← Embedded Finance Index 2026

OnSeason (ex. Flataway)

“Can vacation rental managers escape OTA commissions by owning AI-discoverable direct-booking channels?”

Founded2023
HQSofia, Bulgaria
FoundersBoris Pavlov, Teodor Todorov
Total raised$534.3K
Latest roundPre-Seed, 2023
IndustryVertical SaaS / Hospitality

The story

Founded in 2023 as Flataway by former operators of one of Europe's largest short-term rental management companies. The team first built Calry, a unified PMS API, then pivoted to a broader hospitality direct-booking platform rebranded as OnSeason. The current thesis is that AI travel agents (ChatGPT, Claude) will disintermediate OTAs, and property managers need AI-discoverable direct-booking websites to capture that shift. Payments are outsourced entirely to Stripe — the company is a SaaS layer, not an embedded finance player.

Last 12 months

—

Product timeline

2023

FlatAway Ltd. founded in Sofia, Bulgaria; raised pre-seed led by Eleven Ventures· founding

2024

Built Calry, a unified PMS API connecting 40+ property management systems· product

2025

Rebranded from Flataway to OnSeason; launched AI website builder (Staycy), zero-commission booking engine, and distribution network· pivot

2026

Positioned as AI-discoverable direct booking platform (ChatGPT, Claude, AI travel agents)· product

The stack

1 layer disclosed in OnSeason (ex. Flataway)’s embedded-finance stack

Payments / PSP

Stripe

Accounting gap: none

OnSeason (ex. Flataway) — frequently asked

Who is OnSeason (ex. Flataway)'s payment processor?

OnSeason (ex. Flataway) processes payments through Stripe.

Who founded OnSeason (ex. Flataway)?

OnSeason (ex. Flataway) was founded by Boris Pavlov and Teodor Todorov and is founded in 2023, headquartered in Sofia, Bulgaria.

How much funding has OnSeason (ex. Flataway) raised?

OnSeason (ex. Flataway) has raised $534.3K in total (latest round: Pre-Seed, 2023).

Benchmark your own stack

Request an embedded finance strategy assessment

Get a read on where your own stack stands against OnSeason (ex. Flataway) and the rest of its category — what they built versus bought, which providers they use, and where the gaps in your own strategy and competitive set actually are.

Your category, mappedHow your stack compares to OnSeason (ex. Flataway) and the other companies in its category.
Build vs. buyWhere a provider relationship would close a gap faster than building it.
A named analyst, not a form replyA short call to scope what's actually worth assessing for you.