here and my role has also evolved as the business needs evolved and with the strengths they bring. I started as a generalist, helping with all things events and employee experience and hiring. As we needed to scale the team, I took on more of a hiring hat, and now I'm the senior talent business partner. All things hiring and then helping Sasha support our leadership team with performance management.

Chris Ronzio (06:29):

Awesome. Well, I want to get into, maybe at the end of the conversation, we'll circle back and anybody that's ever applied to work at Trainual in the last couple years has probably talked to you. You've had more Zoom calls, more phone calls than probably anyone here, probably more than our sales team I would even venture to guess. I want to know some of the tips and tricks of how to be awesome as a candidate through the process. We'll talk about that, but that'll be like, you can think about that in the background.

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Stage 1: The Owner Phase

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(06:59):

But first, let's go through these stages. All right, so we'll start at the owner phase at the beginning. Chelsey, you were here as person number one or two if you include me, I guess. But even in those early days, when you were taking on some of the administrative work around the business or some of the customer work and doing some customer support, I was really the one at the beginning doing most of the interviews, but you were there with me. What do you think is important for the owner to do at the beginning of the business? When I interviewed you, what was important? How do you do a good job finding your first few people?

Chelsey Krisay (07:37):

I think one of the biggest things was just really setting expectations for culture. I know we were super aligned the first time we ever met on what we wanted out of business, what we liked doing, what we didn't like doing. When I started coming into interviews when we were super small, it was more of a cultural screening. I was making sure that the people we were bringing on were good fits, they matched our core values and that they would be fit in really well with the team.

Chris Ronzio (08:04):

Yeah, at the beginning, you kind of don't know what to do other than it's... I feel like I'm a terrible interviewer. You're all better than me at this. I just want to talk to people and find connections with them. It's almost like dating in a weird way or a first date, which Sasha, you're like, "No, I'm not dating all our employees. I understand I'm not supposed to say that," but it is a little bit like you're sitting down and you're just trying to build rapport with someone and say, "Can I, can I see myself working with this person?" But then you start to get into the skillset. Are there tips or tricks for somebody that's like a one, two person shop that's just trying to find those first few people? How do you do it right?

Chelsey Krisay (08:50):

Yeah. Another thing I would add in too, is going along with the core values, I think we are looking for people who are going to help us build the team. We wanted good leaders early on that would then hire good people to work under them. I think that's another really important part.

Chris Ronzio (09:06):

Do companies at that stage use any HR tools? I'm trying to think back. I don't really think we had any. It was maybe a project management system, something like that.

Chelsey Krisay (09:18):

We had Breezy.

Chris Ronzio (09:20):

Oh, the applicant tracking system?

Chelsey Krisay (09:23):

[inaudible 00:09:23] Yeah.

Chris Ronzio (09:23):

Yeah. That was a little later. That was when you were more starting to get involved. At the very beginning, when I found you, I had my email inbox. That was my whole system. Yeah, I think you're right. At the beginning, it's at the owner stage, it's really just about finding those first few people that see the vision, that are willing to take the risk, that are willing to come on board, that are willing to work for basically nothing. Shout out to you. Thank you for your flexibility. We were joking, because you just passed your anniversary and your anniversary in our HR system was like the date you got health insurance, not the date you actually started. It was like the date we formalized it all, right?

Chelsey Krisay (10:09):

Yeah, I think I had a two-week trial period to make sure I was going to fit in.

Chris Ronzio (10:14):

Yeah, yeah. Something like that. All right. But over time, after the first few, the first year or something, you did take a more active role in starting to interview people and help people. What was your role? You mentioned Office Manager, Operations Manager. What was your core focus in those early days, when you were taking a lot of this stuff off my plate?

Chelsey Krisay (10:36):

Yeah, so really, I mean, the biggest hat that I was wearing when we launched Trainual, was running the CX and sales department. Starting to build out those functions, I don't think we technically brought anyone on until the end of our first year, but that was a really instrumental hire. We were getting to a point where we had so many inbound sales tickets, that it was just impossible for one person to handle them. Then we started to bring on support reps as well. But I think that was the biggest, like I said, biggest thing I was doing at the company and helping to start scaling that.

Chris Ronzio (11:12):

Yeah, at that time, we didn't really have a ton of best practices. When we found Sarah, who was our first salesperson here, she was a very experienced sales rep and she taught us a lot of what we were supposed to do. I think at the beginning, a lot of times you are hiring for that external experience to bring into the building, because you don't really know what you don't know, right?

Chelsey Krisay (11:39):

Oh, totally. I had never run a CX team before. It was all new to me. I've always been good at figuring things out, but we are definitely looking to hire people that knew it better than we did.

Chris Ronzio (11:50):

Yeah.

Chelsey Krisay (11:50):

It's kind of a weird feeling, but it's also something that you have to do, because you'll never grow if you're not bringing on people that have more experience than you.

Chris Ronzio (11:58):

Yeah. We brought on Sean, who was a learning and development experience, which we had nothing of. We brought on Becky, who had, they'd been doing all the marketing coordination, and slowly we started bringing on people that knew things that we did not know that could fill the gaps, that we really just didn't know what we were doing. We did know how to do events, though. We were good at that at the beginning. That was definitely... Is that an HR function? It's kind of, right?

Chelsey Krisay (12:30):

Yeah. I mean, that's a People Ops thing.

Chris Ronzio (12:30):

Yeah.

Chelsey Krisay (12:33):

I always loved doing that at my previous job when I worked in marketing. I planned a lot of events for clients. I was really good at getting a process down, coming up with fun ideas, and it was really cool to be able to set the foundation for that, with such a small team. We did a lot of fun stuff. We went to spring training games, we went to a Sur La Table cooking class. We did a lot of different really fun things, hiking, everything. I got to plan our first retreat to Lake Tahoe back when the team had eight people, I think.

Chris Ronzio (13:04):

Yeah.

Chelsey Krisay (13:05):

That was Alex's first day, one of our support reps. But lots of fun things early on.

Chris Ronzio (13:10):

Yeah, and then we also did set up the building blocks. Even at that stage, we set up things like our 401k and health insurance with a broker and basic payroll and HRAS system. We were using Gusto at the time, so we had a lot of those foundational things. I'm curious, Marlowe, Sasha, do you think that we were ahead of the curve in doing those things or by the time you have five or 10 people, should you have a lot of that foundation set up?

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The Basics of HR & People Ops For Early Stage Businesses

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Sasha Robinson (13:43):

I think that some of the stuff that you were doing was stage appropriate and some of it was pretty advanced. I think it's pretty normal to have a payroll system when you have five or 10 employees and ensuring you have health coverage. I think 401ks are typically something that are brought on later as an added benefit. When I joined the team, when you were 15 employees, I was really impressed that you'd already had that established and baked that into the cost for every employee, because that was important to you. I do think that Trainual, more so than any other place I've worked, invested earlier in some of the people first initiatives or benefits for sure.

Chris Ronzio (14:22):

Yeah, some of that came from the consulting work I was doing before, where I would hear from employees of other companies that the benefits they didn't have and that they wish they had. It became a goal of mine to provide those benefits, because I knew if we could check this box, and we can check this box, and we could bring people on cool events, and we can do a retreat, and we can communicate like this, then each of those boxes that we check will avoid a pothole that I saw in a different consulting place. Chelsey, when I was delegating some of this to you, what do you think I was still the most involved with in those early couple years?

Chelsey Krisay (15:07):

I would say hiring. I feel like you kind of handed over the reins with events and culture, those kind of things. The office, I feel like you gave me total autonomy to run that, and I think we collaborated really well in a lot of the early policies and procedures that we had. There was a lot that we had to do. We were reactive with things. We didn't have a bereavement policy, we didn't have a sick leave policy. There was a lot that we had to work on together with that, but I think you always stayed really involved in the hiring process, just to make sure that we had the right fit.

Chris Ronzio (15:42):

Yeah, I remember hearing a podcast of some founder, it was a SaaStr podcast, and they were saying that the founder still did the interviews up until they're 500th person or something, which I thought was like, I didn't know if that should be a goal of mine or if that was absolutely insane. I remember when we were getting to 10, 15 people, right before Sasha came on, I was feeling like I'm getting to my max of doing interviews, because every one of those people that you bring on, you're probably interviewing 20 times more people to get to that one person that you eventually get to or maybe more than that. It took up my entire week. It's hard to do that. When you're trying to grow a business and you're really focused on sales and marketing and are we growing our revenue, it's very hard to also be dedicating 20, 30, 40 hours a week to interviewing. But it's hard to let that go, too.

Chelsey Krisay (16:44):

Also, I think back when we were really small, I think you got some pushback from people too, because we didn't have much of a team. We didn't have much of a product yet. I know I remember you getting a lot of questions from people. Well, tell me more, it was very unknown.

Chris Ronzio (17:01):

Oh, about like having to sell them on [inaudible 00:17:03].

Chelsey Krisay (17:02):

Yeah.

Chris Ronzio (17:03):

Oh, totally. Yeah. At that beginning stage, you're right, it was more of a sales pitch to explain why somebody should choose Trainual, because Trainual was an unknown product or whatever. It was like we didn't have all the PR at that time, and we didn't have the funding at that time. Hiring people was they were taking a big gamble. Everyone that was here before we raised any money for sure was like, "Well, this might be a fun project for a few weeks, but let's try it out." Sasha, let's talk about when you started to ease onto the scene.

Sasha Robinson (17:40):

Ease onto the scene, the eight-month ease.

Chris Ronzio (17:45):

Yeah, because before you came on full-time, which you mentioned you were number 15, you recommended I think employee number nine and number 11, and you had this network of people and you started sending people our way. You were doing some side consulting and advisory work. What was your perception of the eight or nine employee Trainual, and why was it too early for you at that stage?

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When To Hire A Full Time People Ops Employee?

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Sasha Robinson (18:17):

My first impression was I was very impressed. I got to meet Chelsey first, I think, outside of you, and I was like, "This girl is so cool." She would talk about all the stuff she'd already done, "They are so ahead of the game. They're already doing all of these things. Why are you even talking to me? Chelsey's got it on lock," and I think the reason that I pushed back against joining the team earlier, was because you hadn't raised money yet and the velocity at which you were hiring was a little bit slower, which is totally cool.

(18:44):

But for someone to come in and own that role full-time, like you didn't necessarily need me, you didn't need the systems or any of the infrastructure that my skillset lends itself to. When you started talking about raising external money and accelerating the pace at which the business was growing, thus necessitating more hires, "All right, I'm in, I got you. I can take whatever you've built in this beautiful foundation and ensure that we can scale that from 15 employees to 100."

Chris Ronzio (19:12):

For you, it was really the velocity of hiring and the fact that if we're only going to add a role here and then wait four months and then another role, we don't need someone that's all the time focused on People Operations, not just hiring and recruiting, but managing the team. Is there a magic number for anyone that's listening to start thinking about when they need to make that first full-time hire?

Sasha Robinson (19:35):

I really wish I had a magic number. I think it's more of an art than a science. I think it depends on a lot of different factors in your business. One is your current headcount. You could have five people on your team, but be anticipating adding 500 the next year. You might need to add someone now. You could have 30 people on your team and add five people the next year. You might be good with someone like Chelsey who can have HR and People Ops as part of their role, given that it's only a piece of what they do. I think it's taking a look at your business, how many people you have on the team, how many folks you may be adding, and then looking at your product, your employee base, the types of issues you're running into. That would determine when you need to hire someone and the type of person that you would hire and what their background should be.

Chris Ronzio (20:21):

Chelsey, do you remember when I started talking about hiring Sasha, and what was your thought? Was there something that you were ready to get off your plate or what was it that you think tipped the scales that we needed her in a full-time capacity?

Chelsey Krisay (20:36):

Oh, definitely. I mean, I think I remember we were sitting down in the conference room in one of the first offices and we were just talking about culture and you were throwing out ideas like the donut app on Slack, and I was like, "Oh my gosh, it's a genius. We need to do that." You really understood how to interview someone. I'm with you, Chris. I don't love interviewing people. I don't think I'm great at it. Sasha is. She had a track record of doing it. She had a really good network in the valley. I didn't know anyone that worked in tech and Sasha just had so many good things to bring to the table. I was super excited for that, and my new best friend.

Sasha Robinson (21:11):

Yeah, thanks. I feel like it was total hype Sasha session. I'm loving this.

Chris Ronzio (21:17):

Well, no, Sasha, I think you interviewed me harder than anyone has ever interviewed me about the business. I was nervous talking to you, as if you were an investor or something. I figured if you're going to interview me that hard, you'd probably do a good job interviewing other people. It was a good skill to have.

Sasha Robinson (21:37):

Well, thank you.

Chris Ronzio (21:39):

All right. When you came in, what was strong here in terms of People Ops and what was weaker or not yet established that we really needed to focus on as we came into that 15, 20, 25 person phase?

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People Operations At 15 - 25 Employees

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Sasha Robinson (21:57):

I joined in the fall of 2019. At the time, the Trainual team was exclusively based in Phoenix, Arizona. We all came into the office every day. I think something that [inaudible 00:22:07] I walked into a really good situation for all of those reasons.

Chris Ronzio (22:54):

It was pretty cushy. Pretty cushy.

Sasha Robinson (22:55):

It was very cushy. Yeah, I told people that all the time. Cushiest gig I could have walked into.

Chris Ronzio (23:02):

You mentioned the events. I know we talked about that, but is it faux pas to interview people at events? I'm curious, Marlowe, you got to chime in, but I remember we... Like Nick, our videographer literally interviewed hiking a mountain with us. We invited him. He did not know what to expect and ended up just on like... Yeah.

Chelsey Krisay (23:26):

Not just a mountain, camelback. [inaudible 00:23:27].

Chris Ronzio (23:27):

Yeah, hard mountain. I know a lot of people listening probably aren't here, don't know what that is, but it's a grueling hike. You'd be very winded at the top. He was not a hiker. He made it to the top of the mountain. We got him up there, and along the way we were able to really understand his personality, hear his stories, understand what he is into, his passion for video production, the stuff that he had done in the past. It was this extended social interview that I think you can't really do it scale, but we did a lot of it in the early days. Good or bad, Marlowe? I need to know.

Marlowe Everett (24:05):

I would be so fit if I hiked a mountain every time I had to interview somebody.

Chris Ronzio (24:11):

That's what we should do.

Marlowe Everett (24:12):

At scale, I would say not the best practice. We really want that consistency. But I think at that stage, it obviously worked out and here we are with Nick.

Chris Ronzio (24:21):

Yeah.

Sasha Robinson (24:22):

But I think we've been able to replicate looking for what motivates folks through different questions that we ask in the interview process and ensure that they are passionate about small business and the problem we're solving and passionate about the role and the team they'd be walking into. Even if we're not gathering that information while hiking.

Chris Ronzio (24:37):

Yeah, yeah. Okay. All right. Then Sasha, as you dug into what needed to be done, what were the areas that we were maybe weaker in that were underdeveloped?

Sasha Robinson (24:49):

Yeah, so for me, I think it's really important to think about fairness as you're constructing systems or processes and you're scaling and not thinking about individual people. One thing in particular was our compensation philosophy. I know Chris is really passionate about rewarding people for the work that they're doing. The first day I walked in, I was like, "All right, so talk to me. How you think about compensation?" He is like, "Well, anytime someone's doing great, let's give them some more money." I was like, "Oh, interesting. I love that you love the team and you want to motivate them, but that gets a little tricky when some people may feel less comfortable bragging about their accomplishments or asking for more money, and that can create disparities."

(25:31):

I think that was one of the first projects I worked on. How do we systematize how we think about compensation? What is our compensation strategy, building comp bands and properly leveling the team that we had, to ensure that there was fairness and parody across the team, not just for the 15 of us then, but then as we've added 75 new folks to the team.

Chris Ronzio (25:50):

I remember the slide deck you put together where it was the GIF of Tim Allen in the Santa Clause, walking down the North Pole, and you were like, "No more Santa, Chris. You can't just give out bonuses and raises whenever you want to. We need to have a system for this." I appreciate that. What else was weaker?

Sasha Robinson (26:15):

As we were getting ready to hire more talent, I think Chelsey talked about this, hiring exceptional people and skillsets that we didn't already have on the team, we needed to pull from companies that had been there and done that or seen that next stage of growth. They were typically series A, B, or C stage SaaS companies, and they typically were offering more robust benefits packages, slightly more compensation. It was evaluating our benefits offering and ensuring that if I got on a phone, or got on the phone with a candidate, could I convince them to leave their job at a company that was maybe a couple stages ahead of us, but we were at least meeting their baseline expectations?

(26:52):

It was revamping our benefit offering and compensation bands and then you already had the foundation for career conversations and growth with the team. We called them 90-day check-ins at the time. Every 90-days you talk to everyone on the team yourself and like, "Hey, how are things going? What could be better? How do you like your role?" Building on that to a more formal process and that's been iterated many, many times over the last three years.

Chris Ronzio (27:21):

Yeah, let's talk about that a little, because I think that's one of the things that we did do pretty early. Chelsey, we had those when there was just four of us maybe, I don't think when it was just you, but when there were four of us, I'm pretty sure we were already doing those 90-day check-ins, right? The 90-day check-in process was really simple. It was a PDF that if anybody's listening and really wants this, I'm happy to send you the old version, just DM me on LinkedIn or something and I'll send you the old version.

(27:51):

But it was a PDF that was a self-assessment for people to rank one to five their happiness in certain things. It was like the environment, the work environment, do they feel challenged with their job? Do they still see themselves here in the next couple years? Do they feel like they're compensated fairly? It was these hot button issues that we wanted to consistently prompt people with, to make sure that they were happy and to give them that space to vent or to give feedback or to have a tough conversation.

(28:23):

Because if you don't ask, a lot of people just won't bring those things up. Then, when they leave and you find out in the exit interview that it was something that could have been avoided, you're kind of kicking yourself and you think, "Why couldn't we have solved this?" We had a version of this in place, but Sasha or Marlowe, can you talk about how this has evolved?

Sasha Robinson (28:43):

Yeah, I'll give a quick answer and then I'll let Marlowe speak to some of the work that she's done more recently and taken it to a whole new level. But we built on the 90-day check-ins, and I would plug this for any small business, building a foundation, even if it's super small, a PDF with a couple questions and whether that's for performance management or how you think about events, doing something small and setting the cultural expectation that this is part of our DNA is so important, because the next step when I say, "Hey, we're going to formalize this in a fancy system and we're going to do this in a cadence every quarter and we're going to add this extra step," it's not so shocking.

(29:21):

It's just an extra step and the next layer to whatever you're doing, versus, "We've never done this before, 50 people, get on board with this whole new performance management change." That again, was so lucky walking into the foundation already set, because we were able to roll out a system. We were able to roll out a specific cadence, not only for the 90-day check-ins and downward and upward performance management, but a self-reflection cycle and an engagement survey to solicit anonymous feedback a couple times per year.

Chris Ronzio (29:55):

I was going to ask Marlowe, what would you add in there and the evolution, because you've seen this over a couple years.

Marlowe Everett (30:01):

Yeah, so I think from the beginning, I've seen places that get to 50, 60 people and everything's on fire and they're, "Oh, we should have hired HR." I think we did a really good job of setting the foundation of 30, 60, 90s when you start really setting that expectation and then obviously the 90-day check-ins and some of the things that Sasha was mentioning with self-reflections and upward and downward feedback and also peer reviews.

(30:27):

For me, in that evolution, it's really looking at how that ties to the hiring process and making sure that we are being really crystal clear on giving feedback, so people know when they're winning and when they have an opportunity to change something so that they can win. It's really hard to do that early, especially when you're still in a role where maybe you're the first one in the role and we don't know what that looks like. We don't know what success is going to look like in 12 months.

(30:51):

Where now with our process, we look at a role and we say we generally know what this person needs to do when they get come in. We also have a good idea of what they need to be doing in six months, 12 months, and hopefully beyond to be successful in that role. Our performance management will match that as well as our hiring process.

Chris Ronzio (31:09):

Yeah, I think what you're getting into a little bit is this the performance management and the career path and career ladders. I think that's been more formalized in the last couple years, but we didn't have any of that the first 20 people or 40 people or whatever. It was sort of like, "What do you mean career path? We just hired you for this job."

(31:29):

At the beginning you're basically just, you're living kind of a week at a time and a month at a time, and you're not really thinking about people's long term trajectory in the company. I'm thinking about how I just hired you and plugged that hole, now what's the other hole I've got to go plug? To have to come back and to have a career discussion with this person is like what? I can't even think about that.

(31:54):

That's definitely something that we started doing as we got bigger, as we had more resources. Sasha, how did the team evolve from you into a larger team now? Can you talk through what is a people operations department start to look like? How did you subdivide the different hats that you were wearing?

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How To Start Building A People Ops Team

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Sasha Robinson (32:15):

Yeah, so I'll speak to what happened on the Trainual pops team, but I think the most important thing if you were the first person on a pops team is evaluating your skillset and your strengths, not only what you're good at but what you enjoy doing. I'm a little salesy. I love recruiting, I love Trainual, I love being able to sell it and build relationships. I could recruit eight hours a day and still go home and work and be really happy. I wanted someone who could help me with building policies and answering benefits questions and things like I didn't love doing as much, but I could do, but I didn't necessarily want to.

(32:52):

I brought in someone who that was their skillset and they were phenomenal. They would help with onboarding behind the scenes and running that, benefits questions, building policies. Then it reached a point where I could no longer handle the number of open rules we had. I started cross-training her to be in talent acquisition. That would be my one piece of feedback looking back. I wish I would've hired Marlowe earlier, because Marlowe is incredible and has such a phenomenal background in talent acquisition.

(33:22):

If you're hiring at the velocity that we were 40 to 50 people a year, it's really hard to do that solo. It's really hard to do that while training someone else, hiring someone who has done it before to support you. When Marlowe got fully ramped after her 90-days, that was the biggest weight off my shoulders, knowing I had a partner who'd crush it and bring in incredible people too. Marlowe was my second hire on the team, when the velocity reached a point where I was struggling a little bit.

Chris Ronzio (33:53):

Okay. There was the benefits administration, the HR generalist stuff, then there was the recruiting and bringing new people in and helping onboard them. Then more recently, there's been the culture and experience side of it, right? Can you talk about that a little?

Sasha Robinson (34:09):

Yes. I think it's a little unique to Trainual, that part of our cultural DNA is time spent in person, but with COVID, we've decided to be a remote first team. We invest really heavily in both remote optimized and in-person quarterly events. We do an incredible week around the holidays, bringing the entire team in, and then we do a retreat offsite once a year as well. Then we do these phenomenal onboarding sessions in person at the office and we put so much care into all of those experiences.

(34:40):

We have someone who their full-time role is onboarding new folks, handling all of the planning and execution for the retreat, for the parties, for the events. She also owns diversity, equity, inclusion and how that weaves into some of the events with our affinity groups and ensuring that everyone feels like they have a place at Trainual, regardless of how extroverted or how much they like parties, that may not be a full-time role at every small business, but for us we knew that was super important for building relationships based in trust, so we could operate really fast when we were actually working.

Chris Ronzio (35:15):

Love it. Okay. Marlowe, you got sort of soft roped in I think as well, like I had brought Sasha in, you were talking with Sasha outside of the business or something, always be recruiting. We knew we needed some help bringing more people into the fold. When you came in, do you feel like you just hit the ground running right away looking for roles? Or what was your indoctrination into Trainual like?

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Hiring Marlowe, POPS Generalist To Talent Acquisition

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Marlowe Everett (35:45):

Oh wow, it feels like that was so long ago. Yes and no. I think there were things that felt very familiar, which was obviously the recruiting piece. Put me in a role, put me in coach. I am that person when it comes to talent acquisition. I think we start to see very early success there. I think there were parts of the role, like the HR stuff and the generalist of benefits, where I was like, "Okay, wait a minute. I need to answer people's actual benefits questions that I need to know what I'm talking about." That's a little difficult for me, so there were learning curves at that.

(36:17):

But to Sasha's point, you know where your strengths are, and I knew where mine were. We very early on plugged me into the recruiting and then had project work and time aside for me to learn the things that I maybe wasn't so well versed with. Yeah, I think I hit the ground learning with certain areas and there were some that I still, benefits questions are still challenging for me, because I don't do it every day. But it's been a bit an evolution for sure.

Chris Ronzio (36:44):

As a business is growing and hopefully you're starting to make a brand for yourself and people are interested in actually working with your companies, what systems did we have in place, or what would you suggest that people have in place to maintain a great recruiting process?

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How To Maintain a Great Recruiting Process

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Marlowe Everett (37:04):

That's a great question. We're on Levers. Levers is our applicant trucking system. We obviously use Trainual for our need to knows, and we'll send a Trainual to candidates to get to know more about the company, the values, which is really special. Then we use Loom for candidate communication. I think between those three tools, they've been really beneficial for our process, which is very intentional.

(37:25):

I think when you look at building a recruiting process, if you can get an applicant tracking system early on, it will monetize tenfold. I always say that your hiring process should match the type of company you're trying to be. There's nothing wrong with when it's really early stage, it's maybe your first few hires you're meeting at a coffee shop, you're figuring it out and that's okay. But if you want to be best in class or you want to scale really effectively, you'll need a system to help you do that.

(37:54):

I think if you can invest in that, definitely do it, it will help not only get your ducks in a row internally as you're hiring, but it will also provide a much better candidate experience, because there's nothing worse than candidates that don't know what's going on, or they don't have a timeline provided. It's really important to have an applicant tracking system, if you're going to be doing a significant amount of hiring.

Chris Ronzio (38:14):

I 100% agree, and that's why we actually had one. I think Chelsey mentioned it earlier. We had a very basic one, when we had three or four or five people, because even those initial interviews, I just found it so helpful to have a place to write down all my notes, to move someone through the stages of a hiring process, to understand all the candidates that I was sourcing from LinkedIn or wherever, and just to keep that organized.

(38:38):

You can do that in a project management system maybe, but there's systems that are designed specifically for that purpose, that maybe you only even pay per roll that you have open. There's a really easy way to get your foot in the door with some of the more SMB tools. I definitely recommend that that people check those out. You mentioned candidate communication, which is something you are exceptional at, to the point that people that you reject working here, are still super fans and follow along with what we do. Blanket question, but how the heck do you do that?

Marlowe Everett (39:14):

Couple things. First of all, put yourself in the candidate's shoes. We've all been in a position where we want that job, we're really excited about it. Or unfortunately, maybe we've been laid off and we don't know where our next paycheck is going to come from. That's stressful and you are putting yourself out there to get the job. It is a courtesy and it should be a norm that recruiters are also being on top of that timeline. Unfortunately, that's not the case. I've had friends apply or get three interviews in and I never heard back.

Chris Ronzio (39:41):

Ghosted.

Marlowe Everett (39:43):

Ghosted, right?

Chris Ronzio (39:44):

Yeah.

Marlowe Everett (39:44):

I think about that and it's bad enough in the dating world. We don't need to ghost people in the recruiting world, right, so-

Chris Ronzio (39:49):

Full circle, back to dating. See, I told you-

Marlowe Everett (39:51):

It's the same. It's the same. No, I look at that and I think, "Okay, if I were a candidate, what type of experience is important for me?" But really what type of company are you? When I look at Trainual, first of all, systems processes, that's what we do. We have it together. It's really hard for me to look at what we represent as a company and then have a sloppy recruiting process, where I'm not getting back to anybody. That doesn't make sense.

(40:16):

It's really important for me from a values perspective to match the type of company we are with our recruiting process. Then you just never know when somebody is going to be a candidate again. I like to tell people this, "Even in the rejection phase, it's not this role right now only," it is, "Let's get to know each other. Let's build a relationship. I'm a fan of you. You're a fan of Trainual, it's awesome. The right thing may come along at the right time," and then perhaps I circle back six months later, if the right thing opens up. If I would've ghosted you, I probably wouldn't have you as a candidate. Right?

Chris Ronzio (40:46):

Right.

Marlowe Everett (40:47):

Really thinking about that long-term relationship.

Chris Ronzio (40:49):

That's so true and it's like a customer doesn't just see an ad and buy immediately. Sometimes it takes some getting to know the brand over a long time before they buy. I think it's the same with the recruiting process, both from the company's standpoint and the candidate standpoint. Sometimes you get to know each other and you realize, "We really like what you're all about. We think you could be great here, but we don't have, this isn't the perfect role for you. Let's keep in touch." One of the things I think we do a good job with too, is we have that future roles post that's always up. I'm curious, could you talk a little bit about that? Just what it is, how we use it, and how we market new roles to our pool of existing candidates?

Marlowe Everett (41:34):

Absolutely. This comes back to having an ATS, an applicant tracking system. This is very hard to do if you don't have that. We do keep an open role all the time for future openings. Maybe you're interested in Trainual, we're not hiring for what you do right now, but perhaps we will be. People will apply, they get added to that bucket and when I kick off a role, I look in the future applicants first and I see, "Okay, who's here, who's excited about Trainual, maybe it wasn't the right time then, are they looking now?"

(42:03):

You can obviously set really, really nice email triggers to send emails to those folks to let them know what jobs are opening, or when you post a new role, or you go ahead and connect with them. That way when I do post a role on my LinkedIn, those people probably follow me. It's really building that visibility, which is really nice. You never know, again, just because the role is not open, you're missing an entire chunk of people that could be really incredible fits for the company. Or maybe they jog your memory and you see a role coming in that, "Oh, I've been talking to Sasha about that. I know we're going to be looking for that in the next few months here. Let's have a conversation and let's see if there's alignment." It's really good with keeping you on your toes and thinking forward.

Chris Ronzio (42:44):

Yeah, and we've also, over the years, hired a handful of people that we're just like, "I don't know, we'll figure out what you're going to do here, but you're awesome and you need to be on this train." I think there's something to be said there too, that if you are always have your mind open and your eyes open for exceptional people, sometimes you can hit the lottery. That's sort of what happened, I think when we found each of you to some extent, is we had our eyes open. We were having meetings, we weren't necessarily expecting to hire that role, but we did maybe prematurely, because we saw something in each of you.

(43:25):

I think that's a tip for everyone that's listening, is to keep your eyes open when you're in a store or there's a cashier at Starbucks or whatever, that you think, "Wow, this person is awesome, maybe they could be great in my business." You always have to think about recruiting. All right, that's it. I'm curious, any final tips from each of you? Anything else that you think we've done well, that somebody else could snag as a little tactic for their business? In any order.

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3 People Operations Tips

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Sasha Robinson (43:59):

It's less tactical, but I would just plug how lovely it's been working at Trainual, with a team that is fully aligned on the importance of building a people first business and Chris having your full buy-in on everything that we're doing. It doesn't really matter what your comp strategy is or what your performance management philosophy is, but having the alignment and the backing, both from a financial standpoint, I always say emotional, the emotional support from Chris, you're fully bought in and support what we're doing and that's felt throughout the entire organization. I think that is so pivotal to your HR or people team being successful, so it doesn't feel like a supportive or an admin function. It truly feels like a partner to all the other departments and your leadership team.

Chris Ronzio (44:46):

Yeah, I remember you talking about that with me when you first joined, and it was a very important conversation to say, "No, this is a seat at the leadership team, because we value this to at that level. This is not just a side function that is a support role for the business. This is a strategic function in the business."

Chelsey Krisay (45:06):

I would say our emphasis on onboarding, I think we've always done, I mean, I did a decent job of onboarding. I remember the day Sasha just started.

Chris Ronzio (45:15):

You were great. You were great.

Chelsey Krisay (45:16):

We had what, six people start with you and I'm like, "Oh my God, I'm onboarding our head of People Ops." But I think we've really refined that over the years and the amount of feedback we get from the team on how incredible of an experience that is. We really get people into Trainual literally into the product, but also they get to meet all of the different departments, all of the different people on the team. They learn a ton about our culture, a ton about the business. I think that means a lot, because that just sticks with them the rest of their tenure there.

Chris Ronzio (45:50):

Yeah. The onboarding process is your chance to either confirm that people made the right decision when they accepted the job, or to scare people the heck away and make them go home and say, "What have I done?" It is so crucial that you invest the time to get that right. Whenever I'm out speaking, I always talk about the orientation process and how crucial that moment is, those first couple days. I know we've got a ton of great content on our website about that, for anyone that's interested, but your orientation is definitely one of the first things you should start with. Marlowe, anything else?

Marlowe Everett (46:27):

I'll take a recruiting lens on this one. Be authentic with your brand. Your employment brand is a side effect of everything you've been doing. If you want to hire incredible people, it's not just making an incredible job posting, it's all of the things that you've been doing in the culture you've created and how that shows in the market. I think you have to look at it this way, candidates are making just as big of a decision as we are. This is their life and it's our company and we're projecting both of those. Everything you do will trickle into how candidates view your company and if they want to work there and if they want to stay.

Chris Ronzio (47:04):

Yeah, great point. Relatively, it is a bigger decision for the candidate than it is for the company. As a company, we have a lot of people and if someone doesn't work out, we post a job, we find another person. But for that person, this could be their entire household income, it could be their career path, it could set them on a trajectory that alters their next decade. That is a really serious decision.

(47:29):

That's why I really believe in this people first approach and the culture that we've created. I have all of you to thank for furthering and deepening the commitment that we have to the people first thing. I appreciate all of you being here to share your stages, from owner to operator, to people operator, to People Operations team. It's been a really cool journey so far. Thank you for sharing.

Chelsey Krisay (47:54):

Thanks for having us.

Sasha Robinson (47:56):

Yeah, thank you.

Chris Ronzio (47:58):

All right, everyone else, like you saw, we got a great listener question about how startups should think about HR and People Operations, and this is the type of content that I love doing that I'd love to provide for you in the future. If you have questions about scaling, growing, systematizing your business, I want to hear about it, let me know. Let's connect on LinkedIn, on YouTube, on Instagram, wherever you hang out, I'm probably there. Search for me, Chris Ronzio, I'd love to connect with you. In the meantime, check out all the other episodes and great content that we have here on Organize Chaos. We'll see you next time.