The Trial Wasn’t the First Step. Qualifying the Vendor Was.

The Study at a Glance

• Business question: How could the company encourage more upmarket prospects to contact Sales?
• Audience: Organizations with more than 100 employees.
• Research approach: Begin with sales representatives and leaders, then refocus recruitment on Sales Operations after learning who performed the initial evaluation.
• Focus: How evaluators researched vendors and what information they needed before booking a meeting.

The Challenge: A Trial Funnel Built Around Existing Customers

The company had grown through a product-led model. Prospects could discover the software, start a trial, experience its value, and eventually convert.

As the company moved upmarket, Sales would play a larger role. The team wanted to increase the number of qualified prospects who contacted Sales after starting a trial.

The initial research question followed that logic: how could the trial better move enterprise prospects toward a Sales conversation?

Before evaluating the trial, we needed to understand who was entering that journey and what they were trying to accomplish.

How We Found the Actual Evaluator

We initially recruited sales representatives, the product’s primary users, and sales leaders, who held purchasing authority and budget.

The early conversations revealed a gap in that plan. Neither group typically handled the initial evaluation in the larger organizations represented. That work frequently belonged to Sales Operations.

We restarted recruitment around that role and asked participants to walk through how they would investigate software in the category.

A consistent sequence emerged. Before visiting a vendor’s website, evaluators had documented their current process, identified gaps, and established requirements. They arrived with specific questions to answer.

The person using the product, the person approving the purchase, and the person researching vendors could be three different people.

Finding 1: A Sales Conversation Often Came Before a Trial

Once an evaluator found enough information to consider a vendor viable, the next step was often to book a Sales call and move on to another vendor.

A trial could require substantial setup just to answer basic questions. Speaking with someone who knew the product offered a more efficient way to resolve those questions.

The trial was not part of the initial evaluation sequence described by these participants. Product evaluation could come later, with Sales involved.

The research changed the question: how could the website help an evaluator decide that a Sales conversation was worth having?

Finding 2: Basic Requirements Needed Clear Answers

CRM compatibility was a pass/fail requirement for these evaluators. If the software could not integrate with their existing CRM, it might not make the shortlist. An unclear answer could also be enough to send them elsewhere.

Security and compliance requirements served a similar purpose. Evaluators needed to establish whether the vendor met their organization’s requirements without an extended search.

This suggested a practical design target: make common qualification information, including integrations and security documentation, findable within two clicks. That was a recommendation to test, rather than a universal usability rule.

Finding 3: The Pricing Page Helped Evaluators Check Features

Participants repeatedly visited the pricing page to understand the available feature set. They expected it to offer a consolidated comparison they could check against their requirements.

The company’s detailed feature comparison was gated behind a Contact Sales button. Evaluators therefore had to request a meeting before they could confirm basic fit.

For someone comparing several vendors, that created avoidable work. A competitor with a visible feature list could be easier to qualify.

Make the feature set visible before asking for a meeting.

The website needed to provide enough information to earn the conversation.

Finding 4: Pricing Structure Mattered at This Stage

Exact price was not the dominant concern in these conversations. Sales Operations specialists often were not the final budget owners, and participants expected enterprise pricing to involve further discussion or negotiation.

They still needed to understand how the purchase would work: per seat, by usage, by team, or through a platform fee. What caused the bill to increase?

At this stage, understanding the pricing model helped evaluators assess fit.

This finding did not establish that price was unimportant to the eventual buying decision. It clarified what these evaluators needed during initial research.

What the Company Changed

The company made key qualification information accessible before the Sales conversation.

Together, these changes aligned the website more closely with the evaluator’s job: determine whether the vendor was worth pursuing.

What Sales Reported

The Sales team reported that prospects entered conversations better informed. Reps could spend less of the opening discussion reviewing basic feature lists and more time understanding the prospect’s situation, demonstrating relevant value, and addressing objections.

Other changes to the company’s upmarket strategy were happening at the same time. No specific conversion increase can be attributed to this research alone.

The reported outcome was better-informed Sales conversations. The research contribution was a clearer understanding of what evaluators needed before booking them.

The Journey We Needed to Support

The research shifted attention from improving a trial step to supporting the decision that came before it. That change in focus followed from speaking with the people responsible for the initial evaluation.