Director / VP leader driving business efficiency through data and application — currently leading a 20+ person Data Delivery & Strategy organization with AI-native workflows.
Author of 8 books · Keynote speaker · Freelance trainer · Consultant
20+ years turning complex data into real business gains — data lakes, BI, agentic AI workflows, and LLM/RAG apps built because the problems demanded it.
Owning the product lifecycle from requirements through launch — translating business needs into applications that work.
8 published books, hundreds of keynotes and workshops, and online courses delivering practical tools to practitioners worldwide.
Open to New Opportunities
20+ years of driving business efficiency through data and application — from modern data lake builds and agentic AI workflows to product strategy, roadmapping, and cross-functional delivery. Currently leading a 20+ person Data Delivery & Strategy organization at Palomar Holdings (CTO org). CBAP | CPOA | PSM certified.
Building data platforms and AI-native workflows that drive real business efficiency — from data lakes and BI to LLM/RAG applications and agentic delivery automation.
Translating complex business needs into products that deliver measurable value — owning roadmaps, requirements, stakeholder alignment, and end-to-end delivery.
Proven Impact
Three stories from the work — each one a real business problem, a deliberate approach, and a measurable outcome.
Inherited a newly formed Data & Analytics department spun out of Actuarial — siloed role-based teams (DataOps, Data Engineering, Report Engineering), a roadmap biased toward a single stakeholder group, and not ITGC compliant.
Restructured role-based silos into domain-aligned PODs for faster delivery and clearer ownership. Implemented daily leadership alignment, a strategic roadmap above each POD's individual roadmap, and trained POD leads in product ownership, vision-setting, and capacity planning. Championed and integrated Claude AI into the team's delivery workflows.
Team delivered 270% more output than originally planned, closed the ITGC compliance gap, and gave leadership a roadmap reflecting the full business — not just one stakeholder group.
Inherited a third-party data alignment process for external source data intake that had passed a POC but wasn't holding up in production — the team was routinely correcting data that had already been "processed," with automation providing no net improvement to quality or throughput.
Partnered with compliance and data engineering stakeholders to implement automated validation and SOX checks spanning source data through processed output, streamlining ingestion by 50%. Identified the underlying process model as the root bottleneck and built the case to design a purpose-built, AI-enabled intake solution integrated directly into the pipeline and SOX controls package.
Automated onboarding for new external data source feeds, direct pipeline integration, and SOX compliance built in from the start — solving the root problem rather than compensating for it.
GSTV had no way to connect which ads a customer watched at the pump to whether it drove a purchase — advertising spend was unmeasurable and therefore indefensible.
Partnered with Marketing, Digital Solutions, and Analytics teams to design MAPP — an application combining raw data-logger output (ad play + facial recognition at the pump) with generalized POS data, loyalty tracking, and coupon redemption to close the gap between ad exposure and purchase behavior.
For the first time, the business had a data-backed, defensible way to measure and report advertising ROI — turning previously unmeasurable spend into a demonstrable performance metric.
8 Published Books
Practical, direct, and built for real-world practitioners — from BA and product delivery fundamentals to data strategy and the way we communicate at work.
Master real-world elicitation techniques — asking the right questions, capturing what matters, and turning noise into actionable requirements.
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A practical guide to building relationships, managing expectations, and getting buy-in from the humans on the other side of every project.
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From backlog management to sprint ceremonies — a no-nonsense guide to owning the product and leading the team with clarity and confidence.
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Stop letting scope creep win. A direct, actionable guide to defining boundaries, saying no with confidence, and prioritizing what actually matters.
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Documentation that actually gets read, written, and maintained — because the best spec in the world is useless if nobody opens it.
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Clear, confident communication for analysts and product leaders — how to say what you mean, get heard, and close the gap between intent and understanding.
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A survival guide for data strategy — practical frameworks for governing, navigating, and extracting real business value from your data, without losing your mind or your stakeholders.
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The straight-talking guide to asking better questions, listening without an agenda, and making every stakeholder conversation — and every meeting you run — actually count.
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Visit Amazon Author PageKeynote & Training
With hundreds of keynotes, workshops, and training sessions delivered across IIBA chapters, corporate teams, and global conferences — Deena brings energy, practical tools, and real talk to every engagement.
Send a note with your event details — format, audience size, and any specific challenges you're tackling — and Deena will get back to you quickly.
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E-Learning
Can't make a live event? Deena's most popular topics — Stakeholder Magic, Requirements Gathering Like an FBI Agent, and CommonSensical Technical Documentation — are available as self-paced courses.
Explore CoursesWhen I met Deena, it was like an explosion went off. It was hard for me to believe so much intelligence, common sense, generosity, honesty, and humor could be blended into one human being. She's hands down one of the smartest people I have ever met. (And I know a lot of smart people.)
