How to hire at a startup: 10 hiring habits of great founders

Startups
Written By Landon Howell

A startup is only as good as the people it hires. Employees will account for 50% of your overall expenses, so it’s important to get it right.

Over the past decade, I’ve been fortunate to have a front-row seat to the hiring practices of hundreds of venture-backed startups.

Many of these startups were backed by investors like Greylock, Kleiner Perkins, Accomplice, a16z, Khosla, TTV, Worklife, and Flybridge. Many were graduates of Techstars or Y Combinator.

In this article, I’ll summarize what I have learned from observing and being part of founders’ hiring processes.

10 things to do when hiring for your startup…

  1. Talk to your network

  2. Understand the market

  3. Prepare your team for change

  4. Treat recruiting like you treat customer acquisition

  5. Approach different roles differently

  6. Craft a compelling job post

  7. Post where people actually look

  8. Tap top talent for help

  9. Use your close circle as a final filter

  10. Move with speed and respect

🗣 Talk to your network

A startup’s leadership team will always be discussing personnel performance, team needs, and pain points in its leadership-only meetings.

Once you and your leadership team have identified key personnel needs that require action, notify your closest circle even before you create job descriptions. Your closest circle will most often consist of…

  • Board members

  • Investors

  • Advisors

  • Mentors

  • Founders and leaders at other startups

Startups are built by generalists and scaled by specialists, so focus less on the names of specific roles you might need to hire for and focus more on communicating your pain points to your network.

This gives your network time to...

  • Ask questions about your pain points.

  • Provide you with additional considerations and insights.

  • Introduce you to subject matter experts who can provide unique insight.

  • Recommend people for you to interview. (On multiple occasions, I’ve seen people hired before a job description was even created. I’ve been one of those interviewees on various occasions, and on three occasions the conversation turned into a full-time role.)

🔎  Understand the market

There’s a wealth of free insight into the startup hiring market. Trends on everything from salaries to equity to popular perks are available on a handful of great sites. (See below for some of my favorites.)

Before you draft the job post, make sure you understand the state of hiring. Your network will be valuable in providing insights, but additional research — understanding trends in salary, equity, benefits, and perks — is essential and easy.

This research will help set expectations for yourself and your company about the time commitment and financial implications of hiring.

Understand trends

Hiring great people, especially great engineers and growth personnel, has never been more challenging. Sure, startup and tech salaries are inching ever higher, but you are also competing against ever-aggressive compensation packages and established tech companies who are fully embracing trends.

Offerings that were differentiators just ten years ago are now becoming table stakes.

The good news: the best employees for early-stage startups don’t want to be “one of many” at a FAANG company, or even “one of some” at a Series D company for that matter.

When working on an incredibly hard product, you should seek to hire missionaries, not mercenaries. Besides, the mercenaries have plenty of options.

Utilize free data

These sites are incredibly valuable resources for researching salary, equity, benefits, and the hiring process for companies and roles...

  • AngelList: Best for all early-stage startup roles and their associated salaries and equity.

  • Techstars Job Board: Thousands of job posts from early-stage startups, all of which are graduates of the global accelerator whose job descriptions and comp plans were crafted with insight from leading mentors.

  • Y Combinator Job Board: Thousands of job posts from early-stage startups, all of which are graduates of the Mountain View, California-based accelerator whose job descriptions and comp plans were crafted with insight from leading mentors.

  • Levels.fyi: Helps you understand what you’re up against for engineers in particular.

  • Glassdoor: Get insight into the process and length of interviews in your industry and your area.

📕  Recommended Reading: A Counterintuitive System for Startup Compensation

📢  Prepare your team for change

Successful startups grow fast, and fast-growing startups look like a different company every 6-12 months.

Prepare your company for changes, no matter how small.

The founders and the leadership team have been thinking about potential personnel additions for months, but most of your team members at the startup have not.

“When adding a new team or role, take the time to clarify a few things: What a role is, what it’s meant to serve, how existing people have been making up for the lack of that role, and how their lives are going to be changed by new people coming in — in positive and potentially negative ways." — Cristina Cordova

Discussing these changes provides an opportunity for team members to process the changes, ask questions, think about potential candidates they might refer for a role, and even position themselves for one of the new roles.

One thing to keep in mind: though any new addition is exciting to the founders and the leadership team, for current employees, the thought of new team members can sometimes feel threatening or even insulting, especially more junior employees.

📕  Recommended Reading: ‘Give Away Your Legos’ and Other Commandments for Scaling Startups, from Molly Graham // 23 Tactical Company Building Lessons, Learned From Scaling Stripe & Notion, from Cristina Cordova // High Growth Handbook — Chapter 5: Organizational Structure and Hypergrowth

📈  Treat recruiting like you treat customer acquisition

It takes time, money, personnel, and campaigns to acquire new customers for your startup; the process for finding new teammates should be no different.

  • Build campaigns around candidate acquisition.

  • Set deadlines, milestones, and KPIs.

  • Meet weekly with company leadership and hiring managers to discuss progress and learnings.

  • When the market presents you with new information, consider adjusting your approach.

During a major recruiting season when I was running Growth at Plastiq, as an executive team, we met weekly with hiring managers to discuss progress for key roles, adjusting our approach as we gathered more market insight.

  • We brought in a recruiting firm when our best internal effort wasn’t resulting in meaningful progress.

  • We tested different Subject Lines for LinkedIn messages, making changes when one message led to greater engagement with prospective candidates.

  • We even added to our list of benefits when it became clear that candidates viewed certain “differentiators” of ours as table stakes.

↔️  Approach different roles differently

All roles are important, but a misfire of a Senior hire can set your organization back months and hundreds of thousands of dollars. A misfire of a Junior employee can often be made up for by generalists or teammates eager to learn a new skill set.

When should you hire a recruiting firm or bring on a full-time recruiter? When you can afford it, and the pain is so apparent that you can’t afford not to.

Senior Roles

Whether it be a team lead, a VP, a ‘Head of’, or a uniquely talented independent contributor, I strongly recommend using a recruiter after you tap your immediate network.

Which recruiting firms should you use? Ask your fellow founders for recommendations. There are firms that focus on hiring for specific roles, specific levels, and even specific startup stages.

Keep in mind that what you pay for in niche skill sets pays off exponentially, so don’t let recruiter fees deter you.

Some venture firms also offer recruiting as a service. If any of your investors do, you should absolutely use their services for any and all personnel needs. Not only is this their core competency, but recruiters always have a shortlist of excellent contacts who are looking for specific opportunities at startups.

Junior Roles

For more Junior roles, lean on job positing sites and referrals from employees

Job Posting Sites
There are endless options, but use the ones that are unique to your needs. I’ve listed the best sites here.

Referral Bonuses
It’s smart to incentivize your team with financial bonuses for referrals. Most junior team members are super socially active, and many likely came from other startups where previous coworkers may be looking to leave.

Most referral bonuses fall between $1,000 and $5,000.

📕  Recommended Reading: Jason Lemkin’s ‘What Happens When You Hire the Wrong VP’ post is excellent and terrifying.

📋  Craft a compelling job post

Stand out in a “sea of sameness” by creating a compelling vision of life at your startup.

Job descriptions are notoriously boring and jargon-filled. Use this opportunity to be compelling and authentic, using your brand voice.

Cover the basics

Who are you? Who are they? What’s in it for them?

This is likely the first thing the candidate is reading about your startup. Have fun, but don’t forget to include the essentials in your job post.

🔗  A startup job post needs these 15 things.

Get creative with the application

You can better surface great candidates while discouraging less-engaged candidates through the use of great questions.

Adding unique questions to job applications helps decrease the number of bad applications and better surface great candidates.

🔗  Ask these questions to get better candidates for your startup.

Be bold with benefits

Gone are the days when a free lunch and colorful bikes could be the sole go-to startup perks.

Things that were once unique benefits — flexible work hours, personal development stipends, unlimited PTO — are now considered by most startups to be table stakes in a hyper-competitive, remote-first world.

Let your company values and mission inspire your creative benefits.

🔗  Here are some examples of creative company benefits.

Use projects as a shortcut

Projects are a shortcut to surface the best candidates.

For candidates in the later stages of interviewing, I typically give them a take-home project or real-time thought exercise. 

How they approach a project or thought exercise is more important than their actual answers. You should focus on their problem-solving approach — thought process, demeanor, questions, collaboration, and ability to communicate effectively — more than on the actual outcome.

Think about how their execution aligns with your startup’s values.

  • A good thought exercise should take about 20 minutes.

  • A good project should take about an hour.

🖥  Post where people actually look

The list of sites and services to post your job is endless, so spend your time and money where your missionaries are.

Besides, when was the last time you heard of a trajectory-changing startup hire applying through Monster or Indeed?

Essential sites

  • AngelList is a must for any startup job post, regardless of type or title. The visitor quality, intent, and potential fit for startups are magnitudes greater than any other site or service.

  • Startup.Jobs is also good, despite its definition of “startup” being a bit loose. The search function is incredibly user-friendly. The quality of applicants will be as good as those from AngelList, though likely fewer in quantity.

Great sites when applicable

Essential actions

If you feel like it...

  • ZipRecruiter pushes your posts to dozens of websites, but I’ve rarely seen early-stage startups have success with ZipRecruiter. Why? The uniqueness of startup job expectations and the risk tolerance of those who join early-stage startups are quite different than those who use non-startup-focused job boards.

🥇 Tap top talent for help

Involve only your top talent — your best employees — in the interview process. Your best employees not only excel at providing a great assessment of candidates, but great candidates want to work with top talent.

It’ll hurt a little to pull your best people away from their work for an hour at a time for candidate interviews, but top talent recognizes top talent from both sides of the table.

Collaborate cross-functionally

Since early-stage startups are rightfully obsessed with product and growth, they often make the mistake of only involving the best engineering and growth/marketing employees in the interview process.

The interviewers you involve should stretch across the startup. All have institutional knowledge, a broad set of skills, and an understanding that at a startup, everyone’s work impacts everyone’s work.

Collect feedback instantly, easily

Create a post-interview feedback form. Have interviewers submit feedback immediately, providing a standardized form with a character limit for each question.

  • Immediate feedback ensures that the key takeaways are captured while top-of-mind for the interviewer.

  • A standardized form helps you get the same information from multiple vantage points.

  • A capped form ensures that interviewees focus on being concise and direct with feedback.

Avoid the infamous group sync

A practice I have actively fought against is the post-interview group gathering for everyone to discuss their thoughts on the candidate. I am against post-interview group gatherings because I was an advocate of post-interview group gatherings for so long.

Outside of the leadership team (plus the hiring manager), gathering to openly discuss and debate the candidate is a significant waste of time and resources.

Don’t forget… this is the top talent you have involved in the interview process. They have strong opinions and most relish debate. These are also highly effective, highly paid employees.

You’ve already involved them in a 30-60 minute interview and a post-interview feedback form that takes 15-20 minutes.

  • If the candidate is seen by all interviewers as weak, it will show in the post-interview feedback forms.

  • If all interviewers love the candidate, it will show in the post-interview feedback forms.

  • If one interviewer saw something in the candidate that was a red flag, it will show in the post-interview feedback forms, and leadership can engage the interviewer 1-1 to get additional insight.

They want to get back to work as much as you want them to get back to work.

👤  Use your close circle as a final filter

There is much to gain by involving founders and executives, even advisors and board members in the final rounds of interviews.

Every new hire, especially in early-stage startups, has an outsized impact on company culture.

Founders for all

I believe that founders should be a part of the interview process for the first 500 hires, and I’m not alone.

  • Founder involvement ensures the hiring process is solid as the startup scales.

  • Founder involvement helps attract and secure great candidates.

🔗 Startup founders should interview the first 500 hires

Key people for some

Your board members, investors, advisors, and mentors are in their respective roles due to the trust you have in their experience and insight.

  • For strategic roles (e.g. your first Marketing hire), consider involving your advisors and mentors.

  • For new leadership hires in the final stages of the interview process, consider having them meet with board members or key investors.

Negative or indifferent feedback from advisors, board members, investors, or mentors should not prevent you from making a hire. It’s your company, not theirs, but their insight is valuable as they often bring greater experience to interviews and recruiting.

🚀 Move with speed and respect

I’ve seen trajectory-changing hires go from a first conversation to employment in less than two weeks.

“One of the biggest determinants of candidate conversion is how quickly you interview them and how quickly you can make an offer.” — Elad Gil

Move with speed

Speed is the single biggest advantage of an early-stage startup.

If someone saw your job post, found it compelling, and took the time to submit an application, then you should review the application with haste.

  • Great candidates will not stay on the market for long.

  • Great candidates understand that the hiring process is a microcosm of a company’s culture.

A great hiring experience is one where applicants are led with transparency and pace.

Move with respect

Great startups have a respectful hiring process in that they clearly communicate what the candidate can expect.

A respectful hiring process and timeline can vary by the position being hired for, most often with key executive and leadership roles taking a little bit longer to hire for, as often they should.

Tools to enable speed and respect

A consistent cadence of communication is essential to the applicant tracking process, so get organized in order to keep all your balls in the air.

I’ve found that this Notion table or this Airtable template will work wonders as a quick, effective solution for applicant management.

Do you need applicant tracking software like Greenhouse, Lever, Breezy? Probably not, but if that makes your life easier or improves the speed and efficiency of recruiting, then go for it.

(Please promise me you won’t use a spreadsheet.)

All hands on doc

Founders should be ready to sync at a moment’s notice to discuss any changes or requests from the candidate and the hiring manager.

Have the right documents prepared in advance, with the right personnel prepared to approve the offer and any necessary changes (e.g. start date).

✌️ In closing…

A startup is only as good as the people it hires.

If thinking about a candidate’s potential fit doesn’t make you think 'Heck yes,’ then the candidate should be a 'Heck no.'

At the same time, you will need to balance this mindset while worrying less about making the perfect hire and worrying more about the opportunity cost of having an unoccupied role for an extended amount of time.

  • Hire people you believe to be great.

  • Give them important work aligned to the mission.

  • Agree to KPIs, sync weekly, and course-correct as needed.

  • If the person you hire isn’t the person you hired, figuratively or literally, professionally part ways.

In the end… hiring is guessing, and firing is knowing.

Landon Howell
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