When You Need to Start Hiring
Practical tips for hiring (and retaining) new team members.

When You Need to Start Hiring
Being ready to hire is one sign you’ve made it as a startup. People may not celebrate this milestone as much as a funding round or going public, but it’s important nonetheless; it means that you’re growing and you have room for new employees to contribute. So how do you go from here to successfully expanding your team? Follow these steps.
Identify Hiring Needs
Often, startup founders realize they need to hire when the workload becomes too much for their current team to manage. Another sign that it’s time to hire is if everyone in your company hates doing a certain task. Or, you might realize you need to add personnel if one employee is being required to fulfill too many roles and doesn’t have time to see any of them through. And when a particular assignment is starting to take up 20 to 30 hours of somebody’s time, you’re probably ready to bring on a new employee who will focus on just that job. You also might need to hire when you land a big client, launch a product line or enter a new market.
To prioritize roles to hire for, consider which tasks will lead to the worst consequences—like lost revenue or compliance issues—if they’re not done well. Next, you might think about bringing in employees who will directly promote your company’s growth, such as sales and marketing specialists.
Olivia Cowan, chief of staff at NextLink Labs, says that startups that are beginning to expand beyond their founding team often benefit from hiring a chief operations officer, too. “They can start really getting the team together and making things go a little bit further with your current budget or current financial restraints,” she says.

Create a Hiring Plan
Write a job description for each position you want to fill. The description should include the main responsibilities for that role and the skills or experience you expect from candidates.
Do a reality check by comparing your description to other jobs posted on sites like LinkedIn and Indeed. Similarly, compare the experience requirements to real resumes on those sites. Your description shouldn’t ask for a “unicorn” combination of skills that doesn’t exist in the real world. Don’t be that company asking for ten years’ experience working with a software program that’s only been around for five years.
An individual job description can’t cover all your startups’ pain points, so keep it focused. Keith Sims, president of Integrity Resource Management, says organizations often make the mistake of stuffing job descriptions with miscellaneous tasks.
“They put everything in the job description that nobody else wants to do. Okay, just because you come up with a list of stuff that nobody else wants to do does not make it a job,” he says.
Set your budget for compensation, using sites like PayScale and Glassdoor to research average salaries in your industry. And decide what benefits to offer. Unique perks like pet insurance can help your startup stand out.
“Even things like an Uber Eats or food delivery stipend is a really attractive benefit to somebody who's just trying to come up with a reason to go to a new company,” says Rachel Ego, owner of Big Time HR.
Get the Word Out
Manually posting ads to job boards can be a chore, so use the free tier of recruiting software like Breezy or Zoho Recruit to automate that process.
Contact people in your network to let them know you’re hiring, and post your ad on social media. Consider filming a short video introducing your company and encouraging job seekers to apply.
To attract top talent, Ego recommends connecting with candidates at industry events and conferences. She finds that responses on job boards can be more hit-or-miss in comparison.
“You're not going to have the number of high-quality candidates, as opposed to going to a conference and talking with people there and making your need known in the network of people who are in that industry,” she says.
Screen and Interview Candidates
Screen candidates to make sure they’re well-suited to working for a startup. You likely don’t have the organizational scaffolding of a Fortune 500 company, so you should hire people who can thrive in a fluid environment.
“You want people who are proactive in seeking out solutions, new opportunities and ideas, because your first few hires in a small business really do have to be able to pivot quickly. They have to be able to ask questions, and they have to be able to help the company succeed,” Ego says.
You also want to confirm that candidates will mesh well with your culture. Tell them your business’ priorities upfront, and start a conversation about those values.
“If you're in the tech industry, maybe it's shipping fast, or maybe it's creating software that doesn't have bugs. It can be a whole bunch of things. It really just depends on what the industry is. But knowing that the person that you're hiring knows what those core values are and signs on is important,” Ego says.
Sims observes that startups are often in selling mode, and he cautions against spending valuable interview time talking up your own company.
“If you're interviewing somebody who's going to be a staff member of your organization, you should be interviewing that person, not selling them,” he says.
Ask questions about personality and working style, and be open and non-judgmental about hearing bad news from candidates. While it may feel disappointing when a candidate says something that’s a dealbreaker, they’re actually helping you narrow down your options.
“You want to make it easy for somebody to tell you they're not a fit for the job,” Sims says.
Situational questions, such as, “What’s a time you failed? How did you respond?” or “What’s a time you dealt with a difficult customer?” are interview classics for a reason.
“They've been around for a long time because they work. You get a sense of what the employee has done and how they've handled it or what they've learned from it,” Ego says.
Consider inviting the top contenders to do a skills assessment in which they show you how they’d approach a sample task. The results can reveal differences in candidates’ level of preparation for the role and in how they interpret directions and feedback.
“It can be a really telling sign of, ‘Oh, this person could hit the ground running and that could be a huge asset.’ Or, ‘Oh, this person might need a little bit of ramp up time because they’re just not as familiar with some of these pieces,’” Cowan says.

Onboard New Hires
To welcome new hires to your startup, create an onboarding process for them to go through. Provide a tour of your office (or remote workspace), and introduce them to other team members. Assign a mentor to each new hire so they automatically have someone they can turn to for help.
Share a list of all the tools or platforms new hires are expected to use, and make sure they get access and login credentials to everything. Tell them your expectations for how they’ll communicate. For example, let them know if your team uses Slack for quick questions but discusses larger issues on the morning Zoom call.
Plan for onboarding to be an extended process in which you regularly confirm that the new hire has all the information and resources they need to do their job.
“The checklist for onboarding somebody doesn't stop when they start working. You need an onboarding process that leads into 30, 60, 90 days and 180 days. There should be standard check-ins with any new staff,” Sims says.
Give new hires an informal heads-up about the dynamics of the group of people they’re joining. If your team has pet peeves or inside jokes, share that information with the new employee.
“For my own recent onboarding, I was told, ‘Hey, the group that you're coming into, there's some strong personalities. You're going to need to take some time to win people over and demonstrate some quick wins.’ Which I really appreciated, and that really helped me,” Cowan says.
Retain Talent Long-Term
Once you’ve hired someone, you want them to feel invested in your startup and committed to working there into the future.
Foster a collaborative work environment in which employees feel they can speak openly. You might want to have regular one-on-one chats. Or, set up a whiteboard (or a similar virtual venue) where team members can share ideas and feedback.
Give employees opportunities to grow and progress in their careers. That might include paying for professional development courses or sending them to training seminars.
If your startup grows large enough, offering them a path to higher job titles and greater pay can motivate them to stick around. If you don’t have those opportunities for vertical advancement, find other ways that they can take ownership of the work. Let them spearhead a project, train the next new hire or direct your startup’s community service initiatives.
Employees feel valued when they have chances to lead. “It feels more like, ‘We're building this together.’ And not just like, ‘Oh, I'm being told what to do and I don't have anywhere to go upwards,’” Cowan says.
Hiring your first new employees is an exciting step. You might feel like you needed to bring someone on yesterday, but remember the adage to “hire slow, fire fast,” and take the time to get it right. When you find the best people for your business, you’ll reap the benefits of working with a cohesive team.
Being ready to hire is one sign you’ve made it as a startup.
Key Takeaways
Identify hiring needs by assessing workload, employee task overload, and new business demands like product launches or entering new markets.
Prioritize roles that prevent critical issues like lost revenue or compliance violations and promote growth, such as sales or operations positions.
Write clear job descriptions that focus on essential responsibilities and realistic skills, avoiding the temptation to overstuff them.
Research compensation using tools like Glassdoor and PayScale, and consider unique perks like food stipends or pet insurance to attract talent.
Leverage networks and recruiting software to streamline job postings, and connect with candidates at industry events for higher-quality applications.
Screen candidates for startup adaptability, prioritizing proactive, flexible individuals who align with your business culture and values.
Ask situational questions in interviews to assess problem-solving skills, learning experiences, and adaptability to real-world challenges.
Use skills assessments to evaluate top candidates’ preparation, task execution, and ability to interpret feedback.
Create an onboarding process with clear expectations, tool access, mentor assignments, and extended check-ins for 30, 60, and 90 days.
Foster workplace transparency through open communication channels, regular feedback, and opportunities for employees to share ideas.
Offer career growth opportunities through training, leadership roles, and projects that give employees a sense of ownership and purpose.
Hire thoughtfully and strategically, taking time to find the right people and ensuring they align with your startup’s goals and dynamics.

Sarah Brodsky is a freelance writer with 15 years’ experience reporting on business, personal finance and careers for a variety of national outlets. She’s a professional member of the American Society of Journalists and Authors, and she’s a graduate of the University of Chicago. She lives in St. Louis. When she’s not working, you can find her reading or baking pizza.
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