5 Characteristics to Look For When Hiring the Sales-Assist Role

What to look out for when hiring your sales-assist (aka product specialist) team

Rob Falcone
August 4, 2021
5 Characteristics to Look For When Hiring the Sales-Assist Role

Product-led sales is the next generation of sales. New sales motion = new type of sales team. When thinking about building your product-led sales team, it would be a mistake to screen for the exact same qualities and skill sets that you would for a traditional enterprise sales role. 

Why? Because while many of the skill sets are similar, there are still key differences to keep in mind. And, even if some traditional sales reps could successfully transition into great PLS reps, it’s not like you could easily filter their resumes by searching for experience in product-led sales. So, what should you do? You should search for candidates who demonstrate certain superpowers. 

As you might recall from this post, there are three functions within the product-led sales organization: self-serve, sales-assist, and sales. You might also recall that - depending on the company - there are many names for the sales-assist role, including “Product Specialist”. In this post, we’ll be using both terms interchangeably as we explore the responsibilities and hiring techniques for the sales-assist team. 

We sat down with Rob Falcone, a product-led sales leader at Guru, who leads the company’s product specialist and sales engineering teams. Not only is Rob one of the early innovators and adopters of the product-led sales motion, but he is also the author of the bestseller book, Just F*ing Demo!.

Quick primer on the sales-assist team (aka product specialist team at Guru)

The product specialist team bridges the gap between the self-serve team and the sales team, adding value by guiding. 

“Our Product Specialists’ charter is to uncover and eliminate friction for our customers. For those struggling to use the product on their own, this could be a quick one time engagement guide toward success. For others struggling with more strategic challenges - stakeholder buy-in, competitive evaluations, or deeper guided trials -  guiding them to the appropriate expert in sales or sales engineering could be the move.” - Rob

Within this vein of eliminating friction and guiding next steps, the product specialist team essentially serves three functions: 

  1. Accelerate self-serve signup flows. The Product Specialist supports self-serve users to accelerate their time to value in the product. Essentially, the product specialist team helps the user get to their “aha moment” as quickly as possible.
  2. Flag and surface big opportunities. The Product Specialist identifies users within the self-serve pipeline that have a high propensity to buy based on their product usage and their requests. If the user is a high-quality lead, the product specialist team passes the lead to the sales team.
  3. Collect and route user feedback. The Product Specialist leverages its exposure to the users to gather valuable customer feedback. The product specialist team routes the feedback to the relevant team (marketing, product, growth, etc.), allowing them to make improvements. 
The 5 Characteristics of Successful Sales-Assist Teams

To identify candidates who are most likely to be successful in this role, you should screen for applications who have demonstrated the following abilities:

1. Consultative

“Help, not sell” is a common catchphrase product-led sales leaders use to describe the function of the sales-assist team. The Product Specialist is all about understanding the users’ pain points and use cases for the product so that they can help them realize more value out of the product. Typically, great candidates are those who practice active listening and are creative problem solvers.


Sample screening question: Tell us about a time when you uncovered a customer’s pain point, and walk me through the specific steps you took to address it. What was the outcome? 

2. User-centric

In order to properly advise the user on the best way to use the product, and shepherd them on the right path, the sales-assist role must deeply understand the users’ needs. It’s their job to be the expert and internal representative of the users’ pain points. They must interpret what a customer is experiencing (whether or not the user verbalizes it fully) and figure out how the product can serve them. Typically, great candidates are those who demonstrate empathy and are obsessed with improving the customer experience.  

Sample screening question: Imagine a typical user of our product. Describe that user persona, highlighting potential pain points or product use cases that you’d be interested in understanding better. 

3. Cross-functional collaborator & communicator

As mentioned above, since the Product Specialist understands the user better than anyone else in the organization, this team has valuable information to disseminate to different teams internally.  For this reason, the product specialist team needs to be made up of individuals who understand departmental dynamics, can identify and build relationships with cross-functional teammates and know how to translate user feedback into actionable insights. Typically, great candidates are those who are agile networkers and effective communicators.

Sample screening question: Tell us about a role or experience in which you’ve needed to communicate and collaborate with several teams across your organization in order to get something done. How did you do it, and what did you achieve? 

4. Well-Rounded

The skill sets required for this role are a mix of customer support, customer success, and sales. So, how do you find someone who has experience in all three areas? Hint: you don’t (or if you do, hire that person and hang on tightly to them!). Instead of looking for a candidate with experience in these areas, you should optimize for someone who can act as a jack-of-all-trades. They should be scrappy and willing to figure things out as they come up. They should be a mix of customer-facing and analytical. Typically, great candidates are those who are not afraid to dive headfirst into a role, and who can juggle various responsibilities at once. 

Sample screening question: Tell us about a time when your job required you to wear many different hats. Was that generalist experience something you enjoyed doing? 

5. Comfortable with Data

One of the promises of product-led sales is the ability to be more relevant, more quickly, because you have data on how the customer has (or has not!) been using the product.

“In the same way we used to leverage research and quotes to provide relevant demos, we now need to utilize product data. Just like it wasn’t acceptable to have a customer verbally tell you something they care about during a discovery conversation and you demo something completely unrelated, it’s poor practice to show up to a product-led conversation starting from zero. You should come with a point of view on how and where you can help.” - Rob

Sample screening question: Tell us about a time when you leveraged data to inform a decision. How did you analyze the data, what insights did it provide, and how did your findings inform your decision?

Now that you’re up to speed on what the sales-assist/product specialist team does, and which attributes make certain candidates better fits for this role than others, you are ready to start hiring this PLS function into your product-led organization! What are you waiting for? 

Sign up for our newsletter below so that you can follow along and learn about our hiring tips for the PLS sales team next.

Rob Falcone leads the Product Specialist team (sales-assist) and Sales Strategy at Guru. He’s also the author of Just F*ing Demo!, which peaked at #1 on the Amazon sales presentation bestsellers list.

Rob Falcone
Senior Director at Guru
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