How do you start to grow your team?

Here are my thoughts based on experiences of building my first successful startup (https://www.nakedapartments.com/), which was later sold to Zillow Group.

how have you decided who your first hire should be?
I realized I was stretched too thin and needed help. This was about 2-3 years into building the business with a partner and getting it profitable. I evaluated what areas of the business needed my talents and skillsets. Then reviewed what position would provide me more time to focus on what I needed to get done. For me, it was hiring more engineers. As the CTO of the company, I wanted to continue taking care of customer support requests so I could be on the frontlines of hearing customer pain points. That was one of the best decisions we ever made.

what do you class as a hire?
Anyone that will impact our culture.

are they freelance, long term contract or permanent staff?
In the very beginning we used some contractors but for a short time. We quickly moved to a permanent staff.

how do you deal with legalities?

We leaned on a lawyer and also did a lot of research. We had a fully distributed team, so we ended up having to deal with a lot of different state laws. We made mistakes, but fixed them.

do you go for cheap staff, or probably more expensive long term people?

I don't believe in hiring cheap staff. I want to hire people that I enjoy working, who also bring in talents we need to grow the business. It's tempting to hire the cheap folks, I get it. I'd prefer to have a small team, who is paid well and kicks ass vs. a cheap team that requires lots of management.

where do you actually find the people that you hire?

We started in the NYC area, but quickly found it too competitive. We all worked from home, so we decided to look all across the United States. Compared to hiring in NYC, it was so easy to find engineers who wanted to work on an exciting product and get good pay.

do people come to you?

Not with my first company. It took job postings and then working on my sales pitch for them to be excited to come onboard. However, since I've left that company, people do come to me now since they heard about the great culture we had.

is it about getting a job done? or building a great team culture? or both?

Both. You need to build a great team culture, but it's a business. You need to get shit done. Many first time managers focus exclusively on making sure a candidate has the skills to do the job. I'd argue that's the lowest priority. Instead, we looked for candidates who shared common values, know how to get things done without micromanagement, and have extraordinary abilities. Skills can be learned. Work ethic is very hard to change, even with proper motivation.

do you get excited by building a team?
Absolutely! The ability to give people a great job and having them help contribute to an ever evolving amazing culture is very fulfilling. However, I don't measure my success based on the number of employees my company has. I enjoy the relationships and building something great together.

hiring is a mixed bag which most of the times backfire if you don't have a clue. Hiring is not just hiring but so much more, giving people purpose, creating or rather curating their growth etc.

I've gone this route for a few years: If you have a clear task/goal/strict boundaries/a development plan over 2-3 yrs for that person you can hire. The less you have yourself such an understanding and hence, the more freedom you give that person the more the whole thing will blow up very early leading to an hire complaining all day.

We used freelancers for the first couple years of our business, but earlier this year we decided to do our first real hire.

• We hired a specialist because we were spending so much time doing some specific tasks that we knew this position would save us the most time, and let us scale faster.
• A "hire" for us is a full-time, long-term colleague. Not a freelancer or a consultant.
• We wanted to go with a cheap hire, but I'm glad that we found a very competent candidate who was asking a little more than we wanted to pay. She's worth it. Also an ex-Googler.
• Posting on job boards gave us literally hundreds of candidates, but almost all were crap. I manually searched through LinkedIn, filtering down and finally making some offers. We had to convince our candidate to leave her current job and take a bit of a risk with us.
• SO many people come to us. I probably get 5 job inquiries a week, without even looking.
• For us, the primary need was driven by getting a job done. But ultimately, I think it was healthy for our company since we were able to focus, and now every member of our (tiny) company can focus on what they do best.
• I love building a team. I think I'm best when I'm managing people and relationships and partners.