Hiring Your First Employee

Hiring Your First Employee

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.

Best Practices for Managing Virtual Teams

Best Practices for Managing Virtual Teams

Building a virtual team should be a top consideration for every startup, entrepreneur, and online business in growth mode, because expanding your talent search to “everywhere” means access to better job candidates. However, managing a team that’s spread across the country (or the globe) presents its own unique set of challenges. SureSwift’s rapid growth from a team of two to a global company of 80 over the past four years has been like a crash course in managing virtual teams, and this is our guide to doing it right.

Recently, we wrote about why we’re committed to being a fully remote company. Not only has it been a great choice for us, but we also wholeheartedly believe that remote work is the future. And the current research definitely backs us up.

In fact, Gallup’s latest State of the Workforce report found that the number of employees who were working remotely (43%) was higher than ever, with a broader range of working hours, and fewer in-person meetings.

And employees want to work at companies that embrace the virtual office. When surveyed, 82% of employees said they’d be more loyal, and less likely to leave if they had more flexibility in their jobs (Source: FlexJobs).

It’s hard to argue with those numbers, and with remote company success stories like Hotjar, Hootsuite, and Buffer. But if you’ve only ever worked with a team in-person, you might be wondering where to start.

Or maybe you’ve hired a few remote contractors or employees already, but you’re struggling to communicate and collaborate effectively.

Whatever stage of going remote you’re in, we’ve got 5 straightforward tips to help you build your blueprint to managing a high-performing virtual team.

Managing Virtual Teams: 5 Steps to Success

1. Organize With The Right Tools

Technology is a huge help when it comes to managing virtual teams. Make sure you have the right set of tools to communicate and collaborate effectively from anywhere.

Technology is a huge help when it comes to managing virtual teams. Make sure you have the right set of tools to communicate and collaborate effectively from anywhere.

The great news for anyone managing a remote team of any size is that there are a huge assortment of free and low-cost business apps out there to help you do everything from organizing projects, to controlling account access, and tracking contractors’ or employees’ time.

Here’s the main app stack we use at SureSwift to manage our team and our projects:

  • Trello: Break down any project by task with the ability to set due dates, create checklists, and leave comments or ask questions. You can also use Trello to create enhancement or bug-fix queues for a busy developer.
  • Google Suite: Create team and project specific folders to share documents with permissions that can be easily edited anytime.
  • Slack: Create chat channels for teams, projects, or specific types of communications to send and receive real-time updates in a fully searchable, super easy to use system.
  • Zoom: Hold interviews and scheduled meetings with the ability to have video calls or share your screen.
  • Paydirt: Create projects and work categories and have your team track their time along with notes on what they did. You can have multiple contractors and employees in the system, with the ability to approve timesheets or send them back with questions.
  • Zenefits: HR,  payroll, and benefits management for a distributed team.
  • 1Password: Use this app to create separate password “vaults” for business and personal use, or make a vault for each product line you manage, then structure your permissions by person, team, or app category.

2. Find The Right People for Your Remote Team

Whether you’re hiring a freelancer, your first employee, or your hundredth, there are certain qualities that make for a great remote team member.

Whether you’re hiring a freelancer, your first employee, or your hundredth, there are certain qualities that make for a great remote team member. We’re proud to have an amazing virtual team spread across the globe.

Since you won’t be in the same office to oversee their work, you want to be sure the people you hire are proactive and resilient self-starters who have experience managing their time effectively. Include these qualities in your job descriptions, along with the specific experience and skills you’re looking for.

Since strong digital communications skills and attention to detail will be important in any remote job, you should also include some specific instructions on how to apply to help you do an easy first filter of your applicants.

Here’s an example from one of our recent job postings: “Please email us with your CV, cover letter and desired hourly rate, and add “Customer Success Specialist” in the email subject line. Please ensure your CV & Cover letter are shared on Google Drive with a link we can access.”

Once you have a set of candidates you’re interested in, set up video interviews. Video will help you assess things a phone call never will, such as internet speed, professionalism, and body language.

For some jobs, you may want to ask for work samples (writing, design, code, etc.) to see past examples of your candidates’ work. If you decide to go further and ask people to complete an assignment as part of your interview, either keep it under an hour, or be sure to pay people for their time.

3. Put the Right Legal Documentation in Place

Whether you’re hiring an employee or a freelancer, having the appropriate contracts in place can help you avoid major legal headaches (and costs) down the road.

Your freelancer or employment agreements should cover things like at-will employment, Intellectual Property ownership/transfer, non-disclosure/confidentiality, and non-compete terms. You should always consult a lawyer before finalizing your contracts, but you can get started with free templates from UpCounsel.

4. Hold Regular Meetings and Keep Communication Lines Open

Communication is key for any virtual team. Here are two of our team members, Marvin Russell, working from his home office in Chicago, and Martín Centurión, logging in from a coffee shop in Uruguay.

Communication is key for any virtual team. Here are two of our team members: Marvin Russell, working from his home office in Chicago, and Martín Centurión, logging in from a coffee shop in Uruguay.

One of the best parts of remote work is that there tend to be a lot fewer unnecessary meetings. But having a virtual team doesn’t mean you don’t need any regular meetings. Not keeping your team up-to-date or checking in on work barriers is the fastest way to lose their trust.

In a remote environment, visible and transparent leadership is even more important because people aren’t in the office to see what you’re doing all day or pop by when there’s a problem.
Click to Tweet.

If your team is small, you can keep things pretty simple. You may just need one team meeting, or a quick 1:1 with each team member once a week or every other week, with online communications like emails or Slack chats in between.

Set a regular schedule for these meetings for the same day/time/frequency to make sure they actually happen. It’s also helpful to have a predefined agenda so you can stay on track and on time.

As your team keeps expanding, you may hit a point where it makes sense to form a leadership or core team. Letting someone else be in charge of day-to-day operations of specific areas, such as support or marketing, will let you step out of tactical meetings and focus on strategy.

This point will be different for every founder, but trusting your gut and avoiding burnout will benefit your business much more in the long run than waiting too long to delegate.

It’s also worth noting that video is an extremely helpful tool for training and communicating with your virtual team. You can read a lot from people’s expressions and body language that you might miss on the phone or over email.

5. Build a Strong Company Culture

Strong leadership and a healthy company culture will help you retain the talent you spend so much time finding. Pictured above, our CEO, Kevin McArdle, catches up with Chicago-based SureSwift team members.

Strong leadership and a healthy company culture will help you retain the talent you spent so much time finding. Pictured above, our CEO, Kevin McArdle, catches up with Chicago-based SureSwift team members.

Despite the fact that 90%+ of your communications with a remote team will take place digitally, it’s still possible (and we’d argue imperative) to build your culture.
Click to Tweet.

Here are a few tips on how to do it:

  • Be transparent about your vision and goals for the company and let everyone know how their role specifically contributes to them. All of your team members want to feel that their work has value.
  • Communicate clear expectations about response time, deadlines, and milestones at the outset of jobs and projects. If you need to deliver constructive feedback, do that 1:1 on a more personal channel, never in a group meeting or channel.
  • Say thank you, recognize extra effort, and celebrate successes.
  • Set a good example when it comes to work-life balance, and respect your team’s personal time.
  • Get to know your people. Let them know a bit about your life outside of work, and encourage them to share, too. Before you jump into calls or meetings, take a minute to ask how people are doing and what’s going on in their lives. (For team meetings, try keeping a short list of icebreakers to kick things off).

If you can afford it, getting your team together in-person once or twice a year can build interpersonal relationships, help you align on big-picture goals and priorities, and discuss any roadblocks or process issues.

At SureSwift, with our team spread out across 14 time zones and more than 28 different companies in our portfolio, gathering the whole team together in person hasn’t made sense so far. But we make a point of getting a group together if one of us is traveling.

When our CEO Kevin was in Chicago earlier this year, he was able to meet with 5 team members who live in the area. Some of our other team members have found opportunities to meet up when traveling or attending conferences, too.

At the end of the day, not being in the same office has made us that much more focused on hiring and building our culture intentionally, and the pros have been well worth the trade offs.

Managing a virtual team comes with its own set of challenges, but they can all be overcome with the right tools, planning, and leadership. So if you’re in growth mode this year, make it a top priority to consider going remote — you won’t regret it.

Why We’re All in on Remote Work

Why We’re All in on Remote Work

and What It’s Like to Run a Fully Remote Company, by our CEO

People are always shocked when I tell them that SureSwift Capital is a completely remote workplace with 75 people working across 14 timezones. That means we have no office, no set working hours, and no location requirements. Everyone always has a lot of questions about how we got here and how the whole remote work thing… works. It’s a topic I’m very passionate about, so I’m dedicating this post to answering the questions I get asked most.

How the heck did you get here?  

Well, when you acquire other peoples’ businesses, the smart thing to do is to bring on the teams that helped create their success. So, as we’ve acquired 31 businesses over the last three and a half years that’s meant bringing on a lot of people, wherever they happen to be.

Isn’t it hard to build an office culture without an office?

It’s true that a Friday happy hour would be pretty hard to pull off (not to mention cost prohibitive since we’d have to fly everyone in!). But we still manage to have fun and get to know one another on calls and online.

You can still create company culture in a remote workplace. At SureSwift, ours is built by getting to know each other on calls and online.
You can still create company culture in a remote workplace. Ours is built by getting to know each other on calls and online.

In my previous jobs, I found that a lot of time spent in an office can be wasted time. Endless numbers of meetings with large groups of people take up a huge amount of time in most traditional companies, and when you add in water-cooler chats about fantasy sports or the latest celebrity gossip, your whole work day can easily disappear before you actually get anything done.

We use Slack to have those social moments instead, and the thing I love about it is that it’s very easy for people to opt in or out. If I have a crazy week meeting with potential investors and business founders, I can be totally focused on that. If I’m having a more mellow day, I can hop on and join in on our “Photo Friday” thread and let people know what’s been going on in my life and catch up.

Slack = socializing for the remote office. We use it to message each other about work projects too, but our general channel is where everyone can head when they need a quick break or just want to share what’s been going on in their lives.
Slack = socializing for the remote office. We use it to message each other about work projects too, but our general channel is where everyone can head when they need a quick break or just want to share what’s been going on in their lives.

How do you know people are doing what they’re supposed to

I know it’s a bad habit to answer a question with a question, but how do you know the person in the cubicle next to you is actually working and doing what they’re supposed to? The true answer is that you don’t. You just have to trust that good people are going to take care of their business, whether you’re sitting near them or not.

Kevin McArdle, CEO of SureSwift Capital on leading a remote, distributed team.

Of course we have systems in place to track progress against goals. All well-run companies do that.

Our take on individual and team productivity is that systems are necessary, proximity isn’t — we don’t all have to be in the same building to be effective.

Click to Tweet.

In fact, I look at a lot of people who spend 30-60 minutes a day commuting (the American commute has gotten longer every year since 2010, by the way) and feel sorry for all the time that takes away from doing something more valuable — whether it’s working, exercising, spending time with friends and family, whatever. I know a lot of people say, “that’s when I listen to podcasts, it’s not wasted time.” But wouldn’t you rather listen to podcasts from a hammock than from your car in gridlock?

Not commuting is one of our team’s favorite parts of working remotely. It’s adds up to about 30 minutes a day, or 150 hours a year, that we can all use to do something else we actually enjoy.
Not commuting is one of our team’s favorite parts of working remotely. It’s adds up to about 30 minutes a day, or 150 hours a year, that we can all use to do something else we actually enjoy.

Okay…so tell me about the systems that make a remote company work.

The technology stack that powers SureSwift and our portfolio companies deserves its own dedicated post, but some of the apps and tools we use to keep things running are:

  • Slack for in-the-moment communication on projects and socializing
  • Trello for project management and task tracking
  • Google Docs/Sheets for project collaboration
  • Databox for tracking trends
  • Proprietary “Deep Dive” documents to make sure we’re making progress against our 30-60 day goals
  • Zoom for calls
  • Zenefits for payroll
  • HelpScout for customer service

Ultimately all of this technology is just a tool that makes our work processes easier, but without the right people to do the work, we wouldn’t get far. So let’s get back to our great people and how we find them.

How do you hire for a remote company?

As I mentioned briefly above, our model of acquiring businesses has ended up being one tremendous way to find amazing people. We buy “bootstrapped” businesses — meaning that the founder/seller has built the business from the ground up with their own money and runs it on the profits generated from customers.

When the profits of a business are what pay your mortgage and feed your family, you are very selective about the people you bring on to work with you. You only bring people on when a position is truly necessary and will benefit the business, you vet them very closely before hiring, and you only keep them around if they’re pulling their weight. So when we buy a successful business that’s being run by a founder and 2-4 contractors, we assume those people are really good at what they do and important to the running of the business. It makes a lot of sense for us to keep them on and make room for them on our team, no matter where they happen to live.

In addition to hiring people via the sale of the company they worked for (which sometimes even includes the founder), we’ve also hired a lot of people directly.

So when we have the choice, why don’t we hire in Minneapolis/St. Paul, where I’m located and where SureSwift is “based”? The answer to that one is super simple — we follow talent. I love MSP, and if I can hire an amazing person who lives here, that’s wonderful. But (to paraphrase the late Steve Jobs), no matter how big your city is, most of the talented people in the world are outside of it.

Let’s say I want to hire a Ruby on Rails developer (which we may be doing this winter, so be sure to check out our current job openings). There are probably hundreds of Ruby developers in my city, but the employment rate here is very high right now, so the most talented ones are already going to be gainfully employed and harder to attract. The good news is that there are hundreds of thousands of Ruby developers around the world. So why wouldn’t we want to look for the best talent in the biggest pool — i.e. everywhere?

The next developer we hire could be from anywhere — that gives us a huge pool of talent to choose from.
The next developer we hire could be from anywhere — that gives us a huge pool of talent to choose from.

Is remote work really better?

If you’ve read this far, you already know that I’m a big champion of remote work. If I haven’t convinced you yet, here are 4 more reasons it’s been the right choice for SureSwift.

Diversity

In addition to having a bigger pool of candidates than a traditional company with employees who are required to work on site at the company’s office, another benefit of the remote office is that diversity can be wired in. There’s a lot of discussion here in the U.S. about the value of diversity in the workforce  and it’s something I personally believe makes a team and a company smarter and stronger.

Remember our 75 people in 14 different time zones? They grew up with different backgrounds, goals, ideals, and beliefs. And we didn’t need a ‘diversity and inclusion’ hiring program to find them because we weren’t limited by a single location and its existing demographics.

Around-the-clock Customer Support

Another remote work win for us is that around-the-clock support for our customers is attainable without having to ask people to work odd hours. A customer issue in Boston at 2:00 am isn’t a problem when it’s 3:00 pm in Malaysia.

A Worldwide Network

The best source for finding new hires is often the people who already work for us. With a team that’s spread across the globe, we have a worldwide network who’ve become evangelists for our company and can help us recruit.

No Office Overhead

Renting or owning office space is a huge business cost, and one that we don’t have to incur, which means we can put those dollars to other uses that have more value for our business. As a small-ish, but growing company, it also means we’re not held back by outgrowing a space. If we needed to double our team, we could do it without worrying about where to put those extra desks, or having to move to a new space.

I recognize that some people like their offices, and this style of work isn’t for everybody. But me and SureSwift? We’re all in. So if you like to (or need to) drop your kids off at school at 9am? Cool. Want to hit a yoga class at 1pm? Awesome. Always been more productive after 3pm? Great.

If this sounds like something you want to be a part of, hit our Careers page to see our current job openings and tell us why you’d be an awesome coworker.