Paul Gilliam · Product Leader · Teams, Strategy, and Outcomes That Scale
I Rally Teams
Around Problems
Worth Solving.
Not problems that look good in a roadmap. Problems validated in the field, shaped with customers, and worth paying for.
I’ve spent 8+ years working the way founders do: in customer interviews, on sales calls, at trade shows, and in the data. Then I build cross-functional teams around a clear story and ship something that moves the business.
About
The best products start with the right problem and the right people around it.
The best products I’ve shipped didn’t start with a roadmap. They started with a conversation, usually in a customer’s office, on a sales call, or at a trade show booth where someone finally said what they actually needed.
I’ve conducted 200+ customer discovery interviews, personally supported key sales deals, attended industry conferences to stay close to the market, and rallied cross-functional teams of 10+ to turn insight into something real. At SmartMoving I led the adoption of AI prototyping as a core part of how we aligned executives and validated ideas before committing engineering resources, collapsing cycles that used to take months.
Today I continue pushing that edge, using AI to accelerate discovery, sharpen strategy, and build faster than ever. I write about it at The Product Pipeline on Substack.
What drives me is the moment a product clicks for someone. When a dispatcher finally has a clear view of their day. When an assortment planner stops second-guessing a forecast. When a moving company operator can explain their own business using data you helped build. That’s why I do this.
I don't write requirements until I've talked to customers. Assumptions are expensive. Conversations are cheap.
The best product decisions I've made came from getting engineering, sales, marketing, and ops in the same room around the same customer problem.
Every feature, every metric, every decision gets filtered through one question: does this make life meaningfully better for the person using it?
Featured Work
Products built by getting close to the customer and rallying teams around a shared vision.
SmartMoving: From Niche CRM to Operations Platform
SmartMoving Software · Jan 2024 – Jan 2026
Partnered directly with the founder/CEO and VP of Product to transform a vertical SaaS CRM into a full operating system for movers. Owned product strategy, discovery, roadmap, commercialization, and team building end-to-end across seven capability areas, personally contributing to $6M in ARR growth over two years.
- Identified that 63% of customers were outside the ideal profile and consuming disproportionate support with low expansion potential. Led a strategic ICP realignment through 200+ cumulative customer interviews and monthly on-site visits with operators, shifting the mix from 37% in ICP to 80% in ICP over two years and directly contributing to $6M in ARR growth.
- Used AI to rapidly build and deploy lightweight prototypes before engineering was ever involved, sending one-time links to customers to measure whether they completed expected flows and whether they were in enough pain to try something new at all. Built a rapid context engine that synthesized those sessions into structured roadmap inputs, so customer insights went directly into prioritization rather than sitting in notes.
- Convinced leadership to invest in an embedded analytics platform, testing each solution with real customers, negotiating contracts, and presenting a vendor option 10x cheaper than the internal build estimate, redirecting engineering toward differentiated product work.
- Personally led discovery, market sizing, pricing, and GTM across every major capability added to the platform including automation, claims management, dispatch improvements, an ACH payments platform that contributed over $1M in ARR, and an OpenAPI ecosystem that generated $100K in third-party integration revenue.
- Hired and mentored 2 PMs, established every product and engineering process from scratch, and led 3 engineering teams across concurrent workstreams. Conducted over 200 customer discovery interviews, made 8 in-person trips to moving companies.
Capital One: A Semantic Layer for Enterprise Data Security & Optimization
Capital One Software · Jan 2026 – Present
Built a new AI-ready data security and optimization intelligence platform to help enterprises improve their data security and cost optimization postures. Identified a gap across 8+ teams causing confusion for enterprises trying to optimize their businesses, built the business case from scratch, led detailed discovery, and leveraged Claude Code to create lightweight prototypes that verified the problem and solution. This led to a semantic layer solution that reduced delivery time from 3 months to 1 hour and cut duplicate and poorly defined metrics by 30%.
A gap across 8+ teams left enterprises confused about how to improve their data security and cost optimization posture, with no shared way to define or measure the problem.
Built the business case from scratch, led detailed discovery, and used Claude Code to create lightweight prototypes that verified the problem and solution before committing engineering resources.
A semantic layer that cut delivery time from 3 months to 1 hour, reduced duplicate and poorly defined metrics by 30%, and scaled across 4 lines of business.
Special Needs Student Transportation Platform
First Student · 2021 – 2022
Hand-selected to build a new vertical from the ground up, traveling to school bus depots, embedding with districts, and leading a 40-person contractor team to launch a $1M special needs transportation platform serving 1,000+ students across 10+ districts. Reported directly under a VP of growth and strategy to lead meaningful change.
- Defined the full platform strategy spanning a web app, two mobile apps, and cloud infrastructure, owning the vision from concept through launch
- Traveled directly to school bus depots and met with district stakeholders to understand operational realities before defining requirements, focusing on being discovery led, not assumption led
- Partnered with 3 pilot districts to validate the platform in real-world conditions, using their feedback to shape the product roadmap
- Partnered with marketing and sales to define the go-to-market strategy and positioning for broader district expansion
- Led a cross-functional team of 40 contractors, coordinating across engineering, operations, and external partners to deliver on time and on budget
First Student had no platform for special needs transportation. Districts were managing complex, high-stakes logistics with fragmented tools and no operational visibility.
Traveled to school bus depots, partnered with 3 pilot districts before writing a requirement, then led a 40-person contractor team through full delivery with GTM alignment alongside sales and marketing.
Launched a $1M platform spanning a web app and 2 mobile apps, serving 1,000+ students across 10+ districts, on time and on budget.
Building a Product Department from the Ground Up
EverDriven · 2018 – 2020
Joined as a QA advocate and helped found the product department, building the processes, culture, and cross-functional relationships from scratch. Became a driver of better technical solutions for dispatchers, coordinators, and executive teams, turning unstructured operational data into tools people actually relied on.
No product department existed. Engineering and ops made decisions in isolation, with no customer-facing function advocating for better solutions or a coherent product vision.
Started as a QA advocate to deeply understand user pain, then built the product function from scratch including processes, tools, and a cross-functional culture centered on the customer.
30% reduction in operational waste, dispatcher and coordinator workflows transformed, and a fully functioning product department established where none existed before.
Retail Assortment Planning: Making AI Usable
Zebra Technologies · 2022 – 2024
Worked embedded with pre-sales, sales, and data science teams to make the life of a retail assortment planner easier, turning complex AI/ML outputs into intuitive, actionable intelligence inside a larger integrated platform.
- Partnered with pre-sales and sales teams on enterprise deals with clients including JCPenney, The Children's Place, and Evereve, translating customer pain points directly into product requirements
- Recognized that raw data access was creating decision paralysis for assortment planners and led the reframe toward actionable business intelligence, reducing noise and surfacing what actually mattered
- Collaborated with data science teams to shape AI/ML forecasting models that improved retail planning accuracy by 17% across nearly 1,000 variables
- Conducted extensive user research with assortment planners to identify workflow gaps and prioritize features that differentiated the platform from legacy competitors
Enterprise retailers could not trust their forecasts. AI/ML models produced raw outputs that assortment planners at JCPenney, The Children's Place, and Evereve had no way to interpret or act on.
Embedded directly with pre-sales, sales, and data science teams to run discovery with planners in their actual workflow, then reframed the product from a data dump into actionable business intelligence.
17% improvement in forecast accuracy across nearly 1,000 variables, with a platform planners could trust and act on.
Career Timeline
Senior Manager, Product Management
FeaturedCapital One Software · Jan 2026 – Present
Leading strategy for an AI-ready enterprise data security and optimization platform, using Claude Code prototyping to turn a single-team proof of concept into a semantic layer standard adopted across 4 lines of business.
Senior Product Manager
FeaturedSmartMoving Software · Jan 2024 – Jan 2026
Built an Inc. Award-winning analytics platform from scratch with 100% beta retention. Led a strategic ICP realignment from 37% to 80% and helped drive $6M ARR growth through customer-led discovery and cross-functional execution.
Senior Product Manager
Zebra Technologies · Nov 2022 – Jan 2024
Embedded with sales and data science teams at major retailers to turn AI/ML outputs into tools assortment planners actually used, improving forecast accuracy by 17% across roughly 1,000 variables.
Product Manager
Koddi · Jun 2022 – Nov 2022
Embedded with engineering, program management, and Booking.com teams to simplify targeted ad creation for hoteliers inside KoddiOne, driving a 15% improvement in ad targeting accuracy through customer-led discovery.
Senior Product Manager
First Student · Sep 2021 – Jun 2022
Hand-selected to build a new vertical from zero. Traveled to school bus depots, embedded with 3 pilot districts, and led 40 contractors to ship a $1M platform serving 1,000+ students.
Senior Business Analyst
EZLynx · Aug 2020 – Aug 2021
Led growth of an insurance platform integration marketplace, scaled the product ecosystem, and helped grow the product team capabilities alongside the product itself.
Product Manager
EverDriven · 2018 – 2020
Helped found the product department. Built dispatcher planning tools and executive dashboards that reduced operational waste by 30%, starting from an empathetic QA mindset and growing into a full product function.
How I Work
The frameworks, methods, and tools I reach for to build products that matter.
Product Leadership
Cross-Functional Execution
AI and Data Fluency
Team and Process Building
Education
MBA — Business Management
Quantic School of Business and Technology
Platform Economics · Competitive Analysis · Strategic Market Development
B.S. Information Systems and Business
University of Colorado Colorado Springs · 4.0 GPA, Summa Cum Laude
Enterprise Platform Architecture · Strategic Systems Design
Let’s Work Together
If you’re building something
worth building, let’s talk.
I’m drawn to senior and director-level roles where getting close to the customer is the strategy, not an afterthought. Where cross-functional teams rally around a real problem and ship something that makes someone’s day better.
If that’s the kind of product team you’re building, I’d love to be part of it.