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
Traditional prospecting is inefficient and expensive, particularly in a hybrid model with relatively low ACVs (at Calendly, plans start at only $10 per user per month).
But we used to have SDRs set up prospect meetings and qualify for AEs. We’ve replaced SDRs with a marketing-forward approach to prospecting that leans heavily on technology.
We use as much intelligence about accounts as possible to get hand-raisers for sales, including 6sense, intent signals, and product-qualified leads (PQLs). It’s worth calling out that despite our large user base, PQLs at Calendly are still a small (albeit growing) part of our sales leads; they’re gravy, not the meat. Understanding the company's intent and aggregating all the information about how users in a company are engaging with Calendly is where the magic happens.
For example, we could have 1,000 Calendly users at the same company, but our sales team wouldn't know it because they're not in Salesforce. By aggregating both internal and external data points we can see if there are multiple Directors or VPs using and looking for scheduling, and put together an advertising plan that targets that company to drive inbound leads.
Embraced automation to maximize efficiency
Bringing back the efficiency point, how do we deliver on the thousands of prospects every month who want to talk to someone or get a demo in a sustainable way? Luckily for us, Calendly has a routing product with its HubSpot, Salesforce, and Marketo integrations. We’re definitely drinking our own champagne here.
Our “Talk to Sales” form asks users for their name and email and how they plan on using Calendly. We then use Clearbit forms in the background, and if we don’t know their company size or industry from their email, we ask for that too.
That gives us a really good picture of how qualified the prospect is for Sales. We’ve also recently been experimenting with website behavioral data prior to contacting sales to help with qualification, such as time on site, pages visited, and content viewed.
Based on our qualification rules, one of three things happen when a prospect submits a lead form: (1) they’re assigned a new AE, (2) they get sent to their already assigned AE, or (3) they get disqualified from sales and sent to support-assist instead.
A new prospect that is qualified for Sales: Calendly Routing launches a modal to book a time to meet with Sales (and simultaneously creates the lead in Marketo and Salesforce ready for the assigned Account Executive).
An existing prospect or customer: Calendly Routing allows the prospect to book a time with their already assigned Account Executive.
A disqualified prospect: We connect them with support-assist in an embedded live chat. If they don’t engage with chat, then our support-assist team member will send them a follow up email.
The beauty with this system is that there are no dead ends and every customer gets to book a meeting or speak to a person immediately – no waiting for a qualification call with an SDR. Even though our goal was to drive sales efficiency, we ended up increasing the number of qualified meetings booked by nearly 40%.
Disqualified prospects without hurting their customer experience
I believe the prospect’s experience should be guided by what they want to do, not what we want them to do. If the VP of Sales at a huge company wants to sign up for Calendly’s free plan, we let them sign up and we try to create a great product experience for them afterwards that encourages them to raise their hand to talk to sales. I don’t force them to talk to a salesperson first just because that’s more valuable to us.
On the flip side, there are thousands of SMB prospects who want to see Calendly in action but are too small to talk to sales. Most companies would not respond to these customers, but I challenged my team to create no dead ends. Everyone who comes to our website is a potential customer (or detractor) and we need to create a great customer experience while maintaining our target efficiency ratios.
If a prospect who wants to view a demo has been disqualified, we direct them to an existing demo that’s been customized based on their role type. For example, a salesperson will learn about our Salesforce integrations and our capabilities allowing a user to instantly book a meeting. If they still have questions after the demo, they’re prompted to connect with a support-assist rep to hopefully answer their questions and close a deal.
The takeaway is that everyone who wants to talk to someone at Calendly can do so, but on our side, we’re allocating the right resource to ensure efficiency and maximize revenue from that prospect, giving all involved a good experience. The best bit is all the routing logic is handled by Calendly. We literally set the rules in our UI to determine which prospects get routed to AEs, or disqualified and sent to the non-sales experiences mentioned above.
It takes an iterative process to (finally) get it right
There were three requirements to get this to work for us: (1) assigning a dedicated owner responsible for lead routing and lead scoring, (2) rapid iteration, and (3) a tight partnership between sales and marketing.
Our lead routing tiger team met every single week and (thanks to Calendly Routing’s UI) we were able to make lead routing changes in minutes. Many of these changes came from the sales team (admittedly, we didn’t prioritize getting this feedback prior to January).
By talking to sales every week we were able to pick up on a lot of nuances that made a huge difference in dialing in exactly the right leads for each sales team. For example, we are a popular product among colleges and universities. These are huge organizations from an employee perspective so we used to send those leads to our enterprise team. Our enterprise sales reps let us know that universities typically start with small deals so they were passing almost every one of those sales down to the velocity team. We changed our routing rules for EDU and saw an immediately positive change in close rates and a better customer experience.
The TL;DR:
A more efficient go-to-market motion is hiding in plain sight. Go-to-market teams usually pay too much attention to getting new leads and not enough to scoring the ones they already have.
Use technology to disqualify leads before they get to sales. We previously had SDRs set up prospect meetings and qualify for AE’s. We’ve replaced that with a marketing-forward approach to prospecting that leans heavily on technology – and increased the number of qualified meetings booked by 40%.
Redesign the website experience based on the prospect’s intent and awareness. Tailoring our website CTAs increased the number of leads from the website by 50%.
Don’t create dead-ends for prospects even if the deal size might be small. For us, scaled sales assets (like on-demand demos), a support-assist team, and a Chatbot (Ada) allow us to offer a great customer experience while staying lean.
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How they rewired PLG motion to create a well balanced experience for both SMBs and Enterprises is mind blowing. Great insights!
Loved it. Drive value to users first principle coupled with using tech to pre qualify is a magic bullet for improving efficiency in plg driven sales motion.