Hiring your first employee is an exciting, and potentially stressful time for any business. Expanding your team beyond the founders means your company is bringing in enough money to grow, and having help means you can work less in the business and focus more on the business from a strategic level. But if you’ve never hired or managed anyone before, how do you find the right people for your team? We’ve got all the details for you including where to post your jobs, how to filter applications, interview questions, and more.

When Hiring Your First Employee (and All of Your Employees), Go Remote

Step away from the expensive office space… and commuting time, unnecessary meetings, and overhead. Build a virtual team and hire your first employee (and every one after that) remote.

Step away from the expensive office space… and commuting time, unnecessary meetings, and overhead. Build a virtual team and hire your first employee (and every one after that) remote.

First off, if you haven’t already committed to going remote, you should. Most SaaS businesses don’t need or benefit from having a traditional office, and expanding your job search to “everywhere” will give you access to a bigger talent pool with more competitive rates. Hiring remote from your first employee on also means you’ll get all the benefits of remote work, with none of the headaches of trying to integrate an in-person team with a remote team later on. 

Plus, managing a virtual team is easy with the right tools and practices. In fact, SureSwift is a fully-remote company with 80 employees working in 14 different time zones, and we wouldn’t have it any other way. 

But however you decide to structure your business, there are certain qualities that make for a great team member. Small teams and startups don’t have the time or capital for ineffective employees. You need proactive, resilient self-starters who have experience managing their time effectively, and you need to not spend months and months finding them.


How to Write Your Job Description

All of your channels come in handy when you’re hiring your first employee. Use your website, social media accounts, and even your email list if you have one.You don’t need to reinvent the job description. There’s a reason the format is pretty standard. But you should make sure it’s appealing to the best candidates. Here are a few tips:

  • Include a bit about your business. What does your company do, and how do you help your customers or make their lives better? 
  • Include an overview of the job duties along with a brief, bulleted list that includes specific skills, requirements, etc. 
  • If the job is remote, or has flexible hours, include that in the job title. For example: “Remote Customer Support Position” or “Remote Web Developer: Flexible Hours.” (Read up on crafting your posts to attract remote workers). 
  • Keep it simple, but include some instructions on how to apply for the position. Things like a specific subject line, a few questions to answer as part of a cover letter, or including a link to a resume on Google Docs will all help you do a first quick filter of your applications. Attention to detail is important to any job, and this is a great way to help you filter applications (more on that below). 
  • If you have a salary or an hourly range in mind, you may want to include it in your job description. Or, you can ask applicants to include their desired rate in their email. 

Where to Post Your Job

All of your channels come in handy when you’re hiring your first employee. Use your website, social media accounts, and even your email list if you have one.

All of your channels come in handy when you’re hiring your first employee. Use your website, social media accounts, and even your email list if you have one.

  • Even if you’re just starting out you should put the full job posting on your website, and promote via your company’s social media accounts. If the job is remote or has flexible hours, be sure to include that in the title. 
  • Let your professional network know you’re hiring, and ask them to share the posting as well. We’ve had great success with referrals from the SureSwift team.
  • Share the job post with your email list. If people like your product, they might want to work with you to help grow it. 
  • FlexJobs and WeWorkRemotely are two job posting sites dedicated specifically to remote work.
  • PowertoFly is a job board aimed specifically at female candidates, with a remote-specific search. With 56% of women leaving the workforce mid-career, and a good chunk of that churn due to a lack of flexibility, there are some seriously talented candidates out there being left in the job pool by your brick-and-mortar peers.
  • UpWork is a good place to look for entry-level freelancers. If you’re looking for a long-term relationship or more experience, you might be better off creating a freelance job posting using one of the sites above.

How to Narrow Down Your Candidates

Where you post your job and the type of employee you’re looking for will determine how many applicants you get. Sometimes you may just get a few and other times you may have an overwhelming number.

Where you post your job and the type of employee you’re looking for will determine how many applicants you get. Sometimes you may just get a few and other times you may have an overwhelming number.

Here are a few ways to help narrow your list of candidates: 

  • Look for personal referrals and if they meet the job qualifications, put them at the top of your list. Networking is one of the best ways to find good talent. 
  • Eliminate anyone who didn’t follow directions. If you asked for three specific things and they only provided two, it’s likely they’ll do the same thing on the job. 
  • Look for people who go above and beyond. Maybe you ask for a writing sample and they mock up an article that could be used on your website. If they’re willing to go the extra mile for the interview, it’s a good sign they’ll do the same when they’re working for you as well. 
  • Exclude any candidates that fall completely outside the salary or hourly range you have in mind.

Hiring Your First Employee: What to ask in your interviews

Video chat is a great tool for interviews. You’ll learn a lot more from your candidate’s body language and whether they took time to set things up to look professional than you can from a phone call or an email.

Video chat is a great tool for interviews. You’ll learn a lot more from your candidate’s body language and whether they took time to set things up to look professional than you can from a phone call or an email.

In addition to questions that get to your candidates’ experience for the specific role you’re hiring for, here are a few examples of questions that will help you determine if someone is a good fit for your role. 

If you’re hiring for a remote position, here a few basic questions you should ask:

Tell me about your most recent experience working with a remote team. What tools did you use to communicate? 

  • Look for honest answers about communicating across time zones, keeping people on the same page, and whether they seem knowledgeable about some of the web-based communication tools you use.

Let’s pretend you’re in this position. You’re on an important call, and your internet signal starts having issues. What would you do?

  • In addition to how they answer this question, take note of how their signal and setup is for your interview. Did they make sure to have fast enough internet? Did they take care with how they dressed (at least from the waist up)? 

No matter what kind of role you’re hiring for, here are a few questions to help you spot the gems in your candidate pool and uncover issues before you make an offer:

Tell me about your most stressful day at work. What happened, and how did you deal with it?

  • Look for candidates who are skillful at dealing with stress in healthy ways and then moving on. Note the tone of their answer, too. Do they sound bitter and irritated, or are they able to inject positivity or humor into a bad past experience?

Tell me about a big project you worked on. What was your role, how did you approach it, and how did you organize your time? Did you hit any roadblocks along the way, and how did you deal with those?

  • The key skills you’re looking for here are the ability to break big projects down into smaller tasks, creating systems to manage time and keep track of tasks, and letting managers or co-workers know about barriers.

Can you give me an example of a time you had to have a difficult conversation with your boss/co-worker/customer? How did you communicate with them, and what was the outcome?

  • Difficult or nuanced conversations are best held in person, or on the phone, or via video call if you’re working remote. If someone discusses a conflict that happened over email, text, or other electronic communications that they didn’t move to a more personal channel, it’s a good sign you should pass. 

Making the Offer and Preparing for Day One

You’ve made it through interviews and you’ve got your top pick for hiring your first employee. Now what?

You’ve made it through interviews and you’ve got your top pick for hiring your first employee. Now what?

Here are the steps you should take to make an offer, and get yourself (and your new hire) set up for a successful start:

  • When you reach out to your top candidate with a job offer, you’ll want to let them know how much you’re going to pay them and when you would like them to start. Be prepared to negotiate both items.
  • When your top candidate accepts, it’s a good time (and common courtesy) to contact the rest of the people you interviewed and let them know you moved forward with someone else. 
  • If you had other candidates you were really interested in, send them a personal note, and let them know you’d like to stay in touch so you’re on their radar if/when you expand your team again. 
  • Take down your job posting so people don’t continue to apply.
  • Start documenting all of the things you’ll want your new hire to do. You can use tools like Loom to make videos of day-to-day tasks that may be difficult to explain over the phone or email. 
  • Use a project management tool like Trello to help keep track of daily, weekly or monthly tasks and to keep communication around them in one, central location. 

Take a deep breath and celebrate! You’ve reached a huge milestone and hiring your first employee should help you focus on other things. While it’s tempting to put off hiring, or think you can do it all, building lean teams has helped a lot of our founders scale their businesses. Lilia Tovbin hired a small team of long-term freelancers to help her moderate user-generated content when managing the queue was taking her attention away from business strategy. And bringing on a technical partner helped MySiteAuditor founder, Marvin Russell, scale the company to $40,000 in MRR.


Amy Stewart, VP Operations for SureSwift CapitalAmy Stewart | VP Operations
Amy oversees the day-to-day operations that support the fast-paced growth at SureSwift. With a master’s degree in communications, she also leads the “People” side of the organization, which includes the growth of the team. 

Find Amy on LinkedIn