Why I traded everything to join a startup

Two weeks ago, I made a career move that my friends find puzzling. I traded in my job at Boston’s Best Place to Work for 7 years running, my cushy six-figure salary, hundreds of thousands of dollars in RSUs, and my dream apartment in Beacon Hill. In exchange, I joined a 2-person team working out of a living room in Midtown, downgraded to a modest startup salary, received illiquid stock options of uncertain value, and moved into a tiny closet apartment in the Upper East side.

Am I crazy?

I did all this because I believe RocketVisor is going to become the multi-billion dollar business that transforms the way we all work. They are solving the pain that I experienced firsthand, their technology is cutting edge, and I love the company culture. I would know; I was the very first RocketVisor user when they began their Alpha one year ago.

I believe in the problem

Sales is a critical but frustratingly manual task at most companies.  I began my career in sales because I understood that life is selling. What I didn’t know was that the profession involves tedious, repetitive tasks that can drive a person to the brink of insanity…or at the very least drastically affect their productivity. I frequently wished I had more guidance to understand how I could improve, automation to limit the tedium associated with sourcing and prospecting, and actionable data to facilitate coaching with my manager. Right now this doesn’t exist.

If you’ve never been in sales before, let me explain the pain. Each day, I would get my morning coffee, toss on my headphones, and jump back and forth between Salesforce, Linkedin, Gmail, Google Docs, Evernote. I would repeat this ping-pong between my applications dozens of times over. It was not uncommon to have between 20 and 30 tabs open in my Google Chrome. Organization was next to impossible. Workflow was left up to each individual rep to figure out based upon gut instinct. When it came to coaching sessions with my manager, I had no idea where to start the conversation to improve myself. This was a real problem; about half of my paycheck depended on how well I performed. When I looked for a solution, the answer was always “That’s just part of the gig.”

That’s bullshit.  I knew that software could be designed to make people’s lives better and days more efficient. Unfortunately, I found most of the software I used to do the opposite and, quite frankly, burn me out.

Then a friend introduced me to RocketVisor, a one-month-old startup that was on a mission to solve this exact problem. I learned that Yaro, the company’s founder, and the team are on a mission to annihilate the frustration involved in sales processes. RocketVisor wants to help salespeople sell more, and be happier.  After that, they want to build software for all knowledge workers to improve their quality of work and quality of life.  That was a big, meaningful vision that excited me.

I believe in the product

It was exactly one year ago when I became the first RocketVisor Alpha tester, and I fell in love with the product. The difference with RocketVisor was that Yaro understood exactly the pain I experienced because he had hit a similar wall in his previous role sourcing deals at a VC firm.

His solution was simple, creative, and incredibly effective. Since the browser is where all our work now happens, RocketVisor was on a mission to make the browser brilliant. They weren’t building a distracting chatbot or some new tab I had to log into.  I had tried solutions like that, and they only added to the complexity I experienced. They tried to change how I worked, and I didn’t like that.  

What I like about RocketVisor was its simplicity.  I just worked like I normally did, and RocketVisor would help me as I went.  And it didn’t require any technical resources or skills to set up. In turn, many manual tasks involving various company websites, Gmail, Linkedin, Evernote, and Salesforce became much more streamlined. RocketVisor was saving me seconds on steps I would repeat dozens of times a day and hundreds of times a week. It was then beginning to automate these tasks. From using RocketVisor, I was averaging an hour of saved time each week. This was an hour I was getting back in my life. This was an hour I could put toward closing one more deal or heading out of the office a little early to get dinner with my parents. I also felt less frustrated and burnt out.

If the RocketVisor team could accomplish this momentous feat in just a few months while the founder was still getting a Harvard MBA, what was possible if the team started to scale? I knew that RocketVisor was on the brink of solving an enormous problem — not just for salespeople but for the entire future of work. I wanted to be a part of helping other professionals get some of their life back.

I believe in the culture

RocketVisor’s culture is no joke. This is coming from a former member of the company that literally wrote the deck on culture. Company culture is crucial to uniting a team, attracting and retaining talent, and overall, having a happy workforce. HubSpot houses some of the smartest people in Boston. Everything that you read about HubSpot’s culture code and the people doesn’t even do the actual experience justice, but there is a je ne sais quoi about the team RocketVisor is building. Not only does Yaro have a fantastic resume (Princeton Student Body President for 2 years, Associate at a top VC firm, Harvard Business School degree, etc.), but our conversations over the past year truly speak to how seriously he takes the role of culture in building a world-class team and company. I know RocketVisor is a place where I will grow and thrive.

Integrity and honesty

These are the traits that I hold highest above all else. As I came to find, so does Yaro. As we frequently grabbed coffees and talked about entrepreneurship, we often discussed how these characteristics are pivotal. During our more serious conversations about opportunities at RocketVisor, much of our conversation, again, was centered around strong integrity and honesty. When I reviewed the RocketVisor handbook and offer letter, again, integrity and honesty were at the core. A team that so strongly focuses on these traits will find a way to win no matter what happens. I wanted to be a part of that.

Always be learning

Despite a lot of the amazing benefits one receives while at a large, established organization, I found that I was becoming siloed in my daily process and division. This was ultimately impacting my ability to learn, grow, and thrive. Despite learning a lot about a given role, other areas of importance to personal and career growth can fall by the wayside. A core aspect of RocketVisor is to always be learning. Shortly after signing the offer letter, Yaro mailed me 3 new books so I could start learning more about how I can be as effective as possible in the role. I was also encouraged to begin scoping out networking events and conferences that can help my personal and our team development. As long as you constantly learn, RocketVisor believes you will be happier, healthier, more productive, and grow personally and professionally. I wanted to be a part of that.

An incredible network

By joining RocketVisor, I gained access to an incredible network of people and knowledge. The RocketVisor network includes investors and mentors who have built and sold companies to the likes of Microsoft and Oracle, Venture Capitalists that have done due diligence and made investments in hundreds of companies, and VC firms that have backed and helped drive strategic direction for some of this decade’s most successful firms (HubSpot, Snapchat, Airbnb, Stripe, and many more). I wanted to be a part of that.

I believe that we will win

I joined RocketVisor because this is where I am going to solve a serious problem alongside an outstanding (and soon to be growing) team. On one hand, I could continue to overachieve at a corporate company, get amazing benefits, accept that tedium involved in the role, move into management, and retire comfortably. But, an interview with Jim Koch, Founder of Boston Beer Company, challenged this status quo in my mind. He outlines the difference between ‘scary’ and ‘dangerous.’ Getting to the end of your career and saying “‘Oh my gosh. I wasted my life,’ that’s dangerous. That’s very dangerous. Not scary. But really dangerous.”

Picking up all of your things, quitting an amazing job, moving to New York City, learning to walk much faster, having the self-control to not buy the $1 pizza slices at every corner, and dedicating myself entirely to giving professionals some of their life and happiness back: that is scary. I am 150% on board with this challenge and couldn’t be more excited to bring this vision to life. 

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