Funded Administrative Services Startups in Chicago
The 25 most recent funding rounds among Chicago administrative services startups span from Enduvo's undisclosed raise in July 2020 through Nurture Life's S…
The 25 most recent funding rounds among Chicago administrative services startups span from Enduvo's undisclosed raise in July 2020 through Nurture Life's Series Unknown close in August 2025. Activity peaked across 2021 and 2022, which together account for 16 of the 25 entries — including Foxtrot's $100M Series C (January 2022), The Mom Project's $59M private equity round (September 2021), and Hunt Club's $40M Series B (December 2022).
Round types are broadly distributed: seed and Series Unknown labels each appear five times in the dataset, while Series A deals include Site Technologies and Crafty (both $10M, in 2023 and 2022 respectively). Aries Capital ($50M, June 2023) and Chowbus ($40M, August 2023) represent the largest disclosed raises from 2023 onward. The most recent disclosed-amount round is leadership.NET's $300K angel close in June 2025.
Most recent rounds
25 shownRelated listings
Frequently asked
What are the largest disclosed rounds in this dataset?
Foxtrot leads at $100M (Series C, January 2022), followed by The Mom Project at $59M via private equity (September 2021) and Aries Capital at $50M (June 2023). Chowbus and Hunt Club each raised $40M in August 2023 and December 2022 respectively.
When was funding activity most concentrated in this segment?
2021 and 2022 each account for eight rounds in the 25 shown, together making up 16 of the entries. Volume drops notably afterward — five rounds in 2023, one in 2024 (ChangEd, undisclosed), and two as of mid-2025.
Which companies in this group have reached Series B or later?
Hunt Club closed a $40M Series B in December 2022. Foxtrot, Tovala, and The Primo all reached Series C, raising $100M, $30M, and $850K respectively — The Primo's figure suggesting a small or bridge-style close despite the stage label.
What do seed round sizes look like in this segment?
The five seed rounds range from $100K (WinningWise, January 2021) to $7M (Keyo, November 2022). Anthill AI, Anthill, and Quicklly clustered in the $3M–$4M band, all raised between July 2021 and August 2022.
Which rounds closed in 2023 and how large were they?
Five rounds closed in 2023: Aries Capital ($50M, June), Chowbus ($40M, August), Drift Net Securities ($16M, March), Site Technologies ($10M Series A, September), and Varcode ($1M, November). Four of the five carried a Series Unknown label; only Site Technologies disclosed a named round stage.
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