-73%

est. 2Y upside i

HealthcareSeries A

We sell health insurance to small businesses 100% online.

Rank

#2011

Sector

Health Insurance Technology

Est. Liquidity

~3Y

Data Quality

Data: Medium

SimplyInsured operates in a highly competitive health insurance technology market, with an estimated $5.8M in annual revenue and approximately 50 employees.

Last updated: March 10, 2026

Bull (15%)+300%

SimplyInsured successfully expands its platform with deeper HR integrations and captures significant market share from traditional brokers, growing revenue to $20M-$25M by 2028 and justifying a $100M-$125M valuation at a 5x multiple.

Base (45%)+75%

SimplyInsured maintains its niche in the small business health insurance market, growing revenue to ~$10M-$12M by 2028 and achieving a $50M-$60M valuation at a ~5x multiple, but faces ongoing competitive pressures.

Bear (40%)-75%

Increased competition from incumbents and well-funded competitors like eHealth and Zenefits leads to pricing pressure and slower growth. Revenue stalls, and a down round or low acquisition price of ~$7.25M wipes out all common stock value given $8.5M in liquidation preferences.

Est. time to liquidity~3.0 years

Preference Stack Risk

high

Investors hold $8.5M in liquidation preferences, representing 29.3% of the estimated $29M current valuation.

Dilution Risk

high

Given the company's current revenue and funding history, future capital raises are highly likely to fuel growth, which could lead to further dilution for common shareholders.

Secondary Liquidity

none

There is currently no active secondary market or tender offers for SimplyInsured's shares, typical for a company at this stage.

Other — 2 roles

View all 2 open roles at SimplyInsured →

Last updated: February 22, 2026

Questions to Ask at the Interview

Strategic questions based on SimplyInsured's data — designed to show you've done your homework.

  • 1

    “Given the estimated $5.8M in annual revenue and the competitive landscape, what are SimplyInsured's specific growth strategies to achieve significant scale and differentiate from larger incumbents like eHealth and HR platforms like ADP?”

  • 2

    “With $8.5M in total funding and the last round in 2015, how does the company plan to fund future growth, and what is the anticipated timeline and strategy for a liquidity event for employees?”

  • 3

    “SimplyInsured has integrations with Quickbooks and BambooHR. How is the company thinking about deepening these partnerships or forming new ones to expand its reach and competitive advantage against broader HR solutions?”

Community

Valuation Sentiment

Our model estimates -73% upside. What do you think?

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Disclaimer: This analysis is AI-generated and does not constitute financial or career advice. Always conduct your own due diligence.