From Wall Street to SaaS: My Journey in Support Leadership

I don’t expect anyone reading this to be here for my life story. But if you’ve stumbled upon it, I hope it serves as a blueprint, a cautionary tale, or maybe just a source of reassurance—that careers aren’t linear, that pivots can be powerful, and that the best paths are often the ones you never saw coming.

For twenty-six years, I’ve worked in some form of customer support. Eleven of those years have been in leadership, spanning industries like finance, subscription billing, DevOps, fintech, and procurement. I never set out to build support teams or scale global operations. But looking back, every twist in my journey led me exactly where I needed to be.

This is my story—the wins, the hard lessons, and the unexpected detours along the way.

The Accidental Beginning: Wall Street and the Art of the Pivot

In 1999, I was temping as a receptionist at a brokerage firm in Rye Brook, NY. A one-day gig, nothing more. But by sheer luck, the company was hiring for two full-time roles—one in legal, one in customer service. I had a choice: paperwork or people.

I chose people. It was a decision made on instinct, but in hindsight, it shaped everything that followed.

Three years later, I found myself in the heart of New York City, pitching electronic trading systems to brokerage firms, armed with my Series 7 and 63 licenses. If you’ve ever seen The Wolf of Wall Street, imagine a slightly tamer version—but still, a thrill ride for a 20-something navigating the city that never sleeps.

The sales life was exciting, but something felt off. I wasn’t drawn to the pitch, I was drawn to the product. I wanted to solve problems, not just sell software. So, I pivoted.

I moved into API support at the New York Mercantile Exchange, helping global investment banks integrate with our trading systems. I was working the 5 PM to 1 AM shift, supporting traders in Singapore and Dubai, running on adrenaline and caffeine, rarely seeing the sun.

But after a decade in the trenches of Wall Street, I was burned out. The pace, the pressure—it was exhilarating, until it wasn’t.

I needed a change.

Trading Skyscrapers for Sunsets: A Reset in Key West

In 2009, I walked away from the high-stakes world of trading and moved to Key West, Florida—a place where time slows, shoes are optional, and no one cares what you did for a living.

It was paradise.

It was also a career dead zone. No tech jobs. No corporate ladder to climb.

So, I pivoted again. I helped my ex-husband open a restaurant on Duval Street. I spent a year working in hospitality, and let me tell you—waiting tables will teach you more about human behavior than any executive boardroom ever will.

But I missed tech. I missed building things.

So, I used the web design and SEO skills I had taught myself by toying with affiliate marketing for a few years and launched my own digital marketing business. I helped small businesses in Key West build their online presence. I loved the creative challenge, but as a one-woman operation, scaling was impossible.

I needed stability. I needed health insurance.

And then, I discovered remote work.

Breaking into SaaS: The Road to Leadership

In 2014, I joined Chargify (now Maxio) as a Tier 2 support engineer—the 13th hire and the first woman on the team.

My manager, Jay Glynn (RIP my friend), saw leadership potential in me before I did.

When he first suggested I move into management, I was hesitant. I wasn’t sure I wanted to deal with personalities, office politics, and the emotional weight of leading people. But he convinced me it was a natural step. I trusted him, so I took the leap and quickly found that I had a knack for it.

Over the next five years, I built multi-tiered support, customer success, onboarding, solutions engineering, and technical writing teams. I grew into Director of Customer Success, learning how to scale GTM teams in an organization from the inside out.

But like all good things, it came to an end. Chargify had been purchased by a fund and was transitioning customer teams to San Antonio. I didn't have the option of relocating, so I knew it was time for a new challenge.

Scaling Support at CircleCI: The Power of Process

CircleCI was the first professional services package I had sold while building the pro serve team at Chargify. I had made connections within the Operations team and joined CircleCI, a DevOps CI/CD company, as Director of Support Engineering. Never underestimate the power of relationships!

Here’s the kicker: I didn’t have a DevOps background.

But I quickly realized something that changed the way I approached leadership forever:

👉 Support is about process, not just product.

I didn’t need to be an expert in the software to make an impact. I just needed to build the right team, structure, and workflows.

And it worked.

📈 CSAT jumped from 87% to 98%.

🌍 We scaled support teams across NAMER, EMEA, and APAC.

⏳ Response times and resolution times decreased significantly.

🚀 I had the opportunity to build a TAM team, boosting proactive support.

I stopped second-guessing myself. I stopped worrying about not being the most technical person in the room. I knew how to build high-performing teams and talk the talk—and that was enough.

The key takeaway: Support best practices work across industries.

Synapse: A Lesson in Crisis Management

When I joined Synapse as Senior Director of Support Engineering, I walked into chaos.

💀 A massive ticket backlog

🚧 Engineering was siloed

😡 Customers were furious

It took multiple quarters to turn it around, but we did it!

✅ We reduced backlog and escalations by 30%

✅ CSAT soared from 89% to 98%

✅ Support productivity jumped 300%

✅ Built out Compliance Support and Production Engineering

✅ Customers were happier with the support they received

But then, the company started to unravel.

Synapse’s largest customer was threatening to leave. Layoffs were coming. The company eventually filed for bankruptcy—and to this day, people are still trying to recover their lost funds.

It was a brutal experience, but a masterclass in leadership under pressure.

Building from Scratch Again: Tropic

At Tropic, a procurement SaaS startup, I joined a number of previous Chargify coworkers and was hired to build the entire support function from the ground up as the company transitioned from Services to SaaS.

But the hardest part hasn't been team-building—it has been the behavior change.

✅ Customers were used to white-glove service from account teams

✅ Dedicated account teams feared redirecting customers to Support would impact retention

✅ Changing this dynamic takes education, process, and patience

💡 Change is hard. But necessary.

Fast forward to today:

📈 1,000+ tickets per month

⭐ Top-tier CSAT and perfect SLA attainment

⚡ Support is now a competitive differentiator

Behavior change management is still ongoing, but getting better and better with time.

Mission accomplished.

Final Thoughts: Support is Mission-Critical

I’ve had no regrets, and I’ve learned something at every step. I've also been promoted and asked to build teams at every company I've joined. This is a testament to the fact that finding gaps and proposing solutions coupled with hard work and metrics improvements will get you where you deserve to be. Don't forget to campaign for yourself and make it undeniably clear what value you bring to the table!

The unfortunate truth is that Support is often undervalued. Too many companies see it as a cost center. I’ve spent my career proving that Support is the front line of retention, growth, product adoption, and insights for product improvements.

We solve problems. We build relationships. We create loyalty.

And the best teams? They turn every challenge into an opportunity.

I can only wonder where life will take me next… but for now, I’ll keep building.