Being the First People Leader at the Company

Christie Williams, VP of Employee Success, Softdocs

Christie Williams, VP of Employee Success at Softdocs responded to my post about how people leaders can make great COOs. When I learned she’d been the first people person at several companies I had an instinct that she’d be right for the series. Our conversation covered her motivation for doing people work, what it’s like being the first people leader on the team, how she thinks about the technology stack that runs the company, and her advice for other people leaders who are the first. 

We met on LinkedIn. You commented on one of my posts. I immediately went into your DMs and pitched the series. “Would you like to come to talk about your experiences?” I'm so grateful that you were willing to talk to a random stranger on the Internet.

That is exactly how it happened. We were strangers at the time. If the 1990s and 2000s childhood told me anything, it's that no one's really a stranger on the Internet, are they?

Can you introduce yourself?

Absolutely. I'm Christie Williams. I am currently the VP of Employee Success at Softdocs. We are a campus automation tool that removes paper processes on campuses and automates workflows. I joined the team about a year ago. Now, we're getting close to my year mark, and have loved it. I enjoy just getting to be with people and building out new processes and love tech, love the industry that is still growing despite the current economic times. It's amazing to see the way that tech pivots and sort of remains agile which for a lot of companies, that's how they run their product and it's nice to see it in practice across the company. I'm a mom. I have two daughters who are 16 and 18 which it's just wild to have an 18-year-old at this point.

You do not look old enough to have an 18-year-old. I'm staring at you like, "What?"

I know. I know. It's the makeup. (laughs) My daughters are adopted from foster care and they joined our family when they were four and six. A lot of the work that I do is driven by them because I've both wanted to be an example for them to look up to as far as work and life balance and how we help people go. The other side of it is I wanted to be in a position where I could create equitable workplaces for children, teenagers going into their careers, adults who are working with neurodivergence, and all of those types of things, and then you certainly wouldn't pick this up on a call probably but both of my daughters are Black and it's just always been very important for me to work in companies and create companies that they could see themselves working at without any hesitation. So that drives a lot of the work that I do.

That's awesome.

Yeah. They're phenomenal. They both just started their first jobs in the last couple of weeks so it's been cool to see how companies are working with that age group as they transition into what for most of them is their first role. One of my daughters works for our local YMCA as a Before and After School Counselor, and the other works a retail job, and it's just cool to see them step into that part of life and be there to support them with just my background and knowledge too.

How did you come into the people field?

I suppose that my demeanor just always landed me in the people field in some way, shape, or form but my career has been across, I guess, we're getting at 20 years now for a solid career arc. I started in restaurant work. My first job was at an assisted living facility so it was just very cool for me to be around people who had these amazing stories about their lives and learn from them. Then I went to college and started working more customer service-focused roles. I've done so many different things which interestingly enough brings a different insight to the people work that I do now because I've really been on, generally speaking, all sides of the company outside of the development side so it's been a fun journey to get here.

In 2016, I took a role with a local co-working community. I eventually moved into the Director of Development role. We were a small gritty team, I was doing a hodgepodge of work, and helping other small businesses and entrepreneurs build out some of the processes that they need on the front end of their business. So whether that was advising them on health insurance or getting together an employee handbook, just some of the small things that a small business owner may not realize that they need on Day 1. As they start to add headcount, they start to get into more compliance issues, and they have to think about accommodations and the types of benefits that they're offering and ACA sort of came into implementation around the same time that I was transitioning into that role. 

As my career journey ended with that company, I had an honest conversation with my leader who was probably one of the most influential people in my whole career. I said, "I think it's time for me to move to the next thing. I've done a lot here. I've implemented a lot of things and I think it's time," and he was like, "All right. Well, let's think about what you want to do," so I thought I would take more of a project management route and work more project management type roles and on a Sunday night whim on LinkedIn, I applied for a job with a Series A tech company called Onna. I didn't hear from them for a couple of months. I had been interviewing with several companies phase and they called me in January of 2020 and said, "Hey, we'd love to talk to you about this role."

It was an interesting role because it was listed as a workplace experience manager. So it was making sure that people felt taken care of and had what they needed to do their best work with a component of space design which was also in my background has been in the co-working world. So I was like, "Well, I'm doing this job but I'm not doing it for one company. I'm doing it across, at that point, hundreds of companies." So that was an interesting pivot to take out and just be like, "Oh, I'm one person helping a small team locally of 15 people."

I started that job in February of 2020 and about four weeks later, COVID hit. So it was a very quick pivot actually from just being the workplace experience manager to the team being like, "Whoa, Christie can do way more than we thought she could do." So I moved into the people operations manager role there and built out so many different things which eventually led me to be recruited for the role that I'm in now and started about a year ago. A very interesting progression but I've loved it nonetheless.

I can relate as I had an interesting progression into the people side of things. You've now been the first people ops person at several companies, right?

I’ve done it at probably about five at this point. I do like being the first and I say that with probably an asterisk on it. I do like going into a company that has been doing its best to do it right by people even before I start. Whether that's having strong access to equitable benefits or just some of the processes in place that protect the company, employment agreements, and things like that. I do like entering where it's not just wild, wild west, maybe, is the right way to put it but I also really like being able to put my touch on processes and build things out and get it where I want it so that it's efficient, effective and self-service in a way so that I'm not a blocker for people to do their best work.

It makes it a lot easier when there was not much in place. I've found that the teams tend to be very receptive to the change if they don't feel like they're changing from one full, complete process to another that's brand new. When it's new, it's okay. But when it's, "I've done it this way for a long time and now, you're telling me the new thing?" it’s a lot more difficult. I'm working at a company that's 20-plus years old and hadn't had a formal HR function. They were just doing the best they could with the people they had and the tools that they had. It's been a lot of fun to bring structure around it and my team feels a lot of appreciation for the things that I've put in place.

Do you think that this is your niche now or would you take a role where they already had robust practices?

I suppose it just may depend on where I'm at in life as a whole, right? I do like the newness, the freshness, the building it, find the right technologies to support it. My friends joke that I tend to be the cleanup crew. Like I just take whatever it is and make it better. That's not a knock on any of the work that I've done either. I've consulted with companies too that they were doing the best they could with what they had and you can go in and as someone who's done it before really make recommendations. Even then, sometimes I mess up. I'm like, "Oh, I think this will be great," and then it's just not the right thing for that company and you just figure it out along the way.

I do think that I am more driven to go in, fix it, and then parachute to the next thing. My CEO and I have talked about my career. I'm in a VP role, we're a pretty small company, and I don't see us needing to probably take the next step to a Chief People Officer. Functionally, I don't think that it would be much different than what I'm doing, it would just be a title. So we talked about it like what does that look like over the next three, four years? I think what keeps me excited about my current role is we are talking about growth outside of our four walls as well. What would maybe a merger or acquisition look like at some point and finding ways that we can make our tools even more robust through M&A work? That keeps me excited because I know that brings a fresh slate of data and people and new processes to bring in and translate into what we're doing so I think I'm good for now.

I was curious because being the “first” of something is a specific kind of person. Some people don't like it. I mean, I'm similar, where they haven’t really invested in this side of the business or need to because of what’s happening. I think a lot of growing companies, and startups that are in the scaling startup phase are under-invested in the people area. This can lead to organizational debt around people processes, tools, and programs.

What are some of the biggest challenges you've faced in general being the first people leader at a company?

Over the last couple of years, I think the theme that a lot of us have had is how do we keep our team together in a world where we're all physically apart. The theme isn't new to me because I have worked remote roles for, gosh, a decade now. Prior to my role with HQ Raleigh which is now Raleigh Founded, I was an operations manager for a small IT firm. The team was all over the country doing jobs so I still had to find ways to bring us together. That is the biggest challenge, I think, for a lot of companies right now. You were able to mold yourself around a physical space where you could listen to the person next to you on a call and learn from that. You could pop into the break room and be next to the CEO grabbing coffee, and feel like you had a presence where you could influence the team.

We've had people in our teams who have struggled with, "Well, what does my career even look like? I can't even meet people, I don't eat lunch with them. How do I have these conversations without it feeling forced?" Making sure we're very intentional about bringing people together, and giving people opportunities to connect has been a big challenge throughout my career.

The other challenge as the first people person is the tech stack. There are so many tools. Finding the right thing for your team at the space that you're at right now that can also scale with you and not cause you a headache two years down the road when you're at 500 people — those are always the things that I'm thinking about.

I think, "Okay, this might feel like the right decision now but will this be the right thing a year from now or two years from now?" So really looking through our options around the tech stack and then getting the buy-in from the team is always difficult. How do you make sure that whatever you implement, how do you get that adoption rate up? It’s always a struggle at any company and it's not unique to my department, it's every department.

Yeah, for sure. When you say tech stack, do you mean people tech stack or do you mean the whole company?

I mean the whole company. If my people software doesn't really talk to anything else and we can't flow things together or minimize the amount of software use that we need, that’s a problem. There are always additional costs. There's additional implementation and upkeep. So I always try to look at it from, "All right. What does our full company tech stack look like and how many of these things that you're using X, Y, and Z for could I pull into my HRCM? My HR management tool.”

If I can't pull it in there, is there another tool that we're not using right now that pulls together two or three of these components, right? So I look at it more holistically for the whole organization but not every people leader has that opportunity, to be honest, and they're like, "Oh, whoa." Operations are like, "Nope, that's... Your lane is over there. Don't come over here talking to me about what our Salesforce community looks like?” I'm fortunate. I don't have that problem but I've seen it even in slight bits of consulting where people just don't know what to do to get everyone on board.

I don't think people always understand the role of the people area and how it can support the business. There's a legacy. I mean, HR has notoriously done some things and has people see it as like, "Oh, you're just here for legal compliance to protect the company. You don't give a crap," but I know people leaders who do care and are quite sophisticated in their thinking.

Yes. I mean, truly, I think I care pretty deeply about people. I do my very best to make sure that we've done all we can to support people in the roles that they're in or give them opportunities to move into other roles that might be a better alignment to their skills or where they're at just personally in life. It is hard, the whole HR is not your friend mantra and I'm like... From me working in a lot of different departments, I'm like, "Well, what department is the friend department?"It's like the IT department's here to make sure that we don't get hacked, right? And if you're doing something that's going to cause us to get hacked, they're not your friend, right? If you're a software engineer and you're breaking our code in the background, no one's going to be happy with you about that either.

Across the whole company, we all have to think about compliance. Yes, I realize that the HR team at most companies is the messenger, a lot of times, around compliance issues but it is very rare that the compliance issue stems from us. I mean, most of the time it's like someone in a department did something wrong and now we've got to swoop in and course correct for folks so it is tough sometimes to hear people say that.

Tech is a little easier in a lot of ways. I don't really see myself at this point working outside of the tech world. It aligns well with my personal life, and my professional aspirations and the types of people that I get to work with usually are a sort of similar mindset with diversity. I love thought diversity but being on a general same page around how we run a company is important to me.

I’m smiling because when the people side of the business is doing their job well, you don't see us doing our work. When things are running smoothly that there is a ton of work that goes into making that happen. They only see when something goes badly and the people team has to do things they don’t enjoy either. Who likes to let anyone go? It’s the worst.

It's the worst. It's the absolute worst. I have lost many nights of sleep over decisions around who can continue employment with us or is not. It's tough. On the flip side, I think now I have enough perspective across my career to be able to see that sometimes this is not the right place anymore for someone.

I've watched so many people go on to what becomes the exact right role for them, it gives them career progression, or it gives them a salary that aligns more with what they desire. Sometimes it's just not the right fit anymore and then that's the tough part for people when you're in the middle of it. No one wants to be in the middle of it but when most people get to the other side of either being laid off or let go, or just completely fired. I do think that people can generally look back on it and be like, "Okay, that was just part of the story and now, I'm onto the next chapter." Hopefully, they can maintain relationships with the people that they develop relationships with. But yeah, it is tough. Nobody wants to fire anyone.

I've been laid off five or six times in my career. I've had to lay off people and let people go unfortunately in the roles that I've been in. So I've been on both sides of the house. I too have come to that place where I don't enjoy doing it but I know it's best for everyone involved even if it's difficult and I do think there's some nuance there in how that person is treated on the way out.

100%. It's really tough and as we are in this part of the industry right now where we're seeing a lot of layoffs happen across tech and my company even had a very small reorganization around our engineering function recently and it's tough. It is really tough. I wish there was an exact right way to do it but because we are held to so many standards in the tech world in particular around security and operational compliance and having our stockSOC audits and all of those things annually, it's very hard to not do a mass Zoom call.

I want to do right by people and I know that when it comes time for my audit, my auditor's going to be like, "Wait. So you laid off 20 people in the morning and you didn't even cut their access until 8:00 PM once you were able to talk to everyone one to one?" Those are the things, unfortunately, that we have to think about. Those mass Zoom call decisions, it's so impersonal and if you're doing those, you should be opening up one-to-ones immediately with your HR team and the managers for people to jump into.

That's what I did. I had a calendar that went out immediately, you can grab a time with me, let's talk through what this looks like. I tried to help people where I could with resumes and advice. I had a lot of people who had been with us for many years and hadn't really been in the career world in a while. The best you can do is just do right by people — treat them the way that I would hope someone would treat you in that circumstance. So it's tough and it stings and trust me, it's gut-wrenching for anyone who's on this side of the table having to deliver that news. You just have to do the best you can.

How big was Softdocs when you joined? Where’s the company now?

When I joined, we were around 105. We are 120 right now.

So some growth, but not massive.

Yeah. We didn’t intend to have any massive growth. We’re not a VC company. We're private equity backed. As a 20-year-old company, our hiring is driven very much by our sales and the needs that we have to implement our software at primarily higher ed and K-12 institutions. We hire slower and hire more strategically than many VC-backed tech companies. That happened at my last company. I brought in 110 people into that in a year and a half. It was exciting. I love the momentum but even for some of those companies, they've had layoffs and it's tough to see it.

It all comes down to that next round of funding for a lot of these companies. We're fortunate. We have a really strong revenue, our company is doing well, we have a great client base and our retention rate around our clients is 97%. Those things are encouraging. I feel like we have the right size team now for the work that needs to be performed for the client base we have and the new clients coming in by the end of this year.

Scaling fast puts a strain on the operational and people sides of the business that people don't recognize. The experience can erode unless you have already invested in operational and people and the business infrastructure to support that.

Absolutely. My current company was venture-backed in March of 2021 and the founders are part of our board but they're not a part of the day-to-day anymore. They were ready for family life and all of those things. Our board which is Ridgemont Equity Partners, they are just truly a phenomenal group of human beings. I mean, they do so much to support us and understand what we need to grow. Our CEO was hired as part of that process so he joined the company a little over a year ago now. When he came in he was like, "I cannot believe this company doesn't have an HR person. I need an HR person. I cannot be that person." When I met him, I was like, "This is someone I really would love to work with. Someone, I felt like could grow me in my career and my experience.” We were intentional around my title. He didn't want me to be the HR lady and just in the background doing payroll and benefits and nobody ever seeing me. For him, it was much more around career pathing, giving people a great experience no matter how long they're with us, and making sure that we're taking care of people the best we can. I feel like I've been able to implement a lot of those things in a really short amount of time.

You built out the function including the team so what has that entailed? How big is your team now?

I have two on my team. I started with a talent coordinator last fall. He recently moved into more of a people operations and experience role so he's doing a lot more on the individual contributor level. I'm doing much more on the management level as far as those one-to-one relationships and those types of things. He's also building out our onboarding program and working with me to upskill the areas. We just welcomed a senior technical recruiter to our team who will probably be doing most of our recruiting. She and I worked together at my previous company so I was very happy to be able to bring her to my team. We filled a couple of technical roles quickly with her here. We're very excited for the next phase of our software with these roles in place.

What are some of the other things you’ve done to build the function?

During my interview process, I put out a one-year roadmap of what I would be rolling out. One of the big things I did was move a very archaic payroll system to a true HRCM. It has performance management, compensation tools, and our applicant tracking system. I was blown away by how much our company had spent on recruiting over the last year with hiring in some executive roles and of course, just a lot of individual contributor roles. We've experienced turnover like every other company in this industry, right?

So though we're at 120, we've also had a lot of backfills and a lot of changes that have happened and that's just a natural thing that happens after an equity backing anyway. So it was like, "Okay, we've got to get an HR system in. We aren't doing much around performance management, manager training, a proper onboarding with intro sessions across the whole team, really bringing people together." We developed a culture club so we have events each month that bring people together. It's been a lot, honestly.

That is a lot. What was about building the function?

Some things haven’t been tremendously hard because the team was so hungry for it. They were like, "Oh, we want career progression. We want to know what that looks like." We've seen it happen organically and naturally throughout the company where people have been able to move up and move around and move different departments and it's so well supported.

I would say probably the hardest thing, honestly, for me has been the company has many employees who were here prior to the acquisition, and then, we have a lot of new employees. So finding ways that we can encourage our folks with institutional knowledge to stay and see through the change. That's probably been one of the harder parts of my role. Helping them along with my leadership team to understand the vision — to understand where it is today isn't where it will always be. To rally and get them excited about what we have coming down our product pipeline and our clients' stories.

I think we're at the point now where the people who really are excited to stay are here. I mean, we have people 19, 20, 18, and 17 years of employment with this company. It's like working for a new company now. One of the harder things is finding ways to bridge those relationships and that knowledge transfer into our new team and a new way of doing things. It's been exciting at the same time and I do think the team has been primarily receptive to a lot of the changes that we've had.

I think that's typical after a big event like that, trying to blend those things and keep that institutional knowledge. What advice would you give to other folks who are the first people leader at a company? What advice might you give them?

I give a lot of advice to those people so I would say, really roadmap out what your key initiatives are and understand what the timeline and commitment are going to look like to get there. Make sure that you have your leadership team buy-in because nothing that you ever do as a people leader in any department, it doesn't matter if you're on the people team or if you're in professional services or engineering, nothing you ever do will take off if you do not have leadership buy-in. You need them, you need your allies, you need individual contributors who are your allies, who are out there pushing the decisions you made, pushing the products you're implementing, all of those things.

If you’re the first people leader on a team the biggest thing is to roadmap it out — understand where you are now and where you want to be — and then get your leadership team's buy-in around the process to ensure you reach your goal.

If this piece resonated with you, please let me know and give the heart button below a tap.