weSure Digital Insurance Services: Reinventing Small Business Insurance for the Digital Age

Who We Are

weSure Digital Insurance Services, Inc., headquartered at 220 East 42nd Street in New York City, is on a mission to make small business insurance easy, fast, and affordable.

In an industry long defined by paperwork, jargon, and delays, weSure has built a 100% digital platform that lets small business owners get a quote in minutes, choose a plan in seconds, and buy a policy the same day — all without ever picking up the phone or sitting across a desk from an agent.

weSure is not just another insurtech startup chasing a trend. It is the U.S. arm of a much larger, deeply experienced global insurance group. That combination of digital-first thinking and traditional underwriting expertise is what makes the company stand out in a crowded market.

What Sets weSure Apart

Built Exclusively for Small Businesses

Many carriers treat small business insurance as an afterthought to their commercial or personal lines. weSure does the opposite.

Its entire platform, underwriting logic, and product design exist for one purpose: protecting small business owners.

That singular focus means coverage is shaped around the real risks faced by a nail salon, contractor, two-person consultancy, restaurant, retail shop, or professional office, rather than offering a watered-down version of a policy built for large enterprises.

Truly Digital, Start to Finish

From quote to bind, everything happens online.

There are no processing delays, no hours on hold, and no stacks of paperwork. A business owner can secure a policy from their laptop between appointments, after closing for the day, or whenever it fits into their schedule.

Affordable, Transparent Pricing

Plans start as low as $1 per day, with Business Owners Policy plans starting at roughly $49 per month. weSure also advertises savings of up to 25% compared to traditional insurance shopping.

Just as important, pricing is itemized. Customers can see exactly what each coverage costs and opt out of anything they do not need.

There is no bundling of coverage they did not ask for and do not understand.

A Strong Reputation

weSure holds a 4.8 out of 5 average Google rating across more than 3,700 reviews in the U.S. and internationally. That is a meaningful trust signal in an industry where customer sentiment toward insurers is often lukewarm at best.

Backed by Real Financial Strength

Policies are issued through a carrier with an A- AM Best financial rating, meaning the digital-first experience does not come at the expense of financial security or claims-paying ability.

A Global Insurtech Engine, Not Just a Website

weSure’s underwriting and pricing are powered by data analytics and smart algorithms applied throughout the insurance lifecycle, combined with advanced underwriting designed to minimize paper forms.

This technology backbone is developed and supported by weSure Global Tech Ltd. and a weSure Global Capability Center, giving the U.S. business access to engineering and actuarial resources well beyond what a typical regional agency could build on its own.

Multi-Channel by Design

Beyond its direct-to-consumer site, weSure operates a white-labeled, multi-channel distribution platform serving retail and wholesale producers, sub-producers, and affinity partners across B2B and B2B2C relationships.

That means agents and partner organizations can plug into the same technology that powers weSure’s own consumer experience.

Interesting Facts and Company Background

weSure describes its “We” as more than a name. It represents “every mom-and-pop shop on main street, every corner café downtown, and every hairdresser or barber who has become family over the years.”

The company frames its founding purpose around protecting the businesses that hold communities together.

The name itself is a deliberate play on words. The “Sure” in weSure is meant to evoke security, resilience, honesty, and transparency — values the company lists as central to its code of ethics.

weSure’s leadership and senior management bring a combined 200 years of executive experience in insurance, risk management, and technology, with roughly the last 20 years spent working together to modernize how small businesses get insured.

The company’s growth has been fueled by real M&A activity, not just technology buzz. After proving its model through a beta launch in the Israeli insurance market and completing a Tel Aviv Stock Exchange IPO, weSure’s parent group executed a takeover of Ayalon Insurance Holdings, the sixth-largest insurance group in Israel.

That acquisition positioned the combined group as a roughly $1 billion direct written premium global insurance organization.

weSure also operates an India-based InsurTech subsidiary as part of its global technology operations, reflecting the international scale behind what looks, to a U.S. small business owner, like a simple quote-and-buy website.

The company holds registered trademarks across several sub-brands, including weSure Group, weSure Insurance, weSure LTD, weSure Financial, and weSure Technologies. This reflects a structured, multi-entity global operation rather than a single-product startup.

Meet the Founders and Leadership

Emil Vainshel — Co-Founder and Chairman of the Board

Emil Vainshel previously served as CEO of Ayalon Insurance Company, one of Israel’s largest insurers and the same company weSure’s parent group would later acquire.

He has also held VP roles at Harel Insurance Group, Israel’s largest insurance group, and Migdal, the country’s second-largest insurer. He formerly chaired the board of the Israeli POOL Organization.

Sy Foguel — Vice Chairman of the Board

Sy Foguel spent 16 years as CEO of Berkshire Hathaway GUARD Insurance Company, where he launched the Berkshire Hathaway Digital Workers Comp Program, the program that laid the groundwork for what is known today as BiBerk.

His earlier career includes serving as CEO of IDI, Israel’s first direct insurance company; Chairman of the Broadgate Lloyd’s Syndicate; SVP and Chief Pricing Actuary at Arch Insurance Group; and EVP at Clal Insurance Group.

Stefan Stefanov — Chief Operating and Business Development Officer

Stefan Stefanov previously served as General Manager at NTT DATA, where he led business development and sales for the company’s insurance software business across the Americas and Europe.

He has been with weSure since its inception and helped launch the company’s InsurTech subsidiary in India.

Mark Stephenson — VP of Underwriting & Product and Mid-Atlantic Territory Leader

Mark Stephenson previously served as Territory and Underwriting Manager for Small Commercial Accounts at Nationwide, where he was responsible for a $1 billion P&L book of business.

He brings deep distribution experience from managing Nationwide’s national network and aggregator relationships.

Together, this leadership team blends Israeli insurance and entrepreneurial expertise with deep U.S. carrier, underwriting, and distribution experience — a combination weSure describes as its “winning cocktail” for building sustainable, advanced digital insurance for small businesses worldwide.

What weSure Offers

weSure’s core small business insurance products include:

Business Owners Policy

A Business Owners Policy combines property damage and liability coverage into one packaged policy, including general liability and business interruption protection. BOP plans start at $49 per month.

Workers’ Compensation Insurance

Workers’ compensation insurance is mandatory in most U.S. states and covers medical care and lost wages resulting from work-related injuries.

Cyber Insurance

Cyber insurance provides first- and third-party coverage protecting businesses against a wide range of cyber exposures, from data breaches to related liabilities.

General Liability Insurance

General liability insurance protects against customer injury claims, advertising damages, reputational liability, and legal defense costs.

Commercial Property Coverage

Commercial property coverage protects business property, buildings, equipment, and inventory. It may also include coverage for income interruption and equipment breakdown.

Employers Liability Coverage

Employers liability coverage protects against lawsuits alleging employee work-related injury or illness.

Additional Coverages

Optional add-ons include identity fraud protection, money and security coverage, and outdoor sign protection.

Coverage Packages and Industry-Specific Options

To simplify decision-making, weSure offers three tiers of pre-built packages: Essential, Standard, and Premium.

These packages scale from foundational coverage to comprehensive, high-limit protection with bundled endorsements.

Beyond these general tiers, weSure also builds industry-specific packages tailored to the unique risks of contractors, medical and dental practices, service providers, beauty and nail salons, restaurants, retail shops, laundries and dry cleaners, professional offices, and real estate businesses.

For insurance agents and brokers, weSure offers an Agency Appointment program and a dedicated Agency Portal, extending its digital platform and pricing engine to partners who want to offer weSure’s products to their own clients.

The Bottom Line

weSure occupies a distinctive position in the small business insurance market: a digital-first, customer-friendly platform on the surface, backed by a global insurance group with real underwriting depth, actuarial talent, and an A- AM Best-rated carrier behind it.

For a small business owner, that translates into a simple promise: get a quote in minutes, understand exactly what you are paying for, and know that when something goes wrong, there is a financially sound, experienced organization standing behind the policy.