How to prep for a career switch interview

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There are a million reasons to make a career switch- life is short, the amount of time you spend at work is long, and there is a direct link between career satisfaction with your quality of life.

Even though that’s really easy to say, making the decision to pull the trigger on a career switch can be insanely difficult when you’re in the thick of it. There is a fear of the unknown, along with a fear of starting over, but neither of those factors should stop you if you know in your heart it’s the right thing to do.

Tactically speaking, this was something I had to navigate in my own career. I started my career at a real estate private equity firm in San Francisco, was very unhappy in that world and role, and knew that I didn’t want to spend my entire life and career following a path that I didn’t connect with on a deeper level.

Living in San Francisco, all of my friends worked at tech companies, and seemed to be having the best time ever. They were in companies that were fast moving, innovative, full of young, fun people, and were solving problems that impacted millions of people across the world. They wore jeans and t-shirts to work, were growing and getting promoted quickly, and were generally much more excited to go to work every day than I was. I realized I wanted in, but I wasn’t sure how to make it happen.

I had a bunch of interviews at a few of the tech companies my friends worked for, but I wasn’t prepared enough to get those jobs. It stung at first, but I wasn’t deterred- I continued to experiment with different strategies, changed the way I studied and prepared, and ultimately, was able to get a job as an early member of Dropbox’s sales team. That job changed my life- and although a difficult process, it was very possible with the right strategy.

Key #1 🔑— the process of mapping anecdotes to accomplishments becomes even more important when you’re making a career change.

In the Interview Journal study guide, I talk a little bit about the importance of mapping responsibilities to accomplishments. When you’re making a career change, this step becomes twice as important.

Here’s why- proving that you meet the requirements of a role, and have fulfilled similar responsibilities at a high level, is an absolute requirement for almost any job interview. When you stay in the same industry, it takes far less work and far less massaging to find those similarities.

In my case, I was interviewing for a sales role as someone who had never sold anything in my life (or so I thought.)

Requirements for a sales role at Dropbox included:

1. experience closing deals or generating revenue
2. experience pitching value to customers
3. experience objection handling, negotiating, and managing a full sales cycle
4. experience managing and exceeding a sales quota
5. understanding of SaaS based tools and value propositions

If you don’t have experience in this exact industry (as I didn’t,) this can induce panic. But when I looked closer, I saw direct parallels that weren’t obvious to me, or the team interviewing me/reviewing my resume, at first glance.

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Parallels from my role as a real estate private equity analyst:

1. I oversaw and managed a team of LEASING COMPANIES, who were in charge of managing deal flow and selling leases for the buildings that our fund owned. So in this capacity, I was doing a very similar role as a tech sales manager.
2. I strategized with our leasing agents to choose the companies we should try to pitch for our buildings, and helped them research these targets and refine our pitch
3. I helped respond to objections behind the scenes, though not live and on the spot like a true seller would. I also was in charge of evaluating the analytics and pros and cons of certain concessions we might make in a negotiation.
4. I was responsible for making sure key vacancies in our properties were filled, and filled at a lease price that maintained or grew the value of the property
5. Our team used SaaS based tools like Argus to model out different leases and deal types, and Yardi property management software.

Though it wasn’t obvious, all these requirements mapped to something that I had already done in my life.

Key #2 🔑- Customize your resume to highlight the similarities between what you’ve done to this point, and expectations in this new role/career

Customizing your resume to the specific role you’re applying for is important no matter what, but again, it becomes especially important when you’re making a career switch.

In my case, all the similarities I observed above were things I highlighted on my resume for the Dropbox job. If I were interviewing for a role in the same industry, I would have included a completely different set of information, but this set of bulletpoints spoke directly to the things recruiters and hiring managers for a sales role at a tech company were proactively looking for.

A job description essentially telegraphs the experience and language a hiring team wants to see on your resume- so it’s imperative to incorporate this information in the way your word your resume. A typical recruiter might spend five or so seconds on a resume- if he or she doesn’t see the exact terms and exact type of experience they’re looking for, they’ll flip right past your resume.

Words like “leasing,” “portfolio growth,” or “Argus” will not register with a tech recruiter. But phrases like “leasing SALES,” “portfolio growth QUOTA,”and “Argus SaaS tools” absolutely would, as these are concepts they’re incentivized to look for and notice.

Here’s a look at how my resume bulletpoints spoke to the requirements and responsibilities of the role I was applying for, DESPITE coming from a completely different industry:

1. experience closing deals or generating revenue

• Managed a team of leasing agents across 20 properties, responsible for closing leases between $2–4million in annual value for a total of $200M in annual leasing income

2. experience pitching value to customers

• Worked with leasing team to craft customized pitches for our largest prospective customers

3. experience objection handling, negotiating, and managing a full sales cycle

• Final decision maker for all leasing negotiations, modeling, analysis and approvals

4. experience managing and exceeding a sales quota

• Exceeded goal of 3.5% portfolio valuation growth, and annual quota of $80M net new leases annually

5. understanding of SaaS based tools and value propositions

• Used SaaS based tools like Argus Software in core role, and responsible for training entire San Francisco team on Yardi Property Management Software

Without massaging this messaging, I would have looked like a complete fish out of water coming from real estate finance to selling at a tech company. But by massaging my experience, working hard to identify the similarities, and forcing myself to use messaging and language that was consistent with what Dropbox was looking for, I convinced myself and my recruiting team that I already had directly applicable experience.

Key #3 🔑- Gain directly relevant experience proactively, and on the side

If you know you’re looking to switch roles and/or career paths, it’s incredibly important to spend your extra time on some sort of side hustle that provides immediate experience and credibility towards what you’re trying to do.

This can take a million different forms. For example, let’s say there’s a popular blog or podcast in the field you’re looking to get into. Email in volunteering to help them edit their podcast, proofread their articles, anything that provides direct, provable exposure and experience.

The biggest weakness you’ll have as someone making a career switch is a lack of experience in this field. To address it, you should find any way you can to gain that experience. Doing that PROVES to hiring team that you’re serious about this type of role, committed to it, and that you have skin in the game.

One giant worry all companies and hiring managers have is that they’re going to hire someone who is going to leave after a year, and provide a negative ROI to the company. Showing that you pursue this line of work in your spare time helps to dispel that type of fear.

In my case, I actually used my spare time to create an iPhone app (along with my cousin, who was an iOS engineer) that was designed to be a bulletin board for private groups of friends to post photos together. I designed the app, served as the de facto product manager, and cold called/emailed various venture capitalists I followed on Twitter for advice on how to create this type of business.

Was the app wildly unsuccessful, and shut down after less than a year of working on it? Yes. Yes it was. But it signaled to Dropbox that I was very serious about tech despite my finance background, that I cared about collaboration and the way people shared content together, and that I had experience cold calling, cold emailing, and that I wasn’t afraid to roll up my sleeves and do the gruntwork that sales entails.

As a final point, I made sure to identify those similarities ahead of time as anecdotes, and used each of those points in various questions I was asked in my interview.

Key #4 🔑- Be able to explain WHY you want to go this route, and make this change

Again, I talk about the importance of developing a thesis, aka personal pitch, in the Interview Journal collection, and the importance only magnifies as you attempt to make a career change.

A typical personal pitch consists of 3 items:

1. why you want to work at the company you’re interviewing with
2. why you want the specific position you are applying for
3. why you are the right fit compared to the sea of other applicants interviewing for the same role

This format can be altered very slightly in the case of a career change:

1. why you want to work at the company you’re interviewing with
2. why you want to switch from the path you’re currently on, to this position you’re applying for now
3. why you are the right fit, compared to the sea of other applicants who may have more direct experience than you

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A couple key tips- it may seem tempting to disparage the path you’re on or the company you’re with, but you must avoid that temptation. You never, under any circumstances, want to speak negatively about the world or role you’re coming from.

Instead, you must focus only on the positives of the path you’re pursuing.

In my interview, I was asked “why you do want to switch paths from finance to tech?” I explained that I had a passion for technology (which was backed up by my iPhone app side project as evidence.) I pointed out that in finance, you’re solving problems that benefit only a select group of investors, and that I was drawn to the idea that Dropbox was solving problems for millions of people throughout the world.

That finance to tech comparison is not negative or disparaging in nature- it’s simply factual. It’s also an example of an intrinsic motivator, which is always strong in an interview setting.

If I had referenced that I wanted to wear jeans at work instead of a suit, or that I wanted to advance in my career more quickly, or that I wanted equity in a hot company, those EXTRINSIC motivators would have been absolute red flags.

So the final key 🔑- focus on intrinsic motivators behind your career switch instead of extrinsic motivators.

If you feel the desire to switch career paths, there is likely something core to who you are that is motivating that impulse. Figure out the intrinsic motivations (the reasons that thing is internally fulfilling) as opposed to the extrinsic motivators (the superficial reasons that thing might be appealing on the surface) and you’ll be in great shape.

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