PLS Community Spotlight: Rob Falcone

Meet the product-led sales innovator and community all-star.

Sandy Mangat
October 11, 2021
PLS Community Spotlight: Rob Falcone

The product-led movement has ignited new and exciting career opportunities for customer-facing teams, from new marketing and sales roles to entirely new teams, and so much more still to come. We’ve seen these exciting changes first-hand through the eyes of our product-led sales (PLS) community and the members who are leading the path forward in this exciting new category. 

We wanted a way to find a way to highlight and celebrate the forward-thinking work of our PLS community “Product-Led Sales Community Spotlight” was born. 

In this series, we interview members of our community to highlight their career path, how they found their way into the world of product-led, their advice for newbies, and their predictions for the future of product-led sales. 

Meet Rob Falcone, Senior Director Product-Led Sales at Guru

Rob is a product-led sales leader at Guru, who leads the company’s product specialist and sales engineering teams. Rob has worked in various sales roles at SaaS companies for over 10 years as an individual contributor and as a sales leader who has built teams from the ground up. Rob is not only a veteran seller and an early innovator of product-led sales, but he is also the author of the bestseller book, Just F*ing Demo!.

Tell us a little bit about your role at Guru

At Guru, I lead our product specialist (aka sales-assist) and sales engineering functions. They're both super important for companies like Guru that shift from sales to product-led, because they both involve helping customers connect the product's many features and functionalities to their specific company and use case.

Where they differ is in the “who” and “how.” Teams like product specialists do this with a wider breadth of customers, with relatively low touch tactics. Conversely, sales engineers operate with a smaller subset of customers, at much greater depth through demos and guided trials.

Tell us about your current company, Guru

Our customers use Guru to organize all their information in one place and then access it whenever and wherever they need. It saves people a ton of time and stress and makes them more self-sufficient, which is critical in the new remote-hybrid world.

How did you get your start in sales?

I always like to say I got my start in sales when I was a teenager, selling fake Oakleys at the baseball academy where I worked. I’d buy them in bulk, and then sit there in the pro shop with my little Tupperware of shades and a sign that said Replica Oakleys, and sell them for 15 bucks. I think that that's where I got my entrepreneurial bug and sales bug. 

Later on, I got my start in tech as a customer success manager at Monetate. Since I knew the product and how customers were using it, I got tapped to join the sales engineering team. From there I’ve held a number of roles ranging from account executive to VP of Sales.

When did you first hear about product-led sales?

I was actually recruited to join Guru as the company was heading upmarket using a very sales-led approach. I joined to help build some of that value selling rigor: how do we focus on what the customer is trying to accomplish, uncover their pain, uncover their goals and then determine the product solution needed. 

Over time, as the company pivoted towards product-led, my customer success and sales engineering background lended itself to helping spearhead the functional changes that would be required of our sales org. 

In the early days of this shift, one of the first things we did was audit where remnants of our sales-led approach might actually be unintentionally adding friction to our customer’s lives. A simple example was how we’d engage with customers via live chat.  

In the old world, if someone reached out via chat asking for help, we’d typically respond by saying “sure, let’s hop on a Zoom, so we can talk about what you’re trying to accomplish.” It was totally well intentioned - we want to help! - but in a product-led context, what customers want in that scenario is a quick answer so they can get back to their trial.

In response, we re-jiggered our people and processes, so that we’re first getting the customer the information they need as quickly as possible, and then offering a call as a follow up, in the scenarios where it’d be a value add for the customer.

What’s the best part of your role?

This one's an easy one: helping people advance in their careers. 

I definitely have made a ton of mistakes myself throughout my career and have had some awesome people help me along the way, so having the ability to help folks avoid the same mis-steps in the same fashion is super rewarding.

It makes me so happy seeing people on prior teams of mine on LinkedIn, in more senior roles or even leading teams of their own.

What’s your advice to your younger self?

If I was giving advice to myself in my earlier years, it would be to seek balance.  It's one of our core values at Guru but it's something that I've only recently come to understand. 

If you’re constantly going 100 miles an hour at work, it’s going to impact your life outside work. 

It’s going to lead to burnout and stress and unhappiness. 

Be intentional about everything you do. Take a few minutes each day to stop and clear your head. Shut your work down at the end of the day and be present with your family. You’ll be happier, and surprisingly more productive at work.

What about advice for newbies looking to join a PLG company?

To the extent that you can, find a company that you have some personal affinity to. Look for a company whose values reflect your own, a product that solves a pain near and dear to you, or serves customers that you admire.

When I took my first job after college with Monetate, I was drawn to the fact that they served ecommerce companies because I love online shopping. Even though I was very inexperienced in tech, I was able to contribute right away, because I intimately understood how our customers like J.Crew and others were trying to serve online shoppers. 

Fast forward to today … I use the Guru product extensively, and can see what an important problem it solves for people building teams, that I get a certain thrill out of helping our customers see the same benefit.

Can traditional enterprise sales-trained folks make the switch to PLS?

Well, there is absolutely still a need for “enterprise sales reps” in product-led companies. Slack, Zoom, all of these massive product-led success stories now have enterprise sales teams to help penetrate large enterprise customers. 

The key, in my opinion, is the need to evolve, and add new skillsets needed to be successful, kind of like Kobe Bryant over the course of his career. As his speed and bounce started to erode, he started to add new elements to his game. 

The same goes for enterprise sellers. A great example is how data can be used to inform discovery conversations in product-led. Before product-led, you’d go into a discovery call with only the research you could do about a person or company, and your call would start from there. 

Now, in a product-led world where the customer is likely already using the product to some degree, the enterprise sellers that succeed will be the ones who can look at that customer’s product usage data as critical indicators of what they’re trying to accomplish, and start their discovery process there. 

It’s a more relevant and helpful experience for the customer, which in turn has obvious benefits for the seller.

Where do you see product-led sales going in the next five years or 10 years?

In my opinion, the career opportunities for product-led sales professionals will continue to increase in the coming years, for two reasons. 

One, companies starting with a product-led motion now have seen that they can go further, faster, by successfully layering product-led growth and human sales. 

Second, on the flip-side, is the fact that more and more previously sales-led companies are going to to be shifting more toward product-led with some sort of product experience available for customers. Why? Because it’s how humans buy in their personal lives. The fact remains that people want to try things and so I think that more and more companies are just going to be asking themselves how can we get people more hands-on with the product. 

Rapid-fire fun round

Favorite TV show currently? Wu-Tang American Saga

Favorite emoji? I like making my own in Slack

Travel bucket list? Hawaii, Italy, and the UK (in that order)

Thanks for sharing your story Rob!

If you're new to product-led sales or looking to connect with experts, join Pocus' Product-Led Sales community by requesting an invite. Want to nominate a member of the community for a spotlight? Connect with Sandy Mangat on the PLS community slack.

Sandy Mangat
Head of Marketing at Pocus
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