Executive Management

Aaqib Gadit is the Co-founder and former CEO of Cloudways, a multi-cloud managed application hosting platform for SMBs acquired by DigitalOcean in 2022. Gadit now serves as Chief Revenue Officer at DigitalOcean, overseeing all go-to-market efforts directly connected to revenue-generating activities.

Gadit is a hands-on, execution-oriented leader and a serial entrepreneur with expertise in product, growth, tech, customer support, and customer success, particularly in the context of SaaS, Infrastructure, and Open Source.

Adrienne Calderone is DigitalOcean's Chief Accounting Officer. Previously, she served as DigitalOcean's Vice President, Finance. 

Before joining DigitalOcean, Adrienne served as Vice President and Controller at Cotiviti Holdings. Inc., a healthcare analytics company, where she also served as Interim Chief Financial Officer for a period. She has also held senior vice president and vice president level positions at L-1 Identity Solutions, Sirius XM Radio, and PanAmSat Corporation. 

Adrienne received a B.S. in Accounting from the Isenberg School of Management at the University of Massachusetts, Amherst.

Alan is responsible for all legal and compliance matters across DigitalOcean, including corporate transactions and governance, commercial agreements, intellectual property and data protection, international compliance and litigation.

Prior to DigitalOcean, he served for nine years as the General Counsel of Everyday Health, a leading provider of digital health solutions, and guided the company's IPO and subsequent sale in 2016. He previously served as the General Counsel of Jupiter Media Metrix, a publicly-traded digital measurement firm, and NetRatings, a publicly-traded digital measurement and market research company operating across North America, Europe, Asia-Pacific and South America. He also served as an associate at several international law firms.

Alan holds a Bachelor’s degree in political science from Columbia University and a law degree from the UCLA School of Law.

As Chief Marketing Officer, Carly oversees DigitalOcean’s worldwide marketing operations as the company continues to expand its global customer base. In this role, she’s responsible for scaling DigitalOcean’s self-serve and sales-led acquisition initiatives, as well as its global brand, community, and developer relations efforts.

Carly brings more than 20 years of experience to DigitalOcean with a focus on scaling marketing operations and acquisition at high growth technology companies. Most recently, she served as vice president of revenue marketing at SendGrid, leading the development of the company’s self-service, cloud-based subscription model. During her tenure, the company’s revenue increased more than 30X in eight years, from $5M to $190M, and was later acquired by Twilio in 2019. Before SendGrid, she served as the director of marketing at Return Path, an email deliverability and optimization platform for email marketers, for more than six years.

Beyond her work as a marketing executive, Carly is dedicated to giving back to her community, serving as a board member for Pledge 1% Colorado, a network of entrepreneurs who pledge 1% of company equity, founders equity, annual profits, employee time, or company product to nonprofits of their choosing.

Carly is based in Boulder, Colorado, and holds a B.A. in International Business and Marketing from the University of Colorado Boulder.

Gabe Monroy is Chief Product Officer at DigitalOcean where he oversees the product management organization and owns the company’s product vision. Prior to DigitalOcean, Monroy was vice president of the Azure Developer Experience group in Microsoft’s Developer Division. In this role, he was responsible for the application-centric services and tools on Azure, including compute services, platform services and developer tools.

Previously, Monroy was the founder and chief technology officer (CTO) of Deis, which was acquired by Microsoft in 2017. After joining Microsoft, Monroy started Azure Kubernetes Service, the fastest-growing compute service in Azure’s history. As an early contributor to Docker and Kubernetes, and a founding member of the Cloud Native Computing Foundation (CNCF), Monroy has deep experience in open source software and cloud-native technology.

Jeff Guy is DigitalOcean’s Chief Operating Officer. In this role, he is focused on customer success, revenue growth, and overall company efficiency. He currently oversees strategy deployment, customer support & success, business development, product management, UX, business operations, and strategic sourcing and procurement.

Prior to DigitalOcean, Jeff spent nine years at DigitalGlobe/Maxar, an industry leader in space infrastructure, earth observation, and analytic services. He most recently served as Senior VP of Business Transformation, and also held multiple senior level financial, operations, and transformation roles. Prior to DigitalGlobe/Maxar, Jeff spent nine years at Trimble, Inc., a leader in the GPS SaaS technology space, where he held various operations and transformation roles including building out Americas and EMEA fulfilment operations during a period of growth from $300M to $1.2B. Jeff started his career in the Japanese automotive industry where he embraced lean process and Six Sigma methodologies to drive efficiency.

Jeff earned an MBA in International Business from Western Michigan University, a BSBA in Operations/Supply Chain Management from Bowling Green, and is a certified Kaizen facilitator with a Lean Six Sigma Black Belt.

As Chief People Officer, Matt Norman leads the global people team and is responsible for building DigitalOcean’s people strategy to support the company’s continued growth, culture, innovation, and profitability. In this role, he oversees talent acquisition and development, compensation and benefits, diversity and inclusion, facilities, and employee engagement programs.

Matt has broad experience leading multiple functions across vast global locations, with his most recent role as EVP, Human Resources at Denihan Hospitality Group where he was responsible for creating and executing global human resources administration, integration, and strategy over the course of seven years. Matt has transformed people teams, injecting a business mindset into structure, processes, and systems, continually looking to find alternatives to improve, reach further, and drive success. Prior to joining Denihan, Matt held senior human resources positions at Gilt Group, Conde Nast, Universal McCann, DoubleClick (a division of Google, Inc.), and Honeywell. In addition to his extensive human resources expertise, Matt has been an owner and partner in numerous restaurants in New York City and Indianapolis for over two decades.

Matt received his Master’s degree from Columbia University, and his Bachelor’s degree from Wabash College.

Megan Wood is Chief Strategy Officer at DigitalOcean, responsible for keeping the company's various functions and teams aligned on nearer and longer-term plans and execution. Before stepping into this role, she led Business Operations and Analytics functions at DigitalOcean, focused on driving cross-functional growth initiatives. 

Previously, Megan led Strategy & Corporate Development at NerdWallet and Maxar. She also worked as a consultant at Bain & Company.

Megan received an MBA from the University of Chicago Booth School of Business.

As Chief Executive Officer, Yancey drives the overall strategy for DigitalOcean leading the company through its next phase of profitable growth. He brings a wealth of technical, financial, and leadership experience and spent the last 15 years in senior executive roles at technology companies including SendGrid and DigitalGlobe. Yancey started his career working as a manufacturing engineer at Corning Incorporated and The Clorox Company. He also has extensive investment banking experience focused on mergers and acquisitions at JPMorgan, Lehman Brothers, and Thomas Weisel Partners.

Prior to joining DigitalOcean, Yancey was Chief Operating Officer and Chief Financial Officer at SendGrid (NYSE:SEND) from 2015 to 2019, where he profitably grew revenue from $50 million to over $170 million and nearly tripled the company’s customer base. He also helped guide the company through its IPO in late 2017 and its $3 billion all-stock sale in early 2019 to Twilio (NYSE:TWLO). Previously, Yancey was the long-time Chief Financial Officer of DigitalGlobe (NYSE:DGI), where he helped drive revenue growth from $50 million to nearly $700 million and EBITDA of approximately $300 million, and helped guide the company through its IPO in 2009.

During his career, he has advised on and executed over $50 billion of M&A and $4 billion in equity and debt raising transactions. He has previously served on several Boards of Directors of publicly-traded companies, currently serving on the board of directors of Ping Identity (NYSE:PING) where he is the Audit Committee Chair.