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Succeeding As An SMB’s First HR Hire

Raina Sheth
May 23, 2019

It’s more than common for a small business owner to manage HR for their company. In fact, 95% of businesses with less than 75 employees don’t have a designated HR team*. Eventually, it can become too time-consuming for a business owner to manage things like employee benefits, hiring, and payroll, in addition to running a business. We wanted to know more about this transition and what it’s like to be a small business’ first HR hire, so we sat down with Ease‘s first HR hire, Jill Pittman.

When Jill first started at Ease in 2015, there were just 10 employees. Today, there are over 150. As you can imagine, with only 10 employees and no HR manager, there weren’t many processes in place. She talked to us about her biggest priorities when starting an HR department from scratch, resources that helped her along the way, and best practices for succeeding as a small business’ first HR hire.

Starting An HR Department From Scratch

There was plenty of work to do, but Jill had to start somewhere. Jill remembers, “I would spend a lot of time researching and brainstorming new ideas and processes.” Jill shared the first three things she worked on as Ease’s first HR hire.

Adding Benefits For Employees

When Jill started, medical benefits and payroll were being managed by David Reid, co-founder and CEO of Ease. Quickly after joining, she added additional voluntary benefits like dental and disability. She worked closely with Ease’s health insurance broker to understand which benefit offerings would work for a small but growing business. To this day, Ease’s broker is still an integral part of our benefits offering.

Creating A Time-Off Policy

When Jill started, there was no policy in place, as there were so few employees. She got to work setting up a process for employees to request time off. At the time, Ease hadn’t launched time-off tracking, so the process included submitting paper forms to managers. ”It was so old fashioned, but it got the job done”, Jill recalls.

About a year later, Ease launched its first version of EaseHR, which enabled thousands of small businesses to manage more of their HR and company growth online. At which point, all Ease employees could request time-off from anywhere and managers could approve requests directly in Ease.

Creating A Hiring Process

At the time, there was no formal interview or new hire process. Hiring was about to pick up, so Jill needed to put processes in place that could scale. “I used ZipRecruiter to upload job descriptions, find candidates, and keep track of applicants. It was a necessity in preparing for the influx in hiring that was starting”, Jill remembers.

Today, the hiring process has evolved, adjusting to the demands of a quickly growing company, whose offices now span four states, not including many remote employees. Today, Ease has two corporate recruiters, and uses the applicant tracking software, Greenhouse, to manage candidates.

Technology Solutions For The First HR Hire

It’s normal for fast company growth to present challenges for a one-person team—scaling from 10 employees to over 150 employees in four years. Luckily, Jill was able to rely on technology solutions that helped her stay organized, set up processes, and communicate with remote team members. Here’s what Jill had to say about some of the resources she found especially helpful.

Mammoth HR

“Mammoth HR helped me tremendously. It was a one-stop-shop for all things HR. I used it to make checklists, write our employee handbook, learn about employment laws in different states, and more.”


“We were beginning to have teams in multiple locations, across multiple time zones, so Slack helped us all stay connected throughout the workday. It allowed us to have real-time communication with colleagues across the country by making calls and sending files all in one conversation.”


“I was constantly working on creating new processes and scaling existing ones, so Basecamp helped me stay organized and manage all of the moving parts.”

When It’s Time For A Second Hire

Traditionally, HR departments are responsible for a wide range of tasks — from benefits enrollment to distributing IT equipment to event planning. In order to scale these efforts for a growing company, it became time to make a second HR hire.

Making a second hire allowed the HR team to do more things like creating a hiring plan, formalizing record-keeping, and one of Jill’s favorite aspects, establishing a company culture. Soon after, HR formed an engagement committee and had more flexibility for planning company and team-wide events.

Tips To Live By When You’re The First HR Hire

Jill shared her top three pieces of advice to anyone joining a small business as the first HR hire.

Stay organized

“There are a lot of moving parts to oversee, so staying organized is key, and solutions like Basecamp can help you manage your projects.”

Plan For Scalability

“It’s important for processes to be scalable so that you’re not constantly reinventing the wheel. Though not always necessary, it’s helpful to keep in mind.”

Be flexible

“In HR, we wear many hats, especially at a small company. You have to be willing to do whatever it takes to get the job done.”

Reflecting On Her Journey at Ease

Jill’s experience as the first HR hire has been rewarding and the evolution of the business and her role continues to excite her.

“My day-to-day has changed to more of a consultative role, helping answer employees’ questions, interviewing candidates, and meeting with hiring managers.”

When I asked Jill what she’s most proud of over the last four years with Ease, she said it’s the people she works with every day.

“You have to put the right people in place that share the same values. I’m proud that we’ve continued to do that as we’ve grown. My favorite part about managing HR at Ease is being there for employees, to answer questions and walk through challenges. That’s what I love the most — the people.”

Source: Ease internal customer data, March 2019

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