15 Biggest Microsoft Executive Departures In AI, Data, Security So Far This Year

The departures do not appear to have harmed Microsoft’s own recruiting efforts, as seen by some especially consequential hires by the tech giant so far this year.

A corporate vice president for experiences, devices and technology who left for an artificial intelligence upstart, a COO of business applications and platform who retired, and a chief data officer for customer and partner solutions who is now at Google are some of the biggest executive departures Microsoft has seen so far this year as competition heats up in the AI space.

CRN selected executives for this list based on LinkedIn data, their titles, the length of their Microsoft tenure and whether they left for a major rival, including Google and Amazon.

[RELATED: Microsoft Is Doubling Down On AI, Security: Here Are Some Of Its Recent Hires]

Microsoft Executive Departures

The departures do not appear to have harmed Microsoft’s own recruiting efforts, as seen by some especially consequential hires by the Redmond, Wash.-based tech giant so far this year.

The vendor’s executives have also pledged spending discipline as the company invests in data center capacity and AI innovation to stay ahead in the emerging market.

In a July report from Morgan Stanley, the investment firm noted that Microsoft’s employee growth has plateaued since fiscal year 2022 (Microsoft started its 2025 fiscal year in July) while its stability around nearly $1 million in revenue per employee shows better operating leverage on head count by the vendor.

Official job openings at Microsoft remain well below COVID-height numbers, according to the report. Morgan Stanley put the July openings at around 4,000. Microsoft had around 26,000 openings in early and mid-2022.

“We believe that modest job growth and job postings trends corroborate that management continues to invest prudently behind the opportunity without sacrificing operating efficiency,” according to Morgan Stanley.

Read on for some of the executives who have left Microsoft so far this year.

Madhan Arumugam Ramakrishnan

In July, Ramakrishnan became a vice president of product at Snowflake.

Ramakrishnan came to the AI data cloud vendor after about 16 years with Microsoft, according to his LinkedIn account. He left Microsoft with the title of corporate vice president for Microsoft Cloud for ISVs and AI.

His resume includes about six years with Intel, leaving the vendor in 2008 with the title of senior software engineer.

Saurabh Tiwary

Tiwary returned to Google in June, taking on the role of vice president and general manager of its cloud AI business.

Tiwary came back to the cloud vendor after about 12 years with Microsoft, according to his LinkedIn account. He left Microsoft with the title of corporate vice president, working on Copilot experiences.

He previously worked at Google for about three years, leaving in 2013 as a software engineer in the search business.

Gail Giacobbe

In February, Giacobbe joined Google as vice president of product management.

Giacobbe came to the cloud vendor after nearly two decades with Microsoft, according to her LinkedIn account.

Most of her tenure was inside Microsoft’s Office division after first joining the software giant in 2000.

In her latest role as vice president of product for the Microsoft Office Products Group, she led a customer- and data-focused team of product managers, engineers, content creators, designers and data scientists, according to her LinkedIn profile.

Erik Zwiefel

Another Google recruit from Microsoft this year was Zwiefel, who was named a generative AI field solutions architect.

Zwiefel departed Microsoft in April with the title of chief data and analytics officer of the Americas for the data and AI business, according to his LinkedIn profile. He had been with Microsoft for about eight years.

His resume includes about three years with retailer Target, leaving in 2016 with the title of senior lead data scientist.

Hernan Asorey

Asorey is among the Microsoft executives to leave for Google this year.

Asorey left Microsoft in February with the title of chief data officer for customer and partner solutions commercial software engineering, according to his LinkedIn account. He had been with the vendor for more than three years.

In the chief data officer role, he led “the applied Machine Learning global team in engagements with some of our top customers around the world, to tackle their most significant technical challenges through AI and Machine Learning,” according to his LinkedIn account. “My focus is scaling Machine Learning expertise, creating new opportunities with our customers and our products. Building customer moonshots by leveraging intercompany and partner collaboration for transformational solutions.”

At Google, Asorey took on the role of vice president of data science and engineering. In this role, he is tasked with “growing 99,000 information interactions per second while making them more useful, actionable, human-centered, safe, inclusive, and joyful, pushing the boundaries of what applied AI can bring at Google-scale,” according to his LinkedIn account.

His resume includes more than six years with Salesforce. Asorey left Salesforce in 2020 with the title of executive vice president and chief data officer.

Ian Roe

In April, Roe departed Microsoft as its vice president of global strategic sourcing in the Microsoft Windows + Devices Group for a role at rival Amazon.

Roe became Amazon’s director of global robotics supply chain, according to his LinkedIn account.

Before Microsoft, he worked at Intel for about 25 years, leaving the chipmaker in 2021 as vice president of global supply chain and corporate strategic procurement.

Andre Alfred

Microsoft vice president of Azure security Alfred left the vendor in February, moving on to Google security subsidiary Mandiant and taking on the role of senior director of managed defense.

Alfred spent a cumulative nine years with Microsoft, previously leaving in 2017 as a principal product manager for Microsoft cybersecurity platforms, according to his LinkedIn account.

His resume includes about three years with Oracle, leaving the database product giant in 2021 as vice president of compute operations.

Gary Nafus

Microsoft’s vice president of U.S. manufacturing became chief sales officer at SailPoint in May.

Nafus took on the newly formed role after about three years with Microsoft, according to his LinkedIn account.

At Microsoft, “he led a go-to-market team that included the sales, consulting, and customer success functions for one of its global business units,” according to a SailPoint statement from the time.

As SailPoint chief sales officer, Nafus “will oversee SailPoint’s go-to-market field operations globally” and “lead the regional sales, digital sales, and global alliances teams,”

Prior to Microsoft, he spent about two years with Salesforce, leaving in 2021 as a senior vice president. He spent 14 years with Oracle and companies Oracle acquired in various leadership roles.

Raghu Malpani

In May, Microsoft’s corporate vice president for the Microsoft 365 application and data platform became CTO and head of engineering at business automation company UiPath.

Malpani spent about 18 years cumulatively at Microsoft, most recently leading “several global teams responsible for Microsoft Exchange Core, M365 CoPilot Semantic Index platform, and Microsoft Graph” as part of the corporate vice president role.

His resume includes about three years with Facebook, leaving in 2022 as engineering director, according to his LinkedIn account.

Emily He

Microsoft corporate vice president of business applications marketing He moved on in May to become CMO of AI-powered customer data platform provider Gong.

In this role, she “will lead all aspects of Gong’s marketing strategy and execution, helping the company accelerate its Revenue Intelligence category leadership,” according to a company statement at the time.

In the Microsoft corporate vice president role, her responsibilities included the global go-to-market strategy and marketing of the tech giant’s Dynamics 365 ERP and CRM product and Microsoft’s Power Platform product for business intelligence and low-code application development, according to her LinkedIn account.

She previously worked at Oracle for four-plus years, leaving as senior vice president of global marketing. Her responsibilities at Oracle included “global GTM strategy, brand awareness and demand generation of the global Cloud Human Capital Management business.”

Earlier in her career, He worked at Siebel Systems, leaving the CRM software provider in 2006 with the title of senior director of product marketing. Oracle closed its $5.85 billion acquisition of Siebel that year.

Rubén Caballero

Microsoft’s corporate vice president of engineering for experiences, devices and technology, Caballero left this year for an AI upstart that has received funding from the tech giant.

Caballero joined Humane in June as chief of engineering and strategy officer, working on “CosmOS, Humane’s AI operating system, and the Ai Pin family of products,” according to a company statement at the time.

At Microsoft, Caballero “oversaw the development of Mixed Reality Products including Hololens and the IVAS program,” according to the Humane statement.

He also worked at Apple for about 14 years, leading “the hardware team that innovated the first-generation iPhone and later expanded his role to include the iPad, Apple Watch, Mac, and all other hardware products.”

“He also founded Apple’s Wireless Design & Technology Group, eventually growing his team to over 1,000 employees across 26 countries,” according to Humane. “In this capacity, he was responsible for overseeing R&D, roadmap, architecture, design, validation, certification, regulatory, and field, production and factory tests for all Apple hardware.”

In March 2023, Microsoft was part of Humane’s $100 million Series C round of funding. Other participants include Volvo Cars Tech Fund, OpenAI founder Sam Altman and Qualcomm Ventures.

Mo Osborne

This year, Osborne retired from Microsoft after six years as COO of Business Applications and Platform (BAP).

During Osborne’s time with Microsoft, she “oversaw customer experience and support, people operations, web engineering, financial management, data analytics, international localization, content management, and community support globally,” according to her LinkedIn account.

Some of her accomplishments at Microsoft include driving “business transformation that accelerated revenues 550%” and improving “gross margins by 144%.” She also “significantly elevated (the) platform’s competitive positioning and ability to capture business with large enterprise accounts” and “introduced program/process management rigor to all business disciplines, including finance, supply chain, and customer experience.”

Osborne’s resume includes about six years with EY, leaving in 2017 as global CIO, according to her LinkedIn account.

Patricia Obermaier

In August, Obermaier left her role as chief growth officer of Microsoft’s $12 billion health and life sciences portfolio after spending about five years with the vendor.

In a post on LinkedIn, Obermaier said that she had fulfilled “a five-year goal to unlock potential within this amazing organization, serving health and life sciences customers to improve global health.”

“My personal mission has always been to impact 8, 4, 1 (8 billion people on this planet, 4 billion without adequate care, and 1 billion living with disabilities)” she wrote on LinkedIn. “With immense gratitude and humility, I can proudly say this goal has been achieved.”

She said her decision to leave Microsoft “is fueled by my entrepreneurial spirit that continues to burn within me.”

“I will carry forward my journey through my board and advisory work where I hope to unlock potential through innovation in technology and health for improving the lives of 8, 4, 1,” she said.

As part of her role, she “collaborated with customers to understand the emerging needs of provider, payers, and life sciences organizations and mobilized Microsoft resources to support them” and “executed market development investments to capture market share,” according to Obermaier’s LinkedIn account.

She also “led field team integration efforts for Microsoft's $20B acquisition of Nuance and created roadmap for unlocking customer and business value for Generative AI,” according to her LinkedIn account.

Obermaier’s resume includes founding and leading the Resigility strategic consulting firm for about four years. She also worked at Unisys, No. 36 on CRN’s 2024 Solution Provider 500, for about eight years, leaving in 2009 as lead partner for health and human services (HHS).

Mary Ellen Smith

Smith left her role as corporate vice president of Microsoft business operations this year, capping off an 18-year tenure with the tech giant.

She will serve as a fellow in the 2024 Stanford Distinguished Careers Institute program, she wrote in a LinkedIn post.

“The thrill of uncertainty fueled my spirit as I wrapped up the CVP of Business Operations role,” she wrote. “Deep within, I knew there was another peak waiting to be scaled. … Excited to roll up my sleeves, and ready to make a difference while intensely learning and contributing from boardrooms to classrooms.”

During her time with Microsoft, Smith provided “strategic governance for global operations strategy, integrating order to cash processes across all Microsoft products and services generating >$198+B in revenue,” according to her LinkedIn account. She “led global strategy, launch planning, generative AI application thought leadership, physical to digital supply chain transformation, revenue processing and regulatory business compliance.”

Smith “contributed significantly to Microsoft's growth and scale via new business solutions into 190+ markets” and “consistently led the incubation of new business models and capabilities across properties and partner ecosystems.”

Lenny Fenster

Microsoft’s global CTO for Customer Experience & Success (CE&S) left in April for a role with higher education-focused cloud vendor Ellucian.

Fenster finished a 26-year career with Microsoft and will serve as Ellucian’s senior vice president of SaaS innovation delivery, according to his LinkedIn account.

“Microsoft has given me more experience, opportunities, and learnings than I ever dreamt possible,” Fenster said in a LinkedIn post. “I have been very fortunate to be part of many great teams that have made significant and positive impacts to customers around the world.”

In the CTO role, Fenster led “a team of senior Subject Matter Experts across all six solutions areas–Apps, Infrastructure, Data and AI, Modern Work, Business Apps, Security, and Cross Delivery,” according to a bio of Fenster on the website of Remedy Sports, which offers technology to help sports officials.

He coupled “historical and current data with broad strategies from the product group and the sales organization into technical approaches to develop and land consistent technical delivery for the field” and forecast “technology needs for IP, Offerings, and Skilling to help drive accelerated growth and support Microsoft’s customers’ operational health.”

During his time with Microsoft, Fenster worked “with teams like the Visual Studio product group and the patterns and practices team provided him with the experience to author the TFS/Project Server Connector and the book Effective Use of Microsoft Enterprise Library,” according to the bio.