The Executive Interview Series provides readers with exclusive insights from movers and shakers in the payments industry. The payments industry is under continuous transformation. This series offers diverse perspectives on everything from strategy to payments technology and the industry’s future.
In this interview between TSG’s Jon Lennon, Chief Revenue Officer, and Morgan Murphy, Jon shares key leadership principles and industry insights drawn from over 30 years in payments and financial services. His experience spans major companies and startups, emphasizing culture, adaptability, and strategic foresight in driving growth and innovation.
Bio: As Chief Revenue Officer of TSG, Jon drives the strategic direction and growth of marketing, sales, and client success, aligning teams to boost revenue and enhance customer experiences. With over 20 years in fintech and payments and more than 30 years in Fortune 500 leadership at companies including American Express, AT&T, Mastercard, Fiserv, Worldpay, and FIS—where he most recently served as GM, Global Head of Enterprise Payments—Jon brings deep expertise in payments, eCommerce, financial services, SaaS, risk, and M&A. He holds a BA from Union College and an MBA from NYU Stern, and outside of work he is an avid musician, golfer, and tennis player, as well as an active alumni leader and mentor within the entrepreneurial community.
Q. Morgan M.
You’ve led growth at some of the most iconic names in payments and financial services. What guiding principles have stayed consistent for you across such diverse organizations?
A. Jon L.
I’ve been fortunate to spend more than 30 years in this industry, working with incredible teams at American Express, AT&T, Mastercard, D&B, First Data, FIS, and Worldpay. Along the way, I’ve learned a lot from great leaders and experiences, and completing my MBA at NYU while working at American Express further shaped how I think about growth and leadership.
In retrospect, a few guiding principles have stayed consistent for me. First, culture is everything; building a team grounded in trust, accountability, innovation, and a sense of fun creates the foundation for success. Second, hire wisely and invest in your people; when your team thrives, your customers thrive, and the business thrives.
I also believe feedback is a gift, active listening to customers is non-negotiable, and hope is never a strategy, you need a plan and the courage to take calculated risks. I often ask myself, ‘What’s the upside?’ If there isn’t one, you’ve saved time and energy by moving on.
Finally, I remind people that your name is your brand, so align your actions with the reputation you want to build. As a leader, my success is measured by whether my team surpasses me. At the end of the day, treating everyone with dignity and respect is the constant that never changes.
Q. Morgan M.
As someone who’s led both startups and global teams, how do you adjust your leadership approach for each environment?
A. Jon L.
An adaptable leadership approach that has become part of my management philosophy is Situational Leadership by Ken Blanchard. During my 10 years at American Express, the company was an early adopter of this approach, requiring all people leaders globally to get recertified annually on Situational Leadership. The practice is you identify the Skill and Will of the individual for the task at hand through qualifying questions, then apply one of four leadership styles for each unique situation: Directive, Coaching, Collaborative, or Delegating. I’ve consistently found this approach to be beneficial to develop people, as well as collaborating with business groups, strategic partnerships, and clients for the best outcomes. Also, I’ve expanded it to help identify business opportunities faster and make better decisions.
Q. Morgan M.
You’ve mentored CEOs and founders across various stages of growth—what’s the one piece of advice you consistently share with leaders?
A. Jon L.
Lead by example and build trust. You need to hold yourself to the highest standards, hiring people with similar core values you can learn from, taking accountability, learning from mistakes, promoting consistent two-way communication with empathy and transparency, and being a lifelong learner.
Working for more than 20 years in the payments industry, I did not know and appreciate TSG’s full capabilities as a full-service, end-to-end boutique payments consulting firm until I was recruited to become CRO. This taught me the need to help reintroduce TSG capabilities to our prospective and existing clients. Key areas we service include: Advisory & Strategy, GTM & Marketing, M&A Support, Market Intelligence, Profitability Optimization, and Integration & Implementation.
Q. Morgan M.
In your experience, what separates organizations that achieve true cross-functional alignment from those that struggle with silos—especially when it comes to revenue growth?
A. Jon L.
Strong culture, leadership, transparency, fiduciary responsibility, communication, goal alignment, strategy, and clear roles and responsibilities are key attributes of cohesive companies. Each person leads through their own voice. Solutions are presented when identifying challenges, and people assume positive intent. Each organization represents themselves to our customers and prospects as “One Company”. Most importantly, each team member understands her/his role and contribution to the overall results. They need to feel appreciated and valued working as a team, and we have fun as a team.
Q. Morgan M.
What do you see as some of the most pressing challenges facing fintechs, ISVs, and payment companies in today’s hyper-competitive environment, and how can TSG help them navigate those hurdles?
A. Jon L.
With the speed of change combined with the forward thinking required to be competitive in the payments industry, many companies do not have the in-house expertise, experience and exposure (i.e. GTM vision, market insight, customer awareness, investment, strategy, development, staff-augmentation, integration, implementation, technology enablement, etc.) needed to be successful within their specific verticals. TSG can help navigate these hurdles as a trusted advisor and partner to address all these areas as needed for our clients.
Q. Morgan M.
Stablecoins settled over $10 trillion in transactions last year, yet they still represent a small fraction of the overall payments ecosystem. What do you see as the most promising practical use cases for stablecoins today, and what barriers must be overcome for them to become mainstream in everyday commerce and cross-border payments?
A. Jon L.
We’re still early in the adoption curve, but momentum is building, particularly in use cases like cross-border commerce, digital-native merchants, and high-risk segments where traditional rails underperform. The GENIUS Act has paved the way for stablecoins to become mainstream in the U.S.
Institutions need to prepare for selective integration now, while the infrastructure, regulation, and merchant readiness evolve—and prioritized investments to ensure it’s built the right way the first time. Additional barriers include time and expertise, which require a full understanding of the payment ecosystems, regulatory risks, value-added options, embedded payments and finance, investment and acquisition options, and determining how and where to incorporate blockchain technology (led by stablecoin) for the best return on investment.
Q. Morgan M.
With your extensive background in fintech and payments, what other trends do you believe will most impact the industry in the next few years?
A. Jon L.
One of the most impactful trends in fintech and payments is the race to Ubiquity, where consumers expect effortless and frictionless experiences. Cryptocurrency, stablecoin, and Gen AI are just getting started, and there is significant need for regulatory, technology and strategic expertise to ensure these are added to a company’s payment ecosystem with flexibility and security top of mind. In parallel, fintech, ISVs, and payment companies need to take the lead on Embedded Payments to Embedded Finance, to the end game of Ubiquity. Cybersecurity needs to be reprioritized as well for this next evolution of payments