Using Human Judgment in AI-Driven Sales Processes, Ep #491

In this episode, I’m joined by Steve Harding, Senior Vice President of Sales EMEA at SalesLoft and global sales leader, for a deep dive into how AI is reshaping the revenue workflow.

We cut through the hype to uncover the real value AI brings to sales teams, from serving as the “air traffic control” for overwhelmed account executives to accelerating pipeline creation through smarter signal prioritization. Steve shares powerful examples from his own organization, unveils practical AI use cases for prospecting and deal progression, and emphasizes the importance of keeping the human touch front and center.

Tune in for candid stories and fresh perspectives on how sales teams can successfully adopt AI, avoid common mistakes, and leverage technology to enhance, not replace, the vital role of human judgment and relationship-building in sales.

Outline of This Episode

• 00:00 AI-driven sales productivity insights.
• 08:08 Human-centric sales in the AI era.
• 10:42 Content overload challenges modern buyers.
• 15:48 AI-powered sales insights.
• 19:13 AI integration in sales workflow.
• 20:27 AI-driven customer outreach automation.

AI in the Revenue Workflow: Separating Value from Hype

Today, sales teams are inundated with tools and data, making the challenge not just about having information, but about managing it. AI has the potential to become the air traffic controller, helping teams delegate, automate, and prioritize effectively.

AI’s most meaningful contribution is compressing “time to insight.” Instead of manually sifting data or waiting for CRM updates, AI delivers actionable guidance at critical moments in a seller’s workflow. Steve outlines how, at SalesLoft, AI is integrated directly into their platform, which helps account executives instantly recognize the next best action and act at the right time.

This isn’t just theoretical. For example, teams can now pick up signals, both internal, like website activity or content downloads, and external, like missed payments, that indicate where attention is needed. AI then helps sort and prioritize these signals, recommending actions and automating follow-up tasks so teams spend time where it counts. The result: improved productivity and responsiveness, and ultimately, healthier pipelines.

AI that Boosts Prospecting, Qualification, and Deal Progression

What does this look like in practice? Steve shares a recent exercise at SalesLoft when they analyzed every major win and loss across markets and segments, mining rich interaction data captured in their system. When they fed this into the AI, they discerned clear themes that differentiated wins from losses. The findings informed improvements to their sales process, especially around discovery intent, giving teams concrete cues that new hires and veterans alike could watch for.

This real-world application of AI proved results, boosting win rates and adding confidence, context, and clarity to team conversations while preserving the all-important human connection.

The Human Element - Where Judgment Still Matters Most

Despite the buzz, AI is not a panacea for sales relationships. At the end of the day, sales is a human-centric activity, Steve explains. AI serves best as a “wingman or copilot.” It can automate certain workflows, but when the conversation gets nuanced, or the stakes are high, whether it’s handling objections or building deep trust, a human’s judgment, empathy, and experience remain irreplaceable.

Buyers are showing up more informed, or misinformed, than ever before. But the proliferation of high-quality marketing content has led to confusion and caution. Salespeople must now help buyers navigate this information landscape and overcome the “fear of messing up”, a challenge that can’t be solved by algorithms alone.

What missteps do organizations make with AI rollouts? 

Steve stresses two dangers:

• Expecting AI to perform beyond the skill level of a company’s most junior rep.
• Failing to keep humans “in the loop”, validating and verifying a system’s outputs.

Instead, AI should recommend and automate, not dictate, with human oversight at every critical juncture. It’s the old wisdom: “Trust but verify.”

As sales leaders consider integrating AI into pipeline generation or deal execution, Steve recommends starting with the pain points, not the tech itself. Ask where reps are wasting time, then target AI to solve those problems. Then, using AI within your systems, not on the edge (like ad hoc Copilot or OpenAI research). This keeps valuable intel connected to your CRM. While you’re doing this, it’s important to keep a human in the loop to protect your relationships and reputation.

Where AI and Human Skill Combine for Better Outcomes

One standout example is nurturing relationships when key contacts change roles or organizations. AI tools can track these moves and trigger a personalized, multi-step outreach campaign, congratulations on LinkedIn, followed by an email and a phone call. This blend of automation and personal touch lets teams act at scale, re-engage valuable advocates, and build pipeline opportunities that would be nearly impossible to manage manually.

AI is transforming sales workflows, but not by replacing humans. Use AI as an intelligent copilot to prioritize, automate, and scale, but never lose sight of the human skills of empathy, and judgment. 

Connect with Steve Harding

• Steve Harding on LinkedIn 
• Salesloft 

Connect With Paul Watts 

• LinkedIn
• Twitter 

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