AI in Sales: Why the New Playbook Still Starts With Fundamentals

Midway through Startup Boston Week, a room full of founders, operators, and go-to-market leaders gathered at Suffolk University for a timely reality check: AI may be changing how startups sell, but it isn’t changing why sales works.

The session “AI in Sales: The New Playbook for Startups” was moderated by Vanessa Ferranto, CEO and co-founder of Dalbero. She was joined by Jason Ingargiola, Partner at M1 Advisors, and Joss Poulton, CEO and co-founder of ClearSync.

Rather than pitching shiny tools or silver bullets, the panel focused on what founders consistently get wrong when adopting AI, and how to avoid losing time, money, and momentum.

The full event video is embedded below if you’d like to watch the conversation start-to-finish, or keep reading for an overview. 

The First Misconception: AI Is the Answer

Early in the conversation, the panelists agreed on a shared misconception they see across early-stage startups: the belief that AI can replace the hard thinking required to build an effective sales motion.

“AI is not the answer,” Ingargiola said. “It’s an enablement tool.”

Poulton echoed that sentiment, framing AI not as an autopilot but as a co-pilot - particularly in the earliest stages of a company. Human judgment, empathy, and direct customer conversations still matter, especially when founders are learning who their real buyers are and why they buy.

Strategy Before Scale

Throughout the session, the panel repeatedly returned to fundamentals, particularly the importance of clearly defining an Ideal Customer Profile (ICP) before turning on automation.

AI can help founders test messaging, accelerate research, and experiment at scale. But without clarity on who you’re targeting and what pain you’re solving, automation only amplifies noise.

“You don’t use AI to decide who you sell to,” Ingargiola said. “You decide that. AI helps you execute it better.”

For startups with large total addressable markets, AI can be a powerful tool for rapid segmentation and experimentation. For niche or early-stage companies, Poulton advised founders to stay close to the metal, using AI to support research and personalization, not replace direct learning.

Three Ways AI Actually Helps Sales Teams

Rather than listing dozens of tools, the panel broke AI’s real value into practical categories:

1. Sales Intelligence & Research. AI excels at distilling large volumes of information (annual reports, investor calls, market signals) into actionable insights that make sellers more relevant and informed.

2. Pipeline Generation & Prospecting. Used thoughtfully, AI can help identify high-fit accounts, test messaging, and surface buying signals, especially when combined with human judgment.

3. Operational & Revenue Automation. From conversation analysis to revenue reconciliation and forecasting, AI can reduce friction in areas that often slow down early teams.

The key, the panel emphasized, is diagnosis: understanding where your sales process is breaking before layering in tools.

The Real Risk: Losing Momentum

One of the strongest warnings of the session centered on burn rate, not just financial, but organizational.

Startups that rush to adopt multiple AI tools without integration or training risk slowing themselves down. Ingargiola shared examples of teams juggling eight or nine disconnected systems, creating more friction than efficiency.

“Momentum is everything,” he said. “Six months lost can kill a startup.”

Both panelists stressed that AI investments should be evaluated not just on direct ROI, but on whether they shorten sales cycles, improve learning velocity, or reduce cognitive load for small teams.

Training Is the Hidden Bottleneck

Another consistent theme: AI adoption fails without training.

Sales teams are often expected to hit aggressive targets while simultaneously learning new tools - without time, structure, or support. The result is low adoption, poor compliance, and underwhelming results.

“Training is the first thing that gets cut when things get busy,” Ingargiola said. “And it’s exactly what you can’t afford to cut.”

Poulton added that documentation now matters more than ever. As employees increasingly rely on personal AI assistants, clear internal knowledge becomes critical to ensuring consistency, accuracy, and alignment.

Authenticity in an AI-Saturated World

During audience Q&A, a recurring concern emerged: buyers are becoming numb to AI-generated outreach.

Both panelists acknowledged the fatigue. As automated emails flood inboxes, generic personalization has lost its edge. The answer, they argued, isn’t abandoning AI, but using it to create real value.

Successful outreach today requires orchestration across channels, relevance rooted in genuine insight, and offers that go beyond “just checking in.” AI can support that work, but it can’t replace it.

The One Thing to Do in the Next 30 Days

When asked what founders should implement immediately, the advice was refreshingly simple:

• Lean into how your team is already using AI and standardize it

• Audit your go-to-market fundamentals before adding tools

AI works best when layered onto a clear strategy, not used as a substitute for one.

As the session wrapped, one message was clear: the new sales playbook isn’t about doing more with AI, it’s about doing the right things faster, with more clarity, and less waste.

The full event video is embedded above (or you can watch it directly on YouTube) to catch the complete Q&A and founder stories shared from the stage.