Connor Lennon

Product & operations · Charlotte, NC

I find the places where people get stuck, and get them unstuck.

Cold calls, a company of my own, a fintech startup and a big bank. Six years, four cities, and the same puzzle every time. Here's how it went.

Prologue Columbia, SC

A finance kid who liked people more than spreadsheets

I studied finance and international business at the University of South Carolina's Darla Moore School of Business and graduated magna cum laude. I loved the numbers, but I kept noticing that the interesting part was always the people behind them: why they decided what they decided, and what got in their way.

01 2020 · New York, NY

Cold calls in a very strange year

My first job was in sales development at BrightEdge, starting in the spring of 2020. It was a strange time to start anything. My whole job was getting busy strangers to give me a few minutes, and by the end I'd built more than $350K of qualified pipeline.

  • $350K+pipeline built
What it taught me Everyone is busy. Respect their time, and get to the point.

02 2021–2022 · Limerick, PA

Starting something from zero

In 2021 I co-founded Cobblestone Capital Group, a boutique wealth management firm. No clients, no assets, no logo anyone recognized. I earned my Series 7 and 66, did the research, made the calls, and we grew to more than $1.5M under management with 10 new clients, one conversation at a time.

  • $0 → $1.5M+assets under management
  • 10new clients
What it taught me Trust doesn't scale. You earn it one person at a time.

03 2023–2025 · Charlotte, NC

Learning where people get stuck

Next came BrightDime, a fintech startup. I started in business development and marketing, doing customer discovery and competitive research that sharpened how we told our story. That brought in $90K+ in new annual recurring revenue, and our content strategy more than doubled website traffic.

Then I moved into customer experience and looked after 50+ business clients. I spent a lot of time in the feedback and usage data, finding exactly where people dropped off during signup and onboarding, then fixing those spots.

  • 98%client retention
  • +10.6%monthly active users
  • +139%website traffic
What it taught me The data tells you where people get stuck. The people tell you why.

04 2025–now · Charlotte, NC

Making a big bank feel a little faster

Today I'm a Senior Consultant (AVP) on Truist's Client Experience and Digital team. Every new digital product idea starts with an intake request, and those requests were waiting more than a month for a decision. So I redesigned the form and the process behind it, added automatic status updates, and built a dashboard so 650+ people could finally see where their requests stood.

Median time from request to decision
3919 days

51% less waiting, across hundreds of requests a year.

I've also helped evaluate around 100 digital product ideas, built dashboards that connect each idea to what actually ships, and piloted a GenAI assistant that reads new requests, spots what's missing and drafts the follow-up questions, with a human always making the call.

What it's teaching me Sometimes the best product is just a shorter wait.

∞ Next

Still looking for the stuck spots

The thread through all of it: find the place where people get stuck, understand why, and build the thing that gets them moving again. Usually that's a product. Sometimes it's a form, a dashboard, or one well-timed email. If you're working on something like that, I'd love to hear about it.

Say hi

Whether it's a role, a stuck process, or just a good conversation about product, my inbox is open.

LinkedIn

It's in Charlotte