Rilla

Software Development

Apt Insight

They are growing rapidly with an intense, all-in culture where people take on immense responsibility and earn competitive compensation. Headquartered in New York, the startup builds conversation intelligence software tailored for in-person sales and service professionals. They operate as a small-to-mid-sized organization within the tech software space and have expanded their footprint significantly. Active hiring continues across multiple departments to sustain their expansion.

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About

Rilla is the leading virtual ridealong software for outside sales and service. When sales reps or technicians go out and talk to customers face to face. They record their conversations with the Rilla app, and we use AI to automatically transcribe, analyze and give them feedback to help them improve their sales. And to help their sales managers do virtual ridealongs that are 100x faster, better, and more productive than physical ridealongs. If you're interested in joining us in our adventure, we are hiring! https://www.rilla.com/careers

Founded2021

HeadquartersNew York, US

IndustrySoftware Development

Websitewww.rilla.com

Employees139

Total Funding$4M

Open roles at Rilla

3 open roles, newest first.

Software Engineering Intern, 2028 GradsNew York, New York · Onsite

Software Engineering Intern, 2028 Grads New York, New York · Onsite

Product Design InternNew York, New York · Onsite

Why people join & leave

Why join

Accelerated career growth and ownershipHigh compensation and housing stipendsWorking on applied AI for offline salesAmbitious, high-energy startup culture

Why leave

Six-day on-site workweeks and long hoursRisk of rapid burnoutHeavy performance pressure in sales rolesLimited work-life balance

Company Pulse

Headcount

-65%past year

Raised

$4Mtotal

In the News

As founders in our 20s, we worked out a cramped apartment.linkedin.com · Sep 9, 2026

This CEO pays $1.7 million a year so employees can live in one of America’s most expensive areas | Fortunefortune.com · Jul 8, 2026

This AI Founder Pays Employees $18k to Live Near the Officeinc.com · Jul 6, 2026

I Pay Each Startup Employee $18000 a Year to Live ...businessinsider.com · Jul 4, 2026

Rilla records, transcribes, and analyzes in-person sales conversations so sales teams can coach what actually works and replicate their winning process.linkedin.com · Jun 17, 2026

Employee Experience

3.8/5

Career Opportunities

4.0

Compensation & Benefits

4.1

Culture & Values

3.8

Diversity & Inclusion

3.8

Senior Management

3.9

Work-Life Balance

3.5

Quick Take

Strengths

Strong compensation packagesCompensation and benefits are rated at 82, supported by competitive pay and unique perks like housing stipends.

Rapid organizational growthThey expanded into a 57,350-square-foot office space with ongoing hiring across engineering and sales.

Watch out

Demanding scheduleEmployee reports frequently highlight six-day workweeks and long daily shifts in the office.

Note

In-office proximity modelThey offer an $18,000 annual housing stipend to encourage staff to live within a 10-minute commute.

Things to consider

Extreme work hours — Multiple employee reviews and press reports cite intense schedules, six-day workweeks, and workweeks stretching up to 72 hours.

High attrition risks — Reviewers report noticeable turnover, particularly within sales development teams, stemming from burnout and aggressive targets.

Leadership

Mike DavisCEO

What They Build

Rilla develops an AI coaching and speech analytics platform designed for field sales and technicians. The platform captures face-to-face audio conversations, automatically transcribing and evaluating interactions to provide automated feedback and virtual ridealong capabilities. Engineering tackles complex audio processing, natural language modeling, and scalable cloud infrastructure.

Speech Analytics

Conversation Intelligence

Machine Learning

Field Sales Software

Domains

Machine Learning

Backend

Infrastructure

Frontend

Tech Stack

Python

PyTorch

TypeScript

JavaScript

React

PostgreSQL

Redis

Kubernetes