44 Interviews in 56 days. How I Kept My Sanity and Landed My Dream Job

Lisa Besserman
6 min readNov 8, 2020

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After 6 years as an entrepreneur, I was a bit out of touch with what re-entrance to the workforce would look like. Before starting my own company, the last job I held was at an early stage tech startup.

After one interview with the C.O.O, I was hired on the spot.

More recently, I accepted a role at a major tech company, waited 7 months to onboard, then had the offer rescinded due to a re-org and hiring freeze. I was *scrambling* to find another job.

With advancements in HR software, competition in the technology space, and a more demanding interview process, I’ve picked up a few tips along the way.

1. Do not frivolously apply to jobs.

At first, I found myself playing a numbers game. I quickly skimmed through the job description and required qualifications, then submitted my resume. I should’ve been more targeted in my selections and clear on location preferences.

I scored an interview at a top 5 Accelerator fund and was genuinely excited about the role. However, it was located in San Francisco. I was willing to overlook this at first, but after 20+ interviews, I just didn’t have it in me to continue with yet another interview.

I realized that SF was not a place I wanted to live, so I promptly removed all SF based job alerts and declined moving forward with the interview.

2. Set up Indeed/Google/LinkedIn Job board alerts

After manually searching for hours on end, I realized a more streamlined approach was to create keyword searches and have the jobs delivered me, not visa-versa.

Although starting out each day with 20 different job board emails and 100+ openings to sift through is a bit daunting, it does save time and energy in the long run.

3. Write an intro script for interviews

The first question in 90% of interviews is “tell me about yourself”.

Rather than wasting the brain power in retelling your story over and over, write out a script and customize it for each interview.

Just do your best to sound natural, not that you’re reading from a doc.

4. Know when to say no.

At one point I was interviewing with 6 companies simultaneously. Each role was exciting and I had a genuine interest in pursuing them all.

Any opportunities that came my way that I wasn’t 100% committed to, I turned down.

If your heart isn’t in it, your energy is better spent preparing for the roles you’re most passionate about.

5. Take notes

These days most roles require multiple interviews with many different stakeholders. Create a Google doc dedicated to each position and take clear notes when speaking with each of the interviewers.

Many times I was able to use the information on next round interviews, providing me with more context and knowledge as I moved up through the process. It also enabled me to ask more thought-provoking questions.

6. Tap into your network

This is the #1 best piece of advice on this list.

70% of interview opportunities came from my personal and professional network. Let your friends and contacts know you’re looking for work and be clear about the roles you’re exploring.

Tapping into your network is the most effective path towards finding your next opportunity.

That being said, be extremely explicit in your “ask” and do your part to allow them to help you as seamlessly as possible. Be respectful of their time and resources.

(Shoutout to: Lauren Rinkey, Heather Hartnett, Alessandra Henderson, Ian Friedman & Frank Denbow for all of your support.)

7. Know your market value and discuss compensation early on

There were many roles that I was excited about, however, once we reached the compensation discussion, it became clear there was not a good fit.

It’s better to get this information early, out of respect for everyone’s time. The last thing you want to do is participate in multiple rounds of interviews, only to learn that the compensation is too far off to make sense for either party.

It’s become more acceptable to discuss compensation early on in the interview process these days. I recommend doing so in a tactful and respectful manner to ensure everyone is aligned moving forward. Recruiters will appreciate this.

The line I generally used with success was “I hate to bring this up so early in the process, but out of respect for everyone’s time, could you please share with me the range you had in mind for this role?”

8. Prepare (duh!)

Understand the role, the company, the culture and how you fit into it. The goal of interviews should not only be to highlight your experience, but also create a clear understanding of how you fit into the company mission and the value you will add long term.

9. If you don’t get the job, it’s not the end of the world.

As I briefly mentioned, I accepted an offer from a large tech firm and after 7 months of delayed onboarding, a re-org resulted in a hiring freeze and my offer was rescinded.

I was devastated, not only due to the lost time and wages; but because I didn’t think I would find a better role.

Boy, was I wrong. I found a better role 6 more times at 6 different companies, all within 8 weeks.

If it’s not meant to be, it won't. If it is meant to be, it will. Accept that and move on. You have no idea what’s waiting just around the corner.

10. Optimize/customize your resume

It’s important to have the right keywords for different jobs. Also, try to incorporate a nice design element so your resume stands out from the rest.

Keep in mind, HR software has advanced tremendously throughout the years. It’s possible your resume will be overlooked if it’s not optimized for the role in an effective manner. Also, always use PDF format.

11. It’s a marathon, not a sprint

The hiring process takes time. It’s important to prioritize your efforts and stay motivated. There were many times I was fed up and exhausted — physically, mentally, and emotionally. However, you have to recognize you’re in it for the long haul.

The roles I interviewed for were highly sought after and competitive. Just because I didn’t get the offer or make it to the next round, didn’t mean I wasn’t a viable candidate. It just meant someone was a better fit and that’s ok.

It’s important to stay positive and motivated, your attitude is a huge indicator of what your outcome will be.

12. One bonus lesson if you’re deciding between multiple offers —

Trust your gut. You already know the answer, you just have to listen.

My gut told me not to accept the original offer at the large tech company. However, I was too persuaded by the compensation, prestige, and shininess of it all. If I had just listened to that inner voice, I could’ve saved myself months of frustration and disappointment.

Eventually, after 2 months and 44 interviews (I kid you not, I counted), I was happy to receive a few offers at some fantastic companies.

In the end, I felt strongest about an exciting new role at Indeed, as Head of Program at their Global Incubator. I get to work with an incredible team to bring products and ideas to life, while fostering a culture of intrapreneurship on a daily basis.

The moment I stepped onto the Indeed campus, I immediately knew it was the right fit.

My first day at Indeed

Wherever you may be in your job search, I know how challenging it can be. Lean on your friends, family and loved ones to help keep you sane throughout the process.

Who knows? You could just be one phone call away from a life-changing opportunity…

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Lisa Besserman
Lisa Besserman

Written by Lisa Besserman

Founder of Startup Buenos Aires Accelerator (acquired), Business Insider’s “Top 100 Most Influential Women in Tech”. Head of Program, Indeed Global Incubator.

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