Winning Customers and Driving Growth with Chloe Stewart, Fractional CRO

10/10 GTM Episode 26
Transparent sales process - working together
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Welcome to Season 3 of 10/10 GTM: The Podcast for Revenue Leaders!

Our guest for Episode 26 is Chloe Stewart, Fractional CRO, and former CRO at Chloe is an accomplished revenue leader who builds and executes GTM models for high-growth companies. She brings more than 15 years of sales experience to the conversation. 

In this episode, Ross and Chloe discuss the importance of being someone customers want to buy from, the necessity of holding yourself accountable to outcomes and benchmarks, and why you have to be ruthless with qualification criteria. 

Listen to the episode here, and get the key takeaways from our conversation below.

Be someone customers want to buy from

Your job as a sales rep is to prioritize the relationship between you and your prospect, and help them make an informed decision. In order to do this effectively, think about the sales process from their perspective. 

Here are some key questions to help you align with your prospects' perspective:

  • Reflect on a positive buying experience you had recently. What made it great?
  • Did the purchasing process meet your expectations? Why or why not?

Keep in mind, your buyers have their own priorities at each stage of the sales process. Demonstrating alignment with their needs builds trust and positions you as someone they want to engage with. 

“At Eventbrite, we had a salesperson who was a true SME. She did a phenomenal job figuring out early if we could do what the customer wanted. She would guide them through the process, be transparent, and explain how things are done and why. If the prospect wasn’t ready to move forward, 60% of the time they would come back six months to a year later and say, ‘Hey, I haven’t stopped thinking about our interaction, and I think we’re ready to explore how we do it, and the way Eventbrite does it.’ How powerful is that? By creating a positive, memorable experience, you become a person people want to buy from,” says Chloe. 

The bottom line is that although you might not win the deal today, it’s a brand-building exercise for you and will ultimately come back to reap the rewards.  

Hold yourself accountable to outcomes & benchmarks

Focus on a handful of metrics or data points that clearly point to winning and retaining customers, ideally at your preferred velocity. Your team should be well-versed in KPIs such as win rates, time to close, deal size, verticals, and buyer personas, without having to stop and think about them. 


You have a finite number of selling hours per day — use that time to sell. Hold yourself accountable to outcomes and benchmarks so you can optimize your selling efforts and drive sustainable growth. 

Be ruthless with qualification criteria 

No one wants to waste time on deals they can’t win, retain, or expand. As the saying goes, “time kills all deals,” so no matter the temptation, don’t waste time on deals that aren’t healthy for the business, and in turn, the prospect. If you put a customer into a bad experience, they’re going to share that with everyone they know. You don’t want that as a brand. 

“Discovery is a lifestyle, but qualification is life or death,” says Chloe. “You need to be ruthless with qualification criteria and create an environment where qualification standards are always held on to.”

To reinforce this mindset, build a culture around compliance and enforcement of what wins. This sets the stage for sustainable growth and long-term success.

Rapid fire: Chloe’s fast sales insights

In a rapid-fire Q&A session, Chloe shares her insights with us on a wide range of topics: 

What’s the main reason most teams miss their ARR goals?  Lack of alignment across the company, bad leadership, unclear expectations.

What’s your favorite resource for revenue leaders? Old-fashioned get togethers with peers. I’m also a big Chris Walker fan. His podcast helps me keep my marketing chops somewhat on point. 

What’s the number one challenge for revenue leaders in 2024? Having a durable plan that aligns with the strategy of the business. It should reflect what your customers need to buy and want to buy.

SMB, Mid-market, or enterprise? Mid-market. But I love my SMB and Enterprise customers equally. 

What’s the most important org: Sales, CS, or Marketing? These teams should be one org. 

Best way to unplug from the demands of leadership? Spending time with peers. And going outside and touching grass! 

About Chloe

Chloe is an accomplished revenue leader who builds and executes GTM models for high-growth companies. As a Fractional CRO, she spends her days helping growing businesses modernize their financial back office. She also serves as a strategic advisor for Dooly and Showpass.