Integrate Calendaring and CRM for Greater Sales Productivity

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When managing sales, it’s essential that managers and salespeople know who is calling on which prospects or clients and when. Otherwise, companies could run into serious sales mismanagement issues, such as two salespeople calling on the same client, sometimes at the same time, or no salespeople calling on an important client at all.

A big part of the sales manager’s role, therefore, has to be calendaring.

It might sound like an easy task, but that’s not always the case.

Calendaring issues go back to when everything was done on paper or white boards (or some combination of the two).

“Calendaring has always been a basic concept in most sales methodologies,” says Christian Wettre, SugarCRM’s chief of staff. “You want to have some focus on how many interactions you’re having with prospects or customers. The idea is that the more you speak to people, the more opportunities you find to generate business. So sales leaders have always been interested in seeing how many meetings and calls their sales team has.”

Calendaring often starts with Microsoft Outlook or Google Calendar, but others opt for different systems due to ease of use, cost, functionality, or personal preferences,.

And with most employees bringing their own mobile devices to work and using them for business, calendars are often isolated on individual smartphones. This, unfortunately, often leads to situations where the right hand does not know what the left hand is doing and where the sales manager does not know what either hand is doing.

The most direct path to ensuring that all sales team members know who is doing what is to share calendars, says Robert Brill, CEO of Brill Media. By sharing calendars with other people, managers can see the calendar from multiple people on the team, including all the event details, just as easily as they see their own calendar details. This process is great to monitor work performance and to give assistants the ability to schedule time based on their bosses’ availability.

Google makes the process easy. In Google Workspace accounts (if your business email is accessible through mail.google.com), users just need to go to calendar.google.com, click the three dots next to a calendar on the left of the screen, go to settings, choose “share with people or groups,” and select the people with whom they’d like to share their calendars. That gives other people access.

Of course, this method requires that all salespeople keep their calendars up to date and that they all use the same calendaring system. If all reps and managers are on different systems, any sharing strategy won’t work as planned.


While Brill’s recommendation is certainly an essential step for transparency, more insight can be gained into sales team members’ activities by integrating their calendars and CRM systems.

TileCloud, an online tile shopping site, uses HubSpot and Calendly to enhance its operational efficiency, according to Drew Mansur, company cofounder. “Our CRM, HubSpot, is pivotal for tracking the progress of appointments and opportunities from both walk-in customers in our showroom and online inquiries. We’ve created a bespoke setup between HubSpot and Calendly for managing all inbound design appointments. This integration automatically populates a deal in HubSpot with all appointment details once booked, ensuring our team is always in sync and fully aware of who is meeting with whom and when.”

As the Australian company continued to expand, it introduced a unique booking link for trade customers, according to Mansur. “This allows them to offer their clients access to our free design support, further streamlining the consultation process. We’ve also found that Calendly’s automated workflows for appointment confirmations, reminders, and SMS prompts for reconfirmation have been crucial in maintaining a high level of engagement and attendance.”

Additionally, the integration between HubSpot, Unific, and Shopify enables TileCloud to track deal states, from quote sent to sale closed, without manual intervention, according to Mansur. “This, along with daily utilization of HubSpot tasks based on customer conversations, allows us to tailor our follow-ups according to each customer’s renovation timeline, providing a personalized and efficient service.”

Another common practice is to use calendar programs within Salesforce. Coconut Software, a Canadian company that provides customer engagement platforms for financial services firms, uses the DayBack calendar integration with Salesforce, tying sales reps’ Google Calendars with Salesforce records.

DayBack enables users to link events to resources, such as people, equipment, rooms, or a mix of things that need to be scheduled. The user then can link items to multiple resources and organize resources by grouping them into folders. Resources are shown as rows or columns, and users can move events from one resource to another to balance the schedule.

And because field service sales, installation, customer service, and inspection teams each have their own requirements, resources, and workloads, users can filter down to just one area or view them all at once.

DayBack’s Salesforce Connect grants customers and partners access to a salesperson’s schedule even if they don’t have Salesforce licenses. Sales managers can grant field personnel access to just their schedules in read-only format or let them update key aspects, like job status or work order details.

“DayBack sits as a widget within Salesforce and allows our managers to have a high-level overview of what each rep has planned for the day, including all sales calls and internal meetings,” explains Coconut Software account manager Adam Purvis. “You can set up custom workflows on the calendar events to link the calendar event and its contacts to Salesforce opportunities.”

This makes the process of seeing next steps on a deal very simple since the manager can simply click the calendar invite to open the opportunity. The other option would have left people spending time manually navigating Salesforce opportunities and manually cross-referencing with Google Calendar, according to Purvis.

“This has been a net win for our sales organization as it allows our managers to better understand which deals are slipping so they can jump in proactively to provide coaching or support,” Purvis says.

Integrating the calendar with the CRM system has streamlined operations, enhanced team collaboration, and helped drive sales at TeamUp, a provider of fitness management software for in-person and online classes at boutique gyms, studios, spas, resorts, and the like, according to Laia Martin Quintana, the company’s head of marketing and sales.

“Two tools that have proven to be effective in this regard are Yesware and CalendarAnything,” Quintana says. Yesware, an activity dashboard for Salesforce, automatically syncs email activity, calendar activity, campaign activity, and engagement data. This eliminates the need for manual data entry, freeing up valuable time for your team to focus on client interactions.

CalendarAnything, meanwhile offers customizable calendars within Salesforce, allowing for efficient scheduling and management of marketing campaigns, project planning, and opportunity forecasting, CalendarAnything users can create, edit, and move records in Salesforce directly from the calendar, providing a comprehensive view of team activities and client interactions.

“These tools, when utilized effectively, can significantly enhance transparency and efficiency within your organization,” Quintana says.

Wettre has also seen that while Google Calendar and Outlook are excellent calendaring systems on their own, efficiency comes by integrating CRM with those systems. Many of SugarCRM’s customers are manufacturers, and their salespeople need not only the calendaring capabilities but also the product information, blueprints, etc. “That content comes from a calendar meeting, so our focus is to [automatically] bring that information into Sugar so the salesperson doesn’t have to,” he says.

When calendaring and CRM systems are integrated, they usually work very well, but many calendaring programs don’t integrate with CRM platforms or they have limited functionality, according to Nikolaus Kimla, CEO of Pipeliner, who adds that rather than switching between programs, it is easier to have calendaring and other sales and CRM activities within the same program.

Efficiency also comes from being able to have activities, progress reports, appointments, etc., in the same system, Kimla says. Otherwise, salespeople need to manage a handful of different applications in addition to their calendars, and invariably a progress report, essential follow-up, or something else will get missed when switching among the different applications.

The user interface in any calendaring or CRM application is essential, according to Kimla. “If you see something that is easy to understand, then you don’t lose your focus.”

Even managing different windows in the same application can be cumbersome, Kimla says. “Inefficiency comes when you cannot connect all of this stuff together. The efficiency comes when you do not have to have multiple windows for each process. And efficiency leads to productivity.”

Even once a company has a calendaring system that its salespeople are comfortable using, updates can be an issue, according to Kimla. “Some vendors are always changing their [user interfaces]. Then you have to learn it again. This happened to me recently when Microsoft 365 forced me to upgrade.”

Kimla has the Office suite, which includes Outlook for calendaring, in the cloud and on his personal computer. The issue, according to Kimla, was that the upgraded suite was more complex than the one he had been using. Also, the cloud and desktop versions were upgraded at different times, making it cumbersome for anyone using both versions.

“One of the biggest companies in the world forced me to upgrade to a worse system than I had before,” Kimla says. “We try to do exactly the opposite with our customers.”

Though Pipeliner, SugarCRM, and some other calendaring/CRM integrations offer a host of features, many salespeople will only use a portion of them, according to Kimla, likening the solution to Microsoft Excel. Millions of people worldwide use Excel, but most use only the basic functions rather than everything the application has to offer.

“Few people understand everything you can do with Excel. The same is true of other applications,” Kimla says. “But the core of calendar, email, and appointments and bringing that together is essential for productivity within the company.”

Pipeliner, therefore, also enables salespeople to automate email messages based on type (initial greeting, sales pitch, etc.), tone (professional, friendly, etc.), and other options. The user can change options and the email updates automatically.

Wettre says that another essential function of integrated calendaring and CRM systems is the ability to ensure notes from a sales meeting flow through to the rest of the sales team.


Beyond that basic functionality, many other systems add other functionality that can further enhance a salesperson’s production. But those additional features don’t do any good if they’re not being used. While a sales manager can insist that his teams use certain systems, there can be resistance to such a top-down approach, especially for salespeople who are entrenched in their own ways of conducting business.

“There’s instant gratification when they see they are being asked to use something that meets their business needs,” Kimla says. “Salespeople want to optimize their daily work. When you give them something that does that, then you give them real benefits. At that moment, you have them hooked.”

If salespeople can achieve multiple benefits from a calendaring and CRM system, they will use it, Wettre and Kimla agree.

“People will follow the rules if they respect them, if they feel they are valuable for their community,” Wettre says. “With taking notes, if you feel that your bosses and your peers are actually reading them and they are being used for [their intended purpose], you will comply. If you feel that nobody is reading them, then you will make your own decision on whether taking them is worth the effort.”

The key for any calendaring system in today’s environment is to be very user-friendly and very visual, Kimla adds. He credits Apple for helping to drive visualization as a key component of applications inside and outside of the Apple ecosystem.

The benefits of having integrated CRM and calendaring systems will increase as artificial intelligence, particularly generative AI, automates note taking, summarizes notes, and produces further insights from the data that those systems collect, according to Wettre. 

Phillip Britt is a freelance writer based in the Chicago area. He can be reached at spenterprises1@comcast.net.

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