VP of Information Technology • Technical Program Executive Leader
Scaling Teams, Platforms & Culture
- Directed over $75M in technology investments, balancing innovation with risk
- Cut build time by 80% through streamlined A/B testing and release strategies
- Increased mobile engagement by 10% across a 60M+ active user base
- Led UX improvements for 60M+ users of enterprise HCM software
- Drove product and platform decisions that scaled globally across fintech and SaaS
Career Highlights
Tom Sikora is a technology and product leader known for turning complexity into momentum. Early in his career, he was the fixer—brought in when teams struggled and platforms stalled. Over time, he became the builder—scaling systems, teams, and business impact across fintech and B2B SaaS.
From modernizing core banking infrastructure to launching a fintech startup and leading UX improvements for 60M+ users of enterprise HCM software, Tom brings clarity, empathy, and a bias for execution.
He doesn’t just ship products—he shifts trajectories.
Core Skills
Strategic Technology Leadership
Digital Transformation
Enterprise Architecture
AI & Machine Learning
Data Science & Analytics Product Development & Innovation
Project & Program Management
Cloud Infrastructure (AWS, GCP, Azure)
Vibe Coding React
A/B Testing
Data Engineering
Regulatory Compliance
Team Building & Leadership
Process Automation & Improvement
Industries
Banking
Fintech
B2B SaaS
Challenge:
A global HCM platform with over 60M users had stagnating mobile engagement. The mobile org was under-resourced, with a fragmented team of 75 across functions and a fragile delivery pipeline.
Case Study
Enterprise Mobile Transformation
Scaling Mobile Adoption and Engineering at Enterprise Scale
My Role:
Rebuilt the mobile team from 75 to 125, hired key leadership, and established a new DevOps team to support a reliable build pipeline. Introduced performance metrics, A/B testing, and user-centered iteration.
Outcome:
Increased mobile adoption by 10% year-over-year and restored confidence in mobile delivery. Mobile became a core pillar of the product experience.
Challenge:
A critical mortgage servicing platform conversion—impacting over 8 million customers—was more than two years behind schedule. The delays threatened broader alignment with the domestic bank’s conversion roadmap, where missing a delivery window meant waiting quarters, if not years, to re-sync.
Case Study
Mission-Critical Delivery
Turning Around an 8M-Customer Mortgage Platform in 9 Months
My Role:
Brought in to lead the turnaround. Rebuilt team structure, reset delivery expectations, and aligned cross-functional dependencies across product, engineering, and the broader bank program. Created a clear execution plan with incremental milestones and accountability at every layer.
Outcome:
Delivered the mortgage conversion just nine months after stepping in, aligning with the bank’s timeline and avoiding costly delays across the larger enterprise migration effort.
Challenge:
The company was under legal pressure from existing enterprise customers due to accessibility gaps—and was actively losing sales opportunities in competitive deals where accessibility mattered. It was a known weakness across the product suite.
Case Study
Revenue-Driven Accessibility
Transforming Accessibility into a $100M Sales Advantage
My Role:
Built a cross-functional accessibility team within product and engineering to partner with design and delivery orgs across the company. Established scalable accessibility standards, integrated automated accessibility checks into the build pipeline, and provided tooling and training to support adoption across teams.
Outcome:
Closed out legal pressure from existing customers and repositioned accessibility as a strength in the sales motion. The company became best-in-class among competitors and attributed over $100M in ARR to deals won where accessibility was a key decision factor.
Task/Activity:
Key Actions Taken:
- Analyzed the proposed workflow and identified inefficiencies
- Documented an optimized workflow focused on clarity and automation
- Presented a revised solution with visual flow diagrams in Jira
- Collaborated with the Purchasing Manager to review and refine the approach
Case Study
Optimizing Jira Workflow for Product Launch Efficiency
Situation:
The development team was tasked with building an automated Jira workflow to support the Purchasing Team in tracking tasks for new product introductions involving over a dozen team members. The initial proposed workflow was overly complex and inefficient, relying heavily on manual notifications.
Results:
- Implemented a streamlined Jira workflow that reduced unnecessary notifications
- Improved task clarity and accountability across multiple departments
- Increased operational efficiency in the product launch process
Testimonials
What People Say
“She understands business and with her vast technical knowledge and management capacity, she has successfully lead her team and rewrote our website, created countless internal applications, adapts 3rd party software integration and she is able to complete multiple tasks and projects with favorable results. She shows her team the way by example and her dedication is impeccable.”
” I admired her capability to take some of the newer technologies surfacing from the direction of web-driven needs and turn them into powerful applications. She worked in figuring out the new database connectivity objects which gave our entire group perspective on the shaping of this technology for the future. Along with Linda’s programming skills, her personable approach and friendly nature made working with her a pleasure.”
Beyond The Office
Outside of work, I’m a lifelong runner—these days, almost entirely on trails. Whether weaving through redwood forests, climbing mountain switchbacks, or chasing views of the San Francisco Bay, trail running is where I reset, reflect, and stay grounded.
When I can carve out the time, a long solo run in the Marin Headlands is my favorite kind of reset.
The rhythm of the trail—focus, grit, and forward motion—shapes how I lead: steady, intentional, and always moving toward what’s next.
Publications
Must -Know Details About the Military Lending Act
In July of 2015, the MLA rule was expanded to include a wider range of credit products and the rule more closely aligned with the definition of credit specified in the Truth in Lending Act. Ultimately it offers further protections for our military members and subjects to civil liability and administrative enforcement for MLA violations.