Booking and payment breakthroughs: Executive coach saves 10 hours per week with Calendly + Stripe

My name is Colleen DelVecchio, and I’m the founder of Maxady — a leadership development and executive coaching firm that helps people and organizations lean into their natural gifts.

At Maxady, we partner with companies across industries to offer high-impact training, team coaching, keynotes, and executive coaching. Many of our clients are women in or approaching C-suite roles who want clarity, confidence, and practical tools to lead well. We also work with HR teams and learning & development departments to deliver workshops on everything from team communication to inclusive leadership.

We’re a small but mighty operation. I’m the only full-time employee. I’m supported by a part-time program coordinator and a bench of eleven contracted coaches and facilitators who deliver our services globally. On any given day, I’m coaching clients, speaking at conferences, running our podcast, or helping teams navigate big changes.

With so many moving parts — and no time to spare — I needed a system to handle the day-to-day admin without breaking the flow of client experience. Calendly has become one of the most powerful tools in my business. It’s the engine behind how we schedule, how we stay in touch, and how I get paid for the work I do.

Challenge

The system depended entirely on me

Before Calendly, scheduling was always challenging. Every new coaching engagement required multiple meetings just to match clients with the right coach. I was blocking off time on my calendar for appointments that never got confirmed. When clients finally circled back, the slot was often gone, and we’d start all over again.

Reschedules were constant. Confirmations got missed. I was burning out. Even more frustrating was what happened after formal coaching engagements ended. Clients would reach out for quick advice or “a short call,” and I’d hop on without thinking much of it. But those quick calls often turned into full-blown coaching sessions — completely unpaid. I wanted to support them, but I needed a boundary.

Solution

Automations that protect my time and help grow my business

Calendly changed everything. I started with the basics by letting people grab time on my calendar with my scheduling link, but quickly adopted more powerful features.

“The real breakthrough came when I connected Calendly with Stripe. I set up a paid coaching link for one-off sessions.”

Colleen DelVecchio

Founder at Maxady

Now, when former clients reach out, I simply send the link. They pick a time, enter payment, and get an immediate Zoom invite. No chasing invoices. No wondering if they'll show up.

I also created multiple Event Types, each tailored for different types of meetings I host: free consults for new prospects, paid sessions for returning clients, strategy calls, podcast interviews, and even urgent training needs. Each one runs on its own Calendly Workflow, with custom reminders, follow-ups, and confirmation emails. And I never have to worry about forgetting something because Calendly automatically adds Zoom links and syncs across all my calendars — personal, business, and client-owned.

Another way I save time is with Calendly’s browser extension. I can quickly share the right meeting link without leaving the tab I’m working in — whether I’m replying to a DM, email, or social message.

“And for channels like TikTok or our podcast, my Calendly links are embedded in our Linktree so people can book, and even pay, without me needing to lift a finger.”

Colleen DelVecchio

Founder at Maxady

Results

Time saved, revenue secured, and a better experience for everyone

Calendly now saves me five to ten hours a week — time I used to spend answering emails, tracking payments, and double-checking my calendar. I used to pay a coordinator $25/hour to help with scheduling. Now she focuses on more impactful work like marketing and finance.

Clients get a better experience, too. They book when it works for them. They get reminders. They can reschedule without waiting on a response from me. They feel taken care of from the very first click.

The payment integration has been especially transformative. I’ve completely eliminated unpaid consults and made it easier for clients to work with me on their own terms. When someone needs a quick session weeks or months after their engagement ends, they don’t have to email me. They just click, pay, and schedule.

I also don’t waste time on Sunday nights anymore making sure my Zoom links are in order. Calendly handles it all, flawlessly.

“If Calendly disappeared tomorrow, I honestly don’t know how I’d replace it. I’d need three or four different tools just to piece together what I’ve built — and none of them would work this smoothly.”

Colleen DelVecchio

Founder at Maxady

When people ask what software is worth paying for, Calendly is always the first thing I mention. It’s been a game-changer for my business and for my peace of mind.