Holly Flaherty
Bradenton,FL
Summary
Accomplished Principal Technology Seller with 40 years of experience in the technology industry, specializing in the application of automation, AI, and data-driven solutions for the insurance and financial services sectors. Proven success in driving growth, efficiency, and client satisfaction by delivering innovative and tailored technology solutions. At IBM, I collaborated with global business and IT leaders to consistently achieve exceptional results, contributing to both client’s and IBM’s success. Known for a consultative, results-driven approach, I have successfully led multi-million-dollar projects and developed long-term, strategic client relationships.
Overview
39
39
years of professional experience
Work History
Principal Technology Seller
IBM
09.2022 - 12.2024
- Led the account team for IBM’s largest US Group Insurance client, aligning technology solutions with strategic business objectives
- Successfully closed over $200M in hardware, software, and services, driving transformative projects in IT infrastructure, cloud, and containerization, including:
- Repatriation of mainframe, storage, and software
- Power Server estate refresh
- Two Enterprise License Agreements (ELAs)
- Implementation of CloudPaks and RedHat OpenShift as the standard platform
- Large-scale cloud agreement and Apptio catalogue deployment
- Negotiated a 2-year QROC extension prior to the transfer of trade to Palo Alto
Automation Technology Seller
IBM
01.2022 - 09.2022
- Led the global Automation and Integration portfolio for a major Financial Services client, positioning IBM’s automation solutions as a key enabler of business growth
- Exceeded sales quota by 150%, generating over $1M in new revenue within the first half of the year
Certified Client Executive, Global Markets
IBM
03.2018 - 01.2022
- Led business development and project management for a global payment processing company, contributing over $20M in services across fraud prevention, AI solutions (including Watson), risk compliance, and hybrid cloud projects
- Successfully deepened client trust and delivered measurable business outcomes through tailored solutions
Certified Global Client Executive
IBM
01.2011 - 03.2018
- Directed all sales and client management for a multi-line global property and casualty insurance company
- Developed C-level relationships and closed complex, multi-brand projects, achieving over $150M in annual revenue
- Key accomplishments:
- Closed two major infrastructure outsourcing deals totaling over $350M
- Drove customer satisfaction through strategic, solution-oriented sales approaches
Client Representative/Executive
IBM
01.1986 - 01.2011
- Led sales and strategic support for a major international Life, Annuities, Investments, and Property & Casualty insurance company, delivering over $50M in annual revenue
- Notable achievements:
- Closed a $100M nationwide technology rollout for agents/offices
- Proposed and closed a $12M Data Warehouse project
- Delivered a $100M Life Insurance agency productivity solution for 1200 US offices
- Expanded IBM’s footprint in 9 international markets, contributing $10M+ in new revenue annually
Systems Engineer
IBM
09.1985 - 09.1986
- Specialized in telecommunications, data communications for a major US Life Insurance client
- Successfully led and closed multiple hardware and software projects, generating over $15M in revenue within the first year
Education
Client Executive Certification Program
Harvard Business School
Boston, MA04-2007
Life Insurance
Life Office Management Association
06-1997
Bachelor of Science - Marketing Management
Rider University
Lawrenceville, NJ05-1983
Skills
- C-Level Relationship Management
- Enterprise Sales & Business Development
- Automation
- AI
- Data
- IT Infrastructure
- Digital Transformation
- Client Relationship Management
- Solution Delivery
- Cross-Functional Team Leadership
- Revenue Growth
- Strategic Sales
Affiliations
- Life Office Management Association (LOMA), Member (FLMI, ACS)
- Certified Weight Watchers Consultant
Hobbies and Interests
- 40-year member of the Green Pond Women’s Club and two-time President – community and charitable organization devoted to the betterment of society
- Active community involvement and participation in charitable events
- Married with two children, committed to continuous learning, professional and personal development
Timeline
Principal Technology Seller
IBM
09.2022 - 12.2024
Automation Technology Seller
IBM
01.2022 - 09.2022
Certified Client Executive, Global Markets
IBM
03.2018 - 01.2022
Certified Global Client Executive
IBM
01.2011 - 03.2018
Client Representative/Executive
IBM
01.1986 - 01.2011
Systems Engineer
IBM
09.1985 - 09.1986
Client Executive Certification Program
Harvard Business School
Life Insurance
Life Office Management Association
Bachelor of Science - Marketing Management
Rider University
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