ICYMI - Meet the Team

Our Leadership Team

Meet the Team

Our Leadership Team

Niamh oversees the entire Group Marketing team, which includes central and functional Marketing teams.

Chief Marketing Officer (CMO)

Niamh Fox

Amanda oversees all of our Customer Success development and strategies

Chief Customer Officer

Amanda Lee Cascitelli

Chief People Officer

Cathy Donnelly

Cathy is responsible for our People (HR) function.

Erinn is responsible for all of our Finance function worldwide.

Chief Financial Officer (CFO)

Erinn O'Sullivan

Craig oversees the entire Calypso group.He grew up in Northwest Missouri and attended Brown University where he established his first SaaS business, which happened to be an education technology company. He then spent a short stint in Silicon Valley at the height of the “.com boom” working in tech sector investment banking and private equity. Craig then returned to Boston to SaaS-ify a company, in the ed-tech market, that he had started while an undergrad at Brown. He resides in Boston with his three children - Jack, Ella, and George. Craig describes himself as a “dad, country music lover, mediocre golfer, lover of people, and coach”.

Chief Executive Officer (CEO)

Craig Powell

Jonny and his team look oversees the management and implementation of technology strategies

Chief Information Officer

Jonny Gribben

Ryan is responsible for the technical side of our business - products, developers, etc

Chief Technology Officer (CTO)

Ryan Graham

Tim oversees the development and innovation of our product offerings

Chief Product officer

Tim Alvis

Gus oversees all of our Sales team worldwide, both for the Education and Workplace sectors.

Chief Revenue Officer (CRO)

Gus Schmedlen

Chief People Officer (CPO)

Cathy Donnelly

Cathy, our Group Chief People Officer, leads the HR strategy, focusing on Team Development, People Operations, and Talent Acquisition. With prior experience at companies like Liberty IT and IKEA, she brings a wealth of knowledge in building strong, inclusive workplace cultures. Cathy is dedicated to creating a world-class employee experience, ensuring everyone is supported to reach their full potential.Outside of work, Cathy has been married to Seamus for 28 years and has two children, Marcus and Daisy. She loves outdoor adventures with her family, travel, and is a big fan of good food, reading, and playing guitar.

Martin actively supports large-scale initiatives, company growth, Workplace expansion, and neurodiversity inclusion. He’s committed to transparent communication, fostering an inclusive environment where every team member can contribute to our success. Outside of work, Martin enjoys good food, wine, and traveling with friends. Married to Fiona for 25 years, they have two children, Emma and Jamie. He loves the outdoors, spending summer fly fishing and winter hunting.

Executive Chair & Founder

Martin McKay

Gus leads Revenue Growth, Revenue Operations, and Sales Enablement, focusing on key metrics like ARR, NDR, and CSAT while fostering a strong sales and customer success culture. He enjoys collaborating across teams to solve customer challenges and drive growth. Outside of work, Gus lives in the Philadelphia exurbs with his wife, Rian, their daughters Tatum and Lindy, and their labrador, Pinky. He’s passionate about supporting education-related nonprofits locally and globally.

Chief Revenue Officer (CRO)

Gus Schmedlen

Craig oversees the entire Calypso group.Craig's primary responsibilities are; integrating both companies to make a bigger and better business that can drive real impact in our market. This includes overseeing the unification of operational systems and corporate cultures to ensure a seamless transition for all teams and stakeholders. Craig is focused on leveraging the strengths of both teams to optimize what we deliver for customers and expand market reach, while also ensuring financial stability and sustainable growth. Craig describes himself as a “dad, country music lover, mediocre golfer, lover of people, and coach” and resides in Boston with his three children - Jack, Ella, and George.

Chief Executive Officer (CEO)

Craig Powell

Erinn, our CFO, oversees Accounting, Finance Operations, and Strategic Finance, focusing on balanced growth and financial stability. She champions finance as a strategic partner, using data and insights to guide business decisions and forecast future opportunities. Based in London (though she’s often visiting Antrim, Boston, Copenhagen, and Huron), Erinn enjoys time with her niece, Elva, and balances city life with outdoor escapes, whether it’s walking or the occasional camping adventure.

Chief Financial Officer (CFO)

Erinn O'Sullivan

Tim joined n2y in 2024 as Chief Product Officer, overseeing Product Marketing, Product Development, and Product Content. Previously, he led product and technology at SPINS, where he grew the business, culminating in its sale in 2021. With a passion for improving education, Tim brings people-focused, pragmatic product leadership honed through roles at Amazon and Microsoft. Tim has two daughters, Sylvia (12) and Cora (10). Together, they love exploring historical sites and nature, visiting museums, and riding bikes.

Chief Product officer (CPO)

Tim Alvis

As CIO, Jonny leads Internal Products, Data Strategy, and IT/Compliance to ensure seamless operations and effective data management. He oversees the company’s internal systems, IT infrastructure, and data practices, providing teams with the tools and insights needed for strategic growth. Outside of work, Jonny enjoys time with his wife, Rebecca, and their children, Joshua (11) and Lydia (8), often exploring the North Coast of Northern Ireland and enjoying good food.

Chief Information Officer (CIO)

Jonny Gribben

Ryan leads our Product Engineering, Infrastructure, and Innovation efforts, overseeing teams of engineers, testers, and support staff to deliver high-quality, scalable, and secure products that our users love. Passionate about user experience, he ensures that our customers' needs come first, focusing on creating innovative, high-quality features that truly enhance their experience. Outside of work, Ryan has been married to Rachel for 10 years and is a proud dad to Theo (4) and Lily (7). He loves spending time outdoors with his family, often exploring the Northern Ireland countryside on long walks with their dogs. A music enthusiast, Ryan enjoys attending gigs and playing guitar. He’s also a dedicated Liverpool FC fan and has a keen interest in crafting the perfect espresso!

Chief Technology Officer (CTO)

Ryan Graham

Amanda, our Chief Customer Officer (CCO), brings over 14 years of experience from Motus, where she led teams in Implementation, Support, Customer Success, and Renewals, helping grow the company from under $10M to over $150M in Annual Recurring Revenue. She’s passionate about building high-performing teams and driving customer value. Outside of work, she supports women in leadership through her involvement with Chief. She is originally from Guilford, Vermont, but she now lives in Miami with her husband, a Venezuelan-Italian chef, and their two sons. She enjoys traveling, learning languages, and staying active.

Chief Customer Officer (CCO)

Amanda Lee Cascitelli

Tim joined n2y in 2024 as Chief Product Officer, overseeing Product Marketing, Product Development, and Product Content. Previously, he led product and technology at SPINS, where he grew the business, culminating in its sale in 2021. With a passion for improving education, Tim brings people-focused, pragmatic product leadership honed through roles at Amazon and Microsoft. Tim has two daughters, Sylvia (12) and Cora (10). Together, they love exploring historical sites and nature, visiting museums, and riding bikes.

Chief Product officer (CPO)

Tim Alvis

Craig oversees the entire Calypso group.Craig's primary responsibilities are; integrating both companies to make a bigger and better business that can drive real impact in our market. This includes overseeing the unification of operational systems and corporate cultures to ensure a seamless transition for all teams and stakeholders. Craig is focused on leveraging the strengths of both teams to optimize what we deliver for customers and expand market reach, while also ensuring financial stability and sustainable growth. Craig describes himself as a “dad, country music lover, mediocre golfer, lover of people, and coach” and resides in Boston with his three children - Jack, Ella, and George.

Chief Executive Officer (CEO)

Craig Powell

Ryan leads our Product Engineering, Infrastructure, and Innovation efforts, overseeing teams of engineers, testers, and support staff to deliver high-quality, scalable, and secure products that our users love. Passionate about user experience, he ensures that our customers' needs come first, focusing on creating innovative, high-quality features that truly enhance their experience. Outside of work, Ryan has been married to Rachel for 10 years and is a proud dad to Theo (4) and Lily (7). He loves spending time outdoors with his family, often exploring the Northern Ireland countryside on long walks with their dogs. A music enthusiast, Ryan enjoys attending gigs and playing guitar. He’s also a dedicated Liverpool FC fan and has a keen interest in crafting the perfect espresso!

Chief Technology Officer (CTO)

Ryan Graham

Martin actively supports large-scale initiatives, company growth, Workplace expansion, and neurodiversity inclusion. He’s committed to transparent communication, fostering an inclusive environment where every team member can contribute to our success. Outside of work, Martin enjoys good food, wine, and traveling with friends. Married to Fiona for 25 years, they have two children, Emma and Jamie. He loves the outdoors, spending summer fly fishing and winter hunting.

Executive Chair & Founder

Martin McKay

Erinn, our CFO, oversees Accounting, Finance Operations, and Strategic Finance, focusing on balanced growth and financial stability. She champions finance as a strategic partner, using data and insights to guide business decisions and forecast future opportunities. Based in London (though she’s often visiting Antrim, Boston, Copenhagen, and Huron), Erinn enjoys time with her niece, Elva, and balances city life with outdoor escapes, whether it’s walking or the occasional camping adventure.

Chief Financial Officer (CFO)

Erinn O'Sullivan

Chief People Officer (CPO)

Cathy Donnelly

Cathy, our Group Chief People Officer, leads the HR strategy, focusing on Team Development, People Operations, and Talent Acquisition. With prior experience at companies like Liberty IT and IKEA, she brings a wealth of knowledge in building strong, inclusive workplace cultures. Cathy is dedicated to creating a world-class employee experience, ensuring everyone is supported to reach their full potential.Outside of work, Cathy has been married to Seamus for 28 years and has two children, Marcus and Daisy. She loves outdoor adventures with her family, travel, and is a big fan of good food, reading, and playing guitar.

As CIO, Jonny leads Internal Products, Data Strategy, and IT/Compliance to ensure seamless operations and effective data management. He oversees the company’s internal systems, IT infrastructure, and data practices, providing teams with the tools and insights needed for strategic growth. Outside of work, Jonny enjoys time with his wife, Rebecca, and their children, Joshua (11) and Lydia (8), often exploring the North Coast of Northern Ireland and enjoying good food.

Chief Information Officer (CIO)

Jonny Gribben

Gus leads Revenue Growth, Revenue Operations, and Sales Enablement, focusing on key metrics like ARR, NDR, and CSAT while fostering a strong sales and customer success culture. He enjoys collaborating across teams to solve customer challenges and drive growth. Outside of work, Gus lives in the Philadelphia exurbs with his wife, Rian, their daughters Tatum and Lindy, and their labrador, Pinky. He’s passionate about supporting education-related nonprofits locally and globally.

Chief Revenue Officer (CRO)

Gus Schmedlen