Open. Probe. Confirm. How AI Is Transforming the Craft of Selling

After nearly four years at Phenom, including two leading North America account management, Jeremy Bono oversees one of the company’s largest and most critical businesses: roughly 470 customers representing approximately 80% of revenue.

At an applied AI company like Phenom, the mandate for account management goes deeper than relationship stewardship. The real work is value realization: making sure what customers invest in the platform actually shows up in measurable business outcomes.

To find out how that all works, I invited Bono to “Unusual Attitudes.” To learn more about what fuels this sales executive, watch the podcast, listen on Spotify, or continue reading for some quick takeaways.

From Undefined Function to Outcome Engine

When Bono stepped into the role, account management at Phenom wasn’t clearly defined. His first task was to codify what the function is, who it serves and what kind of talent is required. That began with a clear profile and hiring scorecard for account managers centered on three pillars:

One, deep platform fluency, including how AI works throughout the product.

Two, the ability to deliver outcomes, not just sell or maintain relationships.

And three, an applied AI mindset, where AI is used systematically to improve performance and customer results.

In Bono’s view, the traditional separation between technical solution experts and commercial sellers is dissolving. The future account manager will understand product, process, and value at a much deeper level.

“It's not just about hiring,” he said. “It's about looking at your existing talent and then determining ‘How do we help this team get to where we think we need them to go.’”

The New AM Profile: Willingness, Skill and AI Literacy

For Bono, the first screening criterion is not competency, but intent: does the person actually want to grow into this more demanding hybrid profile? The skills he seeks are often split across roles today. Some people excel at relationship and commercial work, others at product and process, so he focuses on both hiring new talent and enabling existing team members.

The model he’s building accounts for vertical complexity, customer tiers and differing adoption needs. In Phenom’s “major” segment, where customers may invest less but face challenges similar to large enterprises, Bono experimented with placing account managers who are eager and able to go deeper into the product and drive adoption directly. Early results have been positive, proving that targeted specialization within account management can accelerate value realization.

AI literacy is non‑negotiable. Bono expects account managers to use AI to do their jobs better by defining repeatable processes, automating parts of their workflow and accelerating research.

That expectation even shows up in the interview process during the final panel presentation.

The difference between a scripted, read-out presentation and a dynamic, AI‑supported conversation is obvious, and it signals whether a candidate has done the homework needed to thrive in an AI‑driven sales environment.

The Rule of Five

Bono anchors his team in value‑ and outcome‑based selling, built on what he calls a “rule of five”:

1. Identify the true business issue (for example, cutting costs by a defined amount or growing revenue by a specific percentage)

2. Map problems and issues to a solution not just within Phenom’s platform, but across the customer’s entire toolkit, including competitive products

3. Quantify value clearly and simply, avoiding overcomplicated business cases

4. Engage the right executive stakeholders with authority to say yes or no

5. Co‑create a plan with the customer to realize and measure the outcomes

In this construct, knowing the product deeply is essential. Without that fluency, an account manager cannot credibly map business issues to specific capabilities or quantify value in terms the customer will recognize. Bono prefers straightforward value stories such as reducing hiring cycle time dramatically and unlocking revenue over elaborate models that distract from the core impact.

Crucially, he distinguishes between product conversations and executive conversations. The latter are business discussions about goals, priorities, revenue drivers, customers, timelines and value creation for employees, customers, and shareholders. The ability to walk into that discussion requires research, curiosity and the discipline to understand a customer’s business as if one were an employee there.

AI accelerates research, but it doesn’t replace salespeople. Instead, it elevates them by giving faster access to insight that can be woven into a compelling narrative.

Questioning as a Core Craft

To support these executive‑level engagements, Bono invests heavily in questioning skills using the Open–Probe–Confirm (OPC) framework.

Open: Ask broad, open‑ended questions to surface business issues and context

Probe: Dig deeper into specific problems, drivers, and constraints

Confirm: Play back what was heard to ensure shared understanding and alignment

He views OPC as more than a technique. It’s part of a broader go‑to‑market alignment that he hopes to extend across functions. When account managers master this cadence, they move from pitching products to co‑diagnosing problems and co‑designing outcomes, which strengthens trust and improves the odds of success.

Leadership in a Time of Constant Change

Despite the rapid evolution of AI and sales practice, Bono believes the fundamentals of leadership have not changed. Leaders are responsible for delivering outcomes for their teams, companies, and customers. 

Patience is central to his style. While he acknowledges there are intense moments and real pressure, he wants customers, employees, and even his family to feel first that he cares.

His purpose is to make a difference in someone’s life every day, and that orientation shapes how he coaches, how long he is willing to invest in someone’s development and how he navigates the inevitable frustrations of scaling a complex business.

Progress often only becomes visible in hindsight through structured reflection on what the team has accomplished over a year. And that retrospective lens reinforces grit, commitment and belief in the long game.