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Don’t Be Afraid to Ask for It with Stephanie Brookby {Hey Salespeople Podcast}

July 11, 2019

Being scrappy and not being afraid to ask for what you want are traits that can get you far in your career.

Stephanie Brookby is no stranger to doing just that. She is the Director of Customer Value at, but it’s a role she prepared for with 8 years at Google where she learned about value engineering. Throughout her career, Stephanie has developed the invaluable skill of carving out a niche for yourself.

In this episode, Jeremey Donovan, Salesloft’s VP of Sales Strategy, and Stephanie explore the concept of value engineering – what it is and how to implement it. Stephanie also shares some great advice for those who are new in their careers, including tips on identifying a mentor.

Stephanie Brookby, Director of Customer Value at Pendo.

Listen to this episode for answers questions like:

  • What characteristics does she look for when hiring?
  • How advice does Stephanie have for identifying a mentor?
  • What exactly is value engineering?
  • How did Stephanie succeed at coming in brand new at Pendo and changing the GTM strategy?
  • How can you involve the champion in the buying process and inspire them to co-present the solution?

Keep reading for some of the highlights from this episode below.


Jeremey: Like you, many of the folks that I’ve spoken to had some sort of hustle growing up. Is that something you look for when you’re hiring people?

Stephanie: I always look for some essence of scrappiness, whether that’s like a side hustle or not. I look for people who go into even larger organizations and find an area of opportunity to either become an expert or to really refine their skills and almost carve out a practice for themselves.

That scrappiness and being able to see opportunity and generate a concept around it as a really important skill in sales. It’s something that I think sets apart great reps from average reps.


Stephanie: I had a really great mentor who really encouraged me to have my seat at the table and be confident in the things I knew. I was encouraged to be a little bit of a disruptive voice when I needed to be because this was new territory. That helped me a lot.

Jeremey: I know a lot of listeners are at different stages in their careers. For those who haven’t yet cracked the code on finding a great mentor, what advice do you have?

Stephanie: I was always encouraged to seek out people that you admire, seek out the people you want to be in the next 10 years. Never be afraid to ask for time, but do it judiciously and be respectful if they say no, or that their time is limited. But don’t ever be afraid to ask.

When I started at Rosetta, I was really mindful about putting five minutes on someone’s calendar for coffee. I also asked people’s opinions about the senior leadership they thought were doing interesting things or had interesting perspectives. That really pushed me to just explore and be open to speaking with different people and seeking out different perspectives.

My mentor there, his name is Jim Halladay, was a truly innovative thinker, but also a very empathetic manager. I really respected how he treated everyone within the organization. Getting time with him and having the ability even just to pick his brain for a few minutes was just hugely valuable. It definitely shaped the way I think about my management style and how I look to build a team, the qualities I look for in others.

Advice for new grads

Jeremey: What other advice do you have for new graduates?

Stephanie: Number one, just never be afraid to ask. I think if I hadn’t honed in on this opportunity and sought it out, I would have been so bored and not pushing myself to my full capabilities. It’s a tough road when you’re the lowest man at an agency. Finding other opportunities to expand myself and my skill set was super formative and important.

The advice I give to young graduates is to find opportunities where you’re not going to necessarily go super deep into one skill, but you’re going to get exposure to a lot of things and wear a lot of hats. That just makes you so much more flexible and agile in the next step you take in your career.

Value Engineering

Jeremey: How did you start on your value solutions or value engineering journey?

Stephanie: We built up a super strong account management and account strategy function at Wildfire in the months prior to the acquisition by Google. We brought in a new head of enterprise sales, a gentleman named Paul Embry, who was incredibly transformational at Wildfire. One of the first things he did upon joining was to build out a sales engineering team and a value engineering team.

In order for us to win upmarket, in order for us to really capture the mindshare of big strategic customers, we can’t just sell on the value of our technology working. We need to sell on the value of what our technology will transform for our customers. That was a huge change in our sales muscle. As an organization, it helped us grow up and become far more transformational in how we approached our customers and the engagement with our customers.

Jeremey: Why build both a sales engineering team and a value engineering team? Why not have that be the same team?

Stephanie: It’s about the constituents that those functions serve. They’re absolutely a sister team. There’s overlap, and they work best in tandem to uncover the business issues and achieve the outcomes we’re trying to drive.

I think it’s just a different skill set. In younger sales organizations, those can absolutely be the same person. When you get into an enterprise sale, it’s really important for those roles to be differentiated, because they’re speaking to different people. Their work output is specific to the audiences they’re serving.

Building out a value engineering function

Jeremey: Now you’re the Director of Customer Value at Pendo. What advice do you have for someone who wants to build out a value engineering function?

Stephanie: First and foremost, I think the number one thing that enables a value engineering team to be successful, is leadership support. I’m talking all levels of leadership: sales management, customer support management, all the way up to the CEO. It’s really important because it is changing the way your entire organization thinks about how they communicate with prospective and active customers.

You’re going to come in and you’re going to ruffle a lot of feathers because you’re just disrupting the status quo. You’re telling people that how we used to sell is great, but it isn’t going to work anymore. And you have to take a step back, and you might have to slow down in order to be more effective in the long run. Having leadership support around that, and constantly echoing to the sales force that this is how we are going to go to market from here on out. We’re going to lead with business outcomes and then support with solutions is really, really critical to the success of this function.

Number two, you’ve got to be ready to be scrappy in order to build out the ROI. To understand the impact of a piece of technology on a customer, you’ve got to dig into data. So when I say scrappy, you got to find the people who know the data really well. They will be your advocate and your helper and actually turn that into meaningful insights for your customers. The minute I came in, I found out we had a data scientist. I have a weekly stand up with her because she knows our data, knows the impact we can have better than anybody.

On top of that, I wanted customer stories and understanding how customers are stretching the limits of a platform or getting the most value out of the platform. Even though the majority of my focus is pre-sales, being closely aligned to the post-sales team, who lives and breathes our customers was also mission critical. Really getting in and understanding what this narrative looked like.

Lastly, partnering really closely with customer marketing and our marketing team. I wanted to make sure everything that I was doing on the front lines in active deals was then being translated into how we thought about our positioning, and really how we thought about being top-of-mind when it comes to our enterprise and strategic customers.

That’s all been the framework, the things I needed to have in place to be successful. Like every great startup, it’s just about hustling and doing more than you ever thought you could do in the span of 10 hours.

THERE’S A LOT MORE AFTER THIS! Listen to the full podcast for more on value engineering and engaging a value consultant. 

If you have a passion for the art and the science of sales, are looking to further your career, or just want to hear some great, practical tips, ‘Hey Salespeople’ is the podcast for you. Subscribe so you can follow along as Jeremey interviews the brightest minds in modern sales to bring you immediately actionable advice. Listen and subscribe here.