Rilla

Market position

Rilla is described as a leading conversation intelligence platform for in-person sales, in a segment that remains underpenetrated. Its closest direct competitor is Siro, founded in New York around 2020 and also focused on in-person sales coaching for home services contractors; the two companies raised a combined $118M within a single month in mid-2025. Sacra estimates Rilla holds roughly a 3-4x revenue lead over Siro, while noting Siro launched real-time coaching before Rilla Live and has deeper integration with ServiceTitan, a widely used home services operating platform. Rilla's revenue per employee is estimated at about $400,000, roughly twice Gong's at comparable stages.

Rilla focuses specifically on in-person field sales rather than phone or video calls, using only a rep's existing smartphone and compressing a manager's multi-hour physical ridealong into a roughly three-minute reviewable clip, which allows every appointment to be reviewed rather than sampled. It layers real-time coaching (Rilla Live) and cross-company analytics drawn from its in-person conversation dataset (Rilla Intelligence) on top of the core recording and analysis product, and models are tuned to each customer's own top performers. Its commercial model — annual prepaid contracts, no free trials, five-seat minimum — supports a lean team and high revenue per employee.

Technology

Mobile app-based audio capture on reps' existing phones, speech-to-text transcription and AI analysis that generates call scores, behavior-tagged moments, talk-to-listen ratios and open-ended question counts. Rilla Live provides real-time transcription and in-call coaching prompts; Rilla Intelligence applies analytics across what the company describes as the largest dataset of in-person sales conversations, and includes an AI roleplay simulator for practice. Models are tuned to each customer's sales process and top performers' behavior.

Go-to-market

Rilla runs a demo-led enterprise sales motion — the website's primary call to action is scheduling a demo — with annual contracts paid upfront and no free trials. The founder has described experimenting with trade shows, cold outreach and paper contracts, structuring demos around discovery, storytelling, short product reveals and Q&A, and selling outcomes rather than features. Partnerships extend distribution: a March 2026 press release announces a combination with Neighborly to serve plumbers and HVAC technicians.

In-person and field sales organizations, including home services (such as HVAC), home improvement, home building and remodeling, automotive, dental practices, senior living, and multifamily property management. Customers range from home services contractors to large enterprises; The Home Depot was announced as a customer in January 2026.

Geography

Headquartered in New York City, with an in-person office culture; company offsites have been held in San Diego, Cape Cod and Palm Springs. Guidance on recording consent references US two-party-consent states including California, Massachusetts, Connecticut, Florida, Maryland, Illinois, Washington, Montana, Pennsylvania, New Hampshire and Oregon.

History

Rilla operated at a loss for years while cycling through markets including political canvassing, retail pilots and field marketing, keeping the product largely unchanged while searching for fit. Early capital included two small accelerator checks of $10,000 each in 2018 and 2019 and a $100,000 seed check from ERA in May 2020, followed by a $3.7M Series A in December 2022 led by Crew Capital and an undisclosed Series A1 in December 2023. After settling on field sales, the company recorded $130,000 of revenue in its first month in the new vertical and raised pricing from $30 per month to roughly $5,000 per license per year on annual prepaid contracts. A $68.5M Series B led by GV closed in June 2025, followed by the launches of Rilla Live in September 2025 and Rilla Intelligence in October 2025, The Home Depot as an announced customer in January 2026, and a March 2026 partnership with Neighborly.

Risks & controversies

The product depends on recording customer conversations, which raises consent and compliance considerations; Rilla states recording is legal but that customers must be informed in eleven listed US states and publishes recommendation guidelines. Competitive risk comes from Siro, which launched real-time coaching before Rilla Live and holds a deeper integration with ServiceTitan, a distribution advantage among home services contractors. The company also describes an unusually intense work culture — roughly 70-hour weeks, six days a week fully in person — which it acknowledges is not a fit for everyone.