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Mainstay

Mainstay

Private
Boston, MassachusettsEnterprise Softwarehttps://mainstay.com/

Last Round

M&A

Mar 24, 2026

Total Funding Raised

$26.45M

Company Overview

Mainstay is an educational software company that provides an AI-powered engagement platform designed to support students and employees through behaviorally intelligent chatbots.

Sector

Enterprise Software

Verticals

NLP & Conversational AI, Vertical SaaS, Customer Experience, Workflow Automation

Business Model

B2B

Customer Profile

Subscription SaaS

AI Layer

Application

Keywords

student engagement platformAI chatbotstudent retentionhigher education softwareconversational AIedtechstudent success coachingSMS marketingvertical SaaSworkflow automationstudent sentiment analysisAI copilotstudent support automationbehavioral nudgingSaaS

Historical Pricing

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Caplight Momentum Score

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Mainstay Comparables

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Mainstay comparables — related companies by embedding similarity
CompanySimilarityMarket Cap
EdSights
92%
Element451
86%
GeckoEngage
85%

Mainstay Funding Rounds

Historical fundraising activity

Data table
RoundDateAmount RaisedValuationInvestorsSources
M&AMar 24, 2026
Series BFeb 16, 2021
Series AJan 28, 2020
SeedJan 11, 2017

Key People

Founding team and executive leadership

Andrew Magliozzi

CEO

Executive Team

Tony F.

Chief Executive Officer

Executive Team

Mainstay Investors

Notable investors and investment history

Mainstay investors
InvestorRounds
The Kresge FoundationSeries B
TechstarsSeed
Bisk VenturesSeed
Salesforce VenturesSeries B, Series A
Reach CapitalSeries A, Seed
Rethink EducationSeries A, Series B
Google Assistant InvestmentsSeries B, Series A

Market signals

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  • Mar 14, 2025

    Added Tarleton State as a new customer.

  • Feb 16, 2021

    $16M round led by Rethink Education.

Mainstay Filings

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Mainstay filings preview — column headings only; records require access
TypeDateAmount OfferedAmount SoldFilingPagesDownload

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Firmographic Details

HeadquartersBoston, Massachusetts
Employee Range92
Year Founded2014
Last FundingMar 24, 2026

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