Massimo Pennisi

Principal at Greycroft

📍 Santa Monica, California, United States🔄 Updated September 2026💼 4 investments📅 13 years investing🗓 Last invested Apr 2025𝕏 @upgrade_to_unlock
VC🌍 United States
4
Total investments
0
Early stage
2
Mid stage
1
Late stage
13y
Years active

Portfolio

4 investments · sorted by recency
All investments
Early stage
Mid stage
Late stage
Board Observer
Apr 2025
Prezent is a leading AI-powered business communication and presentation productivity platform. Our mission is democratize great business communication. At Prezent, were not just about saving time—though we do that exceptionally well. We’re also dedicated to enhancing the impact and professional appeal of every presentation our clients create. We’re committed to improving team communication skills because we know that strong communication is the cornerstone of any successful enterprise. Prezent has earned accolades from industry experts, including prestigious awards like the Edison Awards and The SaaS Awards. Our customers love us for our innovative products and services, as well as our unwavering commitment to customer satisfaction. Our AI-powered platform supercharges presentation productivity by combining audience empathy, business understanding, and eye-catching design. Members have cut down 60% of their costs and gain back 70% of their time by building better slides with Prezent. Teams and leaders can now showcase their ideas with well-structured, hyper-personalized and 100% brand-compliant presentations in a fraction of the time.

Board Observer
2022
Betterfly is an employee benefits platform built on insurance — designed to make it easy for companies to invest in their people and rewarding for people to invest in themselves. By combining insurance, preventive health, and technology, Betterfly turns traditional coverage into something people actually use — helping organizations create healthier workplaces across Latin America, Europe, and now the United States. From day one, employees receive real protection, personalized health insights, and rewards for healthy habits. Meanwhile, employers get a simple way to drive engagement, understand workforce health trends, and build stronger, more productive teams.
mid stageInsurance
Board Observer
2018
Semrush is a leading online visibility management SaaS platform used by 10,000,000 digital marketers worldwide. Back in 2008, Semrush started as a small group of SEO and IT specialists united by one mission—to make online competition fair and transparent with equal opportunities for everyone. In 17 years, weve grown into an all-in-one marketing suite consisting of more than 55+ products, tools, and add-ons that help companies market better online. Our vision is to create the only tool a digital marketing team would ever need to improve their online marketing results, ensure a smooth workflow between team members, and save time on routine tasks. Semrush is a trusted data provider. Our information on online behavior is used by the largest media outlets around the world such as Bloomberg, The Washington Post, Reuters and others. Semrush in numbers: → 55+ products, tools, and add-ons → 143 databases globally → 25.9 billion keywords → 43 trillion backlinks Visit our "Jobs" section if you want to work for us!
Investor
2013
Greycroft is a seed-to-growth venture capital firm that partners with entrepreneurs who are striving to build category-defining companies across intelligent consumer and enterprise applications, AI infrastructure, sustainability, and consumer products. Greycroft has raised over $3 billion in capital and has made over 400 investments since inception.
Experience · 6 entries
All (6)
Investments (4)
Board (3)
2025
Board Observer
Apr 2025
Prezent is a leading AI-powered business communication and presentation productivity platform. Our mission is democratize great business communication. At Prezent, were not just about saving time—though we do that exceptionally well. We’re also dedicated to enhancing the impact and professional appeal of every presentation our clients create. We’re committed to improving team communication skills because we know that strong communication is the cornerstone of any successful enterprise. Prezent has earned accolades from industry experts, including prestigious awards like the Edison Awards and The SaaS Awards. Our customers love us for our innovative products and services, as well as our unwavering commitment to customer satisfaction. Our AI-powered platform supercharges presentation productivity by combining audience empathy, business understanding, and eye-catching design. Members have cut down 60% of their costs and gain back 70% of their time by building better slides with Prezent. Teams and leaders can now showcase their ideas with well-structured, hyper-personalized and 100% brand-compliant presentations in a fraction of the time.

2022
Board Observer
2022
Betterfly is an employee benefits platform built on insurance — designed to make it easy for companies to invest in their people and rewarding for people to invest in themselves. By combining insurance, preventive health, and technology, Betterfly turns traditional coverage into something people actually use — helping organizations create healthier workplaces across Latin America, Europe, and now the United States. From day one, employees receive real protection, personalized health insights, and rewards for healthy habits. Meanwhile, employers get a simple way to drive engagement, understand workforce health trends, and build stronger, more productive teams.
mid stageInsurance
2018
Board Observer
2018
Semrush is a leading online visibility management SaaS platform used by 10,000,000 digital marketers worldwide. Back in 2008, Semrush started as a small group of SEO and IT specialists united by one mission—to make online competition fair and transparent with equal opportunities for everyone. In 17 years, weve grown into an all-in-one marketing suite consisting of more than 55+ products, tools, and add-ons that help companies market better online. Our vision is to create the only tool a digital marketing team would ever need to improve their online marketing results, ensure a smooth workflow between team members, and save time on routine tasks. Semrush is a trusted data provider. Our information on online behavior is used by the largest media outlets around the world such as Bloomberg, The Washington Post, Reuters and others. Semrush in numbers: → 55+ products, tools, and add-ons → 143 databases globally → 25.9 billion keywords → 43 trillion backlinks Visit our "Jobs" section if you want to work for us!
2013
Investor
2013
Greycroft is a seed-to-growth venture capital firm that partners with entrepreneurs who are striving to build category-defining companies across intelligent consumer and enterprise applications, AI infrastructure, sustainability, and consumer products. Greycroft has raised over $3 billion in capital and has made over 400 investments since inception.
2012
Summer Associate
2012
CLEAR CAPITAL ADVISORS is a premier independent provider of strategic and financial advice on mergers, acquisitions, sales, private capital solutions, and strategic growth initiatives. Our clients are the founders and owners of leading middle market and emerging growth companies in technology, internet & digital media, tech-enabled services, and other high growth business services. Bringing strong track records, creativity and passion, we are intensely focused on the success of every assignment.
Show all 6 entries ↓
Investment activity
2013–2025 · 4 investments
20131201812022120251
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