In 2025, I completed the full interview process for Ashby, which included a “challenge” interview project to develop an enablement strategy specifically targeting the Discovery Pillar of their Sales Process. The strategy was designed to help combat the issues laid out by the Ashby team including reps failing to remain in Discovery throughout the sales process, resulting in poor conversion.
Candidate, Head of Sales & CS Enablement
Ashby - 2025
⭐ Supplemental Content:
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Thought Leadership on Revenue Operations & Enablement
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Ashby leverages a few unique approaches to their sales strategy, including a Sales Excellence model, and viewing the process in “pillars,” rather than focusing on steps or milestones.
The sales leaders at Ashby believe there is a significant opportunity to improve discovery. Their assessment is that AEs often move too quickly into product demonstrations before fully understanding the customer’s challenges, priorities, and broader business context.
The Opportunity & Objective Statement were as follows:
In designing and building out the strategy, the approach began with assessing what was going well with the current state of the sales team, and identifying where there was opportunity for improvement.
In order to do this, I was provided with a few resources including a few documents detailing Ashby’s Discovery Pillar, Ashby’s Sales Methodology, Qualifying a Deal, (links available upon request), and a couple examples of “not great,” and “pretty good” Discovery Calls via Gong recordings.
Below are the main takeaways of what I characterized as Effective vs Ineffective in this element of the Sales Process.
| 👍🏽 EFFECTIVE | 👎🏽 INEFFECTIVE |
|---|---|
| Strong Technical Understanding | Deep Curiosity & Business Acumen |
| Effectively Represents Product | Clear Understanding of the "Why" |
| Leveraging Existing Tools & Resources | Risk Aversion in Big Deals |
| Manager Coaching & Reinforcement | High-Quality Questions |
| Continuous Learning Mindset | Balancing Qualification vs. Rapport |
| Limited Competitive Awareness | |
| Second-Order Business Impact | |
| Uneven Skill Development Across Segments | |
| Reevaluation & Ongoing Discovery |
From reviewing the aforementioned documents, as well as conversation with the hiring team, which included the VP of Sales and Director of Revenue Operations, I gathered a few key details on what the Ashby Sales Team may be doing relating to the Discovery Pillar that could be considered effective or ineffective.
On the effective side, I learned that AEs demonstrate a strong technical understanding, effectively representing the product to customers. They are leveraging the existing tools, and managers have a strong commitment to reinforcing positive behavior and promoting continuous learning.
On the ineffective side, I gathered that AEs are not always great at digging deep to get to know the customer. Ashby is a big product, typically replacing multiple solutions, so it’s important we’re training reps to understand the depth of the problems we could be solving.
This could be due to a risk aversion mindset, or lacking a clear understanding of the “why” behind a surface level issue a customer may be facing.
We’d like to coach the team to ask more intentional open-ended questions, as well as high-quality questions in order to get to the second-order business impact for a customer and continually build relationships over time.
Through an emphasis on relationship building, we’ll also weave in the concept of continually evaluating and confirming the landscape of the deal, balancing qualification with building rapport.
At a more nuanced level, we will also address competitive awareness and ensure we’re developing skills effectively across sales segments.