More than One Way to be Rich

There’s more than one way to be rich, and perhaps even better ways. 

To most, the name “high roller” evokes an image of one who has amassed a small fortune — in the traditional sense anyway. Kyle Gross, Managing Director of memoryBlue’s Seattle office, proves that there is more than one way to be rich, and it’s the result of building a community of top performers.

After graduating from Virginia Tech in 2017 with a BA in Marketing and Management, Kyle knew he wanted to be a leader and even dreamed of becoming an entrepreneur. Kyle decided to begin his career at memoryBlue as a Sales Development Representative, where he would get ample training and become in control of the path to his ideal future.

“I wanted to be somewhere new, in a company I could grow with. The ideal place would offer management and leadership opportunities and be invested in my future.”

Beginning his journey to leadership meant preparing, planning, strategizing, and maintaining a growth mindset when any challenge presented itself. Learn how Kyle pushed past “The Dip” in his first sales role and propelled himself to leading an entire memoryBlue office in Seattle.

Pushing Past The Dip

We call Kyle a High Roller now, but earning that title required a lot of work and resilience in the face of many challenges along the way. Like most entering the field of sales, Kyle started as an SDR. He came aboard eager and full of competitive confidence, but starting out in any new job comes with a learning curve.

 “When I first started at memoryBlue, I sucked. There’s no nice way to say it. In my first three months, I was 50% under quota. I wasn’t hitting the benchmarks that people who started after me were, and it drove me crazy.”

For someone accustomed to successfully improvising, this reality was crushing. He had two options: Stick it out or quit– and Kyle’s not a quitter.

He came in early, quit strategies that were not working, took advice from experienced coworkers, and put in a tremendous amount of extra work. And it paid off; Kyle hit quota 6 out of 7 of the following months. He felt on top of the world. But for Kyle, this would be the first of a few hurdles, and the fall that came next seemed much more punishing.

After 6-months of crushing his quota, Kyle hit the dreaded “dip,” as Seth Godin describes in his famous book. “The Dip” is that seemingly insurmountable obstacle on the path to greatness. Kyle fought self-doubt, entertained other possibilities, and even came close to throwing in the towel.

“I stuck it out. I trusted the process, kept pushing, and eventually started hitting or exceeding quota consistently. It wasn’t long after that I took my first promotion to Client Delivery Manager and was leading a team of SDRs.”

Being in the trenches as an SDR and intimately knowing the difficulties of the position proved to be Kyle’s most valuable asset in making him a great leader.

A Natural Leader

It’s hard to best advise someone in a position you’ve never had, help them overcome challenges you’ve never faced, and put things into perspective when you’ve never stood in their shoes. With nearly a year of direct SDR experience and two years managing a team, Kyle’s leadership skills and his team thrived. Just shy of 3-years at memoryBlue, Kyle had demonstrated his talents as a Client Delivery Management and was offered a position that would be the capstone achievement of his career thus far: opening and managing the new memoryBlue office in Seattle.

His commitment to himself and memoryBlue allowed Kyle to achieve his dreams of running a business and empowering people to actualize their own dreams. Now, leading an office of Client Delivery Managers and their SDRs, all while maintaining client facing responsibilities, he makes sure his entire team is engaged by asking them:

“What is your why? What motivated you to be here? I wanted the opportunity for growth — that was my why. And here, we offer very clear and structured growth paths. Come into our program and work hard, and these are the doors that open to you.” 

 

Long-Term Gains 

Being vulnerable, honest, and transparent about your struggles in addition to your victories is imperative — it’s human. Guiding others to success, helping them achieve their goals, and building a network of lasting and meaningful relationships allows Kyle to continue his why vicariously.

It’s hard to remember the light at the end of the tunnel when you’re stuck in the dark, but stick it out, and you can reap incredible rewards. For Kyle, the long-term gains from overcoming those moments of insecurity and frustration have been exponential.

    In 2017 Kyle joined memoryBlue as a Sales Development Representative (SDR)

    In under a year, Kyle was promoted to Client Delivery Manager (DM) in the DC                          headquarters.

    As a Client Delivery Manager, Kyle supervised and developed over 35 SDRs and                          delivered results for a portfolio of over 20 clients.  

    In January of 2021, Kyle was tapped to open memoryBlue – Seattle as the Managing                Director (MD).

    Within 10-months, memoryBlue – Seattle promoted 3 managers due to exceptional                 performance.

     In less than a year, the Seattle office has grown to over 30 employees, setting the                       record for fastest-growing office in the company.

“We’re not teaching you what to sell; we’re teaching you how to sell in the world of high-tech. We provide the opportunity to sell for a variety of different clients and allow you to figure out what you do like, and perhaps more importantly, what you don’t like selling.”

The right place to begin a career conveys investment in your success by offering you opportunities to grow, learn, and prosper. And more than that, it’s a place to build the lasting connections that matter most.

Living the Rich Life

For Kyle, true value comes from elevating his team, his clients, himself, and the company. Within five minutes of conversation, his pride in running the Seattle office and positively impacting the careers of so many feels tangible.

“There is nothing more rewarding than seeing the growth and development of the people I’ve managed. Many of them, as quickly as two years after being on my team, are now sales executives. It means a tremendous amount to me that I’ve played a significant role in their achievements.”

Kyle’s leadership style of operating with a deep understanding and respect for the individual needs of his employees gives a return on his investment, making him rich in more ways than one.

Take Your Next Step

Interested in following in Kyle’s footsteps? memoryBlue is hiring multiple motivated Sales Development Representatives (SDRs) across each of our six offices in DC Metro, Austin (TX), Boston (MA), Denver (CO), Silicon Valley (CA), and Seattle (WA).

Jumpstart Your Career 

Start your rich life with a career in tech sales at memoryBlue.

 
Check Out Some Other High Rollers: Jack Klaas | Deng Phua | Shannon Pierce