Second Alpha

Second Alpha Partners is a New York-based private equity firm established in 2012, specializing in secondary investments in private companies. The firm purchases shares from existing shareholders, including founders, executives, angel investors, venture capitalists, and corporate investors. Second Alpha Partners focuses its investment strategy on growth equity in middle-market and late-stage venture-backed companies, primarily within the telecommunications, media, and technology sectors. The firm also invests directly in private companies, concentrating its efforts on opportunities in the United States and Canada.

Richard Brekka

Co-Founder and Managing Partner

Eugene Galantini

CFO and CCO

Joseph Hickey

Analyst

Ryan Kober

Senior Principal

Jim Sanger

Managing Partner and Founder

Nico Serpa

Associate

13 past transactions

tvScientific

Series B in 2025
TvScientific is a performance advertising platform focused on making connected TV (CTV) advertising accessible and measurable for brands and applications of all sizes. The platform utilizes data to demonstrate the true value of TV advertising while simplifying and automating the processes of CTV buying and optimization. TvScientific offers real-time reporting that allows users to monitor campaign performance effectively, ensuring that their advertising efforts achieve optimal results. Additionally, the platform features Always-On Incrementality testing, which provides insights into the incremental value generated by CTV campaigns, further assuring users that their marketing strategies are effective. By combining intuitive campaign management with digital-like measurement and attribution, TvScientific enables businesses to harness CTV as a scalable performance channel.

Xoxoday (formerly Giifty.com)

Series C in 2021
Giift operates a loyalty marketplace that enhances the value of loyalty programs by facilitating interaction between customers and diverse loyalty initiatives worldwide. By leveraging advanced technology, Giift has established a unified platform that allows for the exchange of loyalty points, miles, and gift cards across various programs globally. Its innovative approach integrates mobile payment technology with a single loyalty point system, ensuring ease of use and broad accessibility. Giift's marketplace serves multiple sectors, including hospitality, food and beverage, airlines, insurance, retail, banking, and payments, thereby creating a comprehensive ecosystem that fosters customer engagement and strengthens brand loyalty. Through its robust loyalty program management services, Giift helps organizations attract customers and build lasting relationships.

HealthCare.com

Series C in 2021
HealthCare.com is an online health insurance company that offers a data-driven shopping platform to assist American consumers in enrolling in individual health insurance and Medicare plans. Founded in 2014 and headquartered in New York City, the company utilizes artificial intelligence and machine learning to enhance user experiences, enabling customers to find, compare, and purchase insurance products that best meet their needs. HealthCare.com also markets proprietary health insurance and supplemental insurance products under the name Pivot Health. Its services include a comparison platform that provides expert advice, data, and personalized recommendations, empowering users to make informed decisions regarding their healthcare coverage. The company has been recognized as one of America's fastest-growing businesses, earning a spot on the Inc. 5000 list multiple times.

Bespoke Post

Series B in 2021
Bespoke Post is a subscription-based service that delivers curated lifestyle products to modern customers, primarily targeting men. Each month, subscribers receive a themed box containing a selection of limited edition items related to style, grooming, food, drink, and gear. The service allows customers to customize their selections by adjusting colors and sizes, adding extra products, or opting out of a box at no cost. Bespoke Post aims to enhance daily life by providing high-quality goods that align with individual interests. In addition to the subscription boxes, the company offers a shop with a variety of standalone products. The business emphasizes customer satisfaction with features like free shipping and easy returns.

SmarterTravel

Series B in 2021
SmarterTravel is a technology-driven company that aims to transform the travel and leisure industry, which is valued at $1 trillion. As part of TripAdvisor, SmarterTravel operates an online travel booking platform that provides a range of travel sites to help users find suitable trips at competitive prices. Utilizing artificial intelligence and machine learning, the platform offers personalized travel recommendations and facilitates instant bookings, enhancing the user experience. Additionally, SmarterTravel features a subscription service that grants access to discounted hotel rates and membership benefits for frequent users, regardless of the hotel chain. The company fosters an innovative and collaborative environment, prioritizing data-driven decision-making and continuous improvement to meet the needs of modern travelers.

DailyPay

Series D in 2021
DailyPay is a New York City-based worktech company that provides an earned wage access solution, aiming to enhance the payment experience for employees across various sectors. By offering a digital wallet system and on-demand pay technology, DailyPay enables workers to access their earned wages before the traditional payday, allowing them to transfer funds directly to any bank account and purchase goods and services as needed. This service acts as a voluntary employee benefit, fostering stronger relationships between employers and their workforce while promoting financial well-being. DailyPay's innovative platform is designed to motivate employees to work harder and remain engaged in their jobs.

Coursera

Venture Round in 2021
Coursera, Inc. is an online education platform that provides access to a wide range of courses offered by over 140 universities and organizations globally. Founded in 2012 and headquartered in Mountain View, California, Coursera serves more than 20 million registered learners with over 1,000 courses spanning various fields, including arts, business, computer science, data science, and personal development. The platform enables users to engage with educational content through video lectures, interactive quizzes, and peer-graded assessments, promoting both career advancement and personal enrichment. Coursera operates through three segments: Consumer, Enterprise, and Degrees, with the majority of its revenue coming from individual learners seeking practical skills and professional certifications. The company aims to make education affordable, accessible, and relevant, leveraging technology and data to enhance the learning experience.

HealthCare.com

Series B in 2019
HealthCare.com is an online health insurance company that offers a data-driven shopping platform to assist American consumers in enrolling in individual health insurance and Medicare plans. Founded in 2014 and headquartered in New York City, the company utilizes artificial intelligence and machine learning to enhance user experiences, enabling customers to find, compare, and purchase insurance products that best meet their needs. HealthCare.com also markets proprietary health insurance and supplemental insurance products under the name Pivot Health. Its services include a comparison platform that provides expert advice, data, and personalized recommendations, empowering users to make informed decisions regarding their healthcare coverage. The company has been recognized as one of America's fastest-growing businesses, earning a spot on the Inc. 5000 list multiple times.

Code42

Private Equity Round in 2018
Code42 specializes in data loss protection, visibility, and recovery solutions designed to safeguard critical information from various threats, including insider breaches. Its platform offers a secure cloud service that continuously and automatically collects data via a lightweight agent installed on devices, ensuring comprehensive protection for files on laptops and desktops. The company's solutions enable security, IT, and compliance professionals to quickly detect threats, meet regulatory requirements, and accelerate incident response without complex policy management or hindering user collaboration. By focusing on ease of use and effective data management, Code42 helps organizations maintain a secure environment while fostering a collaborative workplace culture.

EverQuote

Series B in 2017
EverQuote is an independent insurance marketplace that provides a free service for consumers to compare quotes on various types of insurance, including auto, home, and life insurance. The company operates an online platform that connects consumers with a wide network of insurance providers, enabling them to find relevant options tailored to their individual needs. By leveraging data science and technology, EverQuote enhances the insurance shopping experience, saving both consumers and providers time and money. The company focuses on delivering a data-driven approach to help consumers secure the best prices and coverage available in the market.

CaaStle

Series A in 2016
CaaStle is a pioneer in the "Clothing as a Service" (CaaS) model, providing a subscription rental platform that enables retailers to offer clothing rentals to consumers. The company delivers a comprehensive, cloud-based service that includes technology, reverse logistics, and operational support. This approach fosters a new relationship between retailers and consumers, focusing on access to apparel instead of traditional ownership. By leveraging its platform, CaaStle helps retailers attract new customers and re-engage lapsed ones, creating a relationship-based experience that enhances customer loyalty. This model allows brands to optimize inventory returns while increasing revenue and profits.

Everbridge

Venture Round in 2015
Everbridge is a global software company specializing in critical communications and enterprise safety applications. It provides a comprehensive event management platform that assists government organizations and businesses in anticipating, mitigating, responding to, and recovering from critical events, such as public safety threats and IT outages. The company's SaaS-based platform enables over 3,000 global customers to deliver contextual notifications swiftly and reliably to millions of people simultaneously, reaching more than 200 countries and territories through over 100 communication devices. Everbridge's solutions, which include Mass Notification, Incident Management, and Safety Connection, are designed to be user-friendly, secure, and highly scalable. The company serves a diverse clientele, including eight of the ten largest U.S. cities, major investment banks, leading global accounting firms, and numerous busy North American airports. Headquartered in Boston and Los Angeles, Everbridge also has offices in San Francisco, Lansing, Beijing, London, and Stockholm.

Everbridge

Venture Round in 2015
Everbridge is a global software company specializing in critical communications and enterprise safety applications. It provides a comprehensive event management platform that assists government organizations and businesses in anticipating, mitigating, responding to, and recovering from critical events, such as public safety threats and IT outages. The company's SaaS-based platform enables over 3,000 global customers to deliver contextual notifications swiftly and reliably to millions of people simultaneously, reaching more than 200 countries and territories through over 100 communication devices. Everbridge's solutions, which include Mass Notification, Incident Management, and Safety Connection, are designed to be user-friendly, secure, and highly scalable. The company serves a diverse clientele, including eight of the ten largest U.S. cities, major investment banks, leading global accounting firms, and numerous busy North American airports. Headquartered in Boston and Los Angeles, Everbridge also has offices in San Francisco, Lansing, Beijing, London, and Stockholm.
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