Our Origin Story

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I’ll never forget the disastrous interview that inspired me try to figure out a better interview prep methodology. The interview was at a tech company where several of my friends worked, and I remember asking them for preparation help beforehand.

“You’ll do great,” one of my friends advised.

“Just be yourself,” advised another.

I asked a ton of questions, tried to figure out what the subject matter would be, and tried as hard as I could to figure out how I was going to be evaluated. It was like a bad dream- the more questions I asked my friends ahead of time, the more nebulous the process became.

In retrospect, I now realize my friends had no idea what the interview was going to be like. They had interviewed so long ago that they had forgotten, and because interviews are so frenetic and energy consuming, people don’t tend to retain a lot of that experience.

So despite my best efforts to prep and build a gameplan, my intel was terrible and I didn’t get anywhere. I felt underprepared, and after my first two conversations in the actual interview, I realized I was indeed underprepared. That made me even more nervous than I already was, and it showed.

After the interview, my friend at the company explained that I didn’t get the offer, and shared some of the feedback. One piece of feedback: I seemed nervous.

“But I was nervous,” I explained. “Why did being nervous and seeming nervous have anything to do with how qualified I was?” My friend shrugged. I now know the answer to that question*, but at the time, it was just another mystery in a frustratingly opaque process.

It’s one thing to get rejected from a job offer- rejection is a part of life, failure is a part of life, and I had taken enough lumps in sports to understand that concept. But failing so publicly, when three of my friends at the company knew I was interviewing there, was absolutely brutal and impossible to shrug off. So that experience stuck with me- I was never going to let it happen again, and I was never going to let it happen to someone I cared about either.

Fast Forward to Dropbox

When I interviewed at Dropbox in 2013, I was on a mission. I wanted the job more than anything I had ever wanted in my entire life, and the stakes were as high for me professionally as they had ever been (and likely, higher than they ever will be again.) It was a critical point in my career where I was trying to change trajectories (from real estate finance to tech) which was a difficult transition that would only get more difficult as I got older.

So I decided to study for my Dropbox interview like it was the SATs, AP tests, and finals all rolled into one. Because it was such an experimental process with such high importance, the time commitment was astronomical. I’m not exaggerating when I say I worked on that interview for over 100 hours. Hours a day for several weeks- failure wasn’t an option at this point.

Why such an egregiously high amount of time? The answer was that I knew I’d be at a disadvantage for a few reasons:

1. I was interviewing for a sales role, and had never sold anything in my life
2. The hiring bar at Dropbox was well known, at the time, for being absurdly difficult
3. Dropbox had about 400 employees at the time- so the importance of each person hired fitting in with the culture perfectly was enormous
4. The last tech interview I had ended in absolute, unmitigated, traumatizing disaster. I also had absolutely zero experience working for a tech company.

Building out the team at Dropbox

Getting hired at Dropbox, after the work I had put into the interview preparation process, might be the accomplishment I’m proudest of to this day.

The atmosphere was like nothing I had ever seen or experienced- the smartest people I had ever met working in every single corner of the business, 400 employees managing a business that had exploded organically to 300 million users (at the time.) A full time “Tuck Shop” serving three gourmet meals a day, a private shuttle that took everyone to and from work every hour on the hour, and maybe the best perk of all, I was allowed to wear jeans and a t-shirt every single day.

I was a founding member of our Mid Market sales team, which started as a complete experiment. My job wasn’t just to try to sell Dropbox for Business (which was a brand new product at the time)- it was to figure out the process and build our methodology from scratch.

How would we divide territories?

What would be the value proposition?

How many activities should we try to get done each week?

How should we recruit people to build this team?

What were the mechanics of the sales funnel, and how quickly did we have to move potential customers through it?

It was strategic, exhilarating, and an absolute blast. As we started to get rolling, it became clear that recruiting and interviewing was going to be our far and away most important task to achieve the hypergrowth that Dropbox’s investors were looking for. So above all else, our team had a mandate: figure out how to quintuple the size of the team so we could make an even bigger bet on the outbound sales experiment.

The head of our team asked me to take a lead role in recruiting and interviewing for our team, and our management instituted a policy where each successful referral, by anyone in the company for any new employee at the company, would be rewarded with a $3,000 referral bonus. So at that point, I couldn’t have been more incentivized to get people prepared for interviews.

Friends and Family

After a few years, I had conducted dozens and dozens of interviews on Dropbox’s behalf. It was my job to weigh in on whether or not we should extend an offer to a candidate, and I took each decision incredibly seriously.

Dropbox had a ridiculously deep pool of talented candidates who wanted to work there, and it truly didn’t make sense to extend an offer unless they were a near perfect fit. So I developed an extremely discerning and critical eye at the interviewing table. The company culture we had built was something I was so proud of, and we knew that each individual new hire would change that dynamic is profound and unpredictable ways. So if we extended an offer, it had to be a near unanimous decision, and it had to be a decision that nearly everyone was super excited about.

So that was the filter I used to prepare my friends and family when they had an interview to prepare for- I wanted to help them put their best foot forward and come off to any team they were talking to as a near perfect fit. I wanted to take away any vulnerability that could be used against them in the interview debrief- anticipate the concerns that could arise, and squash them before they had oxygen.

So each time I prepped someone I cared about, I’d build a fresh curriculum from scratch (which took an incredibly long time) ask them to study the materials I had prepped (which took an even longer time) and then, we’d sync back up to discuss, quiz, and drill (more time yet.)

Each individual prep session was slightly different, and had slightly different results. But the overwhelmingly most common result was that I pushed people in our prep sessions to overprepare, and by the time they arrived at the interview, it felt low key to them by comparison. They were able to relax, stay in the moment with their interviewer, and enjoy the experience- in large part, because they knew there were very few stones we hadn’t already turned over together, and virtually zero scenarios we hadn’t addressed in at least some capacity.

The Idea for InterviewX

In late 2016, I had just made the transition from Dropbox to Slack, a company I was incredibly excited about that was entering the same sort of early hypergrowth phase at which I had joined Dropbox. They were just starting to build out a sales team to tackle the enterprise space, and I was fresh off my own interview prep process for the first time in four years.

As I onboarded, Slack assigned me several modular courses online, which were designed to teach me specific aspects of their product and sales process. I found that it was a fun way to learn that aligned with how I preferred to master concepts in school- with a clear set of materials that brought me along gradually, and interactive questions to keep me engaged and helped me retain what I was learning.

At a certain point, with both ideas fresh in my mind, I made the connection that this type of modular learning could be a much easier, more scalable way to prepare myself (and prepare my friends and family who I devoted a ton of time to coaching) for the rigors of an interview process. I didn’t have a ton of time during the week, but nearly every Saturday and Sunday of 2017, I loaded up on coffee first thing in the morning and got to work.

Product Evolution

Over time, as I tinkered with the product and the format, the idea began to take shape. The first thing I did was reach out to a bunch of different colleges, specifically, their career services department, to learn more about some of the challenges students were facing in preparing for the job interview process. I also tried to learn more about the challenges that career services professionals were facing in preparing their students for this process.

One thing that crystalized in this process was the need for efficiency- my initial product included long form articles (kind of like this one) for how to interview more effectively, and almost every career services team told me that they were looking for something that could easily hold someone’s attention. Long form articles just weren’t going to do that at scale, and it was a lesson I’m glad I learned sooner rather than later.

Minimum Viable Product

The first iteration of the product we’ll be releasing over the coming months will be modular in nature, and will take candidates through a series of seven exercises, or sections:

1. Your Personal Pitch
2. Resume & Achievements
3. Interview Flow
4. Company Research
5. Behavioral Questions
6. Technical Skills
7. Risk Management

These sections crystalized for me when I examined the materials I had built in a one off fashion for my friends and family- I took a ton of time to figure out what all these plans (regardless of industry and role) had in common, and the lessons that I thought could be applied to almost any role.

The modules are a mix of educational information, and inputs by the end user, to build a comprehensive preparation plan. For example, in “My Personal Pitch,” the user is asked to map out the requirements and responsibilities of the role, one by one. After that, they are asked to provide an example of how they fit these requirements or responsibilities given their experience to that point.

Each preparation process, for each specific company, will require custom preparation, and InterviewX’s Pro and Premium plans allow for the creation of multiple study guides at once to easily toggle between your opportunities. That way, you can save and revisit each specific set of materials, and get in the right mindset for the interview of the moment.

There is a certain amount of any product that can’t be fully explained in print, and must be experienced first hand. Our first version is truly a jumping off point, and will definitely evolve over time. One thing is certain: we will vigorously collect feedback, incorporate that feedback over time, and continue to listen to our users as we try to de-mystify the interview process.

Our Goal

The end goal is to make interview preparation seamless and stress free- we provide the template and lesson plan so you can focus on what matters.

In my own experience, I turned my interviewing career around by treating each interview process like it was a final exam. If that’s the case, if a job interview actually is a final exam, InterviewX wants to be your study guide.

Post Script (Why Did Nervousness Kill My Chances?)

(*Why did nervousness kill my chances in that first interview I mentioned in this story?

An interview is a selling process- you’re selling yourself as a fit for a role. In order to sell effectively, you need to have a firm command over what you’re selling, and have confidence in that product. When you’re nervous, you can’t project confidence in what you’re selling, and there’s no sense from the person you’re selling to that they’d be missing out by not buying.

It’s exceptionally hard to bond with someone and form a connection with them when they sense that you’re nervous- it’s unnatural and uncomfortable for the other person. At the end of the day, your interviewer needs to make a judgement call that they’d be excited to work with you, so nervousness stands in the way of forming a meaningful connection and conveying a strong personal presence.

The lesson here: even if you don’t feel confident, or feel nervous, you have to focus on not letting anyone see that. Trick yourself into believing that you don’t feel nervous, and it will become reality.)