My story starts with my grandfather, Papo. He came to the United States from Cuba and lived the American Dream. He worked as a dishwasher, cab driver, valet, dock worker, and milkman to get established.
The fintech industry is rapidly evolving, blending technology and finance in innovative ways. This evolution demands leaders who are not only tech-savvy but also adept at navigating the unique challenges of the financial sector. Effective leadership in this dynamic environment is crucial for success. What does it take to excel as a C-Level leader in a fintech company? What are the skills, mindsets, and strategies required to lead a fintech organization to new heights? As part of this series, we had the pleasure of interviewing Joseph Elias Phillips.
Joseph Elias Phillips is the Co-Founder and Co-CEO of Payabli. Payabli was built to be AI-native. Their team launched the Payabli MCP server and AMIGO, the AI product. They think about AI agents in three categories: agents that their ISV partners build on top of Payabli, agents they pre-build for them, and internal agents that make their own operations faster.
Thank you so much for joining us in this interview series! I know that you are a very busy person. Our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?
My story starts with my grandfather, Papo. He came to the United States from Cuba and lived the American Dream. He worked as a dishwasher, cab driver, valet, dock worker, and milkman to get established.
As a milkman, he spotted an opportunity. He started selling jewelry on the side to the homemakers on his milk route. That side hustle grew into Roberto Martinez Inc., a wholesale jewelry business specializing in Latin and religious jewelry. I grew up in that business in Downtown LA, and the entrepreneurial bug bit me early.
I was always the kid with a side hustle. I sold X-Men and baseball cards, candy, and lemonade. I even ran a landscaping business for beachfront properties that I called Sandscape.
At Clark University in Worcester, Massachusetts, I joined the first class of the school’s new entrepreneurship program. George Gendron, the Editor in Chief of Inc. Magazine, founded it. While at Clark, I sold jewelry to the local community. I also started a rap battle series every Thursday night that became a campus favorite.
After graduation, I knew I wanted to start a business. I also knew the best way to start something was to learn from other entrepreneurs first. I joined SeamlessWeb, one of the first online food ordering platforms, as an entry-level sales consultant.
Seamless gave me the chance to lead its national expansion. For several years, I traveled from city to city launching new markets. I lived in eight different cities, building the team and restaurant network in each one.
That journey brought me to Miami. In my second week there, I met Will Corbera at a salsa club in Brickell. We became fast friends and bonded over entrepreneurship. Neither of us knew we’d one day build a company together.
I later moved back to LA to earn my MBA at the USC Marshall School of Business. Through my relationship with the Founder of Seamless, I connected with the founders of ServiceTitan. One week after graduating, I started as their first Head of Sales.
ServiceTitan was an MBA in itself. I had a front-row seat to building a decacorn. About a year in, we started running into issues with our payment processor. I introduced Will to our Head of Growth, who was leading the effort to define our payments strategy. Will went on to help architect what is today ServiceTitan Payments.
ServiceTitan Payments became a massive success. It created a better customer experience and unlocked hundreds of millions of dollars in new revenue. That experience inspired Will and me to build Payabli. We wanted to help other software companies run the same playbook, with modern payments infrastructure purpose-built for platforms to embed and monetize payments.
Today, Payabli powers payments for vertical SaaS platforms across property management, HOA, home services, legal, construction, and government. We’re backed by partners like Visa, Fiserv, Amex Ventures, and QED Investors.
It has been said that our mistakes can be our greatest teachers. 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?
About three months after Will and I started Payabli, we signed our first software partner. We were thrilled. We thought we were on our way to making it big.
It took about six weeks to get the partner live. As luck would have it, their first merchants launched the same week I took my wife to Mexico City for her birthday. The first few days were incredible. We ate our way through the city and visited the museums and cultural treasures it’s famous for.
Then Wednesday came, and the partner started emailing me that something was wrong. As the week unfolded, we found the problem. The processor’s embedded JavaScript payment component had a bug.
A customer was paying their utility bill by ACH from their bank account. The widget kept timing out, so they kept clicking “Process Payment.” Their bank account was debited about 50 times, and they ended up overdrawn by more than $5,000.
The issue finally landed on my desk. I got on a call with the customer’s very upset husband, who demanded answers. We were petrified. We thought we were going to lose our very first partnership.
I spent that entire Friday in our hotel room in Cabo San Lucas untangling the mess while my wife spent the day by the pool alone, and she was not thrilled about it!
We got through it, and today we look back on that week fondly. It would have been easy to give up and admit defeat. Instead, we sacrificed, owned the problem, and earned back that partner’s trust.
Six years later, that partner is still with us. It’s been a lucrative partnership, and more importantly, a relationship we cherish to this day.
The lesson stuck with me: in payments, the little things count. One timeout and one missing safeguard against duplicate payments turned into a real family’s financial headache. That week shaped how we build. It’s also why we run to the fire when something breaks, no matter where we are.
And yes, I still owe my wife a do-over birthday trip.
Are you working on any exciting new projects now? How do you think that will help people?
We’re building Payabli to be AI-native. Our team launched the Payabli MCP server and AMIGO, our AI product. We think about AI agents in three categories: agents our ISV partners build on top of Payabli, agents we pre-build for them, and internal agents that make our own operations faster.
This matters because our partners serve small businesses: the plumber, the HOA manager, the law firm. When software companies can launch payments and automate the busywork around them, those business owners get paid faster and spend less time on admin. That’s how we power the entrepreneurial economy.
We also see a massive opportunity in agentic accounts payable, and we’re investing heavily there. Traditional bill pay runs on legacy technology. It depends heavily on people doing tedious, time-consuming work, which creates friction for both customers and vendors.
Our Agentic Vendor Enrichment and Vendor Enablement products change that. Our agents identify how each vendor wants to get paid, then pay those bills autonomously. They can log into a vendor’s payment page or portal and complete the payment. They can even call the vendor directly and walk them through accepting a virtual card or another digital payment method.
The result: businesses pay their bills faster, vendors get paid with less hassle, work that used to take hours now happens in minutes, and platforms can monetize the money movement.
Thank you for that. Let’s now shift to the central focus of our discussion. The fintech industry is known for its fast-paced and ever-evolving nature. How do you lead your team through periods of significant change or disruption? What strategies do you use to maintain team morale and productivity during such times?
It all starts with a strong sense of purpose. We call it our “Why” statement: to empower the entrepreneurial economy by making every software company a payments company.
Our five core values complement that purpose. They’re our operating system. They reinforce the behaviors and character we want every team member to embody.
Our strategy and priorities may shift from month to month, or even day to day. The foundation stays the same: why we do what we do, and how we do it. That consistency has been our biggest advantage in navigating a dynamic industry.
The other piece is modeling the behavior we want to see. When Will and I raised our Series B, we saw AI becoming a bigger part of everyday life and business. We wanted to be on offense, not defense.
So we made it a priority. We hired a Head of AI to serve as the internal steward of this new technology and strategy. Will and I also dove deep into the tools ourselves.
We use every conversation with our team as a chance to share what we’re doing with AI and why we’re excited about it. We answer questions openly. We also hosted hackathons at our two most recent offsites. Those hackathons helped spread the technology across the entire organization, not just engineering.
When leaders show up with curiosity instead of fear, the team follows. Change stops feeling like disruption and starts feeling like opportunity.
How do you come up with goals for your area of responsibility within the organization?
This is a work in progress, and it’s something that fascinates me. We’ve always done a strong job of setting goals. Where we’ve had room to grow is reinforcing those goals and managing the business against them day to day.
To close that gap, we recently brought in an amazing VP of People. She’s helping us operate the business more consistently, with OKRs as the central mechanism for hitting our goals.
Our process starts with setting audacious company-level OKRs. From there, we meet with our leaders and work through how those OKRs cascade down to each department and the people on their teams. We usually do this in Q4, heading into Q1.
Our team understands what our OKRs are. Now we’re focused on weaving them into the regular operating rhythm of the business.
We’re also evaluating EOS, the Entrepreneurial Operating System. Many entrepreneurs have recommended it to us. We’ve already adopted a few pieces, like the Level 10 meeting, and they’ve helped. This is an area where we’re still improving.
Thematically, our goals fall into four buckets:
Volume growth. Gross managed volume, or GMV, is the north star metric for our business. We set an audacious target for the volume we want to activate. When we hit it, revenue follows.
Security and reliability. We call this OKR “Protect Fort Knox.” It’s all about making Payabli the most secure and reliable platform in the market.
Operational efficiency. Last year, our goal was to “operate like an F1 pit crew.” Sales, product, operations, customer success, and engineering overlap constantly. Running like a well-oiled machine is critical.
Culture. Our goal is to build the happiest team in fintech. We care deeply about our team members’ well-being. We want Payabli to be a canvas for each person to do their best work and have a formative experience in their career and life. That’s why we call out a specific cultural OKR.
How do you manage reporting to your board?
We’ve been very fortunate. Our investors are trusted partners.
Will and I bootstrapped Payabli for two years. We didn’t raise capital until we had grown and achieved product-market fit. At that point, we started seeing larger and larger opportunities.
Bigger prospects were excited about our technology. Even so, they wanted a more established player as their payment infrastructure. We knew a strong balance sheet and institutional credibility would help us win those deals. That’s what led us to raise capital.
Because we never needed outside capital to survive, we took our time. We looked for investors we had strong rapport with. They knew our business well and understood our business model and long-term strategy. We trusted them to stand with us in good times and bad. As a result, we’ve built a very strong board.
Our board members also sit on several other boards together. That gives them great chemistry with each other, and it shows in every meeting.
Our rhythm is simple. We email a monthly update on the previous month’s performance. We hold a board meeting every quarter. In between, we stay in close contact. We reach out for guidance, help with recruiting, or an intro to a deal. We never let the formal meeting schedule get in the way of working together, and our board is always responsive.
We send our board deck 72 hours before each meeting. That way, we handle questions up front and keep the meeting itself focused. We use part of the meeting to share exciting new developments, connect personally, and give newer senior leaders a chance to present and build relationships with the board. We spend most of the time on strategic conversations about what will move the needle for the business. That approach has worked really well for us.
Above all, we’re an open book with our board. We never shy away from hard news or sugarcoat it. Being vulnerable with our board has built deep trust. They know we’ll never hide or downplay what matters in the business.
That’s my biggest piece of advice for other founders. If you have a board you trust, keep them fully informed, because they can help you. A board relationship is a long-term partnership. Break that trust, and the relationship stops being productive.
Investors understand that businesses are complex and go through many chapters. The earlier you build rapport and trust, the stronger your board will be for the long haul.
Do you have any specific strategies that you use to manage your teams?
Across the organization, we’re building a leveling framework centered on ownership. Rather than a long list of competencies, we treat ownership as the defining trait at Payabli. Every other skill rolls up into it. Growth means owning bigger problems, not collecting bigger titles.
Will and I divide responsibilities between us. Will leads Product and Engineering. I lead the commercial and operational sides of the business. We each step into the other’s functions when it’s needed.
On my side, the number one thing I do is hire resourceful people. I look for people who are comfortable operating in ambiguity and in fast-changing environments. I give them clear direction on the outcomes we want, then let them fly. I provide as much support as they want, and I step in if I see them struggling.
I’ve also leaned heavily into AI to drive accountability and visibility across the organization. I have agents that track all of our deliverables and keep team members accountable to their commitments. I’m also obsessed with customer experience. I have agents that monitor our Slack channels to make sure we follow up with partners quickly and helpfully.
Will brings two mantras to how he leads.
First, the co-CEO model. Our product organization runs on three Ps: Pay, Payout, and Pay Ops. Each business line has a product leader and an engineering leader who act as co-CEOs. They’re expected to run that business together.
Second, “inspire and require.”
Inspire means motivating the team, explaining why the work matters, and leading from the front.
Require means going beyond motivation. It means verifying the work gets done right and holding people accountable to their commitments.
Finally, we work hard to stay connected to the whole team. Our door is always open. We take anonymous questions at our weekly all-hands. Any team member can book time with either of us. Will and I also schedule check-ins with people across the organization at random. We use them as a pulse check on what’s working, what’s not, and how we can improve.
Fintech companies often disrupt traditional financial services by focusing heavily on customer experience. Can you describe a customer-centric initiative you spearheaded at your company and the impact it had on your business?
A few years ago, I attended one of our partners’ user conferences. Jesse Cole of the Savannah Bananas gave the keynote. His talk inspired me. It also put words to something we’d been thinking about for our own customers: creating memorable, “you wouldn’t believe it” experiences.
Today, we run a full Savannah Bananas initiative at Payabli. We look for opportunities to delight our customers in uncommon ways. We still have room to improve, but generally we do this well. It’s one of the most rewarding parts of building Payabli.
We look for moments of customer friction, or chances to put our “Little Things Count” value into practice. A small, thoughtful gesture can have an outsized impact.
PCI compliance is a great example. Every merchant has to complete a tedious annual certification, including a complicated self-assessment questionnaire. Most processors offer little or no support. Many merchants give up and get charged a non-compliance fee. The industry widely sees that fee as a junk fee.
Early on, we decided we didn’t want to earn money from junk fees. We wanted to give merchants a better experience instead. So we oversee the PCI compliance process for all of our partners’ merchants, and we turned it into a game.
Our Risk Operations team calls each merchant with a challenge. They say: “We know you’re busy, and your annual PCI assessment is due. Skipping it means financial penalties. The good news is that it’s easy. Give us five minutes, and we’ll finish the questionnaire together. If the call runs longer than five minutes, we’ll send you a $10 Starbucks gift card.”
You’d be surprised how well it works. As soon as our CSMs start the five-minute timer, merchants lean in and fly through the questions. A tedious chore becomes a fun break in their day.
That’s one Savannah Bananas moment, and we create them constantly. We give our team members the authority to make these calls themselves. When a partner hits a big milestone, our team celebrates it with a care package or memento. When a partner goes through a hard time, like an illness or loss, our team shows up for them too. Those gestures have made a real difference in our relationships.
Decision-making in fintech involves assessing various risks, including technological, financial, and security risks. How do you approach risk assessment in your role, and can you give an example of a tough decision you made that involved a significant risk?
At Payabli, security and reliability are our top priority. Innovation is a fast follow. We spend a lot of time thinking about how to prevent unreliable or insecure experiences on our platform.
First, we resource it properly. We’ve hired a sophisticated risk team, and we spare no expense on the technology and tools they need.
Reliability has been an ongoing journey. We now operate at a scale where small issues can compound and create friction for customers. We’ve become much more aware of the second- and third-order consequences of our decisions, especially in product and engineering.
Recently, we revamped our software development life cycle and our release checklist. The process is now much more formal and requires manager sign-off. Before anything ships, a manager confirms we’ve done the right testing and have the right observability in place. That way, releases go smoothly and don’t cause downstream issues elsewhere on the platform.
Our platform is robust, and it’s also interconnected. We’ve seen how one change can cause unintended issues somewhere else. So we’ve become far more meticulous.
One of our biggest decisions was to build our own risk engineering team. This dedicated unit builds our risk, compliance, and underwriting tools.
Instead of relying on third-party vendors, we built everything in-house, including our own proprietary models. That was a significant investment and a real bet. We believe it will pay off. Our models are trained on our verticals and our own payment activity, which gives us an edge no off-the-shelf tool can match.
This investment helps more than our existing partners. We’re also packaging these tools as standalone products. Partners can get them bundled with our core offering. Other financial institutions, fintechs, and payments companies can also license them to tap into our best-in-class technology.
Based on your experience and success, what are the “5 Things You Need To Be A Highly Effective C-Level Leader Of A Fintech Company?” How have these 5 things impacted your work or your career? Please share a story or an example for each.
1. Run to the fire.
I always say it’s easy to be a good partner when things are going well. Your true partnership reveals itself when things go wrong. I take great pride in doing what’s right, not what’s expedient. Our partners will tell you that when something doesn’t go to plan, we’re the first to take ownership and course correct quickly.
One strategic partner wanted to go live on a tight timeline with our new device offering. Our product team underestimated how long certification with the processor and card networks would take, and that put our delivery date at risk. We escalated through every channel we had, including our investors, to get it unblocked.
We also kept our partner closely informed. We didn’t sugarcoat the potential delays, and we assured them we were doing everything in our power to hit the deadline. In the end, we set a record for the fastest hardware certification and got our partner live right on time.
2. Be a truth seeker.
Fintech runs on trust, and trust starts inside the company. I ask our team to bring problems forward with an honest assessment, even when it’s uncomfortable.
The bigger you grow, the further you get from the front lines. That’s why it’s important to zoom in regularly. You need to fully understand the problems your team and customers face and take a sober view of where you can improve.
3. Sweat the little things.
One misconfigured field can stop a merchant from getting paid. “Little Things Count” is one of our core values because in payments, small details carry big consequences. I talk about it with our team constantly and reinforce it every chance I get.
4. Build a true partnership with your co-founder.
Will and I are fortunate to be best friends as well as co-founders and Co-CEOs. The model doesn’t work for everyone. For us, 1 + 1 = 3. We complement each other in meaningful ways.
That only works with deep trust and healthy debate. We don’t always agree. When we’re not aligned, we don’t sweep it under the rug. We take the time to understand each other’s perspective, look at the same data, and work toward alignment.
As a company scales, people may try to form factions around each founder’s sphere of influence. We work hard to make sure that never happens.
5. Stay a student.
Relentless Curiosity is another one of our core values. Find mentors and listen to them. We have advisors, mentors, and coaches who help us spot our blind spots and work through the challenges we face.
We constantly ask ourselves “why.” We pressure-test our assumptions and biases, and we try not to be dogmatic about anything.
We also keep learning by building. Earlier this year, I built a jiu-jitsu training app with Claude Code to better understand AI tools firsthand.
Looking ahead, what do you believe are the key trends that will shape the future of the fintech industry? How are you preparing your company to adapt to these trends, and what role do you see your leadership playing in this adaptation?
Embedded finance becomes the default. The future of financial services is embedded and verticalized. Vertical SaaS is the modern distribution channel for financial services. As AI makes per-seat pricing obsolete, software companies will need new ways to sustain their businesses. They’ll build tailored payments and financial services experiences for their verticals. That’s exactly what Payabli is built to power.
AI agents will move money. Agents will initiate, reconcile, and manage payments on behalf of businesses. That requires infrastructure built for machines, not just humans. That’s why we launched our MCP server and are investing in AMIGO and agentic AP.
Banks and fintechs grow closer. Our work with Huntington shows that banks want modern distribution through software. We’re positioning Payabli as the bridge between them.
My role is to set the direction, remove obstacles, and make sure our team has room to experiment.
You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)
That’s a great question, and a hard one.
I was fortunate to grow up with several positive male role models who shaped my character. My grandfather was one of them. I owe much of my success, and the pride I take in the life I’ve built, to them.
Now, as the father of a young son, I think a lot about how I can be that role model for him. It’s an interesting time to be a boy or a man. Young men hear a lot of conflicting messages about what masculinity and manhood should look like.
That’s where I’d focus my movement: helping young men build fulfilling, productive lives they can take pride in, and play a positive role in their families and communities. Mentorship changed the course of my life. I’d love to help more young men find the same kind of guidance I was lucky to have.
How can our readers further follow your work online?
This was very inspiring. Thank you so much for joining us!
