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Jack Schwabeland

Jack Schwabeland


Program Manager - Sales Enablement

Personal Information

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School: University of Maryland

Major: Economics

Career Information

Company You Work For Now: Flyhomes

Title: Program Manager - Sales Enablement

Brief Description of Duties / Responsibilities

My job is to level up our 300+ person, nation-wide sales team at scale. I focus on systems and processes that could be made more efficient in order to help each sales rep get that extra deal each month. Practically this means I design sales training programs, implement software tools, and find ways to automate mundane tasks.

What Has Been Your Proudest Accomplishment Post-CWP?

I had terrible money habits in college. Post-college, many of the organization and discipline habits I learned at CWP helped me develop a frugal mentality, save a big chunk of my earnings, and buy 2 homes in awesome locations.

CWP Career Impact

In one sentence, what has CWP meant to you?

Words can not define the meaning of the deep friendships, invaluable lessons, and countless great memories that spawned from my time at CWP.

How did your CWP experience impact your career? Immediately after graduation? Now?

CWP made me comfortable going door to door, so it was only natural for me to show up at the door of Flyhomes and apply in-person. A little while after I was hired, the COO told me that after I handed in my resume, the recruiter breezed it over and discarded it. He, on the other hand, had watched my interaction with the recruiter from across the office and thought there was something special about someone who shows up in person, in a full suit to apply for a job. So, he went over and looked at my resume. In a wonderful stroke of luck, he knew about College Works. When he told me this story, his exact words were "anyone who can make it at College Works can make it at Flyhomes." And so, I was hired. Flyhomes is a unicorn in the startup world. When I joined, we had well under 100 people. Today we have 1000. If I hadn't done CWP, my resume would still be in the proverbial trash can...or at least it would have stayed there til I knocked on that door again...again...and again!

What do you want to tell your clients about what it meant to work with them and how it has helped you get to where you are today?

My favorite client is still my friend to this day. His name is Flo. He is an eccentric guy and gave us a big job on his awesome house in DC. After we completed the work he told me we did a terrible job, but he liked me anyway. So, he offered me a job once I was done with CWP. Over the following year he helped me build my resume, introduced me to some cool people, and set me up with multiple job opportunities out of college (which I would have taken had I not randomly up and moved to Seattle). When I am back in DC I still hit him up and hang out with him. He is always telling me to start a company so he can fund it and join forces with me. I've learned a lot of lessons from Flo and having a guy of his status and stature who has so much confidence in me really means a lot.

What was the greatest lesson you learned from your CWP experience?

The ability to apply sustained effort to a challenge can take you just about anywhere.

If you had to come up with an one line slogan for CWP, what would it be? :)

An invaluable grindstone to stick your nose on.


What advice do you have for potential CWP participants? Current CWP participants?

Put in the effort and have fun

Many college students struggle to choose between an internship specific to their target industry or doing CWP. What advice would you give them on this subject if they wanted to enter your career field?

Many internships are just recruiting tools for companies to make you think working at their company is fun. CWP is an internship designed to hone and sharpen your skills and possibly even show you skills you didn't even know you had. You can leverage skills into name-brand opportunities. You can not leverage a name on a resume into skills. Now that may not even matter in getting your first job. You can get your first job on just names on your resume. But you only get the one freebie. Your future promotions and future opportunities will rest on your skills.

What's your best advice for someone interested in entering your career field?

Read Books - sales enablement can be fairly abstract and big-picture. You have to consider how many different types of people will interact with a product or solution and account for as many of the possibilities as you can. Thinking in these terms of systems and structure is foreign to most people who have not worked in the field before. Therefore, my best advice is to leverage the knowledge of those who came before you to get a jump start on tackling the complex problems you will face in sales enablement.

What's your favorite memory from CWP?

In Cancun there was a guy selling some wares on the beach. I was trying to haggle with him, but we did not understand each other until we connected on a common word, "Nike". He had spotted my friend's Nike slides in the sand (my friend was swimming at the time) and so the salesman offered to trade his stuff for the Nikes. I said deal and sold my friends shoes to this guy for his beach wares. Great deal and great time!

Last words of wisdom

Life itself is an absurdity. Enjoy it and be playful