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Heyday, founded in 2017 and acquired by Hootsuite in August 2021, was a leading conversational AI platform. It specialized in providing AI-powered chatbot solutions for e-commerce and retail businesses to enhance customer service, automate responses, and drive sales through personalized interactions on messaging apps and websites. Heyday aimed to bridge the gap between brands and consumers by offering seamless, AI-driven communication tools, ultimately integrating into Hootsuite's suite to bolster social commerce and customer care capabilities.
The Montreal headquarters served as the central hub for Heyday's research and development in conversational AI, product design, engineering, sales, marketing, and overall business operations.
Likely a modern, open-plan office space designed to foster collaboration and innovation, characteristic of tech startups in dynamic urban centers. Specific architectural details are not widely publicized.
Heyday fostered an innovative, fast-paced, and customer-centric work culture. It emphasized technological advancement in AI, collaborative problem-solving, and agility to meet the evolving demands of the e-commerce and customer service sectors.
Montreal's strong AI talent pool, vibrant tech ecosystem, and supportive environment for startups made it a strategic location for Heyday's growth and development as a specialized AI company.
Before being acquired by Hootsuite, Heyday supported a global customer base, providing its AI chatbot solutions to e-commerce and retail businesses across North America, Europe, and other regions. Its platform was designed for international use, supporting multiple languages and integrations with various e-commerce platforms and messaging apps used worldwide. While its physical R&D and operations hub was in Canada, its market reach and client services were global.
7236 Rue Waverly (Former primary office)
Montreal
Quebec
Canada
Address: N/A - Operations largely centralized
Focused on leveraging Montreal's AI talent and tech infrastructure, with remote support capabilities for international customers.
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As of April 2025, Heyday' leadership includes:
Heyday has been backed by several prominent investors over the years, including:
In the 12 months prior to its acquisition by Hootsuite in August 2021, Heyday's existing executive team remained focused on scaling the company and its AI platform. The acquisition itself represented the most significant change, with key leaders transitioning to roles within Hootsuite. No major external C-suite hires were publicly announced during this period.
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Prior to its acquisition, Heyday, operating with the heyday.co domain, likely utilized standard professional email formats. Common patterns for tech companies include [first_initial][last]@[domain] or [first]@[domain].
[first]@heyday.co (e.g., john@heyday.co) or [first_initial][last]@heyday.co (e.g., jdoe@heyday.co)
Format
steve@heyday.co
Example
75%
Success rate
Hootsuite / PR Newswire • August 4, 2021
Hootsuite announced its acquisition of Heyday, a Montreal-based AI platform specializing in personalized customer experiences through messaging. The deal, valued at CAD $60 million, aimed to integrate Heyday's technology into Hootsuite's social media management offerings....more
BetaKit • September 10, 2020
Montreal-based Heyday secured a $6.5 million CAD seed extension round led by Innovobot, with participation from existing investors. The funding was aimed at advancing its AI-powered customer messaging platform for retailers....more
Montreal Times / MTL NewTech • May 29, 2019
Heyday, a Montreal startup using AI for virtual retail assistants, raised a $2 million seed round. The funding, led by Desjardins Capital with participation from other investors, was intended to expand its team and develop its conversational AI solutions....more
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