Optina LLC / DataGlyphic Inc.

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 Senior Product & Strategy Leader (2022–2025)
Product Innovation | SaaS Strategy | HCM Ecosystem Leadership

As Senior Product & Strategy Leader at Optina and co-creator of DataGlyphic Inc., I led the evolution of a boutique HCM services firm into a scalable SaaS platform and data intelligence company—delivering measurable business outcomes in the UKG partner ecosystem. I oversaw the end-to-end product lifecycle, built cross-functional execution engines, and navigated complex organizational shifts while protecting innovation, client relationships, and long-term product value.

This role combined product leadership, operational execution, and strategic navigation, culminating in the launch of DataGlyphic—a platform now recognized as one of the most advanced HCM data conversion tools in the enterprise payroll and workforce management space.

• Launched DataGlyphic from concept to market, transforming a manual consulting model into a cloud-based SaaS product designed for complex enterprise data migrations in the UKG ecosystem.
   
• Drove 5X revenue growth, scaling from ~$500K to $2.4M through a blend of technical consulting, platform monetization, and strategic partner development.
   
• Owned end-to-end product vision, including customer discovery, feature prioritization, roadmap alignment, and successful go-to-market delivery—serving both direct clients and partner channels.
   
• Built and led cross-functional squads across engineering, services, QA, and product operations, aligning teams to iterative outcomes while maintaining high execution velocity under lean startup conditions.
   
• Created repeatable systems for client onboarding, implementation, and post-launch analytics, boosting platform stickiness and improving time-to-value across B2B deployments.
   
• Protected business continuity and intellectual property during a period of high disruption—maintaining client trust and product delivery while navigating governance breakdowns and operational threats.
   
• Stewarded executive operations as interim CEO, managing finance, legal, and partner communication while preparing the business for post-turnaround stability and future growth.

• Product-Led Growth & Innovation – Transitioned service-based delivery into a scalable platform model; aligned product strategy with market gaps and revenue opportunities.
   
• Voice of Customer & Market Discovery – Regularly interfaced with enterprise clients, UKG partners, and internal teams to validate hypotheses, prioritize features, and shape platform evolution.
   
• Roadmap Ownership & Cross-Functional Execution – Balanced vision with technical feasibility, negotiated trade-offs with engineering, and drove outcomes across sprints and releases.
   
• Lean Startup & SaaS Commercialization – Navigated bootstrapped constraints with resourcefulness; launched MVPs, drove adoption, and refined monetization strategy in real-time.
   
• Client-Centric Product Design – Built tooling that mirrored client processes, reduced onboarding friction, and automated high-risk, high-volume workflows.
   
• Organizational Agility & Crisis Leadership – Stabilized core operations and product delivery during founder-led turbulence, retaining talent and customers through strategic alignment and transparency.

 Product Manager & Chief Strategy Leader (2015–2017)
Seed-Stage Startup | Employee Retention & Engagement Analytics | Predictive HR Tech 

As Co-Founder and Chief Strategist at WorkJibe, I helped launch a seed-stage startup focused on reimagining employee engagement, recognition, and retention through a social and predictive HR technology platform. The product was positioned to disrupt legacy feedback models by leveraging machine learning, sentiment analysis, and commercial-grade workforce analytics—a new category we framed as Life + Work Technology.

In just under 12 months, I secured initial funding, led product design and development, conducted ethnographic research, and brought the MVP to market with pilot users and early-stage revenue traction.

• Secured angel funding and negotiated a follow-up investment round, supporting a rapid product development cycle and a lean operational model.
   
• Led platform strategy and architecture, blending social feedback loops, organizational analytics, and predictive retention insights into a cohesive UX.
   
• Developed and validated a new market category, positioning WorkJibe at the intersection of HR systems and employee well-being through next-gen engagement analytics.
   
• Oversaw MVP delivery and go-to-market launch, achieving early pilot adoption and generating real-world traction from clients in the education, healthcare, and public services sectors.
   
• Directly contributed to the product’s machine learning foundation, partnering with data scientists to embed early sentiment scoring and predictive attrition logic.
   
• Managed user research and persona development, shaping platform priorities through interviews, behavioral data, and enterprise HR pain point mapping.
   
• Orchestrated product exit strategy, navigating investor and co-founder misalignment on bootstrapped growth versus capital-intensive scaling—providing key insights into startup lifecycle and culture alignment.
   

• 0→1 Product Leadership – Brought a product from whiteboard to working MVP, including platform design, data model, monetization, and go-to-market mechanics.
   
• Startup Fundraising & Investor Communication – Structured seed investment pitch, coordinated early-stage capital, and built financial scenarios for phase two.
   
• HR Tech Domain Innovation – Identified and acted on unmet market needs in employee lifecycle analytics and post-hire engagement models.
   
• Cross-Disciplinary Execution – Balanced roles across product strategy, architecture, UX, marketing, and investor communication in a highly compressed timeline.
   
• Lessons in Exit & Growth Strategy – Gained first-hand experience in navigating early-stage misalignment on growth strategy, long-term funding, and organizational vision.

Enterprise Data Services Consultant & Technical Product Leader
Enterprise Data Transformation | ETL Architecture | HCM & Payroll Systems 

 Over nearly a decade at Ultimate Software (now UKG), I held progressively senior roles across data services, implementation architecture, and technical product innovation—ultimately leading the evolution of Ultimate’s enterprise data strategy, onboarding tools, and ETL frameworks. My work served as the backbone for thousands of successful go-lives and helped form the data DNA of what would become UKG’s modern product suite.

I served as Technical Lead and TPM for major enterprise accounts including Tesla, Aetna, Activision, and TJ Maxx, and was central to the design, development, and leadership of virtually every major internal tool in the Ultimate data ecosystem.

• Led data transformation for Fortune 500 and high-complexity clients, building repeatable ETL playbooks for multi-source conversions (SAP, ADP, Workday, PayCom, Paychex, Lawson, etc.)
   
• Designed and deployed multiple internal tooling platforms, including the Activation Console, Image Loader, WST, OB Toolkit, and more—now core to UKG's internal migration engine.
   
• Directed onboarding, training, and mentorship for new technical hires; implemented best practices for data conversion QA, error handling, and rollback assurance.
   
• Developed Ultimate’s Premier Data Service Offering, positioning the team as the go-to technical group for high-risk or high-profile implementations.
   
• Architected extraction and transformation frameworks for payroll, HR, timekeeping, benefits, and compliance modules—delivering end-to-end data confidence and supporting billions of records migrated.
   
• Advanced into leadership and advisory roles, bridging the gap between engineering, client delivery, product teams, and partner integrations during a period of rapid company growth.

• Enterprise ETL Strategy | High-volume Data Migration | Workforce & Payroll Systems
   
• Productized Services | Tool Development | Technical Project Leadership in .NET platform
   
• SQL Server | Oracle | Access | .NET APIs | XML | Informatica | SSIS
   
• Internal Enablement | Customer Success Collaboration | Global Delivery at Scale

As a founding member of The Insight Group, I helped build a high-growth consultancy focused on data transformation, analytics, and product enablement in the public sector. We delivered over 200 client engagements and 5 software development initiatives across a portfolio that included Caselle, Tyler Technologies, Motorola Public Safety, and Harris Computer Systems.

My work included full-lifecycle data strategy from assessment to execution, with deep specialization in ERP, financial systems, permitting/planning, and law enforcement applications. I also pioneered our partner channel strategy, achieving 45% YoY growth by aligning our services with OEM ecosystems.

• Executed 165+ data migration projects across multiple verticals, with high specialization in public ERP, utilities, health, safety, and financial systems.
   
• Built partner-aligned solution bundles with 5 major software companies—resulting in over 200 joint projects and national deployment footprint.
   
• Served as lead architect for custom ETL tooling, designed to support repeatable conversion from legacy systems (e.g., PICK, Cobol, dBase, FoxPro) into modern SQL-based platforms.
   
• Directed client engagements end-to-end, from sales engineering and SOW creation through delivery, QA, and post-go-live analytics.
   
• Mentored junior consultants and created internal training standards, helping scale the delivery team while maintaining quality and margin targets.

• Product-Minded Service Design | Data Strategy Leadership | Scalable Partner Models
   
• Multi-industry Expertise: ERP, Government, Utilities, Public Safety, Permitting
   
• Deep Technical Fluency: SQL, Access, Oracle, Btrieve, Hex/ASCII, FoxPro, Data Junction
   
• Client-Facing Delivery | Cross-Functional Execution | Agile Before Agile