Software · head to head
Pie Insurance vs Bold Penguin
Pie Insurance
Software
Small business workers compensation and commercial insurance sold by online quote
- From
- On request
- Rated
- -
The short version
- Only Bold Penguin has a free tier, so it costs nothing to try first.
- Each has a real cost: Pie Insurance coverage is available in only 39 states plus Washington DC, as of August 2026; Bold Penguin sold to brokers, carriers and MGAs rather than to the businesses buying insurance
Where they differ
Only the attributes on which Pie Insurance and Bold Penguin actually diverge.
| Attribute | Pie Insurance | Bold Penguin |
|---|---|---|
| Starting price | On request | Free |
| Pricing model | quote | transaction |
| Free tier | No | Yes |
| Platforms | Web | Web, Ios, Android |
| Founded | Unknown | 2019 |
Identical on both: user rating (Not yet rated), category (Unknown).
What each one covers
Drawn from each product's published feature list. An absence here means we hold no record of it - not that the product lacks it.
Only in Pie Insurance
Nothing recorded that Bold Penguin does not also cover.
Only in Bold Penguin
- Multi-carrier quoting
- Instant quotes
- Online binding
- Customer portal
- Commission tracking
- Mobile app
- API access
- Reporting
What people use each for
The jobs each tool is most often brought in to do.
Pie Insurance
No use cases recorded yet. See the Pie Insurance review.
Bold Penguin
- Routing and triaging commercial insurance submissionsnot Pie Insurance
- Automating submission to bind through the Terminal platformnot Pie Insurance
- Handling complex middle market submissions with SubmissionLinknot Pie Insurance
- Policy checking with ClauseLinknot Pie Insurance
Where each one falls short
Documented limitations, not opinions. Every one is a constraint you would hit in normal use.
Pie Insurance
- Coverage is available in only 39 states plus Washington DC, as of August 2026
- No base premium is published on the site; only a percentage savings claim of up to 30% is shown, with the actual rate requiring a quote, as of August 2026
Bold Penguin
- Sold to brokers, carriers and MGAs rather than to the businesses buying insurance
- Pricing is not published
Pricing, plan by plan
Pie Insurance
On requestNo published plan breakdown. See the Pie Insurance review.
Bold Penguin
Free- Broker AccessFree
- Multi-carrier quotes
- Instant quoting
- Commission tracking
Which should you pick?
Choose Pie Insurance if
Nothing in the data separates Pie Insurance from Bold Penguin on the points above - pick on price and on how each one feels to use.
Choose Bold Penguin if
- You need multi-carrier quoting.
- You want to start without paying.
- You work on Web, Ios, Android.
- You also want instant quotes.
Questions people ask
- Is Pie Insurance or Bold Penguin better?
- Neither clearly leads. Pie Insurance starts at On request and Bold Penguin at Free, and user ratings are close enough to be indistinguishable. Choose on capability and platform support.
- Which is cheaper, Pie Insurance or Bold Penguin?
- Bold Penguin has a free tier; the other does not. Paid plans start at On request for Pie Insurance and Free for Bold Penguin.
- Does Pie Insurance or Bold Penguin run on more platforms?
- Pie Insurance runs on Web. Bold Penguin runs on Web, Ios, Android.
- Can I use Bold Penguin for free?
- Yes. Bold Penguin has a free tier, so you can try it without paying. Pie Insurance starts at On request.
- What can Pie Insurance do that Bold Penguin cannot?
- Bold Penguin covers Multi-carrier quoting, Instant quotes, Online binding, Customer portal.
Related pages
More on Pie Insurance
More on Bold Penguin
Keep looking
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