Raymond Massey

M&A Consultant

Washington D.C., United States


PricewaterhouseCoopers-US Rackspace, The #1 Managed Cloud Company Robinhood

M&A consultant with experience in Software, Cloud, and Information Technology M&A. Raymond was most recently a Researcher on the M&A team at Robinhood. There he worked with stakeholders to identify, evaluate, and acquire software engineering teams. He was responsible for quantitative/qualitative due diligence on potential acquisition targets, engagement with the startup ecosystem, and developing relationships with founding teams. Previously, he was on the Corporate Development team at Rackspace, an Apollo backed company. Raymond began as an Associate in the PwC Deals platform.

Domain experience

Relevant Total Experience: 4 years

Seniority Level: Manager

Sector Experience: 

Software and Services


Skilled in: Corporate Development

Technical Skills: SQL, Microsoft Excel, PowerPoint

Languages: Spanish, English

Work Experience


M&A Consultant



- Now

Advising startups in Software, Cloud, and Information Technology.


Researcher, M&A



- 1/7/2022

Worked with stakeholders to identify, evaluate, and acquire software engineering teams. Researched acquisition targets. Engaged with startup ecosystem and built relationships with founding teams. Highlights 1) Acquisition of Cove Markets Digital trade execution for a range of digital assets in an easy-to-use, transparent and secure platform. 2) Competitive Intelligence System Architected and built database to track acquisition targets, financial data and product features. Robinhood is a modern financial services app. Its platform has enabled products like dividend reinvestment, fractional shares, and recurring investments (NASDAQ:HOOD)

Rackspace Technology

Manager, Corporate Development



- 01/06/2021

M&A, venture, strategy and partnerships for the leading multicloud technology solutions company (NASDAQ:RXT) Highlights 1) Acquisition of Bright Skies GmbH Leading Central European specialist in Microsoft cloud technologies (Azure, Office 365 and Enterprise Security) 2) Strategic Investment in Platform9 Kubernetes-as-a-Service for multi-cloud, on-premises, and edge computing platforms. Responsibilities • Drove international M&A process by maintaining regional M&A pipelines for the Americas, EMEA, and APAC • Engaged with the cloud M&A ecosystem, scout competitors, prepare CFO's weekly competitor investment report • Created weekly presentation materials for M&A Strategy Council with CTO to align M&A with product roadmap • Managed cross-functional due diligence workstreams from IOI through post-LOI: (1) responsible for building bottoms-up financial models, analyzing comparable companies, data room exploration and analysis, (i) overseeing teams and reporting key issues and proposed resolutions (GTM, legal, FP&A, integration, HR), (i) assist sourcing efforts by preparing pre-LOI materials, evaluating CIMs and summarizing merits/ risks for senior stakeholders. Selected Transactions Acquisition of a Leading Cloud Transformation Company in EMEA (closed) ▪ Collaborated daily with regional FP&A and HR teams across time zones to manage post-LOI due diligence ▪ Analyzed sales pipeline/backlog, created Q4 revenue bridge to rationalize remaining 2020E go-get revenue ▪ Presented Due Diligence Readout materials to CEO/CFO to summarize each BU’s key due diligence findings Potential Acquisition of Leading Cloud Services Consultancy & Microsoft Azure Partner in APAC ▪ Drafted APAC market map, evaluated 38 companies in region, connected directly with top 7 targets of interest ▪ Built bottoms-up financial model with QBR productivity analysis to gain initial pre-LOI support from C-Suite ▪ Forecasted QBR hiring plan, sensitized junior/senior QBR quotas, validated assumptions with VP of Sales ▪ Managed post-LOI handoff of financial model to regional FP&A and assisted with pro-forma P&L impact


Experienced Associate, Strategic Value Consulting



- 01/06/2020

Experienced Associate in Technology, Media, and Telecommunications. Responsible for market sizing, financial modeling and industry benchmarking. Advised public and private tech clients on M&A and corporate strategy.


Associate, Strategic Value Consulting



- 01/01/2020

Associate Consultant in Technology, Media, and Telecommunications. Primary clients included Software-as-a-Service, Financial Technology, and Information Technology. Additional clients in Financial Services, Retail, Logistics, and Industrials. Highlights • Advised strategic partnership with FAANG by a Fortune 500 Competitor ▪ Built 3-Statement Scenario Analysis model with DCF valuation to analyze partnership’s incremental cash flows ▪ Presented ~$120 Billion TAM analysis to incoming client CEO to establish trust and build relationship ▪ Advised VP of Strategy to pursue strategic partnership resulting in ~15% projected EPS growth by 2030


Summer Associate, Financial Modeling (MCoE)



- 01/08/2018

Summer Associate in the Modeling Center of Excellence in Deals.


Summer Associate, Advisory



- 01/08/2017

Summer Associate in Advisory.

Presti & Company, Inc.

Software Engineer (Co-op)



- 01/05/2017

Front end developer (Co-op program)


UVA McIntire School of Commerce

Finance and Real Estate



- 01/01/2019

University of Virginia

Finance and Real Estate

SEO (Sponsors for Educational Opportunity)

Alternative Investments



- 01/08/2020

Received 50+ hours individualized coaching and live instruction to achieve targeted interview, technical, and professional developmental goals. Completed industry-specific training and assessments focused on developing technical skills, institutional knowledge, and attention to detail.

Potomac Falls High School