How to Navigate the First 90 Days as the First HR Hire at a Startup

Andy Cook
July 24, 2017
Interview with Heather Doshay

Heather Doshay is an HR veteran who has worked at multiple startups. She’s seen first hand how rapid growth can either make a company hugely successful or break it apart at the seams.

In Heather’s latest role as the first HR hire at Rainforest,  she’s on the lookout for any cracks starting to form in the company’s culture and processes. Small cracks aren’t always visible or might seem trivial, but if left untreated, they can break apart a company.

Sure enough like all fast growing startups on the verge of success, Heather saw a couple rifts taking shape at Rainforest. As VP of People, she knew it was her job to patch them so the company can grow while preserving what made the startup successful in the first place.

heather doshay

When you conjure up an image of a craftsperson at a company, HR probably isn’t first discipline you think of. But HR is an artful technique in it’s own right.

Helping a startup scale is very much like the Japanese pottery technique Kintsugi.

It’s a method for fixing broken pottery by combining lacquer with powdered gold, then using the mixture to bond the piece back together. The philosophy treats breakage and repair as part of the history of the object rather than something to disguise. The end result not only reassembles the broken object, but highlights the original cracks as a thing of beauty.

kintsugi pottery bowl

Most startups don’t hire an HR team member until they’re at least 50 people. It’s around the time that processes start to feel a bit chaotic and the company needs a person to step in to handle change management along with creating official procedures. Much like Kintsugi, the first HR hire walks a fine line between repairing broken processes or culture and making sure not to contort what’s currently working or pretend there isn’t an existing culture in place.

As Doshay remembers when she joined Rainforest, “most startups are maybe fearful of human resources, so really positioning myself  coming into the company as a resource for both talent and career development allowed me to really do all the right things by people.”

What works for a team of 10 doesn’t usually works for a team of 50. While some of the ideas and processes the founder put in place in the early days have great intent and made the startup successful so far, they might break down at scale.

How do you fill the cracks in your culture with gold to fix them and ultimately make the startup stronger? In this exclusive interview, we’ll learn from Heather about what she did in the first 90 days as the Vice President of People at Rainforest.

Playbook for the first 30 days

Being the first HR hire at a startup can be a tricky job, as Heather knows from first-hand experience at Rainforest. “Usually startups don’t hire HR people when a company is small. They hire them when the problems are already real and apparent”

For someone whose job it is to listen and create systems to help people do better work, it’s tempting to come in and make changes right away. “There’s so many quick wins that you see and you’ll think, ‘Oh, well that’s not a huge problem. We can fix that.’”

But according to Heather, that’s the wrong instinct. “It’s hard to try and decide which things to just jump in and make quick wins on versus which things to wait until you talk to everybody to see how the problem is really best solved.” The beginning should really just be about listening and getting a full picture of all the challenges the company is facing.

“In that first 30 days, no one really knows what you do and you don’t really do a whole lot. You’re kind of just listening. What that does for you is build a foundation so you can move really fast and understand exactly who is impacted by various decisions.”

Building Understanding by Strategically Listening

Heather employed a few tactics in the first 30 days to ensure Rainforest had a successful transition from a thriving startup to a company with more processes in place for sustainable growth. Here are some of the ways she pulled it off:

Setup 1:1s

Heather had a goal to meet with all 51 team members within her first 60 days. “I met with every single person strategically. I put time on their calendars or I asked them to put time on mine.”

She asked everyone in those meetings “what they’re doing in their job today, what they’d like to be doing long term, what kind of skills they’d like to acquire, and how they feel about certain aspects of the company.” At the end, she had a good understanding of what her teammates’ professional goals and preferences were at Rainforest.

Beyond getting to know everyone on a professional level, another important aspect was getting to know everyone personally. “Every time I did a one-on-one with someone, I pulled up a little notepad on my Mac. Basically I have a person’s name and all the notes next to it, so that I could go back and remember what I learned about them.”

“After a month, you should at that point almost be able to name every single person in the company because you’ve sat with them, talked with them. You know something about them personally and professionally.”

Heather’s goal for all these meetings wasn’t to find quick wins. It was to get a 360 degree view of who everyone was at the company and learn what was and wasn’t working. “Ideally, you don’t make any decisions.” Instead, focus on identifying the differences between one-off problems or more systemic patterns.

Send a company wide survey

While scheduling one on one meetings, Heather also sent out a survey to the team to learn how things really operated at Rainforest:  what people enjoyed about the culture, what they’d like to see changed, who they were as  people, and what they would like to see from the company in the future. She aggregated this data to pull insights to help guide her conversations and more easily identify patterns in the future.

  • How supportive is Rainforest QA of your career development?
  • Imagine it’s 2 years from today. What do you hope you are doing professionally?
  • ​How do you feel about your own performance?
  • Do you get feedback?
  • Do you feel comfortable giving feedback?​

Sit in on meetings –  any meeting

Heather explained that at the beginning of the job, she didn’t just go to meetings she was invited to – she went  to all types of meetings to really get a full view of the company. As VP of People, “it’s about making strategic choices with people, their time, how we enable them, the resources we give them, the ways we give them freedom or structure, so that they can be the most successful, so, that the company hits its business goals.”

To get a better understanding of how she could empower people on all different teams,  “I sat in on a lot of meetings that weren’t meant for me. I went to sales training meetings and operations meetings – things like that, to understand every in and out of the company and every team member.”

Making Changes and Mending Mistakes

After Heather talked to the entire team, she knew what changes needed to be made and started rolling them out. After rolling out a few changes, one of the main lessons she learned was that even though she was the first official HR hire, she didn’t need to do everything in the traditional HR way. Using traditional HR playbooks and processes in a startup caused her to stumble on some of her initial changes.

One of the first mistakes Doshay says she made was implementing performance reviews. This had to be done carefully since “no one ever says ‘I want a performance review.’  What people said was, ‘I would like to know how I’m doing and I would like that to be more formalized.’ And so we slowly rolled out performance conversations – importantly calling it a conversation, not calling it a review.”

While employees wanted to have these more strategic conversations about their careers, Heather does admit that mistakes were made when the reviews were first rolled out. For example – using a 1-5 number rating system.

“In most performance conversations that have been had across companies where I’ve worked, you have all the qualitative stuff and then you self rate one to five and so does your manager. And I did that just because I think that it’s the way I’ve always seen them.” As Doshay admits herself in hindsight, “this is probably a really terrible answer.”  What she realized is that people liked the conversations for the most part, but they struggled with that number rating, as they do at many companies. “And I thought, ‘We don’t have to do a number.’ Because at the end of the day, that rating, it’s really not for the team member and it doesn’t help them. A lot of companies will say, ‘Oh, you’re a three and that means you’re doing a great job.’ But a three feels like a C to people. And even if you say it’s not a C, it doesn’t feel great.”

It was important for her to take the good parts of the structural aspects of more traditional companies while having the opportunity to do things a bit differently at Rainforest. She repaired a crack in the company’s processes while also making it beautifully fit into the startup’s existing culture.

Keeping The Good, But Making It Scale

One of the reasons people are attracted to working at startups is that they don’t have a lot of traditional processes and bureaucracy. That ethos usually comes from the company’s founders. “Everything that is put in place in early days by founders comes with the best intentions. No startup founder is trying to do things just to be a rebel. They are doing things because the traditional things don’t work.”

More often than not, the procedures and processes that the founders put in place at 10 people break down at 50, causing unintended effects.

When asked about how you make changes to unscalable systems, Heather responded, “it’s about creating the right structures that enable people to feel supported and resourced and able to speak up without creating so many structure that they feel limited. It’s a hard balance. We’re always figuring it out.”

“It’s really about understanding the ethos and the intent of the item and recognizing what is worth seeing through, even if it fails later, versus what we can make changes for now that maybe have the same intent and potential side effects or wins that are also scalable.”

At Rainforest, some of those programs in the early days had unintended consequences that didn’t scale as the company grew headcount. A good example from Heather follows: flat organizations not actually being so flat.

Flat organizations can’t always scale

Rainforest was a completely flat organization in the beginning. “Our CEO Fred thought, ‘Okay – We’re flat. Everyone’s equal. Everyone will be able to say whatever they want.’”

And until recently, that worked really well. “I started on the same day as our VP of Engineering, who’s amazing. So, we had our co-founder CEO, our co-founder CTO, and one other VP and that was essentially the whole leadership team  I joined.  But the thing was, is that nobody was speaking up.”

After doing some research and talking to everyone on the team, Heather realized a counter-intuitive truth about non-hierarchical org charts.  “One thing that was super surprising was that people think they want a flat organization, but if they were junior, they didn’t actually didn’t want a flat organization.”

Rather than having everyone speaking, you had the voices of the three executives speaking, and assuming that people were sharing things. But they weren’t always sharing things.

The team realized that most people who weren’t “senior level” wouldn’t feel comfortable bringing up issues with the executives. “Most people think introducing VPs or another management layer into the mix to create more structure is bad. People won’t get heard. It can feel much more bureaucratic.”

The reality is that this isn’t the case. Hiring more executive leadership “actually enables people to speak up because they weren’t afraid speak up to their VP. And their VP surely wasn’t afraid to take action and say something at the executive table. Whereas, if you’re a Sales Development Representative, you might not feel safe going directly to the CEO to say, “I don’t like that you’re doing things this way.” But you can sure go to your SDR manager or your VP of Sales and say, “I don’t like that you’re doing things this way,” and they’ll go and make that change.”

While introducing VPs and additional layers like managers might seem more bureaucratic, it actually enables people at every level of the organization to comfortably speak up. As Doshay summarizes it, “Flatness in theory would create equality and openness and everyone communicating. In practice, it stifled opinions of people who are more junior.”

You’re A Coach, Not An Administrator

When asked to give her #1 piece of advice to other inaugural People Ops hires at startups, Heather replied that it’s important to recognize and define what role you play for the team early on.

“I think one way that HR tends to get it wrong is that they tend to be administrative, so people don’t invite them to the executive table. They don’t see them as being strategic. They think, ‘Okay. Well, if we’re gonna do this, I guess we should see if there are other HR issues.’ And they come to this HR person in the corner of a room and ask them. But a lot of things are at core, people issues and resourcing issues.”

Doshay positioned herself early as a coach and strategic partner to senior leadership and continues to do so rather than as an administrative burden. Likewise, she positions herself to the team as a resource rather than a policing agent. She likes to offer one-on-one coaching sessions and career workshops, making herself available to help any employee. “I just try to see myself as a strategic problem solver, and partner, and coach, to really anybody who needs it. But especially to people who are managing teams and executives because I feel like their impact is so broad that they really sometimes need another ear, another opinion in the mix.”

It’s good advice that’s in line with how other Vice Presidents at the company are thinking about their roles. “If you look at a VP of sales, their job is to help the company achieve its business goals through sales, like revenue dollars. And if you look at a VP of Product, their job is supposed to help the company achieve its business goals and revenue dollars through creating the right products. If you look at VP of People, my job is to still help the company meet its business goals and revenue goals, but through people.”

Her advice to early HR hires is to be a strategic coach who empowers the organization. “It’s about making strategic choices with people, their time, how we enable them, the resources we give them, the ways we give them freedom or structure, so that they can be the most successful.”

“Be the person that creates the stuff that will allow people to achieve business/organizational goals just like a salesperson would help people achieve revenue goals.”

It’s a Balancing Act

For Rainforest, carefully crafting their employee experience is working. Entrepreneur recently named Rainforest one of the best company cultures in 2017 for medium-sized companies.

Achieving a milestone like that isn’t easy and joining a startup as the first People Ops hire is a worthy challenge. Not only are you fixing the cracks in the company’s culture and processes, but you’re also setting the tone for how HR will be viewed in the organization going forward.

Like everything with a startup, it’s a balancing act. It’s important to not ignore the culture that existed prior to HR formalities while also repairing the cracks that have formed.

As the first HR hire at a startup, you aren’t just trying to fill those cracks. Your goal is to build a stronger organization that is better for having dealt with its flaws making sure that they’re filled with gold. The best way to do that is by improving upon the intent of existing process and acknowledging what has made the company successful. Doing so will ultimately make the organization stronger, more beautiful and an amazing place to build a career.