Creating faster account expansion is always a priority, particularly in a challenging economy. The key to expansion is continual discovery across your entire go-to-market (GTM) team.

“Rather than being siloed focusing on a single product, you have to always connect to broader business value and the full scope of how you are helping,” says Phil Charland, Chief Revenue Officer at SchoolStatus.

Phil joined SchoolStatus as CRO to rapidly build a shared sales and go-to-market strategy and a clear enterprise value prop across five different product sets and teams (SchoolStatus, Operoo, TeachBoost, Smore, SI&A). 

He understood that feature or product-led selling is hard to differentiate. Instead, he wants his team to use strong discovery to deeply understand the needs of each customer and then map all their product capabilities to build an overall story about value.  

And, Phil asks his team to do this continuously in every single buyer and customer interaction, not just in the early part of the sales process.

I had a chance to talk to Phil recently and learn his key strategies for getting a go-to-market team aligned on enterprise value.

1) Using Discovery as a Differentiator 🔎

Building a strong enterprise value proposition starts with using deep discovery as a differentiator rather than conducting shallow discovery with stock questions. 

Phil explains: “If you can train an entire team to go deeper, to ask better questions than your competitors, that alone is differentiated and goes beyond your product capabilities.”

Good discovery improves every of the buyer or customer conversation by helping to:

  • Activate your buying group for diverse sets of administrator decision-makers and committee-based decisions.  
  • Fully understand the needs of the buying group and map them to each stakeholder.
  • Create value through the sales and customer success (CS) process by truly listening to their needs; understand the buyer and become a trusted advisor. 

2) Aligning Discovery Across the GTM Team

Strong discovery on opportunities for enterprise value only works if you bring your whole go-to-market team together around common playbooks and shared processes.

“It’s hard to harmonize multiple teams without commonality in the approach to your go to market motion,” Phil explains. “It’s critical to have a common set of playbooks, especially, as you’re scaling your organization and bringing together teams with different philosophies.”

Phil notes that the two things that can most strongly connect the whole GTM motion on enterprise value are consistent discovery and customer success stories.

In particular, he recommends:

  • Making sure discovery is not just an upfront thing that happens at the beginning of the sales process. Rather, it should be embedded throughout.
  • Training all your GTM teams to move from shallow discovery, or “top of trees” which all of your competitors are doing, to deeper questions to truly understand buyer and customer value.
  • Develop external stories for use by marketing, sales and customer success teams that feature peer customers who are trying to solve very similar issues. 

“Part of deeper discovery is really making sure you understand the needs of the full buying group, [which now may be 6-8 people according to Gartner],” Phil explains, “You have to get to a level of personalization for each decision-maker to find out ‘what’s in it for them.’”

3) Revenue-Oriented CS Team👂🏽

The other key to an enterprise value proposition is a revenue-oriented customer success process. For CS, being revenue-oriented does not mean selling. It means looking for opportunities to continually expand customer value.

“We are intimately and aggressively trying to make sure we’re supporting our customers. From an implementation standpoint, in the handoff from sales to customer success, we are always a growth-oriented, revenue focused organization,” Phil says. 

Whether your CS team has responsibility for sales expansion or passes it off to sales, good discovery and being able to properly position and map your capabilities to the needs of the customer is key for the entire GTM team. 


Every business will have different needs in connecting their individual product lines to enterprise value. But, all go-to-market teams can learn from Phil’s approach to using deeper discovery to personalize for every buyer and doing it in a consistent way across your go-to-market team.