As a part of our interview series called “Women Of The C-Suite,” we had the pleasure of interviewing Stacey Wiles.
Stacey Wiles is the Vice President of Operations at Delta Payment Solutions where she is responsible for managing operational infrastructure and brand engagement. Stacey is experienced in identifying workflows and building tech stacks that create the shortest distance from prospect to revenue. With over 20 years in the industry, she has shared her expertise with teams across numerous corporations helping companies overcome challenges often faced within the credit card processing industry.
Thank you so much for joining us in this interview series! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?
I actually started my payments career as a merchant, not a merchant services provider. The payments industry, which I didn’t even know existed, was quite literally thrown in my lap one day.
Back on the late ‘90’s I worked for a large women’s clothing retailer that had brick & mortar locations and a national catalogue — a.k.a the original omni-channel. This was a time when Google was still a baby (only true-techies knew what it was), there were no smart phones and MySpace hadn’t even hit the scene, let alone Facebook.
The CFO put a stack of card processing statements in front of me and asked me to determine why our business was paying more fees during heavy return months over high sales months. I was very young at the time and had no idea what a card processing statement was, let alone how fees worked. I remember my reaction to finding out that our company had to pay to accept card payments was a comment along the lines of, “We have to pay to take credit cards? That’s stupid.”
Little did I know, that researching those “stupid” fees for my CFO would open the door to a career in an industry, that up to that point, I knew nothing about. I realized the fee research project was my opportunity to become a subject matter expert on a topic even my CFO was not 100% familiar with. I was young, newly married, had an infant son and worked fulltime. Online education wasn’t a thing yet and I had no real options to pursue higher education at the time. I saw this as an opportunity to gain valuable working knowledge — which was a huge motivator for me.
So, I set out to learn all the things that go into card payment processing — and in the late ‘90’s “all the things” was an incredibly short list in comparison to today.
Using my new-found knowledge and being offered a compelling job opportunity with a payment processor who had been part of my research process, I made the jump from being in merchant sales operations to being over regional sales operations for a payment processor. A few years later I crossed over from operations to sales and it was during my time as an individual contributor I really fell in love with the industry. I learned early on that those who understood and could translate the technical side of a sales proposal would typically be the ones to win the deal — even if it wasn’t the cheapest deal on the table.
Once I won my first deal, there was no turning back. Sales is addicting, especially if you are fortunate enough to work for a company that leads with solutions you can get behind. Twenty+ years later, here I am.
Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?
I wouldn’t categorize this mistake as funny per se, but a HUGE lesson was learned. The moment was so burned into my brain, I can tell you 19 years later what I was wearing and where I was sitting when everything started to unravel.
In the early part of my payments career, I was a Sales Director that specialized in retail and e-commerce merchant services. There was a very large women’s undergarment company based out of L.A. that I had won and we were in the throughs of implementation planning. At the time the merchant had over 200 locations nationwide (with 3–6 cash wraps in each) and operated on a POS that was integrated to the payment processor I worked for. We had all the right people on the planning calls, we had put together a conversion plan with the merchant’s CTO and POS account manager, I had our technical solutions account manager on board, the whole-9.
After weeks of negotiations and planning, we were just days away from converting store locations and I get a call from the CTO that final transaction testing was failing.
I get everyone on the horn to troubleshoot and an escalated tech person from the POS vendor is looped in. Turns out…the POS version the merchant was running was not in fact integrated to the payment processor.
The merchant was using a hybrid version and the acronym that both my team and the merchant’s team had been using had been interpreted wrong. Through a series of fire-drill tech calls and late-night repricing approvals, we were able to resolve the issue.
It was one of the most stressful situations I had encountered up to that point in my career. I had no idea how I was going to explain to my boss that I lost a top-tier, key account because of a misinterpreted acronym. Not to mention we had a custom SLA (Service Level Agreement) with the merchant and ‘lawsuit’ was a word that had been tossed around during our plight to resolve the issue.
I never sold a deal again without having fully defined terms, acronyms and versions of hardware and/or software that would need to be converted. This lesson transcends both the Sales and Operations roles I have held.
None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?
I have been fortunate and have had outstanding bosses and mentors throughout my early career (thank you Vito Kowalchuk, Mark Little and Greg Schaub). The person who started it all for me though was Karl Asplund. Karl was Western Region Sales Manager for Paymentech (pre-Chase) who recruited me to be his Operations Director from the retailer I mentioned at the beginning of this interview. Karl was a Maverick and whether you liked his approach or not, his sales numbers and his near cult-like devoted employees spoke for the type of manager he was.
Even though I was brand new to payments, he trusted that I would figure out the operations side of his sales organization. My job was to figure out how to make it easier for the team to close and convert deals. He wanted me to learn everything needed to do that — from industry knowledge to application submission process — and bring it all back to the team. The end result was a sales machine that killed sales goals and produced a very tight team (many of us are still close to this day). That trust and opportunity that he gave me became the foundation of what eventually became a 20-year career and growing!
In my work, I often talk about how to release and relieve stress. As a busy leader, what do you do to prepare your mind and body before a stressful or high stakes meeting, talk, or decision? Can you share a story or some examples?
I find leveraging both forward and reverse planning strategies is key to keeping stress manageable for high stakes events. Proper planning provides the time needed to adequately prepare for a meeting (researching the topic, meeting attendees and goals of meeting) or successfully launch a product (scenario testing and cross function training) for examples.
Planning also allows you to schedule down-time in between the day-to-day stresses of running a business and a household. It is important to take time to work out, go for a walk, spend time with your spouse and kids — whatever needed to detach for the stress of the moment.
As you know, the United States is currently facing a very important self-reckoning about race, diversity, equality and inclusion. This may be obvious to you, but it will be helpful to spell this out. Can you articulate to our readers a few reasons why it is so important for a business or organization to have a diverse executive team?
It is important for businesses to hire the most qualified candidate for the job. This means qualifications should expand past required education and task specific experience to also include personality type, relevant leadership experience (in and outside work environment) and emotional maturity.
When taking these factors into consideration, it helps identify candidates that could bring unique and valuable perspectives to a leadership team. Leadership teams with diverse perspectives present new ways of thinking, can challenge status quo and provide thought leadership to grow the company.
As a business leader, can you please share a few steps we must take to truly create an inclusive, representative, and equitable society? Kindly share a story or example for each.
I think leading by example is an important first step. Provided the example is a good one that promotes free thinking, encourages thought leadership at the individual level and doesn’t encourage exclusion of any kind. Be a leader that builds trust through action, check your ego at the door and live your life inside and outside of work in a manner that can influence positive change.
Ok, thank you for that. Let’s now jump to the primary focus of our interview. Most of our readers — in fact, most people — think they have a pretty good idea of what a CEO or executive does. But in just a few words can you explain what an executive does that is different from the responsibilities of the other leaders?
Executives have a deeper responsibility to the organization than other leaders as they set the direction, tone, pace and culture of the company. Good executives understand their industry, where their business sits within the competitive landscape and how internal departments should work together to achieve goals. While the leadership team acts upon the goals and initiatives set forth by the executive team — the executive team is responsible for making the decisions that drive the company. This includes things like maintaining commercial relationships, seeking strategic partners, choosing which products to launch (or close), selecting people systems and deciding what the leadership team is made of.
What are the “myths” that you would like to dispel about being a CEO or executive. Can you explain what you mean?
I think a myth that should be dispelled is that a CEO or executive acts alone and can call any shot they want. This is not the case. CEOs and executives have owners they answer to (whether in form of a Board, Stockholders or other). Being an effective executive means you’ve created a team that understands your vision and can successfully execute it allowing you to achieve the goals you told the owners you were going to achieve. Executives have a lot riding on the decisions they make and the teams they build.
In your opinion, what are the biggest challenges faced by women executives that aren’t typically faced by their male counterparts?
It’s not the biggest challenge women executives have to face, but a challenge none the less, is dealing with the cognitive biases that still exist when it comes to how a woman’s professional, qualified opinion is received vs. how a man’s opinion is responded to. And I’m referring cognitive bias from both women and men. In many cases, people don’t even realize they have a bias — so the more awareness brought to the topic the better.
What is the most striking difference between your actual job and how you thought the job would be?
I’ve held similar positions and have ran companies in the past, so from a job expectation perspective, there aren’t any striking differences. What is unique is the challenge of evangelizing a new revenue model to an industry with established money mechanics. I’ve been challenged to develop selling and operating approaches that are fundamentally different, and it’s allowed me to have new failure and success experiences to learn from.
Do you think everyone is cut out to be an executive? In your opinion, which specific traits increase the likelihood that a person will be a successful executive and what type of person should avoid aspiring to be an executive? Can you explain what you mean?
No — not everyone is cut out to be an executive. Executives should be able to conceive and design strategy, leverage analytics and insight to formulate an execution pathway and be able to effectively communicate their views and decisions. For those aspiring to climb the corporate ladder, it is important to understand how empathy and people skills play a role in traits specific to successful executive leaders.I think many times people assume a natural career path is to move into management if you’ve done a job well enough for a long enough period time — this is not the case. Just because you’ve been great as an individual contributor does not mean you will make a good manager. If you are genuinely interested in moving up, take courses that help you hone-in the soft skills.
What advice would you give to other women leaders to help their team to thrive?
My advice is for both men and women looking to lead teams in the payments space. This industry is fast paced and highly competitive. It is critically important that you are an industry knowledge advocate for your team. Strive to create a team of acquiring experts that are constant students of card industry trends who understand how their core services stack up to competitor offerings.
Equally important as a team who understands core services, how to sell them and who to sell them to, is a team that understands what they don’t sell. Teaching your team how to say “we are not a good fit for your company” and walking away from unqualified deals is just as valuable as teaching them how to effectively nail a core services pitch and develop a compelling proposal that closes the deal. Ignoring that fact and allowing your team to work the wrong deals will end poorly for all involved and eventually effect moral as well as sales figures.
How have you used your success to make the world a better place?
I hope I’ve brought some good into the world! In addition to being in positions to help people achieve their highest earning potential, I have tried to be an advocate for my employees to help them develop transferable skills and confidence to pursue their professional interests. I believe this is a positive way to manage and results in good things for them and their families. I take the trust of my staff and the responsibility of doing my best to provide them a secure job with growth potential seriously. I’d like to think that is one way I’ve been able to use my success to bring good into people’s lives.
What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)
1) Use a coaching approach to deliver constructive criticism and suggestions for improvement. There is a lot to know in the payments space and no one person is going to know everything. Using a coaching approach will raise up those that want to learn and do better while also weeding out those that are not motivated or right for the job.
2) Know the difference between a real problem vs. a perceived problem and how to resolve both. People by nature tend to take the path of least resistance and don’t ask probing questions as part of conflict resolution. Lead through objective decision making. Teach your team to do same. Having a staff that understands how to resolve a problem using an objective decision-making process will help maintain a healthy working environment.
3) Shut up and listen. To this day, when I get on a sales call and the salesperson launches into the “about the company and about me” monologue instead of offering customer introductions first, I cringe. If you have not established audience, their positions and background as it pertains to the meeting topic before you start rattling off your payments experience diatribe, you are potentially creating obstacles for yourself. Teach your staff how to listen, properly frame meetings and respect that the customer wants you to listen to them.
Also, newsflash to all who tote it, stating you have “20+ years-experience in the payments industry” is meaningless if you still manage like its 2008 and think the sales process of years ago is even remotely relevant today. (rant over)
4) Learn how to say “no”. Learning how to say “no” is one of the most important skill sets I have ever learned — and it is learned. There is more than one way to say “no” and delivery matters. Teach your staff how to properly qualify what to spend time on and how to professionally walk away from deals that don’t make sense. This skill set helps them effectively manage pipelines and grow as professionals.
5) Know when to be methodical and when to prioritize. When in doubt, be methodical. Payment acquiring is a sector of the finance industry where; businesses close overnight, banks stop remitting funds, pipelines fallout, M&A happens almost daily, new products are introduced constantly, and the industry is brimming with Mavericks making it challenging at times to know where to point your roadmap. I have learned the best way to run a productive payments business that exceeds sales goals is to be focused, not try to be all things to all customers and not get distracted by the noise.
There is always going to be a ‘new-best-unicorn-game changing” show in town — don’t run out and buy tickets. Waiting for the streaming version is usually the right thing to do.
You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.
A movement I could get behind would be emphasizing the need for effective listening in our day to day lives. Effective listening is a skill developed over time and it is not being taught or encouraged enough in many facets of life. My husband and I work full time and manage a family of 6 with 4 kids ranging from elementary school to college. To manage our home (and stay sane) we use every opportunity possible to engage with our kids in a way that can be an example of how to “Listen with intent to understand, not the intent to reply.” — Stephen Covey
We listen to them fully, ask clarifying questions about the topic (or argument) they are presenting and by actually understanding the goals and motives behind the words, we are able to parent through our responses while also teaching an effective listening lesson.
The same practice of listening to understand is relevant professionally as well. Whether in an executive meeting or on a sales call, all too often people are ready to jump into their prepared speech or pitch without framing up the meeting, asking clarifying questions or having a strong understanding of what everyone’s goals are. This practice can create a frustrating and unproductive engagement which can negatively impact professional relationships. How much more productive would we be if we made it a point to listen to understand?
Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?
Gwen Stefani’s 2004 hit “What You Waiting For?” became my motivational theme song and had several “life quote” lyrics as I worked to set aside fear of the unknown and open my first company in 2005.
In the early 2000’s, I had reached a turning point in my payments career. After several years of technical solution selling, I needed to take a next step — unfortunately, there was no growth potential at the company I was at.
The internet was evolving, APIs were becoming more readily available and acquiring operating models were expanding. An opportunity to create a payments platform that provided niche card processing services to the mortgage lending industry presented itself, and although I had never owned a business before, I went for it and started my first company.
I still listen to the song today when I’m mulling over how to design a product, work out the operations and selling approaches! It reminds me of my failures and successes to date and while I’ve had some epic fails, I have also achieved more than I ever thought possible.
We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them
There are a number of business leaders and influencers it would be super to meet in person but having lunch with Gwen Stefani would be epic. Aside from what she has accomplished musically, she is a businesswoman and a Mom who has overcome personal and professional obstacles to remain at the top of her game. If anything, I would want to thank her for putting her own fears down on paper and being an encouraging voice in my head during a time of growth in my life.
