Prospects don’t know how to buy – they need to be led. This sales axiom has never been truer than in the AI era, where technology evolves so fast that even investors and board members struggle to keep up.

One of my roles at BCV is connecting corporate leaders with our AI startups – to facilitate dialogue, and sometimes grease the wheels for transactions.

Before joining the venture world, I built and ran sales teams for tech startups, so I know firsthand the existential urgency founders feel about getting past procurement and into the hands of real users. But with AI, that hill is even steeper.

When I meet with corporate execs, I always ask about the topic du jour: How are you adopting AI? How are you using it today? Where do you see the highest-value use case?

The answers might not surprise you, though they initially surprised me because I assumed most people had it figured out. Instead, I hear a mix of genuine curiosity, trepidatious uncertainty and surface-level understanding from corporate execs.

And that’s a problem because startup founders give me the exact opposite: zealous certainty and an unrelatable depth of understanding. The only thing both sides share is curiosity.

The Real AI Challenge: A Communication Gap

AI adoption isn’t just about the tech – it’s about bridging the fundamental communication gap between executives and founders.

Corporate execs aren’t clueless. Many have board-level mandates to use AI in transformative ways. But most have built their careers on cautious iteration, not disruption. They’re insulated from new tech by hyper-cautious legal, procurement, and security teams that dilute AI’s potential before it even reaches their desks.

Meanwhile, they’re drowning in AI options. In the last three years, they’ve read scores of AI think pieces, met dozens of vendors, and – whether they realize it or not – already have hundreds of AI tools in their environment, from incumbents like Microsoft and Salesforce to niche point solutions.

As Aaref Hilaly, an AI partner here at BCV, puts it:

"What’s different about this tech transformation with AI is that execs aren’t just looking for solutions – they’re looking for sherpas. They need trusted advisors to guide them through what AI means for their business, even if it means stepping out of ‘sales mode’ sometimes."

To help AI founders break through, we polled both startup leaders and corporate execs to understand how to bridge this gap.

Here’s what we learned, ranked in my subjective order of importance. This advice is for high-level pitch meetings with economic buyers, not tactical demos for end users.

1. Good communication starts with understanding what the other party truly cares about. Senior executives want to manage to their Business Unit KPIs, so always as with any B2B sale ground your pitch in actual business value – not features or functionality. The more senior the audience, the more this matters. This can be particularly hard for technical founders, who love to show what their product does from a feature perspective.But senior buyers don’t care what it does, they care why that matters.

Anshul Gupta, co-founder & President of Actively AI, an AI powered super-intelligence for sales teams, counsels: “When pitching corporate buyers, it's essential to anchor the conversation around their employees – the exact tasks they do and how those activities drive business outcomes. Rather than leading with technology itself, start by diving deep into the critical Jobs To Be Done [JTBD], the business impact of doing them better and how AI can unlock deeper human effectiveness.”

Christina Melas-Kyriazi, an AI partner at BCV, adds: “If you’re able, spend the time upfront mapping the prospect’s organization. It’s important to understand who you are selling to, what their objectives are, how they think about their career and how decisions get made in the company. Part of your job is giving them the words and firepower to tell your story very effectively internally.”

I’ll add after witnessing scores of founder pitches about their AI products: You really cannot over-contextualize your solution in the era of AI tool proliferation!

2. Don’t succumb to the curse of knowledge – the cognitive bias in which you presume your audience has the same level of understanding about a concept as you do. Slow down and start by explaining even key concepts before getting into your specific solution. BCV hosted a briefing for senior execs at a large company last year, and realized very quickly we needed to start by explaining what are (to us) basic concepts in AI, like what inference is, or risk losing the room.

Even senior executives often lack deep AI understanding. Always explain core concepts – someone in the room will appreciate the clarity. That person may just be the HIPPO (highest-paid person in the organization), and making them feel ‘seen’ could dramatically increase your receptivity.

3. AI isn’t human, and so the human aspect of sales matters more than ever. Aim to be an advisor on this disruptive and unpredictable shift, and lean into the human-based elements of a pitch, and an interaction. Aaref counsels, “you want to be the person they call when they’re thinking about what to do with AI, even if it doesn’t map to your product. Be more relationship oriented and less transactional.”

Paloma Ochi, head of marketing at Decagon, adds “You have to meet corporate buyers where they are on their AI journey. Success comes from listening first, then building a bridge between their immediate challenges and your technology's full potential.”

My take: It’s important to be authentic and show emotion. ChatGPT writes bloodless words on a screen - only you, a flesh and blood founder, can speak emotionally to generative AI’s potential and, in so doing, break through to the human being you’re pitching.

4. Generate FOMO by highlighting who else is getting value from your product. Executives often don’t engage unless they fear falling behind. Case studies, reference customers and competitor adoption drive urgency – especially in fast-moving AI markets. And be sure to, again, contextualize how your solution fits within the panoply of solutions your audience may have seen.If you don’t have a case study for a company in the same industry as your prospect, then at least include the specific terminology, KPIs and JTBD of the function and industry you are pitching. Learn as much as you can from folks within the new industry before going into a big pitch – and try to take a design partner lens to conversations with at least three logos.

Dan Caputo, an innovation executive at JP Morgan, has seen many AI pitches and advises founders to cut through the noise – and to the chase. He advises, “Be prepared to articulate concisely how you are differentiated than the many competitors in a crowded space. Do your homework on the corporate you’re selling into and leverage your network where possible to make sure you’re talking to the right people, at the right time.”

5. When you do a demo, keep it short and make sure it speaks to your audience. It’s painful for us to admit sometimes, but most software basically looks the same. And even though you built your product from nothing and are proud of what it looks like, you will lose your audience if you spend 15 minutes clicking around and waiting for things to load – even if latency is low.Instead, it'd be wise to prepare a very short demo, or even a video, which is less than five minutes and captures the essence of what you’ve already described. Make sure the data points included are relevant to your audience, ideally custom made for it.

Kamal Shah, CEO of Prophet Security, an agentic AI SOC analyst, emphasizes the importance of a use-case focused demo, rather than a feature dump. “Have a compelling demo that highlights use cases relevant to the buyer versus demoing features,” a mistake all too commonly made by technical founders.

6. AI can be scary for all but the most zealous founders and VCs, so preemptively allay their concerns and anxieties. In pitching to many corporate executives, Rishabh Jain, CEO of Fermat, says, “My primary learning has been that gen AI is still viewed with risk, and so it's important to ensure buyers have control over what goes live – and that they are aware of this control. No one wants the feeling of 'I don't know what this thing is going to do.’”

Kamal of Prophet concurs that you should proactively address common concerns such as hallucinations and data privacy.

7. Address their current tech stack, and why your offering will be complementary versus conflicting. This has a bonus of forcing you to do your homework to understand what technology the prospect is already using, and making sure you in fact can work alongside it. Kamal of Prophet counsels succinctly, “Make it very simple for enterprises to evaluate your offerings in their environment.”

Laura Gram, an operating partner at Bain Capital’s Private Equity fund specializing in supply chain, agrees that understanding the context of a prospect’s existing tech stack is critical. “Pitches that work well map the process the tool is impacting – outbound load planning, for example –, and then zoom in and explain the precise benefit the solution provides, along with how it integrates with, or replaces, existing technology in that area of the process. Poor pitches don’t zoom in and don’t address the existing technology at all.”

One Crisp Note Can Pierce Through an Orchestra of Noise

One corporate buyer we met with recently indicated there were already over 700 AI tools in deployment within their walls. How on earth should they expect to make sense of this all, and then grasp the utility of a specific AI solution being presented to them by an excited early-stage AI founder?

Enabling AI adoption within a larger company isn’t only about explaining how the best technology may work. Success requires clear communication and a high degree of empathy to the executives on the ‘other side of the table.' Founders who translate AI’s power into tangible business impact, reduce the complexity of their pitches and create urgency and relatability will be able to more effectively connect with their corporate prospects.

If you're an AI founder, CVC leader, early stage GTM exec or simply want to talk shop, reach out: jdimento@baincapital.com.