Caylor Norris
Summary
Head of Product with deep experience building and scaling B2B SaaS platforms in regulated and compliance-driven domains. Proven track record owning the full product function, leading cross-functional teams through ambiguity, and translating complex customer and regulatory requirements into outcome-driven roadmaps. Known for scaling product organizations during periods of rapid growth, supporting fundraising and exits, and delivering AI-enabled automation that aligns product strategy with business results.
Overview
13
13
years of professional experience
1
1
Certification
Work History
Head of Product
RegScale
Knoxville, TN
05.2023 - 01.2026
- Joined RegScale at Series A and led product through rapid scale, supporting a successful Series B raise and significant revenue growth.
- Led end-to-end product strategy and execution for a compliance SaaS platform, aligning roadmap, delivery, and GTM with business goals and customer needs.
- Redesigned SDLC and release processes to improve quality, predictability, and throughput while supporting continuous delivery.
- Delivered AI/LLM-powered capabilities that automated core compliance workflows and reduced manual effort for customers.
- Established a phased delivery model to provide incremental customer value and accelerate time to market.
- Formalized roadmap planning, presentation, and centralized status tracking to improve executive and stakeholder alignment.
- Served as release manager, ensuring consistent flow through the release pipeline and proactively managing delivery risks and bottlenecks.
- Oversaw staffing and capacity planning across strategic initiatives and Scrum teams to optimize resource allocation.
- Led a major UX redesign, improving usability, customer satisfaction, and engagement across key workflows.
- Defined and implemented a structured product lifecycle from concept through go-to-market to streamline launches and execution.
- Created a tiered product marketing framework to support scalable GTM execution in a SaaS and continuous delivery environment.
Director of Product Management
RFP360
Leawood, KS
01.2021 - 01.2023
- Joined RFP360 when it operated as a lifestyle business and helped scale product and execution to support a successful exit, delivering a ~6× return for investors.
- Built and led a dedicated product organization, hiring and developing product managers, analysts, and UX designers.
- Defined and executed a clear product roadmap aligned to company strategy, driving cross-functional alignment and consistent delivery.
- Implemented Agile/Scrum processes and weighted prioritization to improve focus, decision-making, and backlog health.
- Transitioned the organization to a continuous deployment model, reducing time to market and increasing delivery velocity.
- Redesigned pricing and packaging to increase average deal size, improve margins, and align internal stakeholders.
- Managed R&D security and compliance requirements, including audit readiness, change management, and security assessments.
- Owned key vendor and partner relationships, including AWS and third-party integrations.
Principal Product Manager
Dell Technologies
Overland Park, KS
10.2017 - 12.2021
- Owned product requirements and roadmap execution for RSA Archer solutions in highly regulated enterprise environments.
- Conducted market research and customer validation to inform prioritization and product investment decisions.
- Translated complex regulatory and business requirements into clear technical specifications for engineering teams.
- Partnered closely with development teams to design, build, and launch new platform capabilities.
- Led go-to-market activities for new features and solutions in competitive enterprise markets.
GRC Solutions Architect
Dell Technologies
Overland Park, KS
02.2014 - 10.2017
- Led design and delivery of RSA Archer solutions across a broad range of Integrated Risk Management and GRC use cases.
- Owned public sector solution strategy, defining requirements for NIST, DoD, DHS, and related regulatory frameworks.
- Designed data models, workflows, and integrations to support complex regulatory and operational requirements.
- Partnered with federal contractors and sales teams to support POCs, solution design, and enterprise implementations.
Team Leader
Kansas Army National Guard
Topeka, KS
11.2012 - 11.2018
- Led and supervised military police teams during operational missions and assignments.
- Conducted risk assessments and implemented mitigation strategies to ensure operational safety.
- Provided physical security for critical infrastructure and high-profile government events.
Education
MBA - Management Information Systems
Friends University
Wichita, KS2017
BBA - Business Administration
University of Kansas
Lawrence, KS2015
Skills
Product Leadership & Strategy
Product Roadmap Development, Outcome-Driven Prioritization, Go-to-Market Strategy, Pricing & Packaging, Stakeholder Alignment, Team Building
Execution & Delivery
Agile/Scrum, Continuous Delivery, Phased Product Delivery, SDLC Redesign, Release Management, Change Management
Domain Expertise
Governance, Risk, and Compliance (GRC), Integrated Risk Management (IRM), Audit & Compliance Workflows, Public Sector Standards (NIST 800-53, NIST CSF, DoD, DHS)
Technical & Data
Workflow Engines, System Integrations & APIs, Data Modeling, AI-Enabled Automation, SQL, Python, HTML, Telemetry & Reporting
Certification
- Pragmatic Management (PMC-III)
- GRC Professional (GRCP)
- RSA Archer Certified Administrator
Timeline
Head of Product
RegScale
05.2023 - 01.2026
Director of Product Management
RFP360
01.2021 - 01.2023
Principal Product Manager
Dell Technologies
10.2017 - 12.2021
GRC Solutions Architect
Dell Technologies
02.2014 - 10.2017
Team Leader
Kansas Army National Guard
11.2012 - 11.2018
MBA - Management Information Systems
Friends University
BBA - Business Administration
University of Kansas