When was Sterling founded?

Sterling was founded in 2012 and raised its 1st funding round 10 years after it was founded.

Where is Sterling located?

Sterling is headquartered in Toronto, Canada.

Is Sterling a funded company?

Sterling is a funded company, having raised a total of $***** in its 1st and only funding round, a Seed round on Feb 22, 2022.

When was the latest funding round of Sterling?

Sterling's latest funding was a $***** Seed round on Feb 22, 2022, with participation from 1 investor.

Where does Sterling rank among its competitors?

Sterling ranks 2nd amongst 29 active competitors, of which 3 are funded. It stands 3rd in terms of total funding among its competitors. The most recent competitor to raise funding was League, which secured an undisclosed amount in Feb, 2025.

Who are the top competitors of Sterling?

Sterling's top competitors include League, myHSA and Shepellfgi. Among them, League secured the most recent funding round in February, 2025.

Sterling - 2026 Company Profile, Team, Funding & Competitors

Sterling is an acquired company based in Toronto (Canada), founded in 2012 by David Haines and Stefan Ionescu. It operates as a Provider of insurance brokerage solutions. Sterling has raised an undisclosed amount in funding from True Wind. The company has 29 active competitors, including 3 funded and 4 that have exited. Its top competitors include companies like League, myHSA and Shepellfgi.

Company Details

Provider of insurance brokerage solutions. The company offers group insurance, group retirement, and third-party administration services. Its features include data-driven insurance product selection, paperless onboarding, and more.

Website: www.sterlingbrokers.com/
Social
Email ID: *****@sterlingbrokers.com

Key Metrics

Founded Year

2012

Location

Toronto, Canada

Stage

Acquired

Latest Funding Round

Seed, Feb 22, 2022, $*****

Investors

True Wind

Ranked

2^nd among 29 active competitors

Investment & Acquisitions

MB Pension & Benefits Group

Similar Companies

Swile & 659 more

Exit Details

Acquired by HGGC (Oct 06, 2025)

View Sterling's full profile

Sterling got acquired by HGGC on Oct 06, 2025.

Click here to take a look at Sterling's acquisition in detail

Sterling has raised funding over 1 round. Its latest funding round was a Seed round on Feb 22, 2022 for $*****. 1 investor participated in its latest round. Sterling has 1 institutional investor.

Here is the list of recent funding rounds of Sterling:

Date of Funding	Funding Amount	Round Name	Post-Money Valuation	Revenue Multiple	Lead Investors	Other Investors
Feb 22, 2022	2181349	Seed	6015107	2644842	8894132	3189592

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View details of Sterling's funding rounds and investors

The founders of Sterling are David Haines and Stefan Ionescu.

Here are the details of Sterling's key team members:

David Haines: Co-Founder of Sterling.
Stefan Ionescu: Co-Founder of Sterling.

View details of Sterling's Founder profiles and Board Members

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Top competitors of Sterling include League, myHSA and Shepellfgi. Here is the list of Top 10 competitors of Sterling, ranked by Tracxn score:

Rank	Company Details	Short Description	Total Funding	Investors	Tracxn Score
1st	League 2014, Toronto (Canada), Series C	Provider of SaaS based digital platform to manage employee health benefits	$242M	TDM Growth Partners, OMERS & 18 others	73/100
2nd	Sterling 2012, Toronto (Canada), Acquired	Provider of insurance brokerage solutions	-	True Wind	41/100
3rd	myHSA 2011, Calgary (Canada), Unfunded	Provider of app to manage employees claims for administration benefits	-	-	39/100
4th	Shepellfgi 2006, Toronto (Canada), Acquired	Online platform for employee benefits administration	-	-	35/100
5th	Sapphire Digital Health 2008, Kitchener (Canada), Unfunded	Provider of AI-based health data management software for patients and employees	-	-	32/100
6th	Caribou 2019, Toronto (Canada), Funding Raised	Automated incentives platform to homecare agancies for staff management	-	Mantella Venture Partners, ventureLAB	31/100
7th	Groupe Major 2002, Gatineau (Canada), Unfunded	Employee benefit administration platform	-	-	31/100
8th	Aya 2020, Toronto (Canada), Unfunded	Provider of digital medical payment solution and card for employees	-	-	30/100
9th	Oliver 2019, Vancouver (Canada), Seed	Online benefits administration and retirement planning software for enterprises	$575K	GroupHEALTH	29/100
10th	Benefits By Design 1996, Port Coquitlam (Canada), Acquired	Customized benefit solutions provider for SMBs and Individuals.	-	-	28/100