How Calendly overhauled their product-led sales motion
CRO and CMO Jessica Gilmartin shares a first-hand account of how Calendly revamped their lead routing, qualification, and GTM org
👋 Hi, it’s Kyle and I’m back with Growth Unhinged, my newsletter that explores the unexpected behind the fastest-growing startups. I’ve been cooking up something exciting: a new Icons series, featuring how the best-of-the-best pair product-led growth (PLG) and sales.
When I think of exceptional PLG businesses, I immediately think of Calendly. I might be biased – OpenView is an investor and I’m an avid Calendly user – but I think it’s more than that. The company launched in 2013 and was initially bootstrapped, costing founder and CEO Tope Awotona “every cent [he] had.” Today, Calendly is better known for its unparalleled viral loop (which I covered previously) and generous free experience, making them one of the rare household names in SaaS.
Calendly attracts not only individuals, but a shocking number of enterprises (86% of the Fortune 500 use it). Under the leadership of CRO and CMO Jessica Gilmartin, Calendly has now built an epic hybrid go-to-market motion to unlock this enterprise demand. I invited Jessica to share how Calendly overhauled their product-led sales approach – and the 🔥 results they’ve seen.
I joined Calendly, the scheduling automation platform, as chief marketing officer in January 2023. It’s hard to find someone in the tech industry who hasn’t heard of us or been sent a Calendly link. Today, we serve more than 20 million users around the world, from solopreneurs to enterprises like Lyft and Dropbox, including millions who sign up for the product each year.
Our funnel was a CMO’s dream – and biggest nightmare.
Originally, we operated like a traditional hybrid business. We had a product-led growth (PLG) motion where anyone could sign up, trial the product, and convert in a self-serve way, and a sales-led growth (SLG) motion where we would generate leads through the sales funnel, in the hope of signing contracts for larger deals.
It worked, but it was inefficient and expensive. There were examples of sales closing $3,000 deals that should have been self-serve. And there were large companies with a willingness to spend tens of thousands signing up for a $192 annual single-seat plan, which then needed a longer-term expansion play to get to real revenue.
In January 2024, I was promoted to be CRO (as well as CMO) and decided to overhaul our product-led sales motion. We changed our whole model of how we score leads, and how we route them instantly to a salesperson or support rep using Ada (chat), Calendly (scheduling), Clearbit (scoring), 6sense (intent data), and other tools. We also redefined our customer journey to get leads into the PLG vs. the SLG funnel based on their characteristics and the actions they take.
These changes dramatically increased our efficiency and meeting rate in only a few months, and, most importantly, provided a better experience for our prospects and customers. Here’s what we did step-by-step.
I only get to write this piece because of the contributions from my team. Special thanks to Sarah Jackson (Head of RevOps), Darren Chait (Head of Growth Marketing), and Jennifer Garcia (Senior Manager of Website Marketing) for making this possible.
Lead routing is make-or-break – and most get it wrong
I’ve probably had the same conversation 20 times over the past couple of months as CMOs are thinking through their lead routing and hybrid sales motions. Nearly everyone admits that their current processes aren’t very efficient or well thought out. I see three common traps:
Paying too much attention to getting new leads and not enough to scoring the ones they already have
It’s much sexier and it feels more tangible to focus on driving new leads than on optimizing existing leads. But the leaky lead bucket is real, and companies waste thousands – if not hundreds of thousands of dollars – on leads that get lost in qualifying, routing, and scheduling purgatory.
Sending too many leads to the sales team, creating inefficiencies
When you have inbound leads, especially when they’re at a relatively low volume, it’s tempting to treat every lead the same and send them all to a human being to close or disqualify. Those economics get out of whack very quickly in a PLG model where annual contract value (ACV) is low and volume is high, so you have to insert technology into every step of the process.
Thinking all pages on your website have equal intent and awareness
I’ve always thought that when someone clicks on a “contact sales” button, it doesn’t matter where on the website they came from as long as they meet the right demographic criteria. Fortunately, my team is smarter than I am and re-designed our user journey and calls to action depending on the web page.
How we fixed it at Calendly
When I took over sales in January and we overhauled our lead process, we had three goals:
Increase the efficiency of our sales and marketing spend
Create a world class customer experience
Build a personalized user journey at (huge) scale
This translated into re-organizing the sales team around how people buy, redesigning our website experience to better capture demand, revamping which leads we send to sales, embracing automation to maximize efficiency, and disqualifying prospects without hurting their customer experience.
Re-organized the sales team around how people buy
We took a first principles approach to reorganizing our sales team, starting with looking back at our historical lead volume across many different dimensions and overlaying that data with how people actually buy. Those insights led us to a three-tiered system:
Support-assist team
Catches prospects who want to talk to an AE, but are too small in size
Salaried team since their primary focus is on customer experience.
In a hybrid PLG model, people often bounce between support and sales. Our support-assist rep’s primary job is to answer product questions, but they also close small deals and route larger deals to our sales team if we get our qualifying wrong.
When we disqualify a prospect on a contact sales form, they are prompted to chat with a support assist rep via an Ada chatbot. We went with Ada because an important part of this strategy was to have one customer experience regardless of whether it was a sales lead being routed to sales or a user that needed support.
Velocity team
Focuses on selling our Teams plan, regardless of company size.
Primarily close low- to medium-ACV deals as quickly as possible, ideally within the same month.
Also qualify deals for enterprise (and get incentives to route these).
In a hybrid PLG model, company size isn’t the primary determinant of deal size. You can have Fortune 500 companies that want to purchase 20 seats for a small team or SMBs with highly sophisticated enterprise-grade requirements. We’ve found that we need to get creative with how we structure our qualifying questions, routing, team structures, and incentives.
Enterprise team
Traditional enterprise sales team that sells our largest, most complicated deals.
This team is focused on closing high-ACV new and expansion opportunities.
Redesigned our website experience to capture demand
At Calendly, like at many other product-led businesses, our website is where we capture demand.
Ultimately, we were able to increase the number of leads from the website by 50%. And we did that while decreasing the money we spent on lead generation, by simply improving the user flow to give prospects the precise next step at the right moment in time.
First, we did user research across our website and looked deeply into conversion rates on each page taking into account site visitor paths. We identified that people visiting calendly.com wanted to either sign up for Calendly, talk to someone, or see Calendly without signing up (i.e. a demo).
Based on these page-by-page insights, we placed CTAs in the right places based on the most common intent in that location. For example, on our pricing and enterprise pages, you’ll see ‘Talk to Sales’ CTAs, but on specific feature pages you’ll see ‘Get a Demo’ CTAs.
We focused these CTAs not just on intent, but also on awareness. We assume visitors on our homepage hero know very little about Calendly. By contrast, by the time someone has gotten to the fourth fold on our website embed feature, we assume they are really getting into how they'd schedule from their website, so we ramped up the product details and tested out different CTAs.
Revamped which leads we send to sales
Keep reading with a 7-day free trial
Subscribe to Kyle Poyar’s Growth Unhinged to keep reading this post and get 7 days of free access to the full post archives.
 | A guest post by
|