Speed, focus, and ruthless prioritization are essential when you're building something new.

The startups that master AI will win. In Superhuman's State of Productivity & AI Report, we found that top performers are saving a full day per week with AI-native tools. Over 66% of leaders expect a 3–10x boost in productivity in the next five years.

What does mastering AI look like in practice? Rilla has grown to $40M+ in ARR over three years with just 60 employees — that's over $500K in ARR per team member, making them one of the most efficient startups in the world.

In a recent virtual event, we broke down their playbook with Sebastian Jimenez, CEO of Rilla, and Spencer Grover, Senior Product Marketing Manager at Superhuman.

The secret? A relentless focus on productivity embedded in their culture, using AI and automation to squeeze value from every workflow.

Growing to $40M+ ARR with only 60 employees

Rilla offers virtual ride-along software for outside sales teams. With a small team they've accelerated from $0 to $1.4M ARR in year one, $1.4M to $10M in year two, and $10M to $40M in year three.

This efficiency rivals the likes of Cursor, OpenAI, and Midjourney — which is even more impressive when you consider that Rilla operates in B2B, not just software.

How did they do it? By embedding productivity into their DNA from day one.

A culture of relentless focus

Three minutes to review a sales call. Immediate follow-ups. Eight demos a day per sales rep. A blistering 10-day sales cycle. 

This efficiency didn't happen by accident — it was born from necessity, focus, and devotion to a productive culture.

"Maximize your productive time has been one of our principles since day one," said Sebastian.

He shared examples from when he was a "one-man sales army", selling the first $2M of ARR himself. His biggest breakthrough was eliminating unnecessary steps in the traditional sales process. Instead of the usual 20+ steps, he condensed it into two: pitch, qualify, and book in-person at conferences, then run a high-converting demo.

"I figured out I could do a pitch at the conference — a two-minute pitch where I explained Rilla really quickly, qualified them on the spot, and booked them on my calendar," said Sebastian. "I eliminated the standard follow-up and intro calls. Just one step."

With Superhuman and custom automations, he reduced friction so he could consistently book demos back-to-back, from 8 AM to 8 PM during busy conference periods.

As the company scaled beyond conferences, Sebastian maintained that same focus: eliminate unnecessary steps and accelerate time-to-close. That's how they scaled from a founder-led effort to a 30-person revenue team without sacrificing speed or deal quality.

When productivity is a core value rather than just this quarter's performance metric, it drives every workflow, customer conversation, and product decision.

AI doesn't replace people — it supercharges them

"Adding tools just accelerates the culture you've got," Sebastian notes. Adding AI and automation to a noisy, disorganized culture will just speed up the noise and disorganization.

Adding AI and automation to Rilla's culture, on the other hand, has made them one of the most efficient startups in the world.

Sebastian breaks down their process for sales call reviews. Every sales call is recorded and reviewed using Rilla's own AI bot, Rick. Sebastian and his sales director personally review every call, using AI playbooks to rapidly surface objections, flag missed opportunities, and deliver targeted coaching.

"We still review every single sales call that our salespeople have — myself included," Sebastian says. "AI helps us do it in about three minutes per call."

Superhuman as a growth multiplier

Sebastian decided every Rilla employee needed to use Superhuman. Here's how they scaled their blistering sales motion:

Instant follow-ups: With keyboard shortcuts and Snippets, Sebastian's team can send follow-ups in seconds, often before the Zoom call ends. Team Snippets ensure everyone uses the same high-converting messaging.

Zero context switching: The Superhuman & HubSpot integration brings deal information directly into the inbox. Reps get the vital context they need without opening another tab and breaking flow.

AI-powered personalization: Write with AI helps craft nuanced responses, often combining outputs from Rilla's AI assistant, Rick, to create personalized follow-ups using live call content.

Superhuman's newer AI-native features like Auto Labels, Auto Reminders & Auto Drafts add more ways for Rilla to get more out of every minute in their inbox.

The result? Sales reps achieve 2–3x more ARR than industry standard. Top performers bring in $5–6M annually.

Build it manually first, then decide how to use AI

The future might bring use cases where AI completely replaces a person, but Sebastian hasn't seen that yet. Rilla tried AI SDRs and dev tools like Devin AI, but found the results underwhelming so far.

What Sebastian sees is "human in the loop" opportunities right now — use cases where AI can help people become massively more productive.

"We always do it manually first so that we understand it with our own hands. Then we automate. Then we optimize."

This approach ensures the workflow or process aligns with the culture before accelerating and scaling across the team. That's why Sebastian built Rilla's call review process manually first. He personally reviewed hundreds of calls to understand what made the difference between good and great sales conversations. Only then did they build AI tools to scale that insight across the team.

The same principle applies to their email workflows, demo scheduling, and customer onboarding. Manual first, then AI-powered.

The Rilla startup productivity playbook

Rilla's story offers a blueprint for modern startup efficiency:

Start with culture: Make productivity a core value, not just a quarterly metric. This drives every workflow, conversation, and product decision.

Build manually first: Understand processes with your own hands before automating. This ensures alignment with your culture.

Use AI to supercharge, not replace: The biggest wins today come from "human in the loop" opportunities in your core tools, where AI makes people massively more productive.

With the right culture and AI-native tools, startups that get traction can move faster, grow more efficiently, and win bigger than ever before.

Ready to start, scale, and stay ahead with Superhuman? See if your startup is eligible for one year free, with our Superhuman for Startups Program.