Product-Led Sales (PLS) AMA: Kenny Vincent

Alexa, CEO of Pocus, hosts Product-Led Sales (PLS) AMAs with PLS experts to share best practices, frameworks, and insights on this emerging category. These AMAs are an opportunity to ask PLS leaders any question — ranging from hiring to sales compensation to tech stack — in a low-key, casual environment.

The PLS AMAs are for members of the Product-Led Sales community, the go-to-place to learn, discuss, and connect with go-to-market (GTM) leaders at product-led companies. The goal of the community is to bring together the most thoughtful and innovative GTM leaders to build the next generation of sales together.

Interested in joining? Request an invite here.

Now keep reading for a recap of what we discussed in this week’s AMA chat.

Introducing Kenny, Global Director of Sales at ClickUp 👋

Kenny Vincent, Global Director of Sales at the lightning-fast growing startup ClickUp, has a track record of leading sales organizations at fast-growing companies. 

Kenny was the first customer success manager (CSM) at Yammer, where he first experienced what was, at that time, an extremely new approach — the bottoms-up, product-led growth (PLG) model.

He then went on to join App Annie as the first enterprise account executive when the team only had about 15 people. Similarly, Kenny became the first sales leader at ClickUp when there were only three sales reps and around 35 employees. Fast forward just a few years and today there are close to 1,000 employees and their sales org has grown to include about 160 people! 

In this AMA recap, we’ll cover some of our favorite parts of our expansive chat with Kenny, including these highlights: 

• How ClickUp transitioned from sales-led to product-led with help from a cross-functional proof-of-concept team
• What it took to get PLG buy-in 
• The process behind defining and operationalizing PQLs at ClickUp
• Balancing automation and customization when it comes to sales outreach
• The details of ClickUp’s self-serve and land-and-expand motions 

Walking Through ClickUp’s Transition From Sales-Led to Product-Led 

Originally, ClickUp’s approach was entirely sales-led. But during the interviewing process, Kenny learned the company was already generating an impressive 10,000 signups a day through their freemium and free trial motions.

Immediately, he saw the potential for them to go product-led. So when he came on board officially, he started to put processes into place to monetize all those leads. 

This is what that process looked like: 

The First PQL 

In early 2021, the ClickUp sales team launched their first product-qualified lead (PQL). It was a simple PQL based on firmographic data — they were focusing on executives in large companies. At this time, they were still focusing mostly on the sales-led motion. 

Seeing Proof and Building a Cross-Functional PLG Tiger Team 

After that first PQL generated some revenue, the ClickUp team decided to take things a step further by putting together a cross-functional team that could model what the product-led motion might look like. 

The tasks this team tackled in order to launch a product-led approach at ClickUp included: 

• Developing and validating a PQL that would produce quantity and quality  
• Operationalize lead distribution among sales reps
• Building out sequences and playbooks that provided education on the core tenets of the product-led approach

And who was on the cross-functional team that made these things happen? In addition to Kenny leading the charge, it also included: 

• A senior analyst from the revenue strategy team 
• Head of revenue strategy
• Head of analytics
• Head of digital sales

Over the past 6 months, this team has been able to introduce a robust hybrid sales approach at ClickUp. 

Kenny: “We put together a tiger team of executives and built out this really large model that was focusing on propping up five to six lead triggers, operationalizing them, enabling the sales group, and starting to bring that product-led motion into focus for the company. It's still a work in progress, but we've successfully moved from a pure sales-led to a hybrid product-led, sales-led motion.” 

How Did ClickUp Get All Those Free Signups? 🔍

Diving deeper into the 10,000 freemium and free trial signups that ClickUp was generating per day before Kenny even joined the team, we wanted to know what made that happen. 

According to Kenny, any growth strategy that you’ve heard about, ClickUp was probably already doing it. Some of their approaches included: 

• Thorough marketing and promotions
• Building a fully functional free version of their product 
• Creating a free trial version of their product

What’s driving signups today? 

• Referrals
• Word of mouth
• Guerilla marketing
• Ongoing branding efforts 

“It was pretty apparent to me my first day on the job, when they said they were getting 10,000 signups a day, that product-led growth was going to be a main strategy. I thought, ‘This is going to be a key growth driver for our company within a year, max.’ ”

What Defining and Operationalizing PQLs Looks Like at ClickUp

At ClickUp, defining PQLs relies on three data sets: fit, intent, and usage. 

In the beginning they tried blending these data sets in different ways in an attempt to make more dynamic personas. However, they soon realized how difficult it was to create weighted averages for different data sets.

Instead, today they stack rank on a high, medium, or low scale to create PQLs.

In terms of operationalizing their defined PQLs, over time they’ve formed a proprietary six-step process that takes them through the persona development cycle. 

Some steps in their PQL operationalization process include: 

• Detailed persona definition
• Validating personas by building a data profile
• Making sure lead automation and routing are working efficient
• A tiger team of sales reps and leaders developing playbooks and sequencing

With this process, they’ve been able to create a systematic approach to getting PQLs live.   

Kenny: “The first trigger we popped up took about six weeks, but then the next one took about a month. The last three or four that we've done have only taken about two weeks. So it's a pretty efficient process right now.” 

Getting Buy-In to Go Product-Led 💰

How did Kenny go from recognizing a missed opportunity to getting the buy-in that allowed him to pursue a product-led motion? 

His approach had a couple of elements: 

• The comprehensive model his tiger team had already built out and seen success with
• Validation from his own experience and what others in the space were doing 

Kenny: “We built out a model that was really comprehensive in nature, and it really showed that through propping up a series of lead triggers, validating the data, building out a playbook that focused on user value, and writing sequences — we were going to generate responses from users.

“And my experience at Yammer, my knowledge around what we did at App Annie, and what I know from what they already did at Dropbox and Slack. Knowing some of the big names in this space were already doing this was further validation that it could be done successfully.”  

What Hiring Looks Like after a Shift to Product-Led 

When CilckUp made the move to a product-led motion, they already had 80 of their current 160 sales reps in place — all of whom had been hired to execute a top-down sales strategy. 

So one of their biggest difficulties when rolling out the product-led approach was shifting the sales culture. Something that helped them make this transition was laser-focusing on hiring reps that understood the PLG model, especially from PLG orgs like Datadog, Slack, Dropbox, Twilio, and so on. 

Kenny: “I’d create a list of the top 20 PLG companies and I would be recruiting directly from them. That’s what I’d be focusing on.” 

Because it’s still difficult to find sales reps with a ton of experience in the product-led motion, he recommends focusing on hires that line up with your core values and exhibit some key characteristics. 

What are the main characteristics Kenny looks for when hiring for product-led sales?

• Grit 
• Energy 
• A hunger to learn and grow 

Kenny: “We tell our sales team that we’re effectively teaching them a cutting-edge sales methodology. It’s going to make them better reps. It’s something they can take with them that will help them with future employers.” 

Automation or Customization in Sales Outreach?

While they’re working to build out smarter automation when it comes to communication to lighten the load for sales reps, what ClickUp is experiencing now is that the email sequences they have in place rarely perform as well as customized messages do. 

So what they do is make sure that reps are well trained on spotting high-value PQLs, so they can prioritize hand-crafting messages for these leads.

Kenny: “For the highest-value PQLs, we’ve taught our reps to always write customized messages that highlight specifics about the lead’s usage, mention how ClickUp will drive value in certain instances, and let the lead know that the rep is their partner and available via phone call for support any time.”

Phone call? That’s right, the ClickUp team is big on phone chats as they’ve observed that calls have a 10 - 12x higher conversion rate than email on the first touch. 

Speaking of Phone Calls… 📲

Considering we’re all a little phone shy these days thanks to bad actors, how does ClickUp go about asking leads for phone numbers without scaring them off? 

They’re actually A/B testing right now how requiring, and not requiring, phone numbers affects the sign-up flow and the quality of signups. 

Kenny is an advocate of not necessarily requiring a phone number up front, but instead asking for it more often, optionally. 

Kenny: “There are multiple opportunities within their lifecycle when a user can input their phone number. So we're trying to put it in more places, and make it optional.” 

On top of this, they’ve layered a hand-raising motion that turns high-value question-askers into leads. This is another area where ClickUp has the opportunity to ask for a phone number before connecting a user with support.

Here’s what that workflow looks like: 

• Using an in-app chat tool, a user selects that they want to talk to a live agent
• Front (a customer communication platform) routes these conversations to ClickUp’s support team
• Support reroutes any conversations that have sales potential
• These convos go to Kenny, who routes them out to the appropriate sales reps

Mapping ClickUp’s Land-and-Expand Strategy

At ClickUp, the PLG motion is primarily focused on high-value leads in their target spaces: small and medium-sized, mid-market, and enterprise businesses. 

Their sales team takes a land-and-expand approach to flow all the way from single users up to decision-makers. Which, as Kenny says, requires a delicate hand. 

Kenny: “It's definitely a delicate balance of support vs. sales. You can't have reps just going in there and hard selling.”

To strike this careful balance, their land-and-expand strategy looks something like: 

• Creating rapport: getting to value swiftly, solving users’ specific pain points
• Building on rapport: supporting the preliminary user(s)  in rolling out the solution to 10 or 15 more folks within the company 
• Leveraging rapport: once you’ve proven value, asking that original core group that you connected with if a decision-maker would like to discuss purchasing the product for the whole team 

Why land-and-expand? Because Kenny learned “way back in the day at Yammer” that the value of an instance increases exponentially in relation to the number of users. So even going from one user to two users makes an instance 2x more valuable, and so on. Reps always strive to tie together as many users as possible, and support their collaboration. 

Kenny: “You don't necessarily need it to write an email introduction, but you can start to delicately approach the matter. You might say ‘Hey, you know there are six other people who are using the product and they're finding value through A, B, and C. Would you be interested in connecting with them and combining forces?’ ” 

In addition, they have another outlet for those leads that fall outside of their PQL definitions — a rich self-serve motion. Here, customer support steps in as needed to help drive users to convert, which they measure as entering credit card info. And, this motion is going pretty well.

Kenny: “The self-serve part of the business is almost as big as the sales-assisted side of the business. So it's a very successful self-service motion.”

Peeking Inside the ClickUp Sales Tech Stack 🖥️

According to Kenny, building out a tech stack that was actually beneficial for reps was a major project. 

Because ClickUp has thousands of features, just signaling to a rep that a user had high intent didn't mean anything. The question was always “High intent to do what?”

Kenny: “We needed to create consumable data and deliver it efficiently to reps, so they actually knew where to focus to drive engagement and adoption.” 

Here’s how sales reps consume lead data at ClickUp today:

• ClickUp’s “global 360 dashboard” is built on Tableau and embedded within the opportunity and lead objects in Salesforce
• Snowflake captures lead data
• Segment organizes and pipes data to the dashboard for easy consumption
• In one click, the dashboard can display a lead’s engagement across the whole domain, in almost real-time

For ClickUp, this level of customization has proven necessary. Before all of this, they did attempt to build out an analytics app within Salesforce, but found it too clunky for their needs. 

How Does ClickUp Quantify That PLG Was the Right Move? 🧮

Thanks to their PLG shift, ClickUp has grown from a low six-figure run rate to a high seven-figure run rate in four months.

On top of that phenomenal growth, PQLs are their largest lead source and their second-largest source of sales-assisted bookings. 

It’s easy to see why, today, PLG is a core element of their sales culture and how they’ve won buy-in from several executives. Kenny even sees PLG becoming the primary growth engine for ClickUp.

What’s Next for ClickUp’s ​​PLG Strategy?

ClickUp views their PLG approach as a two-parter. 

The first phase was all about validating the approach, putting the basic data architecture in place, and making sure it could be operationalized. 

Now, they’re ready to move into phase two. That entails getting the growth, marketing, product, and sales teams all aligned on a cohesive strategy. In addition, they’re “tiptoeing” into PLG for the enterprise. And as if that isn’t enough, they're also modernizing their tech stack — including building out automations that will help them scale into an even more successful sales program.

Kenny: “We're really trying to build sales into a world class program.” 

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Key Takeaways From Our AMA With Kenny

• Part of getting buy-in for a PLG motion at ClickUp was proving it could work, so Kenny built a cross-functional team to model PLG on a smaller scale. The main functions this team had to pull off were: developing and validating a successful PQL, operationalizing lead distribution, and creating sequences and playbooks to educate on PLG. 

• Operationalizing PQLs doesn’t have to be terribly complex. At ClickUp, they stack rank leads on a high, medium, or low scale to define PQLs. Then, they run PQLs through a proprietary persona development process. Every business’ process will look different, but theirs includes building detailed personas, validating personas via data profiles, lead automation and routing, and having sales reps and leaders create playbooks and sequencing. 

• At ClickUp, the sales team primarily focuses on a land-and-expand motion. Reps have been trained to use a delicate hand when building and leveraging rapport. On top of this, a self-serve workflow that employs customer support and a hand-raising motion that relies on in-app chat make sure leads at every level find value. 

• ClickUp’s robust tech stack brings together Tableau, Salesforce, Snowflake, and Segment to create a dashboard that displays lead engagement across the whole domain in one click, and in almost real-time. 

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