Get All Access for $5/mo

20 Leadership Lessons with ZipRecruiter Co-Founder and CEO Ian Siegel How this serial entrepreneur built an online employment marketplace that disrupted the recruitment hiring industry.

By Jason Nazar Edited by Jessica Thomas

Opinions expressed by Entrepreneur contributors are their own.


With tens of millions of Americans out of work due to the pandemic, many are searching for their next role in this tough job market — or inspired to start their own business. For the latest episode of my ongoing leadership lessons series with Entrepreneur, I sat down with an expert in both arenas. Ian Siegel, bestselling author and co-founder and CEO of ZipRecruiter, has a 25-year career in executive product and technology leadership roles at companies including CitySearch, and

Related: 13 Leadership Lessons from Zoom Founder and CEO Eric Yuan

Siegel co-founded ZipRecruiter with three of his friends in Santa Monica, California in 2010, and it has grown to employ more than 900 people and disrupt the recruitment industry since its inception. ZipRecruiter is an online employment marketplace that uses matching technology to connect millions of job-seekers to their next opportunity — over 900 million job applications have been submitted through the site.

It's easy to see why the platform has become so popular. Employers can easily send a job to over 100 websites with one push of a button, while job seekers have one easy-to-search database with a list of roles pulled in from across the internet. When Siegel shares where the idea for ZipRecruiter came from, one can see why it was profitable from the beginning. He spent his entire career working for early stage internet startups, and he experienced first-hand the pain points of his the recruitment hiring industry.

"My teams across the board were too small to have an HR department to do the recruiting, so I had to personally put the same job post on multiple websites," Siegel says. "And to make matters worse, every site had different mechanisms for collecting the candidates." So, he did what everybody did back then; he printed out all of the resumes and put them into stacks to combine all of the applicants for one job into one reviewable list.

"I was spending so much time on this that I decided to pull three friends together to fix this problem, and together we created that magic button where you could send the job to every job board — turning the web into one big job board," he added.

The day ZipRecruiter launched, it was profitable.

"Customers were beating the gates down like it was a Black Friday sale," Siegel jokes. "They came in so fast that we were completely taken off guard."

Bestselling author Malcolm Gladwell (Outliers and The Tipping Point) says this about Siegel: "I've been arguing for years that no part of American corporate life is crazier and more irrational than hiring and job search. ZipRecruiter's Ian Siegel is one of the brave souls trying to fix it."

Here are 20 takeaways from my hour-long conversation with this remarkable entrepreneur who generously shared his key leadership lessons:

1. Build the service that you wish you could use

ZipRecruiter is a rare example of immediate market fit, and according to Siegel, that's because he trusted his gut. "All I did for research to build this business was build the service that I wished existed throughout my career."

2. Focus on telling everyone what your one thing is versus building something new

The vast majority of people think that growing their business means building something else or something new, and that's not always true. Instead, Siegel suggests that the best way to grow a business, after you have found product-market fit, is to invest heavily in all of the different ways you can become ubiquitous. Your business might do and offer many things, but he believes every company is famous for selling one thing, so know what makes you special, and focus on telling as many people as possible about it.

How do you find what your one thing is? Have a current customer who loves you talk to a prospective customer. Listen to the first sentence out of their mouth, and however they described you in that first sentence — that's your one thing. For example, "They post jobs everywhere" is ZipRecruiter's thing.

3. Entrepreneurship is a willingness to throw yourself into the unknown

There can be a lot of discomfort in being an entrepreneur. The thing that you do the best at is the thing you will do five percent of the time. The other 95 percent of your time is spent doing things that you have never trained for or that you might not feel confident in. For example, if you're a chef who opens up your own restaurant, picking a restaurant space, designing the decor, hiring people and designing a menu might not be your forte, because you're a chef. But as a new entrepreneur, you need to learn to take ownership of those things.

Related: 12 Leadership Lessons from Mailchimp Co-Founder and CEO Ben Chestnut

4. You need one million of something to be successful

Siegel gives this advice to anyone who asks about their startups. "If you don't have one million of something, don't try to raise money. You do not have momentum, you have an idea. It can be a one million visitors, one million registrations, one million products sold. Ninety percent of businesses never get to $1 million in revenue, but that is the best proof that you have a real business. Now if you ever get to a million, congratulations. You have truly cracked the code on something, and that is a tremendous milestone."

5. Celebrate version 1.0s and the people with the courage to create them

Version 1.0 is a delicate, fragile thing. You want to create a culture where people are generating ideas. That said, Siegel advises that "1.0s are so easy to crush with a power imbalance. When people give me an idea, I have to train myself to not respond and then figure out a way to say, "yes, and' rather than tell them it won't work. This prevents stifling potentially great ideas, so always listen and support version 1.0s."

6. Things that work, work right away

If something works, it works right away, and you should be able to look at a chart and see the proof in the numbers the day it launches. No matter what your AB tests tell you the outcome was, you should be able to feel it and see it immediately.

7. Think about pricing as a lever of opportunity

Most entrepreneurs Siegel talks with are undercharging for their product. They are afraid to ask for full value, and they don't understand their customers' price insensitivity. Siegel believes it comes down to confidence: "It is an insecurity that they have on if what they built is good enough. They don't have the perspective. Believe in yourself."

8. A lot of business is not about what you choose to do, it's about what you choose not to do

The notion of white space and simplification exists in many facets of business and is a concept that Siegel and his team are disciplined in. White space, or putting as little effect on the screen as possible, is where every additional feature, button and link potentially becomes cognitive overload that can confuse your users and create problems for you. Every year, ZipRecruiter purposefully turns features off. It recognizes that the most challenging place to apply this concept is to product prioritization.

Related: 12 Leadership Lessons from Envoy Founder and CEO Larry Gadea

9. The key to a successful work/life balance is if everyone is 100 percent aligned

Siegel describes that he and his executives have been successful in this arena because they have a clear understanding of who they are as a company and what they are trying to accomplish. "We put out a short list every quarter of things we are going to do without question. If a great idea comes up, we don't touch it until next quarter. We have great ideas that come up all the time, but we have the will and the discipline to not touch it." The key is focusing on accomplishing the goal you have already set before you move onto the next goal.

10. If you want to create an open culture, let people operate like intrapreneurs

If people have an idea that will improve your business, let them freely share it. Never assume that anything is unchangeable. Siegel believes there are only two types of managers; managers you work for and managers you work with. "I'm more of the guy you work with. I will walk the floor. I will sit down and talk to you about what you are working on. I am keenly interested."

11. Write your resume like a caveman

Siegel states that there are fundamental disadvantages to the modern-day job search. He offers nuggets of wisdom found in his latest book, Get Hired Now!

1. Job applications are no longer obtained by humans; robots receive them. The only job of your resume is to get it past the robots. Seventy-five percent of resumes are read by a robot, not a human, for companies of all sizes.

2. Forget the vellum paper. You do not need to write prose and outline the 20 years of experience you have.

3. Use the most simple template possible, and describe your skills and contributions in as straightforward a way as possible using common vernacular.

4. Unconscious bias is prevalent, and we all have it. The key to getting hired once you are in an interview is winning those first 20 seconds. Win that battle, and everything after that is just a validation of their first impression. It's prescriptive.

12. There is a magic sentence to say when interviewing

Siegel recommends using it to win over an interview: I am so excited to be here because… [fill in the blank with something specific to the company]. That fill in the blank can be anything from, I use your product every day and I have so many ideas for you…, or I love your company culture and want to be a part of it.

13. Be a thought partner in any role you are a candidate for

When a candidate thinks about the health and overall wellness of the business, that is the person Siegel want to hire. He elaborates that he's not looking for someone to work for him, but with him. He likes to ask, "What is the worst thing about our business? If you got here, what would you change?" If you are afraid to answer the question, and only offer compliments, you probably won't get hired by Siegel.

14. Growing as a leader sometimes means doing less

Leaders should not be reviewing every decision everyone makes. Leaders are not there to check off boxes. Try to make as few decisions as possible during the business day. Take time to think about the bigger picture at 30,000 feet, and only make the really big decisions. Leave the rest up to your very talented team.

15. Generously give the benefit of the doubt, and listen better

Siegel's New Years' resolution is always the same: Listen better. "When you start to feel upset, give the benefit of the doubt. True malice rarely exists between two individuals inside of a business or as part of your business. Listen better."

16. The trick to hyper growth is taking a breath and maintaining perspective

Effective hyper growth is like a magnifying glass. Problems seem 10 times larger based on the number of people they are impacting. "When you go from 100 customers, to 1,000 customers, to 10,000 customers, to 100,000 quickly, all of a sudden, that small bug that you weren't that worried about at 1,000 customers is a huge deal at 10,000 customers." This affects your prioritization and how you feel about your product.

17. A leader's job is to tell the truth

Siegel says that telling the truth means doing so consistently and calmly, even if it feels confrontational. It's important to give constructive feedback the moment after something difficult happens. Telling the truth is explaining to someone what level they are really at, and how far away they are from the next level.

18. Courage over conviction is what creates an entrepreneur

"Theoretically, I was as credentialed as someone could be to forge ahead with a startup," Siegel shares. "Yet despite my experience, people would constantly ask me if I was qualified and if I could pull this off." He compares becoming an entrepreneur before you have made your first dollar to telling people you are an artist (i.e. How many paintings have you sold? What galleries are you in?). Entrepreneurship is about courage and belief in your experiences amid all the doubt that might come your way.

19. There is a certain amount of experience that you can consider enough before you start your own business

If you have been working hard at your craft for seven to 10 years, that is enough, and you are ready to be an entrepreneur. Siegel reflects, "If I had the courage, I could have been an entrepreneur much younger than I was."

20. Leadership commands you to speak beyond the merits of your business

Leadership often commands you to speak to what is happening to society as a whole. It's not about being right or wrong, just be authentic and available when sharing your truth.

With a new book under his belt and multiple Comparably Award wins for being a top-rated CEO and one of the Best Places to Work in multiple categories, Ian Siegel has created an accessible and powerful roadmap for companies to hire employees and for people looking to get hired. Watch the full webinar to hear more from this incredible leader.

Related: 13 Leadership Lessons with Wondery Founder and CEO Hernan Lopez

Jason Nazar

Entrepreneur Leadership Network® VIP

Comparably Co-Founder & Serial Tech Entrepreneur

Jason Nazar is a serial tech entrepreneur, investor and advisor with two successful exits under his belt. Most recently he was co-founder/CEO of Comparably (acquired by ZoomInfo), a leading workplace culture and employee review site. Prior to that, he was founder/CEO of Docstoc (acquired by Intuit).

Want to be an Entrepreneur Leadership Network contributor? Apply now to join.

Editor's Pick

Business News

Apple Reportedly Isn't Paying OpenAI to Use ChatGPT in iPhones

The next big iPhone update brings ChatGPT directly to Apple devices.

Business News

Sony Pictures Entertainment Purchases Struggling, Cult-Favorite Movie Theater Chain

Alamo Drafthouse originally emerged from bankruptcy in June 2021.


Are Your Business's Local Listings Accurate and Up-to-Date? Here Are the Consequences You Could Face If Not.

Why accurate local listings are crucial for business success — and how to avoid the pitfalls of outdated information.

Growing a Business

He Immigrated to the U.S. and Got a Job at McDonald's — Then His Aversion to Being 'Too Comfortable' Led to a Fast-Growing Company That's Hard to Miss

Voyo Popovic launched his moving and storage company in 2018 — and he's been innovating in the industry ever since.

Money & Finance

Day Traders Often Ignore This One Topic At Their Peril

Boring things — like taxes — can sometimes be highly profitable.


Want to Be More Productive Than Ever? Treat Your Personal Life Like a Work Project.

It pays to emphasize efficiency and efficacy when managing personal time.