The Rise of Revenue Innovators • Oct 12
How Jitterbit Wins Back a Week of Productivity per Rep with Outreach Meetings
Orchestrating a ‘meeting of the minds’ is the goal and lifeblood of any customer-facing team in order to win new customers or support existing ones. But all too often, trying to schedule that meeting can push even the most patient representatives to exasperation.
Everyone has been there: the endless back-and-forth game of email tag, trying to nail down a date and time. The proposals, counter-proposals, and response lag times mean the time you suggested four hours ago has now been filled. Multiply that by the amount of meetings the average Customer Success Manager (CSM) has in a given week, and you have to wonder how they even have time to do their day job after maintaining their schedules.
But as Taylor Cunningham, Outreach Administrator and Customer Success Manager at Jitterbit, learned, proactive engagement using Outreach Meetings is the secret to keeping her customers happy while keeping her team sane, organized, and spending their time wisely.
Meetings: Align in Real-Time
Just as Outreach provides better visibility into internal processes for team members, Outreach Meetings leverages that same principle so external prospects and customers can enjoy real-time visibility into your calendar for more efficient and effective, interactive scheduling across organizations.
As the Outreach Administrator of the CSM team helping nurture relationships with customers, Cunningham and her team are all about scheduling one-on-one time to give clients the personal attention they deserve. But all the customers and scheduling variables mean a lot moving parts, and a big chance for those parts to crash into each other in the form of conflicting dates and times.
“In our customer success role, we have a few standard types of meetings,” Cunningham relates. “But the main reason we use Outreach is for onboarding new customers and holding quarterly business reviews with existing customers. In the reviews, we talk about their business objectives and make sure they’re achieving the value they wanted when they purchased Jitterbit, and what can we do to help them, if they’re not.”
Trying to align everyone’s time to hold these regular meetings is a headache that Outreach Meetings helps alleviate. Compared to the reactive scheduling of email back-and forth, Outreach’s proactive scheduling capabilities allow you to send public calendar links so invitees can see your real-time schedule and book a date and time in one click.
It’s a feature that Cunningham relies on to juggle and manage the process of trying to book time with so many customers at once.
"We’re supposed to do about 30 meetings per CSM per quarter,” Cunningham explains. “And if you’re booking 30 meetings you’re probably reaching out to 45 customers or more just to get those confirmations. Outreach has helped us manage all those moving parts."
Instead of going back-and-forth between 45 different customers at once, trying to align dates when everyone is available, it’s very easy to just drop in the times you’re available and allow [customers] to click the schedule that works for them.
CSMs also rely heavily on meeting agendas to ensure their limited time with customers is productive, but it can be tedious to copy the same agenda over and over again and often isn’t prioritized by every rep. When sending the proposed meeting invite, the convenience of templated information, like agendas and dial-in details, is a huge efficiency boost for Cunningham and team by eliminating the time wasted on mundane tasks that amount to no more than repetitive data entry. Cunningham explains:
“It’s very convenient that, when you go to create the calendar invite for instance, you don’t have to copy your meeting details, drop them in, and then copy the meeting agenda and paste that in over and over again."
Outreach Meetings saves a lot of time that is otherwise wasted on tasks like setting up meetings and pulling together invites. I would estimate that it saves us an hour or more a week per user. That's over a week of productivity per person we’re getting back over the course of a year!
That proactive nature also helps to practically eliminate reschedules and cancellations since the customer has chosen the date that works for them and isn’t being forced into a time that’s based only on the CSM’s schedule.
And when customers do have to reschedule, Cunningham says, “They love having the one-click reschedule feature to say, ‘No these times don’t work for me, but let’s go find something that does.’” The instant notifications sent to meeting owners with Outreach Meetings help keep the CSMs organized with friendly automated email reminders when meetings are set or changed by invitees so nothing falls through the cracks.
It’s not just Cunningham and the team at Jitterbit who have been pleasantly surprised by the ease and convenience of Outreach Meetings. The customers she interacts and who actually receive the invites have also been quick to notice the easier scheduling.
“I did have one customer who I sent an Outreach Meeting invite to and she said, ‘Can you please tell me what this software is that you’re using?’” Cunningham laughed. “Because she had noticed the new interactive scheduling. Of course I said, ‘it’s Outreach, we just switched over to it, and glad you like the calendaring feature!’”
An end to follow-up frustration
Once your meeting is set, planned, and held, what’s next? Ideally, you follow-up as soon as possible. But as any sales or customer success pro knows, the juggling act of contacts, dates, times, and tasks can quickly spin out of control without airtight organization.
For Cunningham and team, since every customer’s needs and issues are unique, their follow-up tasks cascade exponentially over 30+ clients. So, they rely on Outreach to help them manage and organize that as well. While before it was up to individual CSMs to hack together their own personal tracking solution, follow-up tasks and sequences in Outreach relieve that burden by helping them set and track tasks so they don’t fall through the cracks.
“For the CSM team, there tends to be a lot of follow-up tasks that need to be done with our customers after we hold business reviews or onboarding meetings, and it’s pretty hard to keep track of them. Plus, a lot of those tasks have to happen at specific intervals – like do this two weeks from now, and do that two months from now. It’s hard to remember everything without a system in place.
“What I do personally, and what I’ve been trying to show the team as a best practice, is after a business review, write a follow-up email to the customer saying ‘these are the action items that we identified.’ And then with pretty much every email I send, I set up a follow-up task. I also send every email with a reminder using Inbox Bump so it resurfaces to the top of my inbox if I don't get a reply in a certain period of time. Between Outreach’s follow up tasks and Inbox Bump, I'm able to stay on top of hundreds of different tasks!”
Customizing the scheduling of those follow-up tasks is also a feature Cunningham relies upon to keep track of all those moving parts.
“I like that you can customize when you want the task to happen, in advance,” Cunningham emphasizes. “It’s very convenient because instead of always wondering, ‘What’s my next touch-point with this person? Do I have it scheduled?’ I know Outreach will automatically tell me when I need to take action, because I’ve set tasks to remind myself. Outreach even helps me prioritize what’s next by showing me which tasks or prospects I’ve marked as high priority. When I’m done, I can just mark them as complete and move on."
We all say, "We could not stay on top of all of our customers’ needs without the follow-up tasks in Outreach."
A snippet in line saves time
And to make those follow-ups even easier, Cunningham has a snippet of advice. As an added feature for more efficient customization, Outreach’s Snippets offer a speedy way to insert pre written content and information that’s shared frequently -- a common need for Cunningham’s customer-facing team.
“We leverage snippets quite a bit,” Cunningham relates. “There’s a lot of repeatable information that we share as a CSM, like enrollment codes for our training program or how to access support or how to access community forums. It’s definitely more convenient to have all that information located in one place that makes it easy to pull from and put into your emails in one click. I like that I can add a snippet into an email I’ve already started, even if I’m not using a full template. And we can use them whether we’re working in Outreach or Gmail.
A solution that works where Jitterbit does
The fact that Outreach Meetings and follow-ups sync directly with Salesforce and Gmail is the final icing on the cake for Cunningham, who uses Gmail as her main platform for communication.
She explains: “I like that I can create meetings and follow-up tasks in Gmail without having to open Outreach. I spend most of my day writing and responding in Gmail, and that way, I don’t have to keep flipping back and forth between two tabs. Gmail sync is a huge plus, and so is the 360 view, when I am working in Outreach.”
That seamless integration and visibility across systems—whether organizing and following-up on tasks, or managing meetings for 45 different schedules—are two of the key characteristics driving Jitterbit’s proactive customer engagement with Outreach.
Because for Cunningham, it’s all about what empowers her to work smarter within her existing workflow. Outreach fits the bill.