How to Make Your First HR Hire

By far the most common question I get from CEOs is how/when/who to hire as your first HR hire. Here’s what I tell them in terms of practical advice:

1. Prioritize: The temptation is to prioritize everything–recruiting, compliance, exec coaching, office management, etc. Resist this temptation: identify clearly why you are hiring an HR person and what their skillset should be before you hire someone. Your priority list should have no more than 5 items on it and you should ask yourself before you post if anyone you’ve ever worked with previously truly has that skill set–no cheating. More often than not, you know someone who can do 3 of the things you outlined but not 5, so really push yourself on what’s on that list and whether anyone but a unicorn could actually do the job.?
2. Level Appropriately: In addition to prioritizing what you need, you have to be realistic about level. Unpopular opinion: I don’t think you need a Chief People Officer if you’re 50 employees. More often, you need a great external consultant on compliance or employment law and an awesome recruiter and/or office manager. The biggest mistake I see CEOs making is wanting someone who is a de facto exec coach, inspiring company meeting leader, great recruiter, and expert on core HR and compliance and wanting to pay them $80,000 for a blanket “head of HR” role. Price and level the role based on your core priorities and do not try to low ball or “combine two roles into one”--it never works the way you hope it will. You should also be clear on when/if they will be able to build a team and the budget they will get to operate with–both are imperative as part of the investment decision.?
3. Set the tone: The executive team (regardless of size) needs to be ready to prioritize the things in question alongside the HR hire–recruiting is everyone’s job, and you can’t do things like job profile leveling or great compensation strategy without serious investment from your senior leaders. Company culture, recruiting great talent, and leading by example are things every single person who is a leader within the company should prioritize, and it’s your job as CEO to make it clear that hiring your first HR person doesn’t absolve anyone of that responsibility–in fact it ups the ante on the team effort required to achieve these goals.?
4. Chemistry matters: there has to be mutual respect between the CEO and the first HR person (or really any HR leader). Note that this does not mean you have to be friends outside of work, that you like each other all the time, or that you always agree on the best approach on things–in fact, I think it’s likely better if you don’t agree on everything and have a healthy ability to disagree with each other. The reality is, your HR team (regardless of size and stage) navigates tough conversations no one else has to handle or navigate, so you want there to be mutual respect and trust as the foundation of a great working relationship. I do NOT recommend waiting to hire someone until every single person on the executive team is bought in on the person–that will lead to a consensus hire and likely mean you will not hire someone for three years. The most important dynamic is between the CEO and HR leader, and that relationship needs to feel respectful and complementary right from the start.
5. Stage Right: There are a lot of wonderful HR leaders who don’t like to build things from scratch and likewise, there are a lot of really amazing startup HR leaders who detest the growing pains of scale. You really want to make sure you hire someone who is excited about the stage and size of growth you’re in. As an example, are you planning international growth next year? M&A, no matter how big/small? Hiring 3 new executives? Hypergrowth? Steady growth? Somewhere in between? Be realistic about where you are and the stage of growth the person is interested in joining-some of the biggest missteps I’ve seen in first hires is a mismatch in interests in how they want to actually spend their time, so testing for enthusiasm for the stage you’re in really matters.?

To address three questions I often get from CEOs after I share this context:

1. How about unconventional HR leaders, like transferring my head of ops or my office manager into this role? I’m a former marketer by trade, so I’m a fan of betting on people with unconventional backgrounds in the world of HR…with one huge caveat. The first HR hire in your organization needs to uplevel the organization’s acumen on recruiting, core HR, diversity, culture, international growth, and similar topics, and it’s really hard for someone who has never done HR to really excel there. If I were the CEO of a company, I would make my first hire someone with experience (HR business partnerships, exec coaching, compliance, or recruiting, depending on your area of greatest need), then as I scaled the team consider betting on people without traditional HR backgrounds to help the team scale and grow. You can absolutely learn those things as the org grows, but it’s easier to do that when you’re part of a larger team and organization than if you’re a solo operator.
2. Can HR report into finance or legal? They can, but I’ll be honest, I really dislike this model. If you say people are your biggest priority, having your people leader report into one of those functions sends a mixed message. Where I’ve seen exceptions work well is having core operating functions report into a COO (I reported to our President/COO at HubSpot for years and loved it), so I can get behind that option or CEO reporting–reporting into legal or finance often means you just want compliance help, in which case you should call it that versus your first people hire.?
3. How many people should be in the interview process? It’s imperative that people respect your people leader, but this isn’t a popularity contest. You absolutely want someone who engages positively with your team and brings great energy to your organization (particularly as the first/only for awhile), but sometimes people veer too far in bringing someone in who is more fun and games than actually elevating your team and your culture, so just be mindful of finding the balance between likeability and the ability to do the job and make your organization better.?

Four questions to help you (the CEO) and your first people leader align on values:

1. If someone came to HR with a complaint about one of our top performers in the organization, how would you handle it? As a note, if you say “so long as it isn’t X person” you’re not ready for an HR leader yet (and are bound to be sorely disappointed down the line by how this ends).?
2. How do we think about diversity and inclusion as a value in the organization and how is it currently reflected in our practices? Where do you hope it is in five years? A great people leader should be able to give you some ideas to get started, but also a great people leader will want to partner with a CEO who really has a sense of where she stands on this topic and where she wants to invest energy and time herself in DEI as a practice. As a note, I personally like it when people set clear, manageable goals here versus trying to be all things to all people–focus is key in all things startups, and it’s true of diversity work as well.
3. How will we handle it when we disagree? Before you make an offer you should get really clear on how you will handle disagreements and in what contexts. As I mentioned above healthy debate is a big part of great people and business leader partnerships, so you’ll want to make sure you both agree to how you’ll handle these situations with grace and with clear guiding principles.?
4. What do you feel strongly about as it relates to how/when/where people work? This should include a discussion of remote work, flexible work, vacation, and what it means to be a great manager. For context, HubSpot's unlimited vacation policy emerged from Brian and Dharmesh's dislike for onerous paperwork and micromanagement. Speak openly about what you feel strongly about with regard to how people work--it will help ensure you're aligned on what matters most as you scale.

In conclusion, the final question I usually get is “where can I find a great HR leader?” I recommend sharing with your network on LinkedIn, sending personal and thoughtful emails to HR leaders at companies you admire asking them to spread the word or share with their network, asking your investors to share with their networks, and following great HR leaders to see who comments and engages with their content–I’ve listed a few people people (and adjacent spaces) I dearly admire below to make your life easier. Hope this helps, and happy people team building!

Lars Schmidt Mita Mallick Doniel Sutton (she/her) Donna Morris Jennie Rogerson Paaras Parker Pat Wadors Adam Bryant (follow his CHRO series for weekly inspiration) Laszlo Bock The Modern People Leader (their guests are all great follows) Joan Burke Patty McCord Carmel Galvin Jaime Bott Sheela Subramanian to name just a few.