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Startup Deep Dive : Attentive.ai — how a landscaping-measurement startup became a construction-AI company

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The Invincible India Startup Deep Dive featured graphic for Attentive.ai.

In November 2025, Attentive.ai raised $30.5 million to build artificial intelligence for the American construction industry. That single round, led by the New York growth-investor Insight Partners, took the company’s total disclosed funding to roughly $48 million (₹460.8 crore at $1 ≈ ₹96.0, 18 September 2026, Trading Economics) since 2021. What makes the story odd is that the company’s own website, as of this writing, still introduces itself as “the number one property measurement software” for lawn-care and landscaping firms — a description that has almost nothing to do with the construction-estimating product its investors are actually funding.

Attentive.ai is an India-built, India-staffed company that sells to a market it rarely visits in person. As of February 2024, only five of its roughly 160 employees were based in the United States, according to TechCrunch; the rest worked out of India, mostly serving American and Canadian landscaping and construction firms over the internet. That geography split, and the company’s repeated changes of direction — from remote property intelligence for insurers, to landscaping business software, to construction takeoff automation — sit at the centre of how a seven-year-old company ended up as one of Insight Partners’ newer bets in “AI for the built environment.”

Quick facts

Company Attentive.ai (Indian operating entity: Attentive AI Solutions Private Limited, CIN U74999DL2017PTC318076; US entity: Attentive.ai Inc., Delaware)
Founded Indian entity incorporated 18 May 2017, New Delhi (Tofler, InstaFinancials); Delaware entity and current product line trace to April 2021 (TechCrunch, February 2024)
Founder(s) Shiva Dhawan (co-founder & CEO) and Rishabjit Singh (co-founder & CTO), both IIT Delhi graduates; Sarthak Vijay and Aishwarya Maurya are also named as co-founders
Businesses Beam AI (construction takeoff and estimating), BIM CoPilot (BIM project management), Automeasure and Accelerate (property measurement and business management for landscaping/outdoor services)
Latest FY revenue Not disclosed on a consolidated basis; company cited $4 million annual recurring revenue in February 2024 (TechCrunch). Its Indian subsidiary’s FY24 revenue sits in the ₹1–10 crore band per Tofler’s read of MCA filings
Latest FY profit/loss Not disclosed on a consolidated basis
Listed Private (no listing)
Market value / last valuation Not publicly disclosed; total funding raised is approximately $48 million (₹460.8 crore) as of November 2025 (Insight Partners, Inc42)
Key shareholders / CEO CEO Shiva Dhawan; investors include Insight Partners, Vertex Ventures, Tenacity Ventures, InfoEdge Ventures, Peak XV Partners (via Surge) and Redstart Labs

What they do

Attentive.ai builds artificial-intelligence software that reads satellite imagery, aerial photographs, drone footage and construction blueprints, and turns them into measurements a business can bid with. Its customers fall into two groups: outdoor-services companies — landscaping, paving, snow removal and lawn care firms — who use its Automeasure and Accelerate products to measure a property from an aerial image instead of sending someone to walk the site; and construction firms — general contractors, subcontractors and suppliers — who use its newer Beam AI and BIM CoPilot products to extract quantities from blueprints and building-information-model files so estimators can put together a bid faster. As of its November 2025 funding round, the company said it served more than 1,100 customers across the United States and Canada (Insight Partners, November 2025).

The origin

Attentive AI Solutions Private Limited was incorporated in New Delhi on 18 May 2017 (Tofler, InstaFinancials, accessed September 2026), founded by IIT Delhi engineers Shiva Dhawan and Rishabjit Singh. The founding insight, as the company described it when it first surfaced publicly, was narrow and specific: the outdoor-services industry — landscaping contractors and the home-insurance firms that insure the properties they maintain — had barely adopted modern software, and both groups needed the same basic thing, an accurate read of a property’s dimensions, without anyone having to visit it in person (The SaaS News, October 2021). Computer vision applied to satellite and aerial imagery could produce that measurement remotely, cheaply and at scale. The idea, in other words, was not “AI for construction” — that came later — but a much smaller wager on remote property intelligence for two unglamorous, software-shy trades.

The struggle years

The public record shows a company that took years, and several changes of direction, to find a business that investors would fund at scale. Between its incorporation in May 2017 and its first disclosed institutional cheque in October 2021, there is no reported outside funding at all — a four-year stretch that corporate filings and press coverage are simply silent on. The company’s own current telling, repeated in its Series B materials, is that it “started with AI-powered property measurements for landscaping and paving maintenance using aerial imagery” before pivoting to construction (Attentive.ai company blog, November 2025) — but even that landscaping-first phase was not static.

In October 2021, when Attentive.ai raised its first outside capital — a $2 million pre-Series A led by Info Edge Ventures — its own pitch named two customer segments: outdoor-services companies and “home insurance companies,” which it said used its remote measurements to prepare estimates without site visits (The SaaS News; Inc42, October 2021). The insurance angle did not become a disclosed growth line in any later funding announcement. By its July 2022 raise, the company had narrowed to landscaping and outdoor services alone, launching what it called “a first-of-its-kind sales automation platform” for that industry (Attentive.ai company blog, July 2022). By February 2024, it had pivoted again, telling TechCrunch it was moving into construction estimating through a new product, Beam AI, because the underlying computer-vision technology could read a blueprint the same way it read a satellite image. Three customer bets in under four years — insurance-adjacent property data, landscaping operations software, and construction takeoff — is not the story of one idea executed in a straight line.

The turning point

The clearest inflection point in Attentive.ai’s history is the construction pivot that crystallised around its February 2024 Series A. Before it: a $4 million annual-recurring-revenue business with just over 500 customers, of which roughly 300 were landscaping companies, 100 paving-maintenance firms and 100 construction companies — construction was the smallest of the three groups (TechCrunch, February 2024). The round itself, $7 million led by Vertex Ventures Southeast Asia and India, was explicitly earmarked to build out Beam AI, the construction-takeoff product, alongside the older Automeasure and Accelerate lines.

After it: by November 2025, when Insight Partners led a $30.5 million Series B, Attentive.ai’s own materials described it purely as a “preconstruction platform” serving “over 1,100 companies” in “construction and field services” — landscaping was no longer mentioned as a distinct pillar in the announcement (Insight Partners, November 2025). In twenty-one months, the company had gone from a landscaping-measurement business with a small construction side-bet to a construction-AI company that happened to have started in landscaping, its cumulative funding rising from roughly $14 million to about $48 million over the same stretch.

The money behind it

Attentive.ai has raised money in five disclosed rounds since 2021, taking total funding to approximately $48 million (₹460.8 crore) as of November 2025, as reported by Insight Partners and Inc42:

Each lead investor tracks the pivot: Info Edge Ventures backed the earliest, unproven geospatial thesis; Sequoia India’s Surge added conviction around the landscaping business; Vertex Ventures funded the construction bet when it was still a side project; and Insight Partners, a much larger growth-stage investor with no prior India-geospatial exposure, arrived only once Beam AI had become the company’s primary identity. No source in this article states a company valuation for any round, and none could be independently confirmed, so this piece does not state one.

How it makes money

Attentive.ai is a software-as-a-service business: customers pay recurring fees to use its measurement and estimating tools rather than a per-project or commission-based fee. The company itself uses the language of “annual recurring revenue” rather than one-time licence fees when describing its scale (TechCrunch, February 2024), which points to subscription pricing rather than a transaction take-rate. No source reviewed for this piece discloses per-seat pricing, contract length or gross margin.

The numbers

Attentive.ai does not publish an audited, consolidated profit-and-loss account, and neither its Delaware parent nor its Indian operating subsidiary is listed, so multi-year revenue and profit figures for the group as a whole are not publicly available. The only India-specific data point traced for this piece comes from Tofler’s analysis of the Indian subsidiary’s Ministry of Corporate Affairs filings, which places FY24 (year ended 31 March 2024) revenue in the ₹1–10 crore band — a modest figure consistent with an Indian entity that functions mainly as an engineering and delivery centre while most customer billing sits in the US parent. The clearest, sourced measure of the business’s actual scale over time is the growth in disclosed customers, headcount and cumulative funding between its two most recent funding rounds:

Metric February 2024 (Series A) November 2025 (Series B)
Reported customers 500+ (≈300 landscaping, ≈100 paving, ≈100 construction) 1,100+ (construction and field services)
Annual recurring revenue (company-stated) $4 million Not disclosed
Employees (company-stated) ~160 (5 in the US, rest in India) Not disclosed
Cumulative funding raised ~$14 million ~$48 million (₹460.8 crore)

Sources: TechCrunch, February 2024; Entrackr, February 2024; Insight Partners, November 2025; Inc42, November 2025.

Where the money comes from

Attentive.ai’s revenue mix has shifted twice in ways the company itself has disclosed:

The surprise is less about geography — India-built, US-sold is a familiar pattern for Indian SaaS — and more about how quickly the disclosed centre of gravity moved from landscaping, the business the company was named for and still describes itself as on its own website, to construction, which did not exist as a product line before 2024.

The risks

The takeaway

Attentive.ai’s history is a reminder that a founding insight and a company’s eventual business are not always the same thing. The computer-vision capability — reading a picture, satellite image or blueprint, and turning it into an accurate measurement — never changed since 2017. What changed three times over was who would pay for it: insurers, then landscapers, then general contractors. The capability was the constant; the customer was the variable investors kept re-testing money against, and it took until the fourth attempt, construction takeoff, for outside capital to arrive at meaningful scale. For an India-built engineering team selling into a market it has barely visited, that is arguably a more transferable lesson than any single funding round: a durable technical wedge can survive several wrong guesses about who its buyer should be, as long as the team keeps testing rather than defending its first answer.

Frequently asked questions

What does Attentive.ai actually sell?

Software that reads aerial imagery, satellite photos and construction blueprints and converts them into measurements and cost estimates. Automeasure and Accelerate serve landscaping and outdoor-services companies; Beam AI and BIM CoPilot serve construction general contractors, subcontractors and suppliers (company sources, 2024–2025).

How much money has Attentive.ai raised in total?

Approximately $48 million (₹460.8 crore) across five disclosed rounds between October 2021 and November 2025, according to Insight Partners and Inc42’s coverage of the November 2025 Series B.

Who leads Attentive.ai, and who are its investors?

Shiva Dhawan is co-founder and CEO, with Rishabjit Singh as co-founder and CTO; Sarthak Vijay and Aishwarya Maurya are also named as co-founders in company and press sources. Investors include Insight Partners, Vertex Ventures, Tenacity Ventures, Info Edge Ventures, Peak XV Partners and Redstart Labs.

Is Attentive.ai profitable, and what is it worth?

Neither figure is publicly disclosed. Its only reported revenue figure is $4 million in annual recurring revenue as of February 2024 (TechCrunch); no confirmed valuation appears in any source reviewed for this piece, so none is stated here.

Is this the same company as “Attentive,” the US SMS-marketing platform?

No. Attentive.ai (construction and landscaping AI, founded in India) is a separate company from Attentive Mobile, the New York-based customer-messaging platform founded by Brian Long and Andrew Jones, which reported $500 million in annual recurring revenue in 2024. The similar names refer to two unrelated businesses.

Sources

Figures are as of September 2026. Currency converted at $1 ≈ ₹96.0 as of 18 September 2026 (Trading Economics).

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