It's been 18 months since I left Microsoft

When I told my parents I planned to start a Marketing Agency, they questioned what I knew about marketing - after all I was at Microsoft for 13 years. They thought I was in tech, not marketing.  And prior to August 2015, so did I.

My parents are almost always supportive of my decisions but just like it was hard when I quit the high school basketball team, or dropped out of pharmacy school, this one was equally hard for them to digest. I left 2 well paying jobs in the last year on my own accord and was already on month 6 with no paycheck -- now I was telling them I wanted to start a business in a field which they had never heard me talk about before. My mom shared my dad’s concern with me, “What does she know about marketing?”

As much as it sucked to hear, he was right to ask. I had been on a journey of learning who I was and hadn’t taken him along on it. 

I left Microsoft on October 3rd, 2014 - 18 months ago today - because as I like to say, I hit a wall. 6 months prior to that, I was the Chief of Staff for Derrick Connell, Bing.com VP, who was managing somewhere around 3,000 engineers. I had been in that role for 4 years carrying the official title of Principal Program Manager Lead. A technical title on a technical team. With Derrick, we had worked together so long I felt like I knew what he was going to say before he said it, but by year 4 I started questioning his decisions. This was new - he always set the strategy and I executed it - day in and day out. We partnered well together that way until we didn’t. I knew I needed to find a new job at Microsoft so I became Julie Larson-Green’s Chief of Staff.

As a Chief of Staff I did a lot of behind the scenes wizardry to help my boss tell a great story - with PowerPoint slides, producing videos, and product demos - which I would later learn is a key marketing skill. My last major event was the Microsoft Board Meeting. Julie was tapped to do the cross-Microsoft product demo, live to the board of directors. Preparing an executive for a five-minute product demo is one thing, but multiply that by nine and then tack on another one million because Julie was demoing literally ALL the key products across the company. In order to make this a seamless production, I wrote a 25-page script and began prepping with Julie. A few days before the Board Meeting Julie had a practice session at the Microsoft CEO’s Executive team meeting and I was in the room helping her out. Neither of us had much sleep trying to work out last minute bugs but we put on a great show.

The day of the board meeting, I remember being in the board room, it was just Julie and I, waiting for others to arrive and in walked Terry Myerson, EVP of Windows. Julie introduced me and he said, "I know you, I don’t know your name but I remember how great you were in the Satya meeting.” I felt pleased with the recognition and also resentful. After 13 years at Microsoft, I was still an unknown. 

This time it was just Julie in the room for the demo. I sat outside waiting nervously, hoping we had planned for every possible thing that could have gone wrong - I half expected her to run out of the room needing help with a machine. An hour passed and out she walked giving hugs and high fives. She pulled it off!

It was time to go home and unplug my brain for a couple days. 

All I could think was that I was doing all these amazing things and not getting the recognition I thought I deserved. I told Julie I needed to find another job and she knew that was the right thing for me. She found a great Lead PM role for me in the team but I couldn’t get excited about it — it didn’t feel right and I decided to leave Microsoft. 

Looking back on it now, I was yearning for the opportunity to take everything I had learned from these amazing mentors and stretch my wings and see what I could create on my own. 

But before I figured that out, I had one more stop to make at 8ninths digital agency in Seattle. I knew one of the founders and was hired as their Studio Director. Fast forward 8 months and I felt like I was hitting a wall again, just as I had done when I left Microsoft. I finally figured out that the phrase, "it’s not you it’s me” applied more than ever and I left 8ninths in May 2015. 

I had no plans.

I wanted to take the summer off on the floating home I rented for my son and I on Lake Union. I enrolled my son in fun camps and we swam in the lake almost every afternoon. I also knew that I needed to start earning money again at some point so I set a deadline of the end of September to have a plan. This meant, if I couldn’t cut it as an entrepreneur, I had to go work for someone again - at least part time. I was more motivated than ever to figure this out.

With the advice of my good friend and Techstars graduate, Adam Tratt I embarked on a learning journey, meeting new people through the generosity of his network and others. While my son was at camp, I set up coffee meetings and chatted without an agenda - looking for common ground, getting advice, and earning more introductions. To my surprise, many of those meetings ended with, “I have marketing work for you to do.” I didn’t know it at the time, much like my parents didn’t know, but I was discovering my role outside of Microsoft. A Marketer.   

After embracing the concept and throwing myself into re-learning Marketing I was hooked. 

By the end of August I had figured out I wanted to start a Marketing agency but that only gave me one month to go from an idea to getting paid to be a marketer. It was the encouragement of my boyfriend who said, take more time, there’s no rush. He was right, so I gave myself one more month. October 31st was my new deadline to start making money. 

The week of October 26th was stressful. I started reaching out to my Microsoft network to ask for work. I’m sure I sounded desperate. Luckily they ignored me.

My first paying client started with a coffee meeting on Friday October 30th at 1:00pm. As I’ve since learned, he knew I would try to ask for work, which he thought he didn’t have for me, but he agreed to meet anyway. I was asking him questions about his business and as we went on I started to show him the data I was collecting and how I was growing my business. He paused, and the conversation changed. I became the teacher. He offered me $50/hr to help him out for one week, as a trial. Well below what I wanted but it meant I hit my deadline with only one day to spare. I could continue crafting my dream. 

By day 4 he had increased my pay to my desired rate. By month 2 he had stopped working with his existing marketing agency and empowered me to run everything - from web design, to consumer marketing, to advertising and sales, customer support and partner management. I scaled by outsourcing some of the work to local and oversees freelancers. He gave me the freedom to try many creative ideas with his business - and we were growing it. Over the next couple of months he unapologetically used up all my work hours.

One day he thought he was giving me a compliment when he said, "I’m glad nobody else wants to hire you.” I wanted to respond, "I can’t find clients when you use up all my hours!" But I knew the best way to respond would come in the future when I had built my own successful business. The present was for me to continue to learn how to grow a business outside the corporate umbrella of Microsoft. 

But let’s be clear, his comment fueled my fire.

Through extensive customer research and 10’s and even 100’s of marketing experiments I helped my client hone in on his target audience. We’re now executing a more focused marketing strategy - which has freed up a lot of my hours to search for new clients. 

In my first two weeks of meetings, I met with 6 potential clients and all 6 said they wanted to hire me. I’ve closed 2 of them and the others are waiting on contract signatures or we're still in talks.

The other day I had a fleeting thought, “I may have overshot my goal." 

So Mom and Dad, it turns out Marketing's a good fit.

#WomenInTech #Microsoft

Jessica Jobes is Founder of OnTheGrid a Seattle Marketing Agency.