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How I hustled my way to a career change in 3 weeks

Earlier this summer, I decided it was time for a career change. As a young, scrappy, and hungry dreamer who sold enterprise software in San Francisco I felt like I was in a position to take advantage of all the opportunities that my life here had to offer. My networks, expertise, and residence gave me numerous options when I decided to embark on a quest to hire a future employer.

What do I mean by hiring a future employer?

For me, hiring a future employer is a different mindset than simply “looking for a new job.” It allows you, the employee, to mentally flip the script with a different perspective, thus coming from a position of power. In this position you're able to constantly remind yourself of how much value you're bringing to each employer you're interviewing.

I come from a business background which means I like process and order. To help make a more thoughtful decision in my career change, I decided to treat it as an RFP process, a type of bidding solicitation in which a company or organization announces that funding is available for a particular project or program, and companies can place bids for the project's completion. In this case, I was soliciting myself as the program or project for companies to bid on.

Here’s how I issued an RFP for this particular use case:

I created a matrix with various decision criteria and scored each metric on a 1-10 scale. Each decision criteria had specific questions which helped generate a score. Once criteria was set, I asked friends, trusted advisors, recruiters, and the Internet for suggestions on helping me source the most exciting B2B enterprise software startups based in San Francisco.

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The RFP was used to score each potential new opportunity. My research produced a list of 21 appealing companies. From these 21 companies, I submitted my resume to 11 with job openings that fit my experience level. Ten out of these 11 companies called for an interview. Late stage interviews were conducted with four companies and three extended offers. The whole process took three weeks.

Wait, how did this process only take three weeks?

In a few days I applied to all positions, and within the first week I heard back from the first round of applications. By the second week I conducted my first round of interviews. During the third week, I lined up late stage interviews with four employers.

When offers started coming in during the third and final week, I found myself with the potential to hire three companies, and I took another few days to make my final decision. What helped expedite the process? I made it clear to each company the urgency and importance of my process. Companies are more willing to move fast to try to hire someone when they know he/she is in demand.

Choosing one company.

Choosing one company out of the three offers was one of the hardest decisions of my professional career. In the past, I've set my heart on one company (and one company only) and did everything to get the job. While choices are a privilege, it also made my decision more difficult.

This process gave me a behind the scenes peek into some super cool companies, an experience I don't feel that many professionals in my situation often have the privilege of enjoying in their own job searches. The companies I interviewed for represented an array of industries. Industries in IoT, experience management, enterprise mobile apps, cloud communications, and digital marketing. All of which were technologies adopted by iconic Fortune 500 brands. Because of this experience, I’m now more bullish than ever on the growth potential for tech and it’s ability to solve challenging problems.

After I evaluated the three different offers I decided to choose. Drum roll...

Hustle - a one-to-one text messaging platform founded in 2014 that scales and humanizes the way organizations communicate with people. As a social impact company, they've helped organizations like Spelman College, Human Rights Campaign, and progressive political action committees find more efficient ways to organize, increase donations, and evangelize their messaging. Within the past year they’ve expanded to business-to-business service offerings as well. Last month they announced Series A funding which will be used to propel future growth and to better execute their mission.

Going back to my matrix, the reason I chose Hustle was not only based on their overall quantitative score in my process, but also based on qualitative reasons aligned with my own past experiences, current passions, and various signs from the universe.

Here are the top five reasons to consider when you decide to join a new company:

  1. Regret. “Choose the opportunity that you’ll regret the most in three years if you don’t take it.” This advice came from the AVP of Sales at one of the companies that extended an offer. However this was one of the most valuable pieces of information I received throughout the entire selection process. Out of the three offers, Hustle was the opportunity that was too hard to pass up.

  2. Fear. In my podcast interview for Breaking Into Startups, I talked about how Doug Leone from Sequoia Capital uses fear to drive him. What opportunity scared me the most? What company scares you - for all the right reasons. There’s more risk at a very early stage company. Some roles are undefined at a new company. You'll have tasks outside of your usual day-to-day routine. This is a risk in itself and takes you outside of your comfort zone. This said, I decided to do what scared me the most.

  3. For as long as I can remember I’ve sold something. I’ve always had a hustle, and then my side-hustle. I sold popcorn in Boy Scouts, sold mix-tapes in high school, sold sponsorships to my events, mowed lawns, rented homes during the Democratic National Convention, and started my own consulting company. I have been a personal trainer and created a cocktail menu for a new restaurant, etc. These kinds of "side" jobs can let you know that you are an entrepreneur. After I met Ysiad Ferreiras, VP of Sales, and read his story, I realized his experiences highly paralleled my own. I wanted a company that would provide me the chance to go from being an amateur to a professional ‘Hustler.’

  4. Social Entrepreneurship. I caught the social entrepreneurship bug back in 2009 when I joined the leadership team of a non-profit startup focused on fostering entrepreneurship for minorities. During my tenure at the non profit, I witnessed the challenges of fundraising and galvanizing members. I wanted a company that was uniquely positioned to provide substantial impact. Hustle is able to generate recurring revenue while solving problems in a big way that benefit the public good and that's important to me. There’s so many big problems that tech can help solve.

  5. Collectivism. My recent trip to Japan as well as my time living in the Bay Area has taught me the importance and value of community – the advantages of collectivism over individualism. I’ve spent my entire career in sales as an individual contributor which at times can feel like somewhat of a selfish role because of its emphasis on commissions. As Senior Manager of Business Development, I’m now in a position where I will no longer be an individual contributor, but an advocate that is ultimately responsible for engaging new markets and helping our company as a whole. This role gives me the opportunity to align my progress with the company’s overall goals.

I feel incredibly lucky to work here at Hustle, and I'm confident in my decision. I have zero buyers remorse and truly feel that my process did not let me down. That said, I now want to share this process in the hopes of helping others on their journey to hiring their own future employers. ​