Self Love

Ready to Hire a Team? 5 Things You Need to Know

February 3, 2015

Congratulations, sister! You have reached a place in your business where you not only NEED to hire someone… you actually CAN. Before I get into the how-to-dirty-deets, let’s both take a moment to pat yourself on the back. Getting to this place in your business took a lot of blood, sweat and tears on your part. That deserves serious kudos and recognition.

It’s also fucking scary, right? It’s not like you don’t have enough responsibility on your plate running a business and all, and now you’ve gotta add taking care of other human beings to your plate. (Take a deep breath. You got this.)

So, let’s get down to the business of bringing people into your business.

How do you know it’s time?

How do you find the right people?

How do you manage them, once you do?

How do you recruit them when you might have limited resources?

I answer all these Q’s and then some with these 5 critical things to consider when hiring a team:

The Hole: First thing’s first when figuring out who and when to hire: identify the biggest need in your company right now.  As an example, you as the founder might be crushing it in biz dev, or content, or technology. What’s really missing? Perhaps an office manager, a sales rep, a social media marketer, or a super strong designer. My recommendation is that the first investment you make in hiring your first staff member should be in someone who can ultimately help drive and support the production of more sales and revenue, whether directly or indirectly. Sales people are great, and can absolutely bring value to your bottom line if they’re strong enough. I believe no one can sell like a founder, but chances are you’re spending a lot of your time away from driving business because you’re caught up in the administrative details of running a business. Implementing a key team member who can free up your time so that you can produce more revenue is a great strategic hiring play. Look at where the money can come from the quickest and always start with that hole.

The Environment: These days, it’s cool to work in a start-up or a new business. The word “entrepreneur” has practically become trendy. And while the whole “all hands on deck” motto is awesome and can inspire great collaborative energy, structure needs to be in place so that your staff remains accountable to you.  The fact is this: as a founder, you will not be behind a desk most days. You will be on the ground, pounding the pavement, making shit happen. There’s an expression that a fellow Entrepreneurial Babe once said to me: “When the cat is away, the mice will play.” I personally had to learn this one the hard way and it fucking crushed me.  Ensure accountability is upheld at the office, or at your virtual one, with systems for checkins and project management. There are various affordable project management tools out there that are awesome for new and more mature businesses alike.  I personally love Asana,  Team Work and Basecamp as easy-to-implement solutions.

The Peeps: Finding great talent is probably the trickiest part of the whole hiring game. It’s safe to say that no one is going to love your brand or your business as much as you do. Well, almost no one. One of my dearest mentors and advisors once told me that when hiring, look for “Brand Evangelists.” These peeps are rare, but they are easy to spot. There’s a difference between brand fans (there are the peeps who share your content, comment on your posts, they might even refer you to prospective clients) and Evangelists. Evangelists have a hunger. Evangelists dream big as well. Evangelists can (and should) enlighten and inspire you in an interview. I recently helped bring on a new hire for a company I am consulting for and during the interview, I asked him what his biggest passion in business was. His answer? “I like building disruptive technologies that can help serve the customer in a way they’ve never been served before.” #Hired. It blew me away. On one end of my experience, I have interviewed and worked with a handful of expectant and entitled people, looking to enter the workforce without paying their dues. But on the other end, there are plenty of people who are passionate, hungry and committed enough to get involved in a good opportunity when they see one. Keep your eyes wide open for them.

#BEABOSS:  This is a tough one, but so significant. This was another hard lesson I had to learn. We all want to be liked.  At least I do. But being liked and respected can’t happen in tandem. And you guessed which one is more important. The truth of the matter is very few people are innately good at people management. It really does take an immense amount of focus, humility and daily effort to manage efficiently and effectively. As the Boss-lady, remember that the entire office culture and company vibe starts with you. That vibe can no doubt be fun and creative, but you must establish respect from the get-go and that means setting up and maintaining rules and boundaries. Accept the fact you indeed might not be liked at all, or at least for a while. Don’t be afraid to reprimand when it’s appropriate.  You don’t need to go all Meryl Streep from The Devil Wears Prada on their ass, but if your employees think you’re a bitch for a hot-minute, so be it. You need to let those fears and paranoia go. When hiring and recruiting, you want to find people that – yes, you will like and get along with, and could even grab a cocktail with– but you will also be able to draw the line with.  If you’re a compassionate, big-hearted business owner (and I guarantee you are), that line is a verrrry fine one, so keep your #BOSS in the forefront at all times.

The Dollars & Cents: Depending on where you are with your fundraising or revenue rollout, offering equity to top level hires might make sense. This is a very personal decision and goes back to finding the right people. Commissions and bonuses are also a great option for a newer company and can help motivate your team. (I have always loved the philosophy, “Eat what you kill.”) If you’re a little lost on what compensation needs to look like relative to the role and experience level, check out You can do a deep dive search on this website, refining by not only title but by also geo-location. Other resources include finding insurance options, bonus structures and other standard expectations like sick days, paid time off, etc. Make sure you don’t just compare one to one. Do your research on the entire landscape. Finally, money might be tight. Therefore commission, bonuses and equity might not doable. Look to your own company for creative and innovative ways to supplement and enhance the perks and lifestyle of your team. Trade, gift cards, industry hook-ups and simple downright appreciation shown via the gift of time can mean a lot and go a long way. Remember, you’re an Entrepreneurial Babe. You make the rules.

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  • Arielle Miller Levitan

    Thanks Jessica. This is so inspiring for those of us building companies. At Vous Vitamin we are learning so much every day about ourselves and the people we employ. It’s great to see some of the daily struggles “Boss lady” described so well and your suggestions are very helpful. Being an entrepreneur is largely a learn as you go process, but getting some great guidance along the way is so helpful. You start to realize you are not the first woman to have done this. It would also be great to hear your take on working with a business partner since that relationship is also delicate and powerful.

    • Thanks Arielle! I am SO glad you found this helpful. And yes, business partnerships are indeed very delicate and powerful. I’m sure I’ll write a blog on that someday! 🙂