SkyWatch
Techstars '16Plug and Play VenturesWaterloo, CA · Founded 2018 · 21 employees on LinkedIn · 4 known investors
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SkyWatch.ai provides aviation insurance products including drone insurance, aircraft renters insurance, and aircraft owners insurance. The company serves aviators and drone operators in the aviation sector.
Also known as Skywatch Insurance · SkyWatch.AI
Founders & leadership
SkyWatch was founded in 2018 by Tomer Kashi.

Investors · 4
Funding
SEC filings, press & company announcements- Undisclosed amountSeries BJun 2021Source ↗
Source: company announcements and press reports — follow each round's link for the claim.
Company profile
researched Aug 2026SkyWatch.AI sells aviation insurance through a fully online, end-to-end digital process. Its product line covers three customer groups: commercial drone operators, light aircraft owners, and pilots who rent aircraft. Drone policies include third-party aviation liability for bodily injury and property damage, coverage for multiple drones under a single policy, the ability to name clients as additional insureds at no extra fee, and personal injury and privacy claims coverage.
On the manned aviation side, the company writes owner's insurance for light aircraft such as Light Sport Aircraft, gliders, multi-engine aircraft, experimental aircraft and seaplanes, and single- and multi-engine variants. Its non-owned renters product targets flight students, certificated flight instructors, LSA and multi-engine pilots, and rotorcraft (helicopter) pilots flying for training, instruction and flight testing. Policies are described as customizable in features, cost and payment plan, with mid-term policy changes and multiple coverage durations. The company also offers broker consulting meetings with its insurance specialists and operates separate drone and aviation support lines during weekday business hours (9am-6pm EST).
Business model
SkyWatch.AI distributes aviation insurance policies underwritten with top "A" rated insurance capacity, selling directly to pilots and drone operators online with instant quoting, and also engaging brokers through a consulting channel.
Insurance premiums on drone policies sold on hourly, monthly and annual terms, and on aircraft owner's and renter's policies available in daily, weekly, monthly and yearly durations.
▸Full profile — market position, technology, go-to-market, geography
Market position
The company describes itself as the leading commercial drone insurance provider in the United States.
Flexible policy durations (hourly, daily, weekly, monthly and annual), a fully online end-to-end process, mid-term policy changes, multiple drones on one policy, and no-fee additional insured certificates.
Technology
A digital quoting and policy management platform that allows customers to configure coverage and purchase policies online in a few clicks.
Go-to-market
Direct-to-customer online sales with instant quotes and a fully digital purchase flow, supported by phone, email and chat specialists, a broker consulting program, and customer reviews published on the site.
Commercial drone operators across construction, aerial mapping, agriculture, delivery, public safety and drone shows; private light aircraft owners; and aircraft renters including flight students, certificated flight instructors and rotorcraft pilots.
Geography
Headquartered in Waterloo, Canada, with products marketed to United States customers and US-based toll-free support lines.
Compiled by commissioned research from 8 cited public sources — announcements, filings, and press listed under research sources below.
Key figures
latest reportedCompany-reported or press-reported figures, each dated to when it was claimed — not independently audited.
Competitors · 2
by search overlapCompanies competing with SkyWatch for the same Google search keywords, organic and paid, via search-intersection analysis.
In the news
Top Earth Observation Startups by Fundraising (2026) – New Market Pitchnewmarketpitch.com · Jul 2026▸Research sources · 8
primary sources listed
- SkyWatchskywatch.ai · web
8 public sources were cited for this profile; the first-party ones are listed here.
Frequently asked questions
- What does SkyWatch do?
- SkyWatch.AI is a digital aviation insurance provider offering commercial drone, aircraft owner's and renter's policies.
- Who founded SkyWatch?
- SkyWatch was founded by Tomer Kashi in 2018.
- Who are SkyWatch's investors?
- SkyWatch's investors include Bullpen Capital, Techstars, F2 Venture Capital, Plug and Play Ventures.
- Where is SkyWatch headquartered?
- SkyWatch is headquartered in Waterloo, CA.


