Calendly ups IT service productivity by 2X

When it comes to building business relationships, every conversation counts. So it’s vital to quickly get those meetings on the calendar without tedious back-and-forth emails.

Calendly’s robust scheduling platform provides a faster way to connect. Founded in 2013, Calendly is now the world’s leading cloud-based scheduling automation platform with more than 20 million users across 100,000 businesses. Those users are supported by approximately 550 customer experience obsessed employees.

Siloed systems and manual headaches

When Darlene Reina, Senior Director of IT and Business Systems at Calendly, stepped into her role, she inherited a Zendesk setup that was severely underutilized. Internal employee service desks were siloed, processes were inconsistent, and employees were left in the dark when seeking help from the IT, HR, Legal, and Security teams.

“IT was known as the place where tickets went to die,” Reina recalls. “We weren’t just inefficient — we were completely reactive. Nothing was being prioritized properly, and everything felt like a fire drill.”

Calendly’s internal departments — IT, HR, Legal, and Security — operated using four disconnected instances. Requests were funneled through email or Slack, lacking any formal structure or tracking.

“There was no automation, no triaging, and no metrics. Everything was manual,” says Reina. “Even onboarding required someone to manually check off a list in Zendesk and write comments. For a growing company, that just wasn’t scalable.”

Optimizing and centralizing with Zendesk

Fast forward to today, Calendly has transformed its internal service landscape and IT service management using Zendesk’s Suite Enterprise platform, along with key integrations to Workday, Slack, and Okta.

Under Reina’s leadership, Calendly began a full-scale overhaul of its internal service delivery. First, they optimized Zendesk with custom ticket forms, automatic routing, macros, and integrations — turning the platform into a centralized hub for all employee requests.
“Our goal was to have every single employee task or request come through Zendesk,” explains Reina. “That way, we could triage, track, and improve everything from access provisioning to audit compliance.”

With the help of Zendesk Professional Services (ProServe), Calendly consolidated four separate Zendesk instances into one centralized system — and the results have been nothing short of remarkable.

Embracing automation and self-service

Automation played a key role in the transformation. Zendesk was integrated with Workday and Okta to auto-generate onboarding tickets and write data directly into Zendesk for compliance tracking.

Calendly’s use of Zendesk’s help center is a driving force behind the company’s success with employee self service. Functioning as both an employee-facing help center, and the backend for integrated AI tools, employees can now submit tickets conversationally. As a result, many common requests are automatically resolved or routed without human intervention.

Additionally, articles like “How to update your macOS” receive hundreds of monthly views, saving IT time and accelerating resolution for common issues.

Asset management with Oomnitza

Additionally, Calendly now enhances its asset management by integrating Oomnitza’s best-in-class IT management with Zendesk.

Oomnitza’s app on the Zendesk Marketplace is designed to deliver frictionless management throughout the technology asset lifecycle. At Calendly, Oomnitza is pulling information into Zendesk from Jamf, Okta, CrowdStrike and other software, giving the team a clear, real-time view of the company’s device fleet and software vulnerabilities.

Oomnitza also provides Calendly with the ability to slice key data to satisfy the unique needs and interests of IT, Finance, and Security related to company assets.

In fact, the results experienced by the IT department convinced the Calendly Legal team and others to hop on board and get their service operations into Zendesk. Now, IT, HR, Legal, Security, and People Ops are all housed in Zendesk. Role-based access and built-in permissions ensure that each team only sees what their role allows for and requires.

Reporting offers them robust insights that allow them to understand where their teams are spending time, ensuring that it’s not on time-wasters.

Faster resolutions and soaring employee satisfaction

The introduction of automation and self-service across internal systems has delivered impressive results across the business. For instance, Calendly’s IT service desk went from four agents to two–a 2X increase in productivity–while handling a growing volume of tickets. Meanwhile, the other two agents were assigned to handle other IT project work.

Even more impressive is that the leaner service desk team is delivering much faster resolution times and consistently higher satisfaction scores.

Full resolution time dropped from approximately 90 hours to under 14 calendar hours — a reduction of 84 percent. “We used to take four to five business days. Now it’s less than one,” notes Reina. Concurrently, first reply time is 97 percent faster–shrinking from 32 hours to under one hour.

Meanwhile, customer satisfaction scores have soared from the low 70s to a consistent 99 percent, a 28 percentage point improvement. “People are genuinely happy,” offers Reina. “And because we’ve streamlined basic tickets, we can spend more time on high-touch or complex cases.”

Compliance and security simplified

Another key benefit of the transformation initiative has been the support Zendesk provides for audit-ready compliance. Calendly systems can now write all updates and information directly into Zendesk tickets, helping ensure compliance with audit requirements, making it easier to track every step of an employee’s lifecycle.

Zendesk now serves as the source of truth for SOC2 audits, thanks to its integrations with identity and access management tools. “We just export the ticket, and the audit trail is all there,” explains Reina. Permissions and visibility are finely tuned based on team roles, ensuring compliance and security without sacrificing cross-departmental collaboration.

IT as a trusted partner

Perhaps the most telling sign of success is the change in perception. “Before, IT was an afterthought. Now, we’re looped into projects early as strategic partners,” enthuses Reina. This newfound recognition and greater efficiency has allowed the team to deliver on major initiatives—like a company-wide role-based access rollout—in just six months.

“We didn’t just improve service,” says Reina. “We changed the way the company sees IT — and Zendesk helped us do it.”

The success of the modern shared-services model implemented at Calendly has not gone unnoticed. Departments such as Legal and People Ops, which once hesitated to embrace automation, now rely on Zendesk to manage their operations efficiently. “Lawyers should lawyer, security should monitor — and Zendesk lets them do just that,” says Reina.

From reactive to fully proactive

With the foundational systems in place, Calendly’s IT team is setting its sights even higher — aiming to make IT support fully proactive.
“Wouldn’t it be amazing,” Reina imagines, “if we could identify a security patch requirement and auto-generate a ticket, send an article, and track completion — before the employee even knows there’s a problem?”

That’s the future she envisions — and with Zendesk as a trusted partner, it’s one well within reach.