Incipia blog

From Microsoft Corporate Life to Working at a Startup

Gabe Kwakyi | September 15, 2016

Feature Image Credit: My Bing Team at SMX West!

From a Corporation to a Startup

For one full year now, my co-founder and I have dedicated ourselves to creating and growing a brand new startup in the mobile app industry. Prior to Incipia I worked for Microsoft for just over 3 years, serving as an advertising account manager in Seattle and then New York City. At Microsoft, I gained tremendous knowledge managing clients spending in aggregate tens of millions on ads, leading a team and brainstorming on ways to optimize our "rhythm of business" processes, all while having the pleasure of working with some of the best and brightest the world over.

Needless to say, it was been quite a ride shifting from the #3 market capitalized company globally to one with a market cap of #N/A. There have been ups and downs, lucky breaks and disappointments, good decisions and poor decisions. While there are things that we would certainly decide to do differently, overall neither my partner nor I regret making the jump, and in fact, we are doubling down on our endeavor to make even bigger moves in year two. Well Connected Now

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So what are some of the differences between working for a corporation like Microsoft and a startup?

Life at Microsoft

  • At Microsoft, one of the most important lessons was to learn how to operate in ambiguity. There are thousands upon thousands of plans, people and products moving around in a corporation at any one point in time, meaning that no one has a solid picture of everything going on; therefore, it's not uncommon for you to have to make a decision or take a task on with minimal direction or hand-holding. Being able to chart a course in an information vacuum and still accomplish the ask (which itself can sometimes be unclear let alone the approach) is key to doing well in a corporation.
    • This skill has been a godsend in the startup world, which is like the wild west as there are no processes, no data points, no colleagues to show you the way. I used my skill of operating in ambiguity to do things like design and optimize a sales strategy, learn and implement brand marketing tactics and build a process for tracking cash flows (proper cash flow management, by the way, is where companies either live or die).
  • Resources for self-improvement were plenty at Microsoft, from 1:many mentoring programs, to 1:1 mentorships, to trainings, to team brainstorm sessions, to an abundance of colleagues to ask for help, to stretch projects to even funding for continuing education. I took advantage of as many as I could to learn all I could, and relished every opportunity to give back and help others improve as well.
    • Being comfortable continually acquiring new skills, not being afraid to ask for help and learning how to ask the right questions have all helped immensely in running a startup, where nearly all of your time is spent learning to fly the plane as you're building it, and that's nearly impossible to do alone. We found a fantastic business coach through a fellow ex-Microsoft friend's startup and regularly asked friends for help when exploring new functional areas. Reaching out and asking to connect with people is very important when you don't work in a whole office building full of colleagues to share learnings with, help move the business forward and socialize with. The life of an early-stage entrepreneur can sometimes be a lonely one.
Well Connected Now

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  • Working for a large corporation usually affords you the chance to interact with people from all levels of the corporate hierarchy in different situations, and in doing so helps you build composure and poise in communications, confidence in leading initiatives and a need to have goals.
    • My experiences interfacing with director/GM/VP/CVP-level leadership, owning high impact initiatives, as well as being an account manager of large, sometimes intimidating clients helped me to fear nothing in the startup world and know that we had a right to win business even when competing with other, well-established companies. Having the Microsoft logo emblazoned in my LinkedIn profile didn't hurt, either. Additionally, being conditioned to constantly set and make progress towards goals was vital in keeping our company growth on the right track, and if we strayed then determining what we needed to do to get back on track.
  • Yet for all the fun it was to work at Microsoft, there was also the frustration of being in a behemoth organization, with lots of red tape, murky visibility across teams and where getting people onto the same page was a constant challenge. While Microsoft, especially under Satya Nadella made embracing change a priority, working in a corporate environment typically brings plenty of organizational inertia that naturally resists change, given change is expensive to implement and brings with it the possibility of failure. The "fail fast" startup mentality works at startups because there are fewer stakeholders/investors, smaller revenues, smaller brands and generally less riding on the outcome of each change. At corporations, there is also the problem of redundancies caused by several people unwittingly working on the same or similar tasks, while the nature of small startup teams mitigates this risk because information flows through fewer checkpoints.
    • Starting Incipia felt like uncoiling years of energy pent-up by organizational limitations. It's great to be part of such a lightweight organization that is capable of trying out new ideas daily and able to "move fast and break things" and "pivot" as needed. That said, leveraging strategies I had built earlier to still affect change, despite the aforementioned corporate issues, has been a boon in growing Incipia. For example, being diligent in sending agendas and recaps from meetings and erring on the side of over-communication rather than under-communication has helped us to keep both clients and our remote team on the same page regarding project statuses. Taking up more time is an annoyance, while missing critical information can be disastrous.
move fast and break things - mark zuckerberg

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Life at Incipia

  • Working on a startup brings a very welcome degree of flexibility regarding how you get things done, in terms of location (work locations range from coffee shops, to home, to airports to coworking spaces), to timing (we night owls enjoy starting work later in the morning and working later in the evening), to what to work on (see the next point).
    • Working at Microsoft offered a great deal of flexibility as well (being able to take off odd days or hours to take care of personal items, great vacation, the ability to work from home and a nice diversity of stretch projects such as sales excellence, product evangelism and business management), but at the end of the day I still had a singular, core role to do: sales. Having to wear many hats as part of my new job description has been a nice change of pace that I don't think I'll ever be able to give up.
coffee office shop

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  • Every day is an open book running a startup, where there is no guidance from managers or leadership teams. This can be empowering and also frustrating at the same time because there is no validation or sounding board to determine whether what you are working on is the best use of your time. Instead, you must determine for yourself what company goals to build a strategy for, and which data points to analyze your progress-to-goal by. Though once you have your priorities and reports in order, it's quite amazing to be able to steer your ship as you see fit and mold your company, career and life into the shape you like most.
  • Startups can move (just about) as fast as you can push them, and you can see every bit of day-to-day effort put into your company come out on the equity side as your company grows (or not, which leads to the "am I spending my time wisely?" question). While this can be incredibly motivating, by the same coin it can cause you to go overboard, working 7 days a week and every waking hour of the day on a path to burnout. Startup entrepreneurs need to remind themselves to take breaks and time off, delegate work when possible and plan for the long-term health of not only their company, but that of themselves as well as their teams.
  • On the opposite side of the spectrum of corporate red tape is the ballerina-like startup environment (only usually a lot less graceful on a daily basis, just really flexible). A nimble startup team can allow you to much more easily change the way things are done, put sensible new processes into place, adapt to changes in the market or even flip your business model upside-down. While we haven't changed our business model, we have evolved it over the past year, are working on the third iteration of our website and are actively rolling out several new strategies that will shake up how we operate as a company, for the better. It may be a bit less safe at a startup, but there is much more freedom, which echoes the swinging pendulum in the climate of American politics: give me freedom or give me safety, but that is a topic for another day.
All in all, it's been a vast change in work and personal lifestyle moving from a corporation to a startup, and while it's been the most challenging professional task I've attempted yet that will take years to come to a suitable point of fruition, that's exactly what we signed up for and we haven't looked back once. If you are an entrepreneur at heart and have an itch to scratch, I wholly encourage you to take the plunge. Just make sure to:
  1. Save up some cash.
  2. Make sure you have a strong network that is willing to support you.
  3. Find a partner or at least a trusted advisor or two who is willing to play an active role in your endeavor.
  4. Know what you are building, why it is important, how you will build it and what your vision is.
  5. Be ready to work. A lot.

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Just For Fun: Microsoft TLAs & Sayings

  • TLA: Three Letter Acronym
  • BAE: Bing Ads Editor
  • ROB: Rhythm of the Business
  • GSDS: Global Sales and Display/Digital Services
  • BG: business Group
  • MACH: Microsoft Academy of College Hires
  • BoB: Book of Business
  • "Learning to fly the plane as you're building it"
  • "Don't try to boil the ocean"
  • "View things from the 10,000-foot or 10-foot level
  • "Developers developers developers" (Do yourself a favor and watch the Developers remix)

That's all for now folks! Be sure to bookmark our blog, sign up to our email newsletter for new post updates and reach out if you're interested in working with us.

Incipia is a mobile app development and marketing agency that builds and markets apps for companies, with a specialty in high-quality code architecture and keyword-based marketing optimizations. For blog/video or speaking requests, business or press inquiries please contact us or send an inquiry to