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A Former Founder’s Guide to Getting Hired

Less than 6 weeks after closing my last company, I had 2 job offers, one of which was for my dream job. Even while weighing these two offers, I continued to receive invitations to meet successful CEOs and investors about my job hunt.

I decided to write this post because during the 5 1/2 weeks I recruited, I learned a lot. At the onset, I searched for a guide and didn’t find one. I was looking for help recruiting as a former founder. How do you apply for jobs when your most recent experience was as a CEO of a four person team? How does that experience translate into a valuable skill for a larger company? Would people reading my resume appreciate the unique experience I had or would I be slighted because I didn’t have the formal experience larger companies look for?

I didn’t find a guide to this process so I started building it on my own. The advice I give is strictly my opinion and based on my experiences. Others likely have very different experiences and I look forward to hearing their rebuts. I managed to land in the job I wanted in less than 6 weeks and I hope, through this, I can help others do the same.

Embrace your failure

When I shut down my company, I was sad and embarrassed. I felt like a failure in many ways. My partners and I had no doubt it was the right decision but that didn’t make it hurt less. The pain was emotional, while the quality of the decision was rational; these apparent dichotomies actually aren’t opposing at all.

When you close your company, you’ll feel like you failed. And that’s because you did. The important point here is to become okay with that. Failure should be embraced and analyzed as a learning experience but that doesn’t mean you didn’t fail. Look in the mirror and admit to yourself that you failed. That’s the only way you’ll be able to learn from the mistakes you made.

I felt embarrassed because I naturally assumed people would view my failure as something negative. That they’d somehow think less of me because I failed. It took me a few days to get past this and to feel comfortable telling people that we shut down the company.

When we started sharing the news, my first surprise came. People didn’t look down on us. They actually respected our ability to make a decision and “cut our losses”. Mentors I spoke to offered a helping hand and ensured me that I’d have other opportunities to build companies. All of a sudden I started to understand that no-one cared. The people who wanted to help me when I was a CEO still wanted to help me as a newly unemployed and confused soul.

The sooner you learn to embrace your failure, the sooner you can pick up, move on and start learning from the mistakes you made to ensure you won’t make them again.

Make a plan for unemployment

Job hunting is a waiting game. Lots of waiting to hear back from people, lot of submitting and perfecting resumes and while people say it’s a full time job, it’s a full time job with a lot of free time. Your schedule can be unpredictable but there will be full days that you just don’t have anything productive to do.

My advice: do something you’ve always wanted to but felt you didn’t have time for. I decided to train for my first marathon. You can decide to write, read more, learn a new skill or language or anything else. The point is, if you don’t have a goal of some sort — something besides the job hunt — to occupy your mind, it’ll be much more mentally taxing.

Job hunting is a demoralizing and long process. It’s very similar to fundraising as a CEO. You’ll hear 100 “no’s”, but you only need one yes. Find something to focus on in addition to the job hunt, it will make it a lot more emotionally tolerable.

Understand what you like and map out your options

As founders of organizations, we work on 100 different things in a week. Your job title and responsibility often have no correlation. Use this as an advantage to understand what you enjoyed and didn’t enjoy and what you’re good at and what you are not good at.

I’d make a list of the responsibilities/tasks and rank them on a scale by how much you enjoyed them and how good you feel you are at completing them. Once you’ve listed the things you’ve done, I’d think about it like this:

You want to find a job in the top right quadrant, something you enjoy doing and are good at and you absolutely want to avoid the bottom left quadrant, things you don’t enjoy and aren’t good at. The other 2 quadrants are a bit more complicated and I’d like to address both of them briefly.

Something you enjoy but aren’t good at (top left) might seem like a great way to perfect a skill you enjoy and it is. But you won’t find much success applying for jobs you are grossly under-qualified for. For example, if you really enjoy speaking to users, building user personas and designing products, but you don’t have much experience doing that, it will be difficult to land a job as a product manager. Look for Associate Product Manager programs or junior product manager roles. There aren’t as may options but your success rates in applying to these positions will be much higher than regular product postions.

Now something that you don’t enjoy but are good at is a dangerous rabbit hole. If you’re really good at something, companies will often pay you a lot of money to do that for them. But if you don’t enjoy it, you’re going to be misserable. My one caveat to that is make sure you understand why you don’t enjoy it. Is there a specific function in the job you could change so that you would enjoy it? Finding a valuable skill we’re good at isn’t easy so don’t be too quick to give it up but don’t take a job you’ll be miserable at.

Reach out to your network

As founders, a lot of our time is spent meeting with people. Telling them about our company and selling them on our vision. We build relationships around the company and product we are building. So much so, that sometimes we assume that when the company ceases to exist so will the relationship. That couldn’t be further from the truth.

In my experience, everyone who was willing to, and interested in, helping me while I was building my company, was equally happy to help me after we closed. You just have to know how to ask.

Make a list of all of the people you have been in touch with who could potentially help you find your next gig. Start sending emails. Important things to keep in mind for those emails are:

  • Don’t include your CV. People get 100’s of emails with CVs and they usually get thrown into some database never to be found. You’re capitalizing on your relationship with the person, you don’t want to be just another CV. Once they respond, they’ll ask for your CV and that’s when you send it.

  • Not more than 2 sentences (ideally 1) on what happened with your previous company. Unless they were very involved, they don’t really care what went wrong, and if they do, they’ll ask. Offer to get more into detail over coffee but don’t tell the whole story of your company’s demise in an email.

  • Keep it short. This should be a general email rule, but sometimes when we’re asking for something, we get nervous and begin profously thanking the person and explaining why we need them. Don’t do that. Get your ask out, respect the reader’s time and be polite.

  • End it with a clear ask. If you want to meet this person to get career advice, ask to get coffee. If you want this person to hire you, tell her what you want to do and how you can help her. If you want this person to introduce you to someone in their network, explain who and why.

Make a list of companies that interest you

Don’t worry about who is or isn’t hiring for a position you want. As former founders, we have a unique skill set that doesn’t always fit into traditional job postings. Things like Chief of Staff to a successful CEO or Product Lead at an in house innovation lab of a larger company are roles that would be hired for by word of mouth. That’s why you should focus first on companies, not on positions.

Make a list of companies whose mission you connect to. These don’t have to be companies that are saving the world, but a company whose mission or story you‘d like to join. My companies ranged from Lemonade (reinventing insurance) to Spark Beyond (automated research engine for enterprises). The goal is to find companies where you can bring something unique to the table and learn from their leadership at the same time.

As you make this list, start thinking about who you know who could introduce you to the right people at these companies. VC’s are a great resource. One of the things they do is help their portfolio companies hire. If there is an investor you had a good relationship with throughout the life of your company, that can be a door into multiple of her portfolio companies.

And this is where it connects to the previous point. As you map out companies, make sure each company is connected to someone in your network. And as you map out your network, make sure you understand which companies each person is connected to and which of those could be interesting to you. Creating this interconnected web of individuals and companies is what will get you hired.

Prepare for interviews

The most important preparation you’ll do for interviews is the first thing I mentioned, embrace your failure. Don’t only embrace it but craft it into a story. Learn how to talk about the highs and lows and how you overcame diversity. Mention things you did well as a team as well as things you didn’t do as well. Don’t be afraid to volunteer this information, the interviewer knows things didn’t go as planned simply because you’re interviewing with them.

During the interview process, these are a few questions I found repeated themselves in interviews and are unique to former founders:

  • When did you sense things started going downhill? What was the tipping point?

  • Tell me about a time your team counted on you and you made a mistake. How did you deal with that?

  • What’s your relationship with your cofounders like today? (Most people will assume this is why you failed because it often is. Be honest about the relationship but don’t go throwing blame. Take responsibility for the failure and NEVER blame it on your partners.)

  • Why did you fail?

  • What could you have done differently?

  • Why don’t you start another company instead of looking for a job? (A lot of times the real reason behind this is financial. As founders, we worked for a long time with little to no salary and equity doesn’t pay the bills. Be honest about this, but it shouldn’t be your only reason. Come up with an additional explanation as to why you feel now is a good time to join another team as opposed to starting your own again.)

How to actually get hired

When you close your company, one of the first decisions you’ll have to make is what kind of company you want to work at. There is a huge difference between an early stage startup or a larger company. Within these two groups there are a lot of differences worth noting, but for the purpose of recruiting, I’m going to divide it into these two categories.

Early Stage

Companies at this stage are going to hire almost entirely through the founders’ or investors networks. Many of them won’t even post jobs on job boards but only on the Facebook pages of the company and employees. The best piece of advice I’ve heard for getting hired at a seed/A stage company came from a partner at Lightspeed. His point was that companies at this stage have problems and they’re looking for employees to solves those problems. Find the company’s biggest problem that you can solve and solve it for them. Learn everything you can about the company and make a presentation and a plan for how you would solve a certain problem. In other words: show them your value before you even apply.

Companies at this stage need people who can wear multiple different hats, switch between them quickly and take initiative without being told. This is the best way to show them what value you bring to their company. If they need someone like you, this is a huge first step towards joining the team.

Larger Companies

The bigger the company, the more hiring processes they have in place. That means there are certain steps that everyone will have to go through to be hired. That also means that they have certain very specific criteria by which they screen CVs that they receive. For that reason, you shouldn’t submit your resume online. Having a friend forward your resume to HR is better than blindly submitting it online but not by much.

The best option is finding a VP (or senior level employee) who you’ve previously worked with and explaining to them what you’re looking for. You can mention specific jobs the company has advertised but you don’t have to. Explain to the person your skill set and explain why you’d love to join their team. Again, don’t include your resume in the initial email, we’re looking to capitalize on the relationship you have with this person. They get tens of resumes a week, you don’t want to be just another one.

If you don’t have a relationship with a VP at the company, there’s another option. Go through their senior staff and speak to friends who work(ed) there. Try to understand which senior employees value entrepreneurs the most. They exist in every large organization, the trick is just finding them. Two big things to look out for:

  • Executives who sold their companies to the larger company are more likely to appreciate your experience as a former founder. Filter their senior employees by ones who came to the company through M&A as opposed to climbing the corporate ranks.

  • Keep an eye out for high ranking employees who mentor startups. This could be formally at an accelerator or someone whose Twitter bio says that DMs are open and they’re always happy to help founders.

There are other ways but those are 2 that I found worked well for me. These executives will be more likely to hire you based on your entrepreneurial experience than others because they can relate.

Involve Everyone

The amount of time it will take you to land a job is inversely correlated to the number of people you involve in your search. More people = less time, less people = more time.

Take the list you made of people who could potentially help and reach out to all of them. Explain to them what you’re looking for. If they show an interest in helping, keep them updated throughout the process. You don’t want them to continue sending you opportunities 2 months after you’ve started your new job.

During most interview processes, you’ll be asked to complete a homework assignment to show you’re actually qualified for the job. Don’t outsource the homework assignment but don’t be afraid to ask for help. You want to put your best foot forward and sometimes our best foot involves asking other for help.

In conclusion

When I first set out on the job hunt, I expected it to be long, tedious and demoralizing. Instead, I managed to stay on top of things, get a great job opportunity and learn a lot about myself. In my previous company, I was fortunate to have been in a position that required me to meet a lot of people and — hopefully — make good impressions on them. These good impressions and relationships were ultimately the asset that helped me land a job.

We all have networks. We all have people who think highly of us and want to help us. The trick is just finding those people and knowing how to ask them for help. And that’s what I tried to do here, give you a guide on how to cultivate those relationships to discover new opportunities.

I loved being unemployed. I read great books, took steps towards a bucket list item (run a marathon) and got some much needed R&R. I’ll end with the same point I opened on, embrace. Just as you embraced your failure, embrace the situation you’re in now and use it to help you move forward.

Finding a job is definitely more of an art than a science. This is my attempt to share steps that helped me and hopefully will help others. If you disagree, please let me know why. If this helps you in anyway, I’d love to hear about it as well.

I’m reachable at

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