10 Lessons from a Brutal Job Search

Shortly after getting back from the 2015 CPCU Society Annual Meeting in Indianapolis, my boss flew up to meet with me for lunch and informed me that due to recent management changes the decision had been made that Northern California is no longer a focus for the company and thus my position had been eliminated, effective immediately.


I handed over my laptop, company car and corporate card and proceeded to take an Uber home. I really wasn’t too mad, they gave me a fair settlement and even paid for outplacement services. As a young #CPCU with six years of broad industry experience, I was pretty confident I’d be able to find a new role pretty fast. Turns out I was wrong, it took almost four months to find my new role, and it was a crazy rollercoaster ride. Here are the main things I learned:


1. Assume the best, but prepare for the worst:

The average time to replace a professional job is around nine months and a good rule of thumb is about a month for every $10,000 in salary. I was almost completely convinced that I’d have a job within four to six weeks, but out of an abundance of caution, the very next day I applied for unemployment benefits and made a new budget cutting out most non-essential expenses (Starbucks, eating out, etc). I figured out that I was in good enough financial shape to last for at least a few months without too much trouble.


2. Take 2-3 days for introspection to figure out what you want to do next before sending out any resumes:

Regardless of whether you saw it coming or not, you will be in shock after losing your job. The last thing you want to do is send out a bunch of carelessly prepared resumes and unintentionally burn bridges. I woke up the next morning and asked a lot of questions.

“What was it I loved about this job? What did I hate about it? Do I want to stay in Insurance? Yes, absolutely. Do I want to stay in Sales Management? Yes. Would I be open to Underwriting? Yes, for the right company and the right product. Would I be open to Claims? No, probably not, with very few exceptions. Am I ready to become a full time consultant? No, not even close. Can I start monetizing the blog? No, I don’t think it’s the right time. How about a sales role in another industry? No. Do we want to stay in this geographic area? No, I’d prefer to move to an area with better cost of living, but I’d stay for the right role.”

I contemplated many possibilities for a good couple of days and bounced a lot of ideas off my girlfriend also. Obviously, this monologue will be different for every person. The key is to avoid analysis paralysis and excessive autopsies of what went wrong, and instead focus on where you want and need to be in your next role. Once you have at least a tentative path to move forward, begin prepping your resume.


3. Get your resume ready, and customize it for each job:

Once I had a solid idea of where I wanted to go, it was time to get my resume in order. Since I’ve done my fair amount of applying for jobs in the last few years, I had a good draft to work from. I spent a good amount of time researching current best practices and had several people review it, including the outplacement firm that my former employer paid for me. I have always been partial to the shotgun approach, and prefer sending a resume to any job that looks interesting, but the low response rate quickly taught me that it pays to take the time to customize the resume a little bit for the job you’re applying. It’s actually not hard. Print out the job description, highlight the key words and then make sure you include those where applicable in your experience. All of the big insurance carriers use software to screen incoming resumes, and without the right keywords your chances of getting to the desk of a hiring manager, or even an HR recruiter, are much lower. Don’t get lost in the black hole of applicant tracking systems, learn to use your keywords!


4. Activate your network:

You should most certainly send cold applications to every posting you find that might be a good match, but keep in mind that there’s a very good chance once you do find a job it won’t be because of an online submission but rather because somebody recommended you for the job. I have worked diligently through my entire insurance career in growing my LinkedIn network and today it has around 3,300 fellow insurance professionals all over the country (and the world). I took about two entire days to go through the whole list and message any and all who might have had a lead for me. The message doesn’t have to be long, just a short message letting them know you’re available and the kind of job you’re looking for and thanking them for sending any leads your way. I had multiple people open doors for me and help me get interviews or at least initial phone calls. Even interviews that didn’t lead to a job proved to be great practice and really helped me figure out the things I needed to improve and what potential paths might look like (see #10).


5. Reach out to third party recruiters:

Third party recruiters are a reality of job searching today, and in the insurance industry they are everywhere and come in all shapes and sizes. They play a very important role and how to deal with them deserves its own article. For now, just understand that introducing yourself to recruiters expands your network and may help you see what direction you ought to take next. A lot of great jobs don’t get posted publicly at all and the only way in is through a recruiter.


6. Education is helpful, but unfortunately it doesn’t replace experience:

This one was a hard lesson for me. I have my CPCU, AU, ARM, ARe and a bunch of other insurance designations. I’ve gotten a lot of attention in the last few years, and as a young CPCU, I get recruited often. This had led me to believe that my education was the equivalent of several years of underwriting experience, turns out I was dead wrong. After I had decided that I would be open to taking an Underwriting position if I couldn’t find a Sales Management one, I was thrilled to see hundreds of open Underwriting roles all over the country in everything from Middle Market to Inland Marine, Construction and Cyber. I started applying and even got a few calls, but it quickly became clear that everybody wanted three to five years of Middle Market or specialized underwriting experience, preferably in their own niche area, and that my education and one year of small commercial underwriting wasn’t going to cut it. Almost all conversations ended in me not getting an interview, and many applications were simply rejected on the spot because of my lack of actual experience. Recognizing this may help you direct your job search more efficiently, and at the very least, it will help you think about what other strengths you can try to use to overcome this challenge. That being said, if you find the right fit, the company may be willing to train.

7. Find your Achilles Heel and address it in all communication:

I knew from previous job searches that my main weakness is my repeated job hopping. I had six jobs in six years, and even though most of those were at the same carrier, and all of them were for roles higher up in the company, I knew hiring managers get really nervous about it. I was very careful to work on minimizing the damage by letting them know in the first conversation that I was aware of the issue, and that my goal was to find a role to sit in and get good at for the next five years. Also, I sought lots of feedback and learned that there were other weaknesses I had to bridge: lack of underwriting experience (for middle market and specialized underwriting roles) and lack of local brokerage connections (for sales management jobs). Once I realized I had those weaknesses I was able to work on addressing them up front.

8. If a job isn’t right for you, don’t panic and walk away:

There were many times when I felt that I should take a huge paycut and accept a small commercial underwriting or claims, but I realized that I was acting out of fear and stopped myself, and I am so glad I held out for the right role. My goal was to find a role at a great carrier, with similar pay to what I had, where I would get the right kind of experience for the jobs I want in 10 years, and I found exactly that when I accepted a Middle Market Underwriter Role at Liberty Mutual in February of this year. Don’t take a job that doesn’t pay you what you deserve and that doesn’t prepare you for the future you want! At least don’t take it until you run out of your unemployment benefits, and exhaust all other options.


9. It isn’t over until the ink dries on the paper:

38 days into the job search, I accepted an amazing offer to relocate to Atlanta as an AVP of Business Development for a small E&S carrier. After accepting the offer, I cancelled three final interviews with other companies. My dreams had come true. I would be a highly paid 33 year old Corporate Vice President jet-setter. The offer was made verbally with the promise that HR would have an official offer sometime early the following week. It was nice while it lasted, but the official offer letter never came, and it ended up falling through 3 weeks later when they reneged on the already accepted offer. I found myself unemployed, homeless, and backpacking through Europe with no job waiting for me in Atlanta, where we had already shipped our stuff to… (Click here for the whole story). The lesson is clear: Even though, in the US, an accepted verbal offer including job title, salary, location. and start date is technically binding, ultimately they can renege and without a written offer, you might not be able to do much about it.


10. A jobs search is a marathon, not a sprint:

You’ll have to send MANY applications, and it will be disheartening. You should be checking your favorite job search websites (my favorite is Indeed) daily and keeping track of all interesting jobs, sent applications, replies, rejections and interviews on a spreadsheet. This daily routine does several things: 1. Puts your resume out there and gives you a chance at an interview. 2. Helps you over time build an understanding of the current employment market (for me it quickly showed me that everyone is looking for Senior Underwriters with 3-5 years of experience but nobody wants to train a new underwriter and that there are very few Sales Manager/Territory Manager type roles out there). 3. It keeps you sane by helping you feel productive! I can’t overemphasize how important this is. Sending in a few applications every day makes you feel like you are making progress to get to the end of the purgatory of full time job searching. Chances are you’ll end up getting a role that someone recommended you for, not one you applied to online (See #4 & 5), but the process is still important. Give it your best, be smart about it and think of job searching as your full time job and soon you’ll land something. It took me 181 applications to underwriting positions to find the right one and 368 applications total. I applied at Liberty Mutual 42 times before they granted me a single interview. Keep reminding yourself that on average it takes a month per $10,000 of salary and just keep fighting!


About Antonio Canas

Tony started in insurance in 2009 and immediately became a designation addict and shortly thereafter a proud insurance nerd. He has worked in claims, underwriting, finance and sales management, at 4 carriers, 6 cities and 5 states. Tony is passionate about insurance, technology and especially helping the insurance industry figure out how to retain and engage the younger generation of insurance professionals. Tony is a co-founder of InsNerds.com and a passionate speaker.

8 thoughts on “10 Lessons from a Brutal Job Search”

  1. Great article! I think what really separates you guys from similar blogs is how candid, real and transparent you are. It’s refreshing in a world full of self-proclaimed “thought leaders” who just dish out formulaic LinkedIn posts!


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