Strategic accomplishments

Shipping high-stakes, compliance-driven platforms

Results from product ownership, analysis and compliance work across five industries.

97%Onboarding attach rate, achieved among core payroll customers
#1Leader on the G2 Crowd Grid® for Onboarding
0Service disruptions in the SharePoint 2010 to Online migration
4Teams aligned, connecting onboarding, recruiting, HR and payroll around shared priorities
  • Developed the Onboarding solution from Beta through General Availability, reaching a 97% attach rate and the #1 Leader spot on the G2 Crowd Grid® for Onboarding.
  • Delivered a financial patient lending platform on an aggressive timeline, serving as product owner, release manager, QA lead, tester, copy editor, security analyst and trainer.
  • Defined requirements for NACHA-mandated encryption of ACH account data at rest, reaching compliance ahead of deadline.
  • Served on the GDPR Task Force and led compliance and security features (GDPR and I-9 Audit Download); compliance SME on RFPs and customer inquiries.
  • Developed corporate policies and internal control assessments, rolled out enterprise-wide Ethics Awareness training and Hotline, and built an internship program that converted interns into full-time hires.
  • Migrated dealer applications and reports from SharePoint 2010 to SharePoint Online with zero service disruption.

Product principles

How I build products

Four principles I build into every product, from the first requirement to production.

Start with the user

Watch the work before writing the requirement.

When people jump through hoops to get their job done, I find the workaround and remove it, with a feature, a simpler process or better training. Help belongs in context, not in a one-inch manual.

ProofA customer opposed the first phase of a feature, so I put them on the review team before rollout. They became our strongest advocate.

Secure by design

Protect sensitive data from the first requirement.

Personal and financial data, from Form I-9 to bank accounts, is protected in the requirements: masked SSNs, encryption in transit and at rest, secure file upload and one-time passcodes.

ProofDefined NACHA-mandated encryption of ACH data at rest, delivered ahead of the deadline. Served on the GDPR Task Force and led I-9 Audit Download at Ultimate Software (UKG).

Accessible to everyone

Accessibility from day one, not as an add-on.

WCAG contrast, a logical keyboard order and layouts that work on any screen are requirements, not polish. Teaching students with vision and hearing impairments taught me to plan for every learner.

ProofThis website and my student tools are built to work with a keyboard, a screen reader and a phone.

Built to support

Make problems quick to find and fix.

I build in logging and diagnostics that never expose sensitive data, so production support can solve more on its own and engineers can pinpoint the rest faster.

ProofAt Ultimate Software, every feature passed Gut Check and Kick Off checklists covering privacy, security and serviceability.

How I built this site →

Domains and tools

Regulated domains
InsuranceFintechHCMBankingAutomotive
Compliance
GDPRSOXNACHAForm I-9
Integrations
TransUnionPaymentsACH processingReconciliation
Platforms
Cloud migrationMainframe retirementSharePoint Online
Data
SQLOracleData warehousingStatisticsGenerative AI
Delivery
ScrumKanbanAzure DevOpsJira

Professional experience

Product leadership in regulated industries

Insurance, automotive finance, healthcare lending and human capital management (HCM) technology.

  1. CHAOS Disruption, LLC

    Jun 2021 – Present

    Consultant and Trainer · South Florida

    • Technicom Media Group: assist with virtual events and presentations.
    • Technicom Sales & Services: teach Data Analytics to veterans pursuing entrepreneurial careers in agriculture through the AgVet Program (North South Institute).
    • Work with user experience designers to develop a prototype for a new concept.

  2. FM (formerly FM Global)

    Jan 2023 – Apr 2026

    Assistant Vice President, Product Owner · Johnston, RI

    $7.31B mutual insurance company (5,000 employees) protecting commercial property through advanced engineering and risk management.

    • Drove development of remote sensing software that detects and reduces natural-hazard risk for commercial property clients, partnering with engineering, data science and business stakeholders to turn hazard-risk requirements into deliverable features.
    • Provided product oversight for production support and enhancements of the Financial Accounting and Reporting System.

  3. JM Family Enterprises

    Jul 2021 – Jan 2023

    Product Owner / Senior Business Analyst · Deerfield Beach, FL

    $1.49B diversified automotive company (3,800 employees) in vehicle distribution, financial services and retail.

    • Led business analysis across distribution, sales and data migration initiatives spanning legacy and modern platforms.
    • Drove mainframe application retirement and consolidation into a centralized Digital Hub, reducing the legacy footprint.

  4. Bankers Healthcare Group (BHG)

    Feb 2020 – Jul 2021

    Team Lead / Senior Product Owner, Product Development & Innovation · Davie, FL

    $235.6M financial services firm (1,200 employees) providing short-term credit solutions to business enterprises.

    • Became SME for the entire patient lending platform in under six months: applications, portals, APIs, TransUnion integration, amortization, payments, NACHA processing and reconciliation.
    • Mentored and led product owners in defining and enhancing functional areas of the platform.
    • Partnered with Scrum teams to deliver features in two-week sprints using Azure DevOps and Jira.
    BHG MVP Award (Oct 2020) · BHG All Star Award (Jan 2021)

  5. Ultimate Software (UKG)

    2014 – 2019

    Product Owner / Senior Business Analyst / Senior Risk & Compliance Analyst · Weston, FL

    $1.85B global HCM technology company (5,166 employees) delivering HR, payroll and workforce management solutions.

    • Drove features through Agile in Jira with Gut Check and Kick Off checklists covering privacy, security, serviceability and cross-team dependencies.
    • Advocated for the privacy and security of customer data, delivering organization-wide awareness presentations.
    G2 Crowd #1 Leader, Onboarding Team Award (2018) · UltiExcellence (2016) · Five Year Award (2019)

Previous relevant experience

Veretech Holdings

A Hearst Business Media Company · Boca Raton, FL
Senior Business Systems Analyst / Project Manager

BankAtlantic

Fort Lauderdale, FL
Business Systems Analyst III, Information Systems – Systems Integration

Education & credentials

Foundations

Education

  • M.S., Computer ScienceWest Virginia University
  • B.S., Computer Science & MathematicsUniversity of the West Indies, Mona, Jamaica
  • Upsilon Pi EpsilonComputer Science Honor Society

Certifications

  • A-CSPOAdvanced Certified Scrum Product Owner
  • CSMCertified ScrumMaster
  • Project Management CertificatesVillanova University

Awards

  • Adjunct Professor of the YearBroward College, 2025–26 and 2015–16
  • BHG All Star & BHG MVP2021 · 2020
  • G2 Crowd #1 Onboarding Team Award2018 · plus UltiExcellence, 2016
  • NASA Group Achievement AwardSpace Telescope Science Institute, education outreach team

Contact

Let's build something that matters

Open to senior technical product owner and product leadership opportunities. Based in South Florida.

Integrity in every decision.
Excellence in every delivery.

Emailwinsome@winsomemundy.com LinkedInin/winsomemundy ↗