How ClickSend transformed its sales ops and saved a full-time role with Chili Piper

ClickSend is an omnichannel communications platform that enables businesses to send and receive SMS. As Director of New Business Sales at ClickSend, Dan Hughes focuses on scaling efficiently without losing the personal touch. For him, scheduling wasn't just a logistics problem. It was the barrier to growing without compromising the customer experience.

How Calendly was slowing everything down

ClickSend's inbound volume was growing fast, but not every lead needed the same level of hands-on attention. A small business sending a single SMS each month didn't need as much support as an enterprise prospect sending millions.

The problem? Calendly treated every lead the same, no matter their intent or value.

“Spending half an hour on a call about one text a month isn’t the best use of the salesperson’s time, especially with so many demo requests.”

So Dan put a smarter system in place. He introduced a 2-track system:

• A group demo path for smaller use cases
• A 1:1 personalized demo for higher-volume senders

Scaling from one-on-ones to demo groups

With Chili Piper in place, ClickSend was finally able to route leads based on value. Prospects were asked how many texts they planned to send. Anyone who selected over ‘100,000 texts’ was automatically routed to the right AE and paired with  a member of the technical support team to get them set up for success

But ClickSend's sales team didn't stop here. They launched daily group demos across the UK, US, and Australia, with 10 to 15 participants in each session.

“That’s 15 people who would have had a half-hour meeting. That’s 7 and a half hours saved per day. <strong>That’s someone’s salary saved per month.”

3,000 tasks routed monthly with no guesswork

Chili Piper helped ClickSend do more than just save time; it reshaped how the team runs sales and customer operations. Using Chili Piper's Distro in an unconventional way, ClickSend uses field changes to trigger tasks and follow-ups across their teams.

When a customer tops up their balance, a task is created and prioritized with Distor. For example: 

• Low top-up →  Low priority task created
• $3,000 top-up? → High-priority task created
• A customer account gets suspended? → Task is created and assigned to Account  Managers before the customer even knows they’re suspended.

Every month, ClickSend uses Distro to route over 3,000 tasks, covering everything from reactivations to account changes. This gives the sales team a clear roadmap to engage with customers before issues escalate.

“We’re doing 3,000 plus tasks a month through Distro... that’s not just SDRs, that’s CSMs and AEs too.”

Instead of chasing reports or working reactively, the team starts every day knowing exactly where to focus.

“I’m not having to ask for reports. The team already knows what to do based on the tasks they’re assigned.”

Viewing Chili Piper as a smart investment, not a cost

Chili Piper quickly became mission-critical, and ClickSend made that official with a 3-year renewal.

For Dan, the value was obvious. Chili Piper's Distro helps them save countless hours, prevent customer frustration, and give the team the clarity they need to move with purpose.

"We don’t view Chili Piper as a cost. More of a cost saver.”

And Chili Piper is helping ClickSend expand into new markets. As the team expands into France and Brazil, they can route demos to reps working the right hours and with the language ability to support their prospects. 

To help track their expansion progress, Dan’s team is using UTMs inside of Chili Piper to track marketing activity and correlate it to meetings booked. 

“That's another feature of Chili Piper that we've only started to use this week, but we always learn more things about what Chili Piper can do.”

Even Distro's UI contributes to smoother operations and faster decision-making. One of Dan's favorites is the ability to test a Distro flow before publishing it.

“I can grab a Salesforce ID and say, ' would that customer flow through it? I don’t have to turn it all on to test it.”

How ClickSend uses Chili Piper to stay flexible as they grow

For ClickSend, Chili Piper's Distro quickly became the backbone of their operations.

"Salesforce gives you structure. Chili Piper ensures we talk to the right customers, at the right time.”

And when inspiration strikes mid-shower? Dan knows he can send a message to the Chili Piper team and get answers that same day.

Why Dan recommends Chili Piper

Chili Piper doesn't just help one team or use case at ClickSend. It supports their global GTM strategy, from marketing to sales to customer success.

It's flexible enough for simple scheduling linking, but efficient enough for complex global routing. And when the team needs help, Dan sends a Loom to Chili Piper's customer support and gets one back the same day.

"The support is second to none. I’ve never waited more than 24 hours."

For ClickSend, Chili Piper is more than a scheduling solution. It's how they work smarter, stay ahead of demand, and scale without compromise.