This blog is a summary of Jesse Dailey’s episode on The New GTM Playbook podcast. Head to The New GTM Playbook page to watch the latest episodes.
In the world of SaaS, staying ahead means rethinking how we work, sell, and deliver value. Few leaders embody this shift as powerfully as Jesse Dailey, a seasoned solutions professional and the VP of Solutions Engineering and Field CTO at People.ai. With years of experience leading solutions engineering and customer success teams, Jesse has honed strategies to tackle today’s toughest SaaS challenges—scaling solutions, delivering impactful demos, and continuously proving value.
Here are four takeaways from my conversation with Jesse.
Automating for Scale: Shortening Pilot and POC Timelines
Time kills deals, and nowhere is this more apparent than in lengthy proof-of-concept (POC) processes. Jesse shared how automation at People.ai has transformed their approach, enabling their solutions team to deliver impactful experiences without the typical delays. Tools like TestBox allow People.ai to simulate customer environments and offer hands-on experiences at scale.
“We’ve solved two big challenges with TestBox: How do I demo AI effectively, and how do I do it at scale? Now, we can send customers a People.ai environment to explore on their own terms,” Jesse explained. This automation has slashed POC timelines, turning what once took months into weeks—sometimes even days.
The takeaway is clear: leverage automation to give prospects more control while freeing up your team to focus on high-value customer interactions.
The Struggle of Demoing AI
AI is a game-changer, but demoing it effectively? That’s a whole other challenge. AI’s non-deterministic nature—its reliance on big data and context—means traditional demo tactics fall flat. Jesse highlighted the pitfalls of static, scripted demos and emphasized the need for flexibility.
“Customers want to interact with AI, not just see it on a slide,” Jesse noted. “But that’s tricky when AI needs real data to work its magic.”
By embracing tools that create live, data-driven demo environments, People.ai ensures prospects can see the real potential of AI, building trust and credibility in the process.
Rethinking Value Realization: ROI Isn’t Cast in Amber
Too often, the ROI pitched during presales becomes irrelevant after implementation. Jesse identified this as a critical gap, one he’s addressed with People.ai’s value realization framework.
“We mapped out our customer journey into five steps: activation, launch, adoption, value realization, and renewal,” Jesse shared. “At each stage, we inserted value checkpoints to ensure we’re staying aligned with the customer’s evolving business goals.”
One standout addition was the “launch party,” a milestone where People.ai re-engages the economic buyer to validate value and celebrate early wins. This proactive touchpoint ensures alignment and prevents ROI promises from fading into irrelevance.
The takeaway: value isn’t static. Revisit and recalibrate ROi and the value your team is delivering regularly to keep customers engaged and happy.
The Power of Team Selling
Success in SaaS is no longer a solo act. Jesse advocates for a “team selling” approach, where solutions engineers, account executives, and customer success teams collaborate throughout the customer lifecycle.
“At People.ai, we ensure SEs stay involved post-sale. It’s not about overloading them—it’s about maintaining continuity and trust,” Jesse explained. This cross-functional collaboration reduces friction and fosters stronger relationships with customers, ultimately driving higher retention and expansion.
For SaaS organizations, this approach represents a shift from the traditional silos most teams are organized into today. By breaking down barriers between teams, you can create a seamless customer experience that keeps buyers coming back.
Are You Ready to Rewrite the GTM Playbook?
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