About Me

15+ years of Senior Management and Senior Legal Counsel Positions

  • Proven success as an executive leader who possesses the determination, know-how, and strategic mindset for building partnerships, expanding services, balancing various stakeholders, and meeting goals.
  • Generates buy-in from physicians, nurses, and hospital staff by soliciting stakeholder input through a series of systematic transparent steps prior to program launch while ultimately achieving goals, timelines, and ROI.
  • Extensive experience in partnership with trustees, executives and clinical leaders to balance multiple ongoing projects encompassing physician recruitment and employment, regional network expansion, enterprise wide risk management tracking system, real estate expansion, management of academic partners, internal communications, contracts and administrative policies.

Curriculum Vitate


Strategic Development: Directly involved with the strategic development and implementation of a strategic plan and a long-range Master Campus Plan (~33 acres). Work with executive team to timely track and ensure connectivity to legislative priorities and 10-year financial plan.

Network Affiliations: Part of the team that created a neonatal network across west central Florida and later led and expanded the network to include other NICUs, pediatric specialists, surgeons, perinatologists and transport services under a sustainable economic model.

Executive Board | Leadership: Extensive interface with hospital Board of Trustees, foundation Board of Trustees, management boards, Executive Committees, Physicians, Philanthropists, and “C-level” executives.

Project Management: Managed multiple ongoing projects encompassing physician recruitment and employment, regional network expansion, enterprise wide risk management tracking system, real estate purchases, management of academic partners, transition from self-insured retention model to risk retention group, communications, manage all administrative policies for system.

Legal: With a lean team of attorneys, paralegals, licensed risk managers, claims adjuster, corporate secretary, compliance officer, privacy officer provided all health care regulatory and transactional work and managed outside panel of attorneys for labor, ERISA, defense litigation and other specialized advisors.

Compliance: Instrumental in establishing an extensive physician compensation plan, the early version of the compliance program and HIPAA policies, procedures, and gap analyses.

Additional Areas of Expertise

Strategic Planning ~ Communication ~ Organizational Structure ~ Graduate Medical Education Committee Regulatory Compliance Risk Management ~ Plan execution ~ Governance and Board Management ~ Grant Management ~ Contract Negotiation ~ Vendor Relations ~ Policy Administration ~ Medical Staff Bylaws ~ Physician Compensation Plans and Benchmarks ~ Physician Employment and Contracting

Envision Better Health LLC January 2020-present
Focused on providing strategic insight, new growth ideas, and professional business advice to large and small providers, including those in transition and needing to reposition pediatric service lines. Dedicated to cost-effectively working with Florida health systems and practices to translate visions and goals into sustainable initiatives related to collaborations, physician compensation, patient acquisition, organizational structures, and physician/APP recruitment services.

Johns Hopkins All Children’s Hospital, Inc. June 2003-December 2018
Johns Hopkins All Children’s Career Progression

Vice President, Chief Strategy Officer (2014-2018) and Chief of Staff (2016-2018)
Johns Hopkins Health System Corporation Senior Counsel (2012-2016)
Onsite Legal Counsel managing All Children’s Hospital’s Legal Affairs Department and budget (2003-2011)
Outside Counsel as part of law firm team (2001-2003)

Johns Hopkins All Children’s Interim Leadership Roles

Human Resources (January – June 2015) (12.5 FTEs)
Quality Resources (May – September 2013) (13 FTEs)
Environment/Life Safety (March 2013 – July 2014) (2 FTEs)
Radiology and Imaging (August 2013- March 2014) (74 FTEs)
Lab and Pathology (August 2013- March 2014) (105 FTEs)
Sleep Lab (August 2013- March 2014) (7.2 FTEs)
Pulmonary Function Testing (August 2013- March 2014) (3.1 FTEs)

Johns Hopkins All Children’s Vice President, Chief Strategy Officer

Key executive team member with direct oversight of the strategic planning and business development, implementation, and clinical network of academic and hospital affiliates.  Responsible for connecting the legislative priorities plan, community health need plan, master campus plan and 10-year financial plan to the strategic plan.  Supported the President and CEO, President’s Executive Cabinet, the community Boards of Trustees, 7 subsidiary boards, Physician Chairman and Institute Directors, Chief of the Medical Staff, Capital Committee, Graduate Medical Executive Committee and Physician Compensation Committee.

Led a team who managed a network that covered 17-counties, 12 hospital units and many consultative services including coverage for over 17,000 births.  Accountable for value proposition statements for strategic priorities, corporate bylaws, governance including trustee liaison, risk and insurance, enterprise wide risk plan, and administrative policies for all entities (hospital, home care, physician groups, research and grants, foundation, retail / restaurant corporation).

  • Supported two strategic plans (ambulatory footprint and physician acquisition / employment) and designed and managed a strategic plan centered on academic transformation and developed a new plan related to access and growth; monitored metrics for all strategic plans and other business plans and growth strategies and reported same to Board of Trustees Planning Committee.
  • Worked closely with the Board of Trustees Building and Grounds Committee to purchase and bank real estate to amass over 33 acres in adjacent properties for main campus and many outlying properties; supported master campus plan and the connectivity of each institute and department plan.
  • Annually managed over 25 clinical coverage contracts, academic partners and supported hospital-sponsored pediatric residency program.
  • Developed the exclusivity model for the medical staff and affiliates; monitored certificate of need issues, added two ‘second opinion’ vendors, and set the foundation for a Clinical Integrated Network (CIN) and bundled care model.
  • Balanced strategic objectives and initiatives with enterprise-wide risk management plan.
  • Supported the international program, external corporate relationships and phased in the first retail strategy, including for-profit corporation, simulation center and restaurant.

Maintained one of the highest engagement scores of the JHACH executive team each FY despite corporate changes.

Johns Hopkins All Children’s Chief of Staff

Accountable for alignment and coordination of boards, councils, institutes, and departments (internal strategy), Governance, Risk and Insurance, physician relationships / medical staff relationships, physician compensation plan, and the refresh and alignment of administrative policies.

  • Implemented consensus management structure (process flow and decision cascading)
  • Lead point of contact for trustees; managed Corporate Secretary to oversee board and committee meeting logistics and board communications and reporting for nine corporate entities and 13 standing committees; and managed trustee nomination and orientation process.
  • Responsible for physician compensation committee for 200+ physician employed physicians. Teamed with outside vendor and managed internal analyst and senior director who produced FMV opinions (11 in last FY), comp cards with wRVU benchmarks (197 last FY), division restructures, leaves or parity issues, all new hire or candidate offers (~30 last FY), and all extra pay calculations (over 1200 incentive worksheets and 120 extra or exceed bonuses).

Johns Hopkins All Children’s Legal Affairs, Risk Management & Insurance Departments

  • Acted as in-house counsel when hospital was an independent, specialty-licensed children’s hospital with various related healthcare entities including two physician employment companies, a home care company and a research institute. Served as counsel to IRB, medical staff bylaws committee, compliance committee, risk management committee, self-insured retention oversight committee, licensure and regulatory team, HIPAA advisory team.
  • Acted as in-house counsel during multiple years of due diligence and negotiations leading to a sole member substitution transaction between All Children’s Health System, Inc. and The Johns Hopkins Health System Corporation and integration into Johns Hopkins Medicine.
    • Supported all leaders and maintained all legal functions during over 3 ‘quiet’ years of due diligence and negotiations.
    • Initiated special claims such as a BP Oil Settlement that grossed over $4M payable over two fiscal years.
    • Accountable for negotiating and maintaining central repository of all contracts with a focus on mitigation and / or elimination of risk, including, but not limited to, physician practice acquisitions, physician employment, clinical services, academic affiliations, equipment and service agreements, clinical trial / research agreements, hospital policies, space leases, construction, EMTALA, technical (IT), marketing, human resources, HIPAA and special event services / venue agreements.Physician acquisitions and employment agreements resulted in a growth of the employed physician groups from less than 25% of the active medical staff to over 70%
  • Managed legal aspects of hospital’s construction projects to build a new freestanding 9-story specialty hospital, central energy plant, 6-story outpatient care facility and connected parking deck.
  • Directed and grew risk and claims department from two licensed risk managers to four full-time risk managers and a full-time claims manager to elevate the span of influence, increase proactive attention to risk areas, and reduce claim expenses and develop loss control programs.
  • Moved from paper-based incident reporting system to electronic incident reporting system.
  • Managed outside panel and team who managed resolution of PL, GL, Auto and Property claims. Worked with health system treasury to secure other coverages: cyber, D&O, managed care, sexual misconduct, travel, and liquor liability.
  • Provided mandatory training to create awareness and performed proactive risk assessments based on clinician or leadership input as well as new acquisition and strategic organization initiatives.
  • Chaired Risk Management Committee, Claims Management Committee and Adverse Medical Incident Committee; supported survey readiness team; executive champion to one of five (AHRQ) Comprehensive Unit-based Safety Programs.

TRENAM KEMKER PA (2006 – 2011) Shareholder, Health Care Practice, St. Petersburg office

  • Responsible for health system legal department, contracts management and advising health system executives and coordinating legal advisors, including oversight of contracts management for health system, hospital, physician practice groups, and other subsidiary corporations as well as providing advice to a variety of health system / hospital operational committees including: risk management, claims management, adverse medical incident, IRB, patient access team, HIPAA Advisory Team, medical staff bylaws, senior management team and legislative advocacy.
  • Practice acquisitions and Physician alignment strategies.
  • Managed Health Care Privacy / Security matters, physician compensation and other regulatory matters.

 HOLLAND & KNIGHT LLP (2000 – 2006) National Health Care Practice Group, St. Petersburg office

  • Health Care Privacy / Security. Health Care Fraud and Abuse Laws.
  • Regulatory Compliance, Audits, Reimbursement Issues, Research and IRB Compliance.
  • Transactions, Hospital and Physician Agreements.
  • Responsible for health system legal department, contracts management and advising health system executives.


  • Harvard School of Public Health, Women Executives in Health Care (2017)
  • Johns Hopkins Medicine Leadership Program (2016)
  • Stetson University College of Law, JD/M.B.A. (2001), Top 7%
    • Research Editor, Stetson Law Review
    • Teaching Fellow, Stetson University College of Law
    • Law Clerk, the Honorable David Demers, Sixth Judicial Circuit of Florida
    • Best Lawyers in America (Health Care Law) 2011
    • Florida Super Lawyers – Rising Star 2009, 2011
  • Florida State University, B.S. (1997), Top 2%


Children’s Hospital Association, Chief Strategy Officers Section, Member
Florida Bar, Active Member
Healthcare Roundtable for Corporate Counsel
American Health Lawyers Association
American Bar Association
St. Petersburg Bar Association, Past Member
Florida Bar Real Property, Probate and Trust Law Section’s HIPAA, Committee Member
Florida Bar HIT Committee, Past Member
ABA Health Law Section’s eHealth, Privacy & Security Interest Group, Past Vice Chair
ABA’s Young Lawyers Division Health Law Committee, Past Chair


Preserve the Burg, Director
FSU Seminole Boosters, Golden Chief
St. Petersburg Economic Development Council, Former Member
Admiral Farragut Academy, Volunteer
Gulf Beaches Elementary Magnet School, Volunteer
Eckerd Foster Angel Program, Participant
Surgikid of Florida, Inc., Former Trustee
ForAllKids, LLC, Former Manager
All Children’s Research Institute, Inc., Former Trustee
Kids Home Care, Inc., Former Trustee
Pediatric Physician Services, Inc., Former Trustee
West Coast Neonatology, Inc., Former Trustee
A Gift for Teaching, Pinellas Chapter, Former Trustee


Crain, J and Pacini, C. et al “Investigating Healthcare Fraud: Its Scope, Applicable Laws and Regulations”, Wm and Mary Bus Law Rev Pending publication 2019/20

Crain, Jackie, “Academic Affiliations” (presentation to the Association of Administrators in Academic Pediatrics (AAAP) at its winter regional event, St. Petersburg, Florida Jan 2017).

Crain, Jackie, “Compliance for Practice Managers” (presentation to Practice Manager’s Association, St. Pete Chapter on October 2009)

Crain, Jackie, “Health Care Audits” (presentation at the St. Petersburg College Health Informatics Symposium, September 2009)

Crain, Jackie, “EHRs and HIPAA post HITECH” (presentation to Tampa Bay providers and plans sponsored by the Mathews Benefits Group, May 17, 2009)

Crain, J. “HIPAA-A SHIELD FOR HEALTH INFORMATION AND A SNAG FOR ESTATE PLANNING AND CORPORATE DOCUMENTS“. Real Property, Probate and Trust Journal. Copyright American Bar Association, Real Property, Probate and Trust Law Section Summer 2005

Crain, J. “HIPAA – What Is It and How Does It Apply to Estate Planning?” (presentation by The Florida Bar and the ABA Real Property, Probate and Trust Law Section, November 11, 2004)

Crain, J. “Applying the HIPAA Security Rules to Employer Sponsored Health Plans: Complex Issues and Compliance Strategies” (presentation at Florida Bar CLE seminar titled The HIPAA Security Rules: One Year to Go-Are You Ready? April 20, 2004)

Crain, J. “HIPAA and Employee Benefit Plans” (presentation at HIPAA for Employers in Florida organized by Lorman Education Services, March 26, 2004)

Crain, J. “HIPAA After 2003: Focusing on Enforcement and the Security Rules” (12th Annual Employee Health Benefits Conference, January 22, 2004)

Crain, J. “HIPAA Compliance for Employers- Complex Issues and Superhero Strategies” (11th Annual Treasure Coast HR Conference at PGA Educational Center, October 3, 2003)

Crain, J. “HIPAA the Real Issues” (2003 Annual Meeting of Florida Society of Ophthalmology, September 13, 2003)

Shannon Hartsfield and Jacqueline Myles “How Will HIPAA Impact Employers?” 3/03; Vol. 11, The Metropolitan Corporate Counsel

Myles, J. “HIPAA Explained and Answers Given” (a presentation related to HIPAA and employers at the 11th Annual Employee Health Benefits Conference in Martin County on April 24-25, 2003)

Myles, J. “HIPAA Compliance for Small Physician Groups and Solo Practitioners” a presentation organized by the Pinellas County Medical Society on March 3, 2003

Myles, J. “Overview of the HIPAA Privacy Rules” a presentation organized by Lorman Education Services  at the Legalities of Utilizing and Maintaining Computerized Medical Records in Florida seminar on January 29, 2003.

Hartsfield and Myles, “Other Liability” No. 3, p. 17.y – Tort and Regulatory (Chapter 8),” E-Health Business and Transactional Law, BNA Books, 2002 (Contributing Author)

“HIPAA: Repercussions and Solutions” panel presentation to the U.S. Virgin Islands Department of Health and V.I. Equicare, Inc. on November 1-2, 2002.

“Introduction to HIPAA and HIPAA Applied to Schools and Colleges” a presentation to the Florida Community College Attorneys at the Florida Community College System Annual Community College Attorneys Meeting on July 12, 2002


Running, boating, golf, watching my sons play baseball