Turning offline conversations into data: AI coaching for in-person sales
Field sales has always lived in the dark. You know what happens at the kitchen table or on a job site, but the data rarely makes it back to the team. That's changing with AI coaching that records, transcribes and analyzes conversations - then gives feedback in real time.
Rillavoice Inc. is pushing this forward with its mobile app and Rilla Live. Sebastian Jimenez, the company's founder and CEO, says the goal is simple: turn every in-person conversation into a learning loop that helps reps improve faster and managers coach without being there.
What Rilla Live does in the field
Reps use a phone, tablet or Apple Watch to record sales and service conversations. The AI transcribes and analyzes on the spot, then delivers instant coaching cues and post-call summaries. Think live prompts, talk-time balance, and question quality - without slowing the rep down.
Managers get "virtual ride-alongs" that replace a full day in the truck. Reviews take minutes, not hours, and focus on the moments that moved the deal.
As Jimenez puts it: "We use AI to automatically transcribe, analyze and give them feedback... virtual ride-alongs that are a hundred times faster, better, more productive than physical ride-alongs."
Why this matters: most commerce still happens offline
Online gets the headlines, but most buying still happens face to face. Estimates peg e-commerce around a small share of total U.S. retail, leaving the vast majority offline. If you can measure those conversations, you can coach them - and scale what works.
That's the point here: make offline sales as measurable and coachable as your website funnel. If you want a quick reference on e-commerce share, see the U.S. Census Bureau's retail data here.
What top reps do differently (from millions of conversations)
Rilla's analysis across millions of in-person sales talks surfaced a few patterns sales leaders will care about:
- Talk-time ratio: top performers talk 45%-65% of the time. They control the flow without steamrolling the customer.
- Open-ended questions: about 25 per hour vs. 5 for average reps. More "how" and "what," fewer yes/no layups.
- Examples that work: "How does the price affect how you think about this?" and "What makes you feel the price is too high?"
These aren't theories - they're repeatable behaviors you can train, track and reinforce.
How to roll out AI coaching in your team this quarter
- Start with one squad. Baseline their talk-time, question count and conversion rate for two weeks.
- Turn on Rilla Live for live cues and post-call recaps. Set a simple rule: one behavior focus per week (e.g., hit 50-60% talk-time).
- Swap ride-alongs for 15-minute weekly reviews. Managers review flagged moments, leave specific notes and assign one micro-skill.
- Build a living playbook. Tag winning phrases, objections and closes. Share clips. Promote what's repeatable.
- Cover consent and expectations. Be upfront with customers and reps about recording and how the data is used.
For sales leaders: fewer blind spots, faster ramp, tighter consistency
This is about visibility and consistency. You'll spot coaching moments you'd never catch live, shorten ramp for new hires, and reduce variance across the team. The result: more predictable revenue and cleaner customer experiences.
If you're leveling up team skills around AI and sales operations, browse practical options by job role here or see the latest hands-on AI courses here.
From the field: what Rilla's team is seeing
"We're bringing a layer of visibility to outside sales and service that was never there before," Jimenez said. "We just launched Rilla Live where you can get feedback in the moment - you're literally like a quarterback on the sidelines giving feedback."
The vision: index offline sales conversations the way search engines indexed the web - so teams can learn what works and repeat it, everywhere.
Disclosure: TheCUBE was a paid media partner for Dreamforce. Sponsors did not control editorial content.
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