BTU #203 - Air Force Veteran to VP of Operations @ ZipRecruiter (Elliot Wilson)

You never want to burn your bridges. I resigned on a position in Los Angeles and took a new job in Chicago. My manager at the Los Angeles position ended up being the CEO and co-founder of ZipRecruiter. I had a good relationship with him so when he decided to open up his facility here, he reached out to me. My wife and I had never lived in AZ and thought it would be a great challenge.
— Elliot Wilson

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Why Listen:
Elliot has a long history in startups and operations. In this interview, we talk about the hiring process on how to play competing offers off of each other in order to get the best outcome possible. We talk about a variety of ways to get a job. We talk about Elliot’s experience in the General Manager position, a role that may be appealing to many Veterans. We talk about changing one’s job title from a big to a small company and how to approach this. And we talk about operations - operations in a tech startup, as well as operations in the cost-driven physical products world.

About Elliot:
Elliot Wilson is the Vice President of Operations at ZipRecruiter, ZipRecruiter, an online employment marketplace that uses AI to connect employers and job seekers. He started out at the Air Force Academy, after which he served in the Air Force for nearly three years. He has worked as a Senior Product Manager at Pictage, General Manager overseeing 250 employees at Lovejoy, and Area Director of Distribution at Sherwin-Williams. He holds both an MS and MBA from Loyola Marymount University. 

Our Sponsor: 

  • StoryBox- People trust each other more than advertising. StoryBox provides the tools and supports businesses need to take the best things customers say about them, and use them to drive more sales and referrals. StoryBox offers a 10% discount to companies employing veterans of the US Armed Forces.

  • Audible is offering one FREE audio book to Beyond the Uniform listeners. You can claim this offer here, and see a list of books recommended by my guests at

Selected Resources: 

  • ZipRecruiter - use job alerts in case their AI misses your resume or doesn’t know how to work with it

  • Military Mojo - great career conferencing site for Veterans

  • SACC - great opp to find employers and play one employer off of another.

  • Leadership and Self Deception: Getting out of the Box - written as novel about a manager who comes into an organization and is struggling and has a mentor to help him grow in this role. He has used 3 of his previous teams read this.

Transcript & Time Stamps:


Joining me today from Scottsdale, AZ is Elliot Wilson. Elliot is the Vice President of Operations at ZipRecruiter, which is the smartest way to hire and get hired. He started out at the Air Force Academy, after which he served in the Air Force for nearly three years. He has worked as a Senior Product Manager at Pictage, General Manager overseeing 250 employees at Lovejoy, and Area Director of Distribution at Sherwin-Williams. He holds both an MS and MBA from Loyola Marymount University.


How would you explain ZipRecruiter?

We brand ourselves pretty heavily as the smartest way to hire people and cite the statistic that 80% of employers find a qualified candidate in our database within 24 hours. We’re like a job board but use machine learning and sophisticated intelligence to make matches between employers and employees faster and more effective.

This can be intimidating for veterans but what I would recommend for veterans is to set up job alerts so that they can easily find out about new opportunities that they are a good fit for. Also do your networking and build relationships that will provide you access to new companies.


How would you describe your role as VIP of Operations at ZipRecruiter?

I’ll use an Air Force analogy to describe it. It’s like an AWACS plane over a battle space. Our headquarters are in Santa Monica and I’m out here in Scottsdale where our primary contact center is. I oversee our customer service strategy and really see the boots on the ground. It’s a lot of fun.

When I made the decision to join the military, one thing I always loved was solving process problems. I’ll give all the credit for my training to the Air Force but those experience really made me fall in love with leading and motivating people. Operations is an opportunity to solve problems that have to do with people and that’s really exciting to me.


What is a typical day like for you?

I like to start my day a little bit later and then stay later. I usually arrive around 9 or 9:30. I’ll walk across the floor of our distribution or contact center. I like to use an Air Force acronym - OODA loop - observe orient decide act. I like to use that to observe what is happening at these facilities and make decisions based on that.

Then from about 10-3, I have a lot of meetings with various people. In the afternoon, I like to reserve some time to get out of the tactical side and do some strategic thinking.


Do you do a lot of traveling?

In the role I’m in now, it’s better than it has ever been. Operations schedules can be a challenge although tech companies are usually more manageable. When I started here, every operational team was one shift and I was excited about that.


What makes the difference between the pace of a company like Sherwin Williams and a tech company?

Sherwin Williams was a very efficient organization but it was really managing uptime which can be difficult. Here at Zip, I’m not running the IT infrastructure. If I was, it would be more intensive. But I’m more on the person and customer side so the hours are more manageable.


When you got out of the Air Force, how did you approach your first job search?

I’ve acquired jobs in every way you could imagine. Leaving the Air Force, I found some very interesting jobs on job boards. I also worked with Lucas Group and had a pending offer from International Paper. I was able to pin that offer up against another offer I had from a tech company.

I had interviewed with Pictage and they had told me after the interview that they would get back to me. I had also gotten an offer from International Paper at around the same time. I got permission from them to wait a few days to give them a final answer. I then called the hiring manager at Pictage and told them that I preferred that position but that I needed an answer from them about whether or not they could offer it to me. I told them the amount that International Paper had offered me and they matched that number so I went with it.


If you could go back to that time again, would you have handled that situation any differently?

I don’t know that I would have disclosed the amount although I don’t necessarily think it hurt me. When you’re transitioning out of the military, I would focus more on getting the job and role that you want and just using it as an opportunity to learn as much as you can.

A couple years later, in 2008, that tech company was in growth mode. But when the recession hit, they went into preservation mode. I was one of three product managers in my division. They cut the other two leaving only me. I later learned that the other two were making much more money that me. I was new to the industry and just trying to grind and add as much value as possible. That positioned me well during that time.


What attracted you to tech?

It’s a lot of problem solving. I was getting an MBA while I was still in the Air Force and started up a Grubhub type website for our military base. I really enjoyed that process and wanted to keep doing that after I left the military.


What is the product management space like?

For a tech company looking to innovate, product managers are really the brains of the operation. I was really more back-end technical management. I was making sure the product worked well for customers.


Can you describe your move from Pictage to Lovejoy?

For service academy graduates, we were all offered a sponsor family. The family I got in Chicago was from old Chicago money. They had a family company without a fifth generation to run the company. So the opportunity to be mentored by that family and run that company was something I couldn’t pass up. So I spent six months at their German facility and then moved to Chicago to run the company. I was with them for six years before they ended selling the company.

I then went to a service academy career fair which opened a lot of doors for me. I highly recommend service academy graduate career fairs. Military MOJO is another good career fair. I again found myself being able to play competing offers off eachother. One was with Sherwin Williams and the other with Google.

In this case, I didn’t even wait for the salaries. I had interviewed with Google early in the week and with Sherwin Williams later in the week. At Google, if they want to extend you and offer, they have to put your package forward to a board. They do that to make sure managers aren’t settling. This process bought me some time and when I received the offer from Sherwin Williams, I was able to let them know I had a competing offer from Google. This pushed them along in the process.


At Lovejoy, you spent time as a General Manager. What was that like?

It wasn’t just managing your employees but also the shareholders and their expectations. Managing up can be just as challenging as managing down.

There’s the old adage that if you start with a particular title at a large company, you then lateral to small company with a larger title. Then you lateral back to a large company with a larger title than your original title at a large company. That’s kind of what I was able to do at Lovejoy because I had a lot of manufacturing experience at a smaller company.


How did you make the shift from Sherwin Williams to ZipRecruiter?

You never want to burn your bridges. I was working for a particular tech manager in Los Angeles when I moved to Chicago to work for my family sponsor. I thought I was making a good career move but it ended up being the most expensive move of my life because my original manager ended up being the CEO and co-founder of ZipRecruiter. I had good relations with him so when he decided to open up his facility here, he reached out to me. My wife and I had never lived in AZ and thought it would be a great challenge.

When I left Sherwin Williams, I was managing north of 300 people and large manufacturing facilities. When I started at ZipRecruiter, I was overseeing 6 people.


Are there any skill gaps that veterans should make sure they fill before moving into operations?

Storytelling is really powerful. Especially with your first role out of the military, you need to connect what you did in the military to how you can positively impact any company you are interviewing with. Really focus on how you can tell your story of why it makes sense for that company to hire you for that role.


Are there any resources you would recommend to listeners?

One book I’ve had my teams read in the past and would recommend to everyone is Leadership and Self Deception. It’s written as a novel. I really like it because it effectively describes many challenges people will face in the civilian work environment.  

As far as conferences, I really recommend job fairs for transitioning veterans. They help you really think about what you want to do. There are a lot of roles out there that you might not know about it.

For more senior folks that are going for higher level roles, I would recommend reading books that talk about interviewing for consulting firms. You’ll find that higher level roles will ask behavioural type questions that are typical of consulting interviews.


Is there anything else that you would like to share with listeners?

One thing I would say is that there are lots and lots of failures on the road to success. One thing I didn’t mention was that right before I got those offers from Google and Sherwin Williams, I had an interview with Amazon. I thought that job was mine to be had and I kind of assumed I would be given the role. It was my first interview in about ten years and during the interview they came at me with some behavioral type questions. I totally blew those questions. Because of that I was passed over for a job that I still think I would have been a good fit for. So I studied up on my interview skills and was able to do much better after that.


That’s great. Thank you so much for your story Elliot and for joining us today.