Jon Lennon
Jon Lennon is Chief Revenue Officer at TSG, where he leads global revenue strategy and growth across the payments ecosystem. He brings more than 25 years of leadership experience across fintech, banking, SaaS, and financial services, having held senior roles at organizations including American Express, AT&T, Mastercard, Dun & Bradstreet, Fiserv, Worldpay, and FIS. Lennon specializes in scaling go-to-market organizations, building strategic partnerships, and driving sustainable revenue growth across complex enterprise environments.
The payments ecosystem is evolving rapidly as new technologies, shifting macro conditions, and changing customer expectations reshape how companies build and scale financial infrastructure.
Ahead of TRANSACT, Storm2’s Ross Byrne spoke with Jon Lennon, Chief Revenue Officer at TSG, about leadership, market trends, and where the greatest long-term value will be created in payments.
From the rise of embedded finance to the growing impact of AI on payments infrastructure, Lennon shares his perspective on how fintech leaders can prepare for the next phase of the market.
Leadership and Career Perspective
Your career spans global brands and high-growth environments. What leadership principles have consistently enabled you to drive revenue growth and organizational momentum?
Across large global organizations and high-growth environments, the constants are pretty simple: culture, clarity, and accountability.
I’ve seen that when teams are grounded in trust, respect, and shared goals, momentum follows. I also believe in hiring, empowering, and investing in great people. When your team thrives, your customers thrive, and growth becomes repeatable.
Feedback is a gift. Active listening to customers is non-negotiable. And “hope” is never a strategy; you need a plan, measured execution, and the courage to take calculated risks.
Be present and authentic in conversations and collaborations. Lastly, I always remind leaders: your name is your brand. If you build credibility internally and externally, revenue becomes a byproduct of consistency and outcomes.
Looking back, what early career experience most shaped how you lead in an industry that keeps reinventing itself, and what did it teach you?
One formative experience was being exposed early to structured leadership development while operating in fast-moving environments.
I’m a believer in Situational Leadership, the idea that you assess the “skill and will” for a given task and adjust your leadership style accordingly — directive, coaching, collaborative, or delegating.
It taught me that leadership isn’t one-size-fits-all, especially in payments where the industry constantly reinvents itself.
The lesson I still apply is this: build adaptable teams that can learn quickly, make decisions with incomplete information, and stay close to the customer.
How do you balance long-term strategic investments with the near-term realities of revenue execution in an evolving fintech ecosystem? What does that look like in practice?
I think of it as a portfolio: protect the core, scale what’s working, and invest in what’s next without confusing activity for progress.
In practice, that means aligning teams around a small set of measurable outcomes, maintaining a disciplined operating cadence, and prioritizing initiatives that improve speed-to-market while managing risk.
The payments ecosystem is increasingly defined by the intersection of technology, automation, AI, data, and consulting, but those are only valuable when they’re tied to customer outcomes and commercialization paths.
Market Shifts and Payments Trends
When you look 12–24 months ahead, what shift in payments or fintech is most underestimated right now, and how should leaders prepare for it?
The most underestimated shift is how quickly payments is moving from embedded payments to embedded finance, and ultimately toward ubiquity where the experience is effortless and frictionless.
Customers increasingly expect the “right” payment option to appear at the right moment.
Leaders should prepare by investing in:
- Flexible orchestration
- Strong risk and compliance foundations
- Partnerships that expand capabilities without slowing execution
At the same time, emerging rails, including digital assets where appropriate, and AI are forcing new expectations around speed, intelligence, and security.
How are current macro conditions changing what payments and fintech companies prioritize this year? Where do you see investment increasing?
Macro conditions tend to sharpen priorities.
When capital is more selective and scrutiny is higher, companies focus on durable revenue, clear differentiation, and solutions that reduce complexity for merchants and partners.
I see investment increasing in areas that directly protect and expand value:
- Compliance
- Cybersecurity
- Platform modernization
- Data and analytics
There is also selective investment in AI where it is measurable and defensible.
Fintech saw the boom-and-bust cycle (2020–21 funding surge, then a winter). The market is strong right now. Where do you see it going?
I expect continued strength for businesses that simplify payments infrastructure, enable new commerce models, and support merchants with better insights and risk controls.
At the same time, consolidation and specialization will happen in parallel.
Some firms will combine to gain scale, while others will specialize deeply in a vertical or capability.
The through-line is sustainable growth. Leaders who can commercialize innovation will win the next cycle.
AI in Payments
AI is touching every part of the payments value chain. Which area do you expect to see real, measurable impact first, and why?
The first measurable impact is happening behind the scenes, not at the surface level.
We’re seeing AI move beyond analytics and into autonomous decisioning inside payments infrastructure, optimizing routing, pricing, interchange, and performance across portfolios in real time.
Historically, AI in payments focused on point solutions like fraud detection. What’s changing now is that AI is becoming part of the operating system of payments, participating directly in how transactions are executed, not just analyzed.
That shift has immediate economic impact: lower costs, higher authorization rates, and more resilient payment performance at scale.
What is one example of AI creating a genuinely new opportunity in payments, not just efficiency gains?
A genuine new opportunity is the rise of intelligent, adaptive payment experiences that can be monetized.
For example, an AI layer can personalize the checkout and post-purchase journey by optimizing:
- Payment method presentation
- Routing
- Retries
- Fraud friction
- Proactive dispute prevention
All based on the specific customer and transaction context.
That’s not just efficiency. It becomes a measurable revenue lever — higher conversion, higher authorization rates, and lower disputes — which can be packaged as a premium product.
As commerce and payments move toward ubiquity, these intelligence layers become a new category: payments performance as a product.
Strategy: Build, Buy, or Partner?
With consolidation and specialization happening simultaneously across fintech, how should leaders evaluate when to build, partner, or acquire new capabilities?
A practical framework is differentiation, speed, and integration risk.
If a capability is truly core to your differentiation and you can build it faster than the market moves, build.
If time-to-market matters and there are proven providers, partner — especially when the capability requires specialized compliance, data, or infrastructure.
Acquire when the capability is strategic, the economics make sense, and you’re confident you can integrate without breaking focus.
The right answer usually depends on whether you’re buying features or buying outcomes.
In payments, the hidden cost is complexity. Whichever path you choose, ensure it simplifies the customer experience and accelerates commercialization.
TRANSACT and Industry Engagement
TSG is a Gold sponsor at TRANSACT and has been a long-time partner to ETA. What are the top themes or conversations you are most focused on bringing to the show?
Top themes include modernizing payments infrastructure, how companies win in a world moving from embedded payments to embedded finance, and how AI and data are reshaping the ecosystem.
It’s also a great environment to talk about partnerships, and we’re excited to discuss how we are working with Payforge and Adyen.
We’re leaning into meaningful discussions that help leaders reduce complexity and accelerate speed-to-market.
If someone is attending TRANSACT with one goal, what should it be, and what should they do before they arrive to maximize ROI from the event?
Have one clear goal: leave with a short list of high-conviction relationships and next steps, not just business cards.
Before arriving, identify the two or three capabilities you need most — distribution partners, infrastructure, risk, vertical expertise — and pre-book meetings around those.
Come prepared with a tight narrative: what you do, where you win, and what you’re looking to partner on.
TRANSACT moves fast, so your ROI comes from focus and preparation, turning conversations into follow-ups while the context is fresh.
The Future of Value Creation in Payments
From a revenue and growth perspective, where do you see the greatest long-term value being created in payments: infrastructure providers, software platforms, or companies that own distribution?
Long-term value tends to accrue to whoever owns distribution and the customer relationship, but it’s strongest when paired with differentiated software and reliable infrastructure.
Software platforms can create sticky workflows and monetize across services, but only if they can reach customers efficiently.
The best model is often a hybrid: companies that own distribution and software experiences, partnered with infrastructure that gives them flexibility, speed-to-market, and resilience.
In payments, the winners don’t just process transactions — they orchestrate ecosystems that make commerce easier, safer, and more profitable.
