Sacra estimates that Rilla hit $70M in annual recurring revenue (ARR) in April 2026, up from $51M in 2025, after growing from $11M in 2023 to $24M in 2024.

The revenue base is almost entirely annual subscription contracts paid upfront, which means Rilla collects cash at the start of each term rather than ratably. That front-loaded cash profile, combined with a minimum commitment of around five seats per customer, produces a predictable revenue stream from day one of each contract.

The customer base crossed 2,000 accounts in mid-2025, implying an average contract value of roughly $20,000 per year, more than double the implied ACV from early 2024. That change points to both seat expansion within existing accounts and a mix shift toward larger enterprise deployments. The Home Depot, announced as a customer in January 2026, represents a different scale of deployment than the home services contractors that formed Rilla's original base.

Rilla's most recent post-money valuation is approximately $757M, set at its Series B in June 2025, led by Google Ventures (GV). The round raised $68.5M in primary capital. Other participants in the Series B include Bessemer Venture Partners, HubSpot Ventures, PROOF, QuantumLight Capital, and Remarkable Ventures.

Before the Series B, Rilla raised a $3.7M Series A in December 2022, led by Crew Capital, with participation from ERA Fund, Jason Calacanis's Launch Fund, Broom Ventures, Comma Capital, and the NYU Innovation Venture Fund. That round was priced at a post-money valuation of approximately $45M. An undisclosed Series A1 followed in December 2023.

Earlier capital included a $100K seed check from ERA in May 2020 and two small accelerator checks of $10K each in 2018 and 2019.

Total primary funding raised across all rounds is approximately $72M to $79M, with the range reflecting differences in how early accelerator checks are classified across data sources.

Rilla is an AI coaching platform for field sales teams, reps who drive to customers' homes or walk showroom floors to close deals in person rather than over Zoom.

The workflow starts with a rep opening the Rilla mobile app on their phone before an appointment. No additional hardware is needed. The app records the conversation, and after the appointment, Rilla's AI transcribes the audio and generates a structured analysis including an overall call score, flagged moments tied to behaviors like presenting financing options or handling objections, the rep's talk-to-listen ratio, and how often they asked open-ended questions.

A sales manager reviews a condensed clip, roughly three minutes, instead of spending three to six hours physically riding along in a truck. The manager can annotate moments, score the call, and send feedback directly to the rep. For a manager overseeing ten reps each running five appointments a week, that makes it possible to review every conversation rather than sampling one or two per week.

Rilla Live, launched in September 2025, extends the workflow into real time. A manager can watch a live transcript as a rep is mid-appointment, see all active conversations ranked by priority, and push coaching notes to the rep's phone while the call is still happening.

Rilla Intelligence, launched in October 2025, moves from individual rep coaching to company-level analytics. Using what the company describes as the largest dataset of in-person sales conversations ever assembled, it surfaces patterns across thousands of reps, including what top performers say differently, which objections appear most frequently in a given market, and how close rates vary by conversation structure. A Roleplay module lets reps practice against an AI simulation of a customer before actual appointments, spanning practice before, record during, analyze after, and monitor in real time.

Rilla sells B2B software on annual per-seat subscriptions paid upfront at contract signing. Pricing runs approximately $4,000 to $5,000 per seat per year, with a minimum of five seats, putting the floor for a new customer at roughly $20,000 annually before any implementation fees. A built-in 3% annual escalator adds modest net revenue retention lift on renewing contracts.

The upfront payment structure affects working capital. Unlike SaaS businesses that collect revenue monthly, Rilla receives the full annual contract value in cash at the start of each term. At $51M in 2025 ARR with roughly 2,000 customers, the business generates strong cash flow relative to its size, a dynamic that allowed Rilla to describe itself as cash-flow positive as early as December 2022, before it had raised meaningful outside capital.

Gross margins are estimated in the 85–90% range. The primary cost of goods is speech-to-text API processing and AI inference, which runs well under $1 per appointment at current API pricing. As transcription infrastructure costs fall, margin on the core recording and analysis product expands even without price increases.

Expansion within accounts comes from seat additions as customers grow their field sales teams and from upsell into Rilla Live and Rilla Intelligence, which carry premium pricing on top of the base subscription. The implied ACV more than doubled from roughly $9,300 in early 2024 to roughly $20,000 by mid-2025, driven by seat growth and product attach. Revenue per employee runs at approximately $400,000, roughly twice Gong's level at comparable stages, reflecting a lean team and a no-free-trial, annual-upfront sales motion that minimizes pre-sale resource consumption.

Rilla operates in a field that remains underpenetrated and is attracting capital. The two largest players, Rilla and Siro, raised a combined $118M within a single month in mid-2025.

Siro is the closest direct competitor. It was also founded in New York around 2020 and focuses on in-person sales coaching for home services contractors. Siro has raised $75M in total, including a $50M Series B from SignalFire in May 2025, one month before Rilla's own Series B closed.

Rilla holds a roughly 3-4x revenue lead over Siro, but Siro has structural advantages in a few areas. It launched real-time coaching before Rilla Live existed, and it has a deeper integration with ServiceTitan, the dominant operating platform for home services businesses. That ServiceTitan integration is a distribution wedge: contractors already running their business on ServiceTitan can activate Siro's Field Pro product without adopting a separate vendor relationship.

A similar pattern played out in inside sales conversation intelligence, where Gong's standalone recording product came under pressure as Outreach, ZoomInfo (which acquired Chorus for $575M in 2021), HubSpot, and Apollo embedded call recording into broader platforms. That pattern is beginning to emerge in field sales.

ServiceTitan's deep integration with Siro is the clearest indicator. If ServiceTitan were to acquire or natively build conversation intelligence, it could commoditize the home services core of Rilla's business in the same way CRM-native recording commoditized standalone tools in inside sales. Recall.ai and Deepgram have made the underlying transcription infrastructure cheap enough that any platform with distribution could assemble a basic version of the product.

Rilla's response is vertical diversification into home building, dental, retail, and enterprise accounts like The Home Depot that sit outside ServiceTitan's orbit, along with GV and HubSpot Ventures relationships that create counterweight distribution through Google Cloud and HubSpot's enterprise customer base.

Below Rilla and Siro, a set of vertical-specific tools like CraftFlow compete on price and depth within home services, explicitly targeting the sub-$20,000 annual spend buyer that Rilla's minimum commitment has priced out. These players focus on the full customer journey, from the initial CSR call through field appointment to follow-up, rather than Rilla's field-first approach.

These smaller competitors are less of a direct threat to Rilla's current customer base than a constraint on how far down-market Rilla can push without repricing its product. As Rilla moves upmarket toward Fortune 50 accounts, the competitive set shifts toward Gong, Salesforce Field Service, and enterprise AI platforms. None has meaningfully invested in the physical, in-person conversation capture problem that Rilla has spent four years solving.

Rilla's founding wedge, home improvement field sales, addresses a real but bounded market. Its expansion logic is to apply the same product to commercial conversations that happen in person, a larger surface area than roofing and HVAC.

The home services market is large, but Rilla's product also applies in settings where a rep walks into a room to close a deal. The Shore Consulting partnership in July 2025 opened new home sales as a vertical by embedding Shore's sales methodology into Rilla's AI coaching layer and using Shore's existing customer base as a distribution channel. Dental and healthcare practices are another adjacent vertical, where Rilla has documented a case study showing case acceptance rates improving from 10% to 40%.

The Home Depot partnership, announced in January 2026, is the clearest signal of vertical expansion. Home Depot operates over 2,300 stores with hundreds of thousands of associates. The partnership is framed around service and sales professionals, not just field sales reps, which points to a broader frontline workforce use case beyond the kitchen-table sales call.

Rilla's original ICP was the $5M-$50M home services contractor with five to fifty field reps. The move to enterprise changes the unit economics materially. A single Fortune 50 deployment could represent more ARR than hundreds of SMB accounts combined, and a Home Depot-scale customer can help open enterprise procurement paths that would otherwise be difficult to access.

The GV investment and the parallel Google Cloud relationship with Home Depot point to a distribution strategy through the Google Cloud enterprise sales motion. HubSpot Ventures as an investor creates a similar channel into HubSpot's large base of B2B companies that have field sales teams but currently use HubSpot only for inside sales workflows.

Rilla Intelligence represents a different type of TAM expansion: the same customers paying for a higher-value analytical layer built on top of the conversation corpus Rilla has accumulated.

The analogy is Gong's Data Engine, which shifted Gong from a call recording tool to a revenue intelligence platform and drove multiproduct attach to 25% of its customer base. Rilla's dataset of in-person sales conversations would be difficult for a new entrant to reproduce, as it took four years and millions of appointments to build, and the benchmarks it enables become more valuable as the dataset grows. This is the path from a $757M valuation toward the kind of platform multiple that Gong commands at $7.25B.

ServiceTitan bundling: If ServiceTitan, which already has Siro deeply integrated as a Field Pro product, were to acquire Siro or build native conversation intelligence, it could commoditize the home services segment that still represents the majority of Rilla's revenue and force a faster-than-planned migration to enterprise and non-home-services verticals where Rilla has less established distribution.

Consent and compliance friction: In-person sales recording in two-party consent states requires explicit disclosure before the conversation begins, which creates workflow friction that does not exist for Zoom-native tools like Gong, and any expansion of state-level wiretapping enforcement or class-action litigation around undisclosed recording could impose compliance costs or drive customer churn in Rilla's highest-density markets.

Data moat durability: Rilla's core defensibility argument rests on having the largest dataset of in-person sales conversations ever assembled, but if Google, Apple, or a well-funded entrant were to subsidize rapid data accumulation through free or deeply discounted recording tools, the training data advantage behind Rilla Intelligence's pricing premium could erode faster than the revenue base can diversify away from the coaching product.