Customer Success

Customer Success

How one manager took the pain out of scheduling group meetings

Scheduling group meetings can be chaotic. With Calendly, companies are finding a better way.

Masooma Memon

Masooma Memon
May 10, 2022

5 min read


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Herding cats is one of those dreaded “other duties as assigned.” You collect your teammates’ “best meeting times,” invite your client, and then a teammate Slacks you: “Oops, I already booked that time slot.” So you start all over. 

With Calendly, teams are learning it doesn’t have to be this way. Automated scheduling tools mean professionals in marketing, sales, and other fields can bypass the chaos and make scheduling as a team easier. Managers like Winta Habteslassie at digital payment company Square are closing more deals faster, because they don’t have to waste time herding cats anymore.

Easily host group meetings when everyone’s available

Winta, a partnerships manager, says prior to using Calendly “there was a lot of friction on the front end to even get the first conversation on the calendar.”

She hosts two main types of meetings: customer research calls and partnership calls. She kept hitting roadblocks when scheduling partnership calls. The reason? These calls aren’t one-on-one interviews. Winta brings partners on board alongside several members of her company so they can iron out deals together. 

Consequently, scheduling these group meetings became a struggle, as Winta had a tough time finding an open slot that suited everyone’s calendar.

“It was so difficult to manage three or four different calendars across the board,” Winta says.  “And by the time I would find an open slot and a partner would get back to me, I’d have to go back and forth, telling them ‘hey I'm sorry, actually those days and times that I provided to you are no longer available.’”

It’s an all-too-familiar story for project managers, sales reps, and team leaders. Winta was losing lots of time just setting up intro calls and follow-up calls with partners. This took focus away from her important strategic work. And the scheduling delays for intro calls meant Winta couldn’t speak with partners when their interest was at its peak. 

Then one day Winta’s team lead recommended Calendly’s collective scheduling feature (available on all paid plans), which he used at his previous job.

Time back = more success

Calendly’s collective scheduling tool lets you define when all your team members can meet. It’s a great way to schedule group kickoffs and recurring check-ins with your external partners and vendors.

Intrigued by her team lead’s recommendation, Winta created a collective Event Type in Calendly that pooled calendar availability of all internal stakeholders. Invitees could only see (and book) times when every call participant on Winta’s team was available.

And Calendly’s integrations with tools like Zoom and Google Meet means there’s zero chance of forgetting the crucial videoconferencing link in the meeting invitation. Now Winta enjoys:

  • Increased capacity to onboard more partners

  • Less back-and-forth finding meeting times that suit everyone 

  • Time savings she redirects to strategy, tactics, and analytics

Calendly has “literally increased the velocity of the conversations we are scheduling—how quickly we are able to get in contact with partners—because the scheduling aspect and the friction are completely resolved,” Winta says. 

“I don’t have to look at my calendar or anyone else’s to provide someone access to scheduling a meeting with me.” 

In fact, scheduling calls is now as easy as sharing her Calendly link with invitees. 

After having connected her calendars with Calendly, Winta realized she could do more than automating meeting scheduling. Turns out Calendly could solve another one of her problems — setting her availability.  

“Being able to do that on your normal calendar is super manual. You have to literally block the time and have it exist forever, whereas, in Calendly, there’s a feature.” 

Now, instead of having a completely open calendar, Winta’s calendar only shows pre-selected meeting slots when she’s available.  As an added benefit, Winta says the tool helped her create healthier boundaries at work.

Land more deals faster

Using Calendly’s multi-person scheduling options for teams, Winta has not just reduced the time it takes to set up meetings but also increased the number of partnership calls they have.

“The velocity of our deals, the speed at which they’re moving, and the number of deals that we can work on at once have increased,” Winta says. 

“And that indirectly contributes to our ROI because we’re getting to those customers a lot quicker than we would have initially [without Calendly] by manually scheduling calls.” 

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Every quarter, Winta has a set number of partners to bring onboard. Using Calendly, she meets these goals faster—minus the stress of managing multiple calendars.

Explaining how Calendly helps her meet her quarterly goals, Winta says, “The quicker I can get through the earlier conversations, the quicker I get to the contract and agreement, the quicker, I can find a partner.”

What’s more, with the time that Winta saves by using Calendly, she can “focus more on my job’s core responsibilities like the strategy. For example, how we should be marketing the specific partnership—as opposed to being stressed out [about coordinating meeting times].”

Most of all, Winta isn’t overwhelmed with tracking intro meetings and follow-up meetings.

“Sometimes you get bogged down, you’re like oh my gosh I have to schedule all five of the follow-up meetings because I just had five intro meetings,” Winta says. “That’s a big undertaking if you have to do that all manually, but if you use Calendly to do that for you, there’s one less thing on your to-do list.”

Try out our collective scheduling tool with a free 14-day trial of our Teams plan, which also includes automated email reminders and follow-ups, Meeting Polls, and integrations with tools you use every day.

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Ready to make scheduling easier than ever?

Ready to make scheduling easier than ever?

Masooma Memon

Masooma Memon

Masooma Memon is a freelance writer for SaaS and a rookie bullet journalist. When she’s not writing, she’s either reading a fantasy novel or shortlisting an idea to discuss in her newsletter, The Content Workshop.

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