ASKIA ACOSTA
Riverview,FL
Summary
Versatile and results-oriented executive with over 20 years of experience leading enterprise-scale digital transformations, cross-cloud Salesforce implementations, and C-suite advisory engagements across regulated industries. Over the past three years, Askia has driven more than $35M in professional services revenue-primarily within the highly competitive and budget-conscious SMB mid-market-by translating strategic vision into pragmatic, technology-enabled outcomes. Recognized for delivering measurable business impact, he excels at shaping strategic direction, modernizing operations, and unlocking value through innovation. Askia brings a strong record of success in cross-functional leadership, complex program execution, and trusted partnerships with executive stakeholders.
Overview
19
19
years of professional experience
1
1
Certificate
Work History
Senior Director, Professional Services Sales & Delivery
Salesforce Inc.
01.2022 - Current
- Closed and delivered over $30M in Salesforce services by aligning digital strategy with enterprise priorities across healthcare, financial services, and public sector clients.
- Directed cross-cloud digital transformations across Service, Health, and Experience Clouds, ensuring compliance, scalability, and measurable business outcomes.
- Trusted strategic advisor to CIOs and COOs, leading business model redefinition and workforce enablement through Salesforce-driven modernization.
- Delivered executive-level 'Art of the Possible' engagements, aligning vision with practical innovation and platform optimization.
- Accountable for full lifecycle delivery, governance, and customer success for multi-million dollar strategic programs.
Engagement Director
Salesforce Inc.
01.2020 - 01.2022
- Accelerated time-to-value, resulting in 50% faster realization of services revenue
- Secured multiple renewals and expansions valued at $5M+ each by demonstrating tangible business outcomes.
- Led upsell and cross-sell motions that increased average deal size by 25% over 12 months.
Program Executive
Salesforce Inc.
01.2017 - 01.2020
- Delivered $50M+ portfolio of engagements on time and within budget across multiple industries
- Achieved 95% +5 CSAT across multi-year enterprise engagements to increase client success and retention
Senior Engagement Manager, Media & Entertainment Advisory
Ernst & Young LLP
01.2012 - 01.2017
- Led $15M+ in advisory revenue managing complex engagements in digital advertising, supply chain integrity, and healthcare transformation.
- Delivered a $3.8M ICD-10 transformation program for Kaiser Permanente, spanning regulatory remediation and systems modernization.
Senior Consultant, Healthcare Advisory
Ernst & Young LLP
01.2010 - 01.2012
- Led healthcare performance and compliance initiatives.
- Supported $1M–$3M in new client acquisition annually.
Senior Program Manager, New Business Integration
WellCare Health Plans Inc.
01.2007 - 01.2010
- Led enterprise rollout of Salesforce CRM and Medicaid/Medicare expansion, enabling $210M in new revenue streams.
- Reported directly to CIO/CFO on enterprise IT portfolio alignment and delivery risk mitigation.
AVP, Technology Program Management
JPMorgan Chase
01.2006 - 01.2007
- Managed treasury systems acquisition initiatives and conducted enterprise-wide technology audit reviews.
- Improved on-time delivery from 20% to 85% through PMO process optimization and team enablement.
Education
MBA - Business Administration And Management
University of Miami
Miami Beach, FL05.2006
B.A. - Mass Communications
University of South Florida
Miami FL 12.2000
Skills
- C-Suite Stakeholder Engagement & Executive Advisory
- Salesforce Cross-Cloud Strategy & Implementation
- Enterprise Digital Transformation & Value Realization
- Agile Operating Delivery Models
- Regulatory Compliance & Risk Governance in Regulated Industries
Timeline
Senior Director, Professional Services Sales & Delivery
Salesforce Inc.
01.2022 - Current
Engagement Director
Salesforce Inc.
01.2020 - 01.2022
Program Executive
Salesforce Inc.
01.2017 - 01.2020
Senior Engagement Manager, Media & Entertainment Advisory
Ernst & Young LLP
01.2012 - 01.2017
Senior Consultant, Healthcare Advisory
Ernst & Young LLP
01.2010 - 01.2012
Senior Program Manager, New Business Integration
WellCare Health Plans Inc.
01.2007 - 01.2010
AVP, Technology Program Management
JPMorgan Chase
01.2006 - 01.2007
MBA - Business Administration And Management
University of Miami
B.A. - Mass Communications
University of South Florida
Certification
- PMP – Project Management Institute
- Salesforce: Advanced Admin, Admin, Sales Cloud, AI Associate
- ICP-ACC Agile Coaching
- COSO / SOX Compliance Training
Licenses
- Member: PMI · ISACA · NABA · IAB
- Board Member: Community Charter School of Excellence
- Contributor to digital transparency, media measurement, and anti-fraud advisory initiatives.
Affiliations
- Former Board Member: Community Charter School of Excellence (K-12)
- PMI
- ISACA
- NABA
- IAB
Community Leadership
- Jack and Jill of America - supporting leadership development and civic engagement for African American youth
- Girl Scouts of America - Advocate for young girls' empowerment and leadership through Girl Scouts programs
- One Voice Against Cancer (OVAC), Cutaneous Lymphoma Foundation - Volunteer Advocate
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