We sat down with Katie Cascino, a top account executive at Webflow, to discuss Sales at product-led companies. She started her product-led sales career as an SDR at Slack, building a team and then transitioned into being an AE. Her experience working in Sales at product-led companies is a great example why even the best PLG companies need Sales.  

How has selling evolved over the last five years?

I originally started in entry level sales, doing a hundred cold calls a day. I did that for about a year until Slack tapped me to help build their sales development team. That team became a foundational part of capitalizing on product-led growth at Slack.

Now that I'm at Webflow, which is another strong product-led growth company, I'm taking what I learned at Slack and applying it into playbooks at Webflow.

I can also say now, as a sales rep, I would never want to work for another company that's not a product-led growth company. I think it's super sticky for all the sales reps that get into PLG. They all feel this way.

The biggest challenge for a salesperson at a PLG company is creating focus. With so many customers you can talk to, which are the right ones.

What makes you never want to work for a non-PLG company again?

I went from cold calling buyers that don't even know our product or our name to having maybe a hundred warm leads a day, already using my product, already interested in understanding more.

So my job is now to help them understand what value the product can continue to provide their organization and ensure they're on the best plan fit for their business, which isn't necessarily the freemium model. All that opportunity means we don't have to do as much cold outreach as we did before.

A lot of people might have a misconception that PLG means no sales. How would you respond to that?

I love this question. Ironically enough, Slack's CEO used to say – and I think he was misquoted on this – 'we'll never have a sales team.' Of course, now they have a well oiled sales machine, so it is such a misconception that PLG eliminates the sales role.

I think the beauty of PLG is you can use product-led growth to build a customer base, and then when the time is right – for example, what I'm doing at Webflow now – we bring in reps to help users increase their value through a broader deployment.

It takes a village to craft a business case to get these enterprise organizations using our enterprise-tier product. So sales reps are often there to help PLG organizations with taking their product upmarket.

Are there any other big misconceptions around product-led sales you'd like to clear up?

I hear 'it must be so easy' all the time. It must sell itself, because all these folks are already using the product.

There's definitely a misconception that customers come in, already in love with the product from getting that free usage, and they're ready to upgrade without any help. But buyers like a human connection. They want that sales rep to come in and help consult with them on the product. I always say to my customers, my job is to make sure you're on the best plan for your business.

Having a sales rep guiding you through the process can help uncover that a better plan for an organization, whether it's because of security, scale, or dedicated support. If a customer is making the case for a premium tier, having a sales rep guide you through the process is really critical.

How's selling been similar or different between Slack and Webflow?

Slack works for every single line of business, so we were selling to every single persona. Webflow is more of a fit for marketers, designers, and dev team members. But it was nice to have the broader experience from Slack to draw on.

Slack and Webflow also model their packages in similar ways, where we're taking them from these freemium standard plans up to increased security, increased support, increased scale.

It's been easy using my experience from Slack to help Webflow users, primarily IT buyers or dev team buyers, explore the scale and support and security. That experience has been very repeatable.

What types of metrics or signals are you looking at when identifying which sign-ups you want to talk to?

I like to look for a couple of things. The sign up date shows me how long they've been using the product. If they've been using the product for a long time, we can assume they're getting value out of it, right?

I also look at who's using the product. With some organizations, you figure out if the account admins or owners are key decision makers for their orgs. Some of my accounts have been owned by the COO of the organization. When leadership has visibility into your product, they're more likely to take a meeting with you, since they already know your name and your product and what it can do.

Other [signals] depend on your product. With Webflow, we look at how many websites or workspaces they've created with us. We also want to see how many users they have in the product, right? If the entire org, multiple users, [is active], it's another good sign.

How often do you customize your email cadences?

I  take an 80-20 approach to my outreach.

I start with a high quality template, which often gets me 80% of the way there, and I'm typically customizing the other 20%. If I'm contacting C-level executives, I usually customize much more than 20% of my message.

The great thing about product-led sales is I can conduct user interviews and talk to the folks in the product to hear what's working and what isn't. I can take what I learn in these interviews into a customized email to a C-level executive to show I've already talked to their team and already understand their problems.

What do you think are the biggest opportunities to improve prospecting for PLG companies?

That's a really good question. I think there's a world where there's a better way to connect the insights we have within the product to my prospecting workflow.

Let's say Deborah, the CEO of the organization, is the owner on the account. Can I tie that directly into LinkedIn, so I can immediately get Deborah into a sales cadence? Can I click into her profile and send her a direct message?

I look for all these signals in my core application, but when I need to identify who to focus on, I need to switch to other sales tools like SalesLoft, or LinkedIn. Streamlining that workflow to help reps stay focused and tie those signals together would be very helpful.

I think strong workflows are key for a sales rep in general, they're just so critical. Sometimes I have like 17 tabs open and it feels like my brain is spiraling.

What are the best sales tools you use today?

Our number one sales tool is Gong. It's my favorite tool. It makes good reps great. It makes everyone more coachable, and you get insights on how to strengthen your meetings with customers. It's just so critical, especially while we're all remote.

I also like SalesLoft for automating my prospecting, and LinkedIn Sales Navigator too. I don't know how you could prospect without Sales Nav, so it's a really big one.

Finally, what are the qualities of a great product-led sales rep?

Adaptability and innovation. Not everyone has figured this out just yet, right? It's new. You have to kind of come in with a growth mindset and try to figure out new ways to prospect into this lead generation machine. Be eager to learn and grow your sales career with a new motion.