Cheryl Bolton
Corporate Technology Leader
South Padre Island,Texas
You miss 100% of the shots you never take.
Wayne Gretzky
Summary
Transformational IT and Financial Services Executive with a proven track record in corporate finance, analytics, and information technology. Recognized for strategic thinking, building high performance teams, innovative technology deployment, and leadership in large-scale transformations. Adept at steering multi-million-dollar initiatives, fostering stakeholder relationships, and driving operational excellence.
Overview
14
14
years of professional experience
5
5
years of post-secondary education
3
3
Certificates
Work History
Corporate Vice President
New York Life
South Padre Island, United States
08.2015 - Current
- Enabled 50% increase in revenue generation for NYL by pursuing Cigna Group Benefits Group, $6B acquisition.
- Developed and implemented new strategies and policies in collaboration with executive partners to establish and achieve long-term business objectives, providing company with strong and sustainable organizational leadership.
- Aligned organizational objectives with company mission to increase business growth and integrate work strategies.
- Directed $100M annual investment budget across run and grow initiatives that spanned across 50+ corporate applications.
- Pioneered Scaled Enterprise Agile delivery model, achieving 98% participation rate across all corporate value streams.
- Sponsored up-skilling of 1000+ technology workforce comprised of fulltime employees and consultants
Sr Program Manager
Fannie Mae
Dallas, TX
07.2010 - 06.2015
- Led 500-member team with $300M budget, driving large-scale initiatives in credit, finance, and capital markets.
- Achieved cost savings of $200M in Loan Accounting Platform and enabled recovery of over $50 billion from banks.
- Collaborated with development teams, internal customers, and product line management to verify delivery of desired outcomes for system delivery.
- Performed program research and analyzed data collection to develop cost estimates and budgets.
- Mentored and supported cross functional teams to create strong workplace culture.
- Networked in local community to identify business opportunities with loan originators and service partners.
Education
Post Graduate Program Certificate - AI & Machine Learning Program
10.2023 - Current
Executive Education Certificate - AI, Blockchain, IoT, And Negotiations
05.2018 - 03.2021
Bachelor of Science - Management Information Systems
05.1998 - 12.1999
Skills
Strategic Leadership & Development
Technology Strategy & Execution
Enterprise Architecture & Applications
Financial Forecasting & Risk Management
Program & Vendor Management
IT Governance, Compliance & Security
Data Science, AI, and Machine Learning
Blockchain and IoT
Contract Negotiation and Vendor Management
Certification
PMP
Work Availability
monday
tuesday
wednesday
thursday
friday
saturday
sunday
morning
afternoon
evening
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Timeline
University of Texas At Austin - Post Graduate Program Certificate, AI & Machine Learning Program
10.2023 - Current
Certified SAFe 5 Product Owner/Product Manager
05-2023
Massachusetts Institute of Technology Sloan - Executive Education Certificate, AI, Blockchain, IoT, And Negotiations
05.2018 - 03.2021
Corporate Vice President - New York Life
08.2015 - Current
PMP
03-2015
CSM
03-2015
Sr Program Manager - Fannie Mae
07.2010 - 06.2015
University of Texas At Arlington - Bachelor of Science, Management Information Systems
05.1998 - 12.1999