1999: How I Went From Retail Newbie to Youngest Store Manager in $9B Company

Leadership is not granted by title — it is earned through ownership, initiative, and value creation. When you act like a leader before you are named one, performance becomes proof and opportunity follows. The path accelerates for those who choose responsibility over waiting.

“Justin, let me tell you something. Today I interviewed three candidates for the General Manager role at our new Gateway Computer Retail Store”

• A guy who was the Store Manager for seven years at Circuit City

• A candidate with 12 years of large box retail management experience, including 5 years running a Toys R Us store

• A person who owns and operates a few Sonic Restaurants

The VP reviewing my resume, which had several handwritten notes on it, leaned back with a faux confused look.

"From what I can tell, you recently graduated high school and are in your second year of college. You've had some management experience at a couple pizza shops."

I nodded.

"You've been interviewed by three of my people today to end up on my shortlist. As the VP over half the US, I only interview store managers."

He paused for effect.

"Why in the world am I talking to you about the $2-4 million General Manager role for our new Gateway store?"

(Today’s post is long. You can cut to the chase by starting at “New Opportunity” below)

Happy Sunday friends,

This is a personal story linked to The Path of a Leader.  Today’s letter spotlights how the Path of a Leader can work at any stage of your career and accelerate it.

It was 1999.

At the time, you probably went to the theater to watch movies like Fight Club, The Blair Witch Project, Office Space.  You were introduced to Jar Jar Binks in Star Wars The Phantom Menace and something called ”bullet time” from this little sci-fi film called The Matrix with that Keanu Reeves guy.

Y2K was approaching and many anticipated computer issues on January 1, 2000. Napster launched, pioneering digital music sharing.

I was a manager at Domino's Pizza, trying to figure out my career path. I transferred universities to be near my girlfriend (now wife) and was studying business, specializing in Management Information Systems.

People saw me as a "computer guy." I built websites, studied computers, and understood technology.

When my girlfriend's sister showed me a career fair ad, I was puzzled. "What's that?" I asked.

She explained the concept - people just show up and try to get jobs. I was skeptical but made a resume. The idea of working for Gateway Computers was very appealing.

At the time Gateway Computers was booming, with $9.6 billion in sales.

Part of this amazing sales growth was because of the Gateway Country Store retail concept they were introducing into large and medium markets across the US. 

These retail stores rivaled Sears, Circuit City and Best Buy. Gateway Country Stores were aesthetically ahead of their time, creating a very cool environment and customer experience. 

Of course, I didn’t know any of that though. 

I had never seen their retail stores and was literally just replying to an advertisement that was trying to staff the Beaumont Texas store they would open in a few months.

As a 20-year-old, my work history was limited to food experience at Dairy Queen, Domino’s Pizza and Papa John’s Pizza.

My first interview at the career fair was brief.

A young bubbly lady asked what role I was applying for and I said confidently “store manager”. It got a chuckle and that broke the ice. 

“Why store manager?” she probed. 

I answered several questions and talked about my experience managing people at Domino’s Pizza and that I was “a computer guy”.

She was the first filter for pass/fail sorting candidates into which group to interview with.  She told me she liked my enthusiasm for the role and said I should talk to the person interviewing primarily for the sales team.    

About twenty minutes later I’m in my second interview.

“So, Justin, you want to be a salesperson at Gateway huh?” She asked as her quick opening question to get me talking as she scanned my resume. 

“A salesperson?” Did I hear that right?

She nodded and said they were looking to hire 3 or 4 fulltime salespeople and another 3 to 5 part time sales people and made note of my status as college student and that many college students considered the part time role as a great way to balance school and work.

“I’m not a sales guy.” I said firmly.

“I’m here to be the store manager”.

She raised her eyebrows in surprise.

I smiled back. Not changing my answer.

She said something along the lines of ‘ok, I’ll bite’ and advised that instead of asking about my sales experience, what could I tell her about managing people and my experiences with management responsibilities.

I enthusiastically talked about managing labor, food cost, scheduling people, weekly sales numbers, hiring and firing delivery drivers and managing unexpected issues with people not coming to work as planned.

I spoke passionately about working hard and training others to be able to help when it got too busy in peak dinner hours etc. I explained the annual competition for “fastest pizza maker” and why that was relevant to speed and quality.

Several more notes were added to my resume.

“Justin, I like your management style and experience, I think you should interview with another person who is hiring the Sales Manager role, are you open to that”? 

She walked me over to another well-dressed woman in a dark pant suit and red glasses.  We shook hands and she quickly scanned my resume and the notes. 

“Wow, you’ve had a busy morning and a lot of good notes here on your leadership skills, communication skills, management skills, and technology background”.  

She summarized out loud.

“And now you’ve made it to me.  Great! I love seeing ambitious young professionals on the team. Can you tell me why you want to be a sales manager with Gateway?”

I sat there for a moment to collect my thoughts.

“Not sales manager” I said. “The store manager.  I want to be the STORE manager”.

This time, there was a clear shift compared to the previous interviews.

She was not cold, but clearly changed her tone and seriousness.

“Tell me about P&L management and quarterly goals and annual goals, how does that work in the restaurant business”.

I explained how cheese cost and employee labor were the biggest factors in a profitable day, that the goal was to keep a winning streak of profitable days which meant I had to balance making a great pizza customers liked with concern for food cost and waste. I had to be disciplined with labor management and timing how many drivers I had for the nightly rush when we were swamped but also knowing to jump out of the fray to cut people as the rush was slowing. Doing all this and more on a daily basis would lead to quarterly and annual profit growth.

Because I was taught to do all roles from washing dishes to taking a phone order, to delivering pizzas and of course making the pizzas as well as doing the commissary orders and nightly inventory – I had total ownership and autonomy over the store and staff.  

Since the restaurant was a well-balanced eco-system to stay dialed in and profitable, it needed to be maintained deliberately or we’d be unprofitable. Part of how I handled that was to cross-train all employees to do all the roles so people could help on phones, dishes, inventory, and making pizzas so we could optimize labor and tasks. 

She had more questions along these lines of training people, managing inventory, dealing with unexpected issues.

She seemed satisfied in my answers, even surprised.

It turns out, I didn’t know anything about retail, but I knew everything about business and I could articulate it at all levels easily and enthusiastically.

She confided in me that she was sold on me and understood how I could see myself as a store manager at Gateway Computers – and she could too. 

But there was just one problem.

She was interviewing and hiring the sales manager role not the store manager role and I would have to talk to Andy, VP over the Eastern US, to discuss that position in detail. 

And this brings us back to the beginning of this letter.

Who is this kid?

Andy was shocked when we met.

His entire day had been with late 30-somethings up to 50-something year old seasoned professionals and here I was just a 20 year old kid. 

He explained to me how:

• Others had clear operational and retail store management experience.

• Others had responsibility over large teams and annual revenues in the $10 - $15 million range.

• Others had experience opening locations and brick and mortar sales strategies. 

He said he could not ignore the notes on my resume. He trusted his people and could see my potential. Andy even agreed I was the kind of talent they needed.

But…

He could not pass on others with long and successful careers in retail.  

He said very bluntly that he could not recommend me with virtually no retail experience.

But what he could do was hire me immediately in sales so I could learn retail and what mattered most - sales growth and customer experience.

"More importantly," he said, "if you prove yourself a great salesperson, I can promote you to Sales Manager. From there, when it makes sense, you'd be ready for Store Manager."

"Why would I do that?" I asked.

"If I become your best sales guy, wouldn't you keep me there? And if you can't hire me now for manager, how would promoting your top salesperson ever make sense, especially if you want a lot of sales?"

I was confused by his plan.

"It's easy," he said. "If you're my best salesperson, wouldn't it make sense for me to have you train 5, 10, 50, 100 people to do what you do? Who better to teach them than you? That makes you an obvious choice for Sales Manager. From there, you can work with the Store Manager on forecasts and leadership skills needed for that role."

Now his plan was making sense.

“I’m only willing to do this if you can assure me that I can be considered for sales manager as soon as I prove my sales capabilities”.

He laughed enthusiastically, saying I was a natural in sales and negotiations. As a show of confidence, he turned over my resume and wrote out our talking points - “great at sales, train others as Sales Manager, lead well, become Store Manager.”

"I'm the VP of the entire region. I'll keep an eye on you. If you do your part, I'll do mine - I promise," he said.

With a handshake, I committed to salesperson but with the full vision and intention of quickly growing into the Store Manager role.

That’s when I started to understand: Leadership doesn’t start with permission. It starts with ownership. You don’t wait for someone to give you the title. You act in service to the vision, the team, and the outcomes—consistently.

About Sales

Within four months of the store opening, I had been top sales performer three consecutive months. 

At this point, I was working alongside my Sales Manager regularly and he graciously showed me his sales reports and his spreadsheets. I was helping with data entry into the spreadsheet and strategizing on what we could do to increase sales and our closing ratio. 

By month five, I was working with my Store Manager a few times a month.

Turns out, Andy, the VP was in the background as promised and instructed my store manager to expose me to the P&L and to educate me on what he was discussing with Steve, his sales manager (which was my boss).

At the end of month six, with five consecutive months of leading store sales, I was promoted to Sales Manager and asked to open a new store in a new market where I would go on to train forty sales reps around the region and for the new store I opened.

About Sales Management 

In this new store, I walked in with a reputation and track record as well as highly valuable context on how these retail stores worked. 

Where everyone else was being hired into Gateway as a new experience, I was the seasoned “go-to” guy for how staging, training, planning day one, and navigating the point-of-sale system and more. 

My new challenge was figuring out how to lead, train and support a staff that was all older than me.  Some of them were in their late 20’s and early 30’s. 

My answer to that challenge was to make it 100% about them, not me. 

I was there to make them successful and to increase their likeliness of promotions and bigger commission checks.   I set expectations early that I was hands on and would demonstrate what works and coach them, on everything from understanding technology, guiding customers across the showroom, doing discovery on needs, upselling, bundling, making offers and closing deals. 

Establishing trust, cohesion, and expectation was critical for us to work well together.

For me to get where I wanted to go, I had to help them get where they wanted to go. That was the first time I realized that leadership isn’t about you—it’s about helping others grow in performance, build confidence, and rise to their potential.

A New Opportunity

Having already spent six months building up another store and about three months doing sales manager type activities at that location, I had an idea on a better way to drive sales.  It would leverage the best of the previous store and introduce a new idea that I believed would increase sales.

The home office would send us price sheets, packages that had configurations of computers, monitors, and printers etc to arrive at a selling price based on its component parts. 

This is how they ran promotions like the $999 Essentials Package. 

We would roll out new pricing and packages in the store and have shelf-talkers and signage at the various demo stations where people could see it all setup.  These stations included software, cameras, monitors, and various items. 

Salespeople got commission based on top-line revenue plus totaling up any incentive bonuses which we called ”spiffs” from anything that had individual bonuses.  

For example, selling Blues Clues kid software might give you an extra $12 per sell, whereas selling the new $300 digital camera might give you a $55 spiff.

While you couldn’t change the corporate provided pricing and packages, each store had what they called a “Manager’s Special”.

What’s So Special About the Manager’s Special?

This was where you could offer two or three packages that were unique to your store. 

This was the only way to let stores flex to the type of market they were in.

If you were in a small market, you might make the manager’s special be the absolute cheapest package as a way to move them off the more expensive price sheet and still close a sale – even if it was just $699 or whatever.

Because a manager’s special was informal, there was no template or branding. Typically the sales manager made a flyer quickly in power point or a word processor and it was available at the checkout area.

A Different Vision Entirely.

My big idea was to take these Manager’s Special and completely change the way it was created and used. Change their purpose from an after-thought to the leading sales strategy.

As a sales manager I needed to drive top-line revenue, have a high average ticket price, and strive to move a certain minimum volume monthly.  But what I really needed to do was make customers happy and my salespeople great at their job with as big of a check as possible.

This required some intention and specific means to pull it off.

So here is what I did…

Each time we got updated pricing I would work in a spreadsheet to methodically list out everything with a spiff and look at the price and value of what was being offered and reflect on which customers would care about those items.

This would lead me to an insight on how to assemble a single system as a solution package that had as many of these spiff items in it, but thematically be irresistible to a type of customer we had.    

An example of how I did this might have been something like this:

• 15 inch monitor (no spiff) —>19 inch monitor ($65 spiff)

• 400 MHZ Intel Processor (no spiff) —>400 MHZ AMD processor ($30 spiff)

• CD Rom (no spiff) —> DVD player and DVD burner ($10 spiff)

• Stock software (no spiff) —> Microsoft Suite ($100 spiff)

• No extra software (no spiff) —> Gaming bundle ($25 spiff)

• No peripherals (no spiff) —> Creative bundle bigger speakers, digital camera, printer ($150 spiff)

So this package might be $3999 and have $380 in spiffs plus the commission of the sale price.

Because I knew our customers from my own experience, I knew as a package it was great for parents needing a big computer for their first-year college kid, or for middle aged power users.   

My web design experience was an advantage because I would use Adobe Photoshop and Illustrator and make it look like it was a cohesive design with branding and a clear offer, not just a quick flyer like other sales managers did.

Because I saw this as a sales tool and my primary sales strategy, I displayed the Manager’s Special on every computer station not just the checkout area.

During weekly sales training, all Manager’s Special offerings were reviewed component by component. Salespeople were educated on the feature and functionality and the spiffs it created. The reps would quickly do the mental math on potential bonuses and get excited.

We did role playing on trial closes, overcoming price objections with our financing options and scenario-based role playing on how to be at a computer station that matched the customers stated need, lets say a cheap $999 essentials package but then pick up the Manager’s Special as a way to compare and discuss what was the “better” deal for the customer.  And this worked because it either helped move them up to the bigger system, or by price anchoring, made the $999 an easy yes. 

This approach to the Manager’s Special was innovative and impactful.

The result was twofold.

First, we closed more customers.

Meaning, they walked in and purchased vs other stores that would have lookers but not buyers. 

Second, we had highly productive sales reps with exceptional sales metrics. 

In a market where we were expected to do $2M in annual sales, we did $5M and we were the 3^rd most profitable store in the region

It wasn’t just sales. It was systems thinking. Strategy. Value creation. And seeing what others didn’t. That’s what leadership is too. You learn to work on the business, not just in it. 

Champions

My store manager was an amazingly humble and soft-spoken man named Mike Miller.  We connected well and he graciously made space for me in leadership calls and situations that were only for store managers.

About eight or nine months into the new store being open, it was clear that our sales were consistent not just a “grand opening” anomaly.

Mike invited me into the quarterly update call with corporate which included store managers from other areas, upper leadership and it included Andy, the VP that interviewed me at the career fair. At this point I had been employed about 15 or 16 months total.

The call eventually got past all the updates and typical business, and someone said they wanted to address sales performance in a specific region. 

They called Mike Miller out by name and asked him to describe his market for those on the call.  This included details like population, local industry, estimated daily store traffic etc. 

On all accounts we were the smallest by comparison to other markets. 

Next, they wanted to know how it was that our sales numbers were exceptional – what was our trick.

Mike was quick to answer.

“Our trick, is our sales manager, Justin McCullough, he runs an outstanding sales organization and has a unique sales strategy.” 

I couldn’t believe it. 

He didn’t take credit, he didn’t brush it off or minimize it, he lifted me up and put a spotlight on my work.  

“I have him in the room with me, Justin, go ahead and tell them how you do it”.

And with that, he turned it over to me and I was able to describe the metrics I monitored, my approach to training and most importantly my manager’s special strategy and how it worked for customers and for the sales reps. 

I was asked to send examples of my manager’s specials so they could review them. 

Two Things Happened.

First, Gateway leveraged the manager’s special formula I developed and other stores adopted the strategy.

Second, I was offered the Store Manager role for a suburb of New Orleans Louisiana.

From pizza kid to Store Manager of a multimillion dollar market in less than two years.

On the call with Andy, while he was offering me the role, he made a point to tell me I was the youngest, by a longshot to ever take on the store manager role and that he was proud to say it was an easy recommendation for him to make and everyone in senior leadership was on board based on my experience and accomplishments.  I had come a long way from being that pizza kid at the career fair to being a top performing market leader.

But Then…

I did not accept the role. In fact, I decided it was time to leave Gateway altogether.

During all this career advancement and training others, I was also still building websites for businesses at night. That moonlighting work was at an inflection point. I decided that building a web business was my path forward.

It was hard to tell Andy and Mike that I would be going in a different direction, but they wished me well. And if you look at my sales graph at the top, the revenue quickly dropped and shortly after I left they stopped building stores and even began closing smaller market stores and laying people off as they made dramatic changes in the executive team and their business strategy - so it worked out as a wise move on my part.

What has always stuck with me was the high level of integrity at Gateway with people who did what they said they would do.

They created conditions for leadership and growth regardless of title or age.  And they fostered respect and teamwork with an interest in innovation and growth. 

That was twenty years ago.

These experiences had lasting impressions on my leadership style and how I think about others making and impact and doing meaningful work.  

It informs my perspective on trusting others to rise to the occasion and making space for people to flourish and grow.

These experiences shaped the way I lead today. I learned that performance opens doors, but it’s leadership—real, daily, responsible leadership—that earns trust and creates lasting impact. That’s why I coach, mentor, and teach leaders not just how to get stuff done—but how to lead with clarity, conviction, and alignment. Because real impact starts with the leader.

This is very much what it means to walk The Path of a Leader.

#ThePathOfALeader
#GSD

Appreciate you,

Justin