Scaling influence & embracing AI: Chris Mabry on the future of presales in 2025

Remember a time when presales professionals were just considered "the demo people"? Those days are long gone.

Manisha Raisinghani, our Founder & CEO, recently sat down with Chris Mabry on the Wintage Club Conversations podcast, and the conversation revealed just how dramatically the presales function has transformed. Chris, who currently serves as VP of Solutions and Partnerships at Reprise and previously led the Presales Collective (the largest global community for presales professionals), shared a journey that many in the field would recognize.

"I started in a literal basement," Chris told Manisha with a laugh. "We actually called it the dungeon." From those humble beginnings in network engineering, a chance overhearing of a sales call sparked something in him. "I thought, hey, I know all the tech, but I loved what they were doing. I wanted to get really good at that skill and that craft."

That moment of inspiration launched Chris into a decade-long journey through the presales world, where he witnessed firsthand how the role has evolved from technical demonstrator to trusted strategic advisor. His insights offer a roadmap for anyone looking to elevate presales' impact across their organization.

The presales journey: Different stages, different challenges

One of the most enlightening aspects of the conversation was Chris's breakdown of the challenges presales teams face at different organizational stages:

Early-stage

In startups, presales professionals must be the ultimate "Swiss Army knife" - knowing the technology as intimately as engineers while mastering sales and marketing motions. They often represent the company solo at client sites, requiring exceptional versatility.

Mid-market

As organizations grow, the challenge shifts to scaling processes and defining responsibilities more clearly. presales teams frequently face competing expectations, engineering leaders want them to be as technically proficient as developers, while sales leaders expect the same people skills as top sellers.

Enterprise

At scale, the central challenge becomes extending influence across thousands of solution engineers while maintaining a consistent mission. As Chris memorably put it: "What CTO is to CEO is what presales is to sales teams." This encapsulates the ideal relationship, a trusted strategic advisor rather than a tactical resource.

Adapting to modern buyer behavior

Today's buyers have fundamentally changed how they approach purchasing decisions. Chris pointed out that we're all buyers in our personal lives - we can purchase cars from our phones, research products independently, and expect personalization as standard.

For presales teams, this means:

• Generic demonstrations no longer work - "Imagine this is your company" has been replaced by the expectation of seeing your actual data
• Hyper-personalization is non-negotiable
• Fewer scheduled meetings, more hands-on experiences
• Navigating a more complex decision-making landscape

Chris recommends that presales leaders experience their own buying journey firsthand: "Go through the buying journey yourself. Test your system." This direct experience reveals friction points that might otherwise go unnoticed.

The AI revolution in presales

2024 was when we saw AI move from proof-of-concept to production, particularly in presales. 

Chris highlighted several high-impact applications:

• Data transformation: Instantly creating vertical-specific demo environments customized to each prospect
• Content enhancement: Improving storytelling and marketing materials (though with caution around creating noise)
• Task automation: Freeing senior SEs from repetitive demonstrations to focus on strategic work

"Let's get our presales team back to being creative," Chris emphasized. "Let's have creative outreach and connections in real-life events that mean something, instead of seven back-to-back harbor tour demos."

"The ROI of these AI applications can be remarkable - up to 70% productivity improvement in some cases, often at a fraction of the cost of additional headcount."

Presales leadership in 2025: Metrics that matter

Looking ahead in 2025, Chris believes presales leaders need to focus on board-level metrics rather than tactical measurements. This means:

1. Tracking impact on pipeline, conversion, and retention
2. Measuring effect on customer acquisition costs
3. Demonstrating how presales shortens sales cycles
4. Building councils to improve feedback loops between leadership and frontline teams

"The top presales leaders in 2025 already are in that seat," Chris noted. "They're shaping strategy. They're well within the process of having board-level conversations."

Market conditions shaping presales strategy

Several market trends are influencing presales teams heading into 2025:

• Rising customer acquisition costs: Making conversion efficiency more critical
• Declining retention rates: Due to easier software switching
• Cautious expansion: More selective hiring after adjustments in 2024
• Toolkit investment: Focusing on tools that improve productivity rather than simply adding headcount

Final thoughts

Chris's dedication to improving the presales function was evident during this discussion. He envisions a transformation in how organizations perceive and utilize their solutions teams, moving beyond simply enhancing demos or technical validations.

The days of presales professionals being called in just to "show the tech" are fading. In their place, we're seeing strategic advisors who can speak the language of both technology and business value, who can measure their impact in terms that matter to the C-suite, and can leverage cutting-edge tools to deliver the personalized experiences buyers now demand.

As Chris advised before wrapping up the conversation: "Get examples of what good looks like out of your organization. And try to apply it internally. It's gold."