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Enterprise AI Sales Too Slow? Here’s How Top Founders Fix That 

By July 16, 2025No Comments

Struggling with Enterprise AI Sales? – Here’s How Top Startups Fix That

From our B2B AI startup portfolio—dating back to 2017—we’re drinking from a firehose of courageous founders actively inventing the enterprise AI sales playbooks that win. For those jumping in at this point in the journey, here are patterns we’re seeing at Valor that can lift your AI sales trajectory.

Big idea: You’re probably selling your AI solution too low in the org chart.

The battle for enterprise AI sales is in the C-suite. McKinsey’s Superagency in the Workplace report shows why failing to engage leadership is costing you—and your buyers—a massive opportunity.

1. Frontline Startup Love ≠ Enterprise AI Sales Buy-In

McKinsey found employees use AI 3x more than leaders realize—and 47% expect AI to take over ~30% of their work within a year. Meanwhile, younger employees are eager adopters, but older, tenured executives are not. Deloitte reports 79% of early-career workers are excited about AI, but just 66% of experienced team members.

Why the hesitation? At Valor, we see a consistent pattern: the ROI of AI tends to decline with seniority. Here’s why:

  1. Leaders must sift through more noise from junior team members using AI without full context.
  2. They don’t see nuanced, role-specific relevance from GenAI’s statistical outputs–so it bogs them down the more senior, and more expert, they are.
  3. Top leaders gain no lift, and likely more noise, from added coaching time spent managing overconfident, AI-powered teams.

Thus, if you’re selling to mid-managers or team leads, you’re playing small ball. They already want your tool. The real opportunity—and budget and confidence gap—is at the top.

Game plans we see working in enterprise AI sales:

  • Elevate your pitch: “We don’t just boost productivity—we architect enterprise-wide AI adoption that drives the bottom line.”
  • What to solve: C-suite misalignment, missing roadmaps, and governance gaps. Help them see AI as a signal amplifier—not more noise. Bring the roadmap. Better yet, bring a case study. Address the unspoken pain it’s not cool to say outloud incorporate these days: AI can add noise too, especially for the experienced experts at the top.
  • What to say: “Your frontline’s ready. It’s your strategic alignment and industry nuance that’s lagging—and we turn that into multimillion-dollar value through our platform’s process, which is . . . .”

2. Sell Strategy, Not Just Software, in Enterprise AI Sales

McKinsey reports only 1% of companies have reached AI maturity, while 92% plan to increase AI spend. And yet . . .  63% of stalled initiatives stem from poor executive alignment.

We see it often: one department is excited, but the CIO won’t back it. Or a department loves your tool—only to discover a competing pilot in another silo. Billions in AI spend are frozen in these bureaucratic bake-offs.

Skip overworking the mid-level fan club. Bring AI strategy frameworks, business cases, and KPI dashboards straight to the C-suite. Your product is the vehicle, but your value is in delivering enterprise AI results.

Tactical moves:

  • Offer an AI Readiness Assessment—a 90-minute C-suite or board-level advisory that gives you the data to deliver custom projections.
  • Design the deal: your platform, roll-out milestones, and executive-level insights derived from your data no one else can provide.
  • Make sure every department-level pilot has a path to visibility at the top that includes your sales team, and if you design that into your platform as a necessary feature, it becomes reality.

3. How to Bridge the Enterprise/Startup Trust Gap in AI Sales

Employees are eager—but under-supported. McKinsey says nearly 50% want formal AI training, yet 20% get none. Meanwhile, half worry about hallucinations, privacy, and security.

To build momentum in enterprise AI sales, your package must build trust with execs and enthusiasm with teams. That means:

  • Include governance and executive enablement, not just training modules–maybe a twice annual executive summit for top customers and prospects.
  • Tailor C-suite materials to real concerns—don’t rely on genericl AI hype (which is rapidly becoming a turn off, not a turn-on).
  • Foster a peer-powered service layer: enable top users to showcase their brilliance inside a private community. Lightly moderated, this becomes a goldmine. Bonus: an AI-moderated feed highlighting top insights daily and feeds your chat-customer-service interface with real world successes.

Scoring Enterprise AI Sales for B2B Startups

Startup CEOs are right to stay scrappy and close the deals they can today, enterprise ready or not. But if you’re building for the enterprise, the traditional software playbook will let you down.

We’re early in the AI cycle—and enterprise AI sales are already possible at scale. That means it’s time to sell like the visionary you are. AI gives you leverage:

  • Faster customization (via tools like Devin, Cursor)
  • Personalized marketing materials (via Gamma, Canva AI)
  • Rapid compliance (SOC 2 with Delve in days)

Soundboard Your Enterprise AI Sales Strategy with this Custom Startup B2B AI Sales coach

  • Much of what we’ve learned about enterprise AI sales for startups is embedded in our AI sales coach, Caesar.

Use him to role-play, test messaging, or pressure-test your pipeline strategy.

Here’s to your bold vision—and brave execution.

— Lisa Calhoun