Why your AI sales machine aren’t working anymore

This article summarizes an episode of 20VC’s video series featuring Carles Reina, VP of sales at ElevenLabs.

Carles Reina, VP of sales at ElevenLabs / Photo credit: 20VC with Harry Stebbings

Automated outbound emails have made traditional business sales ineffective, forcing buyers to aggressively filter messages. Carles Reina, VP of sales at ElevenLabs, explains that sustainable growth now requires sales teams to pivot toward trust, velocity, and specialized methods.

To survive this saturated market, organizations must treat technology as an assistant for human-led outreach rather than a bulk messaging engine.

Using AI without losing buyer trust

Replacing human sellers with fully automated systems destroys buyer trust and drives response rates close to zero. To accelerate sales without alienating prospects, organizations must use AI as an operational assistant that handles data gathering and drafting, while leaving the final communication choices entirely in human hands.

Implementing these methods requires shifting operational focus:

• Focus entirely on incoming requests to capture buyers actively showing intent.
• Generate automated draft responses, but mandate human review before sending.
• Customize every message using specific contract details and usage data.
• Measure success by individual worker output to curb unnecessary hiring.
• Incentivize software adoption by paying full commissions on AI-assisted deals.

Shifting from bulk automation to human control
Flooding inboxes with automated pitches has trained buyers to block generic messages entirely. Reina observes that most AI sales tools fail because they treat every interaction as a transaction. Instead, effective automation embeds customer data into daily workflows.

Reina’s team built custom AI managers that proactively suggest responses based on contract tiers. “The human goes in in the morning and has drafts, edits them, and sends them,” he explains. Outbound is dead unless you do it humanly.

Hiring fewer people for more money
Reina aims for a 50% productivity increase, allowing him to manage a smaller but highly compensated team.

He encourages AI adoption by promising, “Any upsells or contracts that the AI agent closes, I will pay those commissions as if a human closed them.”

Tying pay to company value

Rewarding early pilot programs often created a sales culture obsessed with quick wins rather than long-term retention. Reina refuses to pay commissions on pilots; reps only get paid once they secure a yearly contract and any subsequent expansions. At the same time, many organizations still treat customer support as a passive department.

Reina argues against this, saying, “Customer success needs to be a money-generation function for the business that works for the customer and works for the business to incentivize growth, expansion, and cross-selling.”

Treating company growth like investing

Saturated software markets punish companies that attempt to enter one market at a time. Leaders must abandon sequential planning and treat expansion like venture capital investing—placing dozens of simultaneous bets, analyzing the data, and ruthlessly shutting down failing markets to fund the winners.

Shortening sales times with brand and partners