Riley Webb

Cybersecurity Advisory | Charity Board Member | ex-Okta | ex-Deloitte | ex-Lionsgate | Identity | Hybrid & Multi-Cloud

Parker, Colorado, United States

About

An accomplished Cloud Solutions Architect with extensive experience delivering technology solutions across diverse industries, including Petroleum Production, Financial Services, Manufacturing, Healthcare, and Entertainment. Proven track record in designing, implementing, and optimizing cloud and enterprise systems to support complex business objectives. Skilled in cloud platforms such as Microsoft Azure and Amazon Web Services (AWS), as well as virtualization with VMware, enterprise systems including Microsoft and Oracle Databases, and Identity & Access Management (IAM) with a focus on Okta. Adept in requirements analysis, enterprise architecture, and software integration, driving scalable, secure, and high-performing solutions.

Experience

  • Board Member - Technology and Platforms at Making An Impact Foundation
    Aug 2024 - Present · 1 yr 11 mos

    As a Board Member at Making An Impact Foundation, I play a pivotal role in leveraging technology to support our mission of ending hunger in Colorado. My responsibilities include managing various platforms that facilitate donations, marketing efforts, and volunteer management. By ensuring robust cybersecurity measures, I help protect sensitive information while enhancing our outreach and engagement strategies.

  • Sr Security Advisor - IAM/CIAM at GuidePoint Security
    Jan 2026 - Apr 2026 · 4 mos

    Delivered my highest-performing sales quarter by supporting multimillion-dollar IAM, PAM, and IGA services opportunities across national accounts. Partnered closely with account executives, technical teams, and delivery leadership to shape client strategy, accelerate deal cycles, and drive measurable revenue outcomes. Helped close a $1.5M opportunity on the final day of the quarter, demonstrating strong collaboration, urgency, and execution under pressure. • Led presales conversations for IAM, PAM, and IGA services across national account opportunities. • Supported multimillion-dollar pipeline development through strategic client engagement and solution positioning. • Helped close a $1.5M deal on the final day of the quarter in partnership with a teammate and account team. • Collaborated with sales, delivery, and technical stakeholders to align proposed solutions to client business needs. • Identified and advanced high-value identity security opportunities across enterprise accounts. • Consistently performed in a fast-paced, high-pressure sales environment with strong focus on client outcomes and revenue growth.

  • Director of Professional Services at Anthropic Identity
    Apr 2025 - Nov 2025 · 8 mos

    Head of Services, Workforce Identity and Managed Services Hands-on, billable services leader responsible for client delivery, technical architecture, team operations, and service strategy across Workforce Identity and Managed Services offerings. While operating at the director level, remained directly involved in client architecture, project execution, and technical leadership. Oversaw consultant performance, standardized delivery methods, improved documentation quality, and strengthened repeatable service offerings during a period of significant organizational growth. • Led Workforce Identity architecture and delivery for enterprise clients, serving as primary architect, engagement lead, and technical project manager across multiple concurrent projects. • Owned key client deliverables, including Architecture and Design documents, Identity Health Checks, technical runbooks, and operational readiness packages. • Managed full-time and 1099 resources, providing oversight, mentorship, assignment planning, and project guidance across staffed and non-staffed engagements. • Directed the MSP+ program, increasing managed services adoption and revenue by 80%. • Helped scale professional services growth from $1M to $4M ARR through improved delivery processes, templates, runbooks, and repeatable service offerings. • Served as escalation point for project risks, architectural decisions, and client relationship management across workforce identity initiatives. • Developed and enforced delivery standards for architecture quality, documentation, and identity best practices across Okta, Ping, Microsoft, CyberArk, 1Password, Okta OIG, and SailPoint. • Supported presales and SOW development through solution design, scoping, and client-facing presentations. • Coordinated engineers, architects, PMs, and vendor partners to drive timely, high-quality delivery. • Implemented internal process improvements that improved project execution, onboarding, and consultant productivity.

  • Senior Manager Advisory Identity and Access Management Practice at Optiv
    Apr 2024 - Mar 2025 · 1 yr

    Brought on as a hybrid Engagement Manager and hands-on Identity Consultant to lead delivery efforts while driving pre-sales growth. Supported and delivered complex Identity & Access Management (IAM), IGA, and PAM initiatives, along with broader enterprise architecture and cloud strategy projects. Split time between client delivery and pre-sales, partnered with sales teams to scope work, build proposals, lead discoveries, and shaped solution architecture. Provided executive-ready documentation, change order scoping, and technical guidance across workforce and customer identity programs. ·         Led end-to-end delivery for IAM initiatives including SSO, MFA, lifecycle management, IGA, SIEM and privileged access solutions. ·         Acted as both Engagement Manager and hands-on technical consultant across workforce and customer identity programs. ·         Developed enterprise architecture documentation and cloud strategy deliverables beyond identity scope. ·         Owned proposal creation, including scoping, level-of-effort modeling, and drafting SOW content for new and existing clients. ·         Managed and authored change order requests, ensuring alignment to project scope, timelines, and client expectations. ·         Served as principal pre-sales engineer for IAM, IGA, and PAM opportunities, leading demos, discovery workshops, and solution design. ·         Created client-facing materials including design documents, runbooks, architecture diagrams, and health-check assessments. ·         Partnered closely with sales and delivery leadership to ensure pipeline accuracy, resource alignment, and successful project kickoffs. ·         Advised clients on identity roadmaps, modernization strategies, Zero Trust alignment, and vendor product selection. ·         Supported internal teams with reusable templates, delivery frameworks, and standard operating procedures to improve efficiency and quality.

  • Okta, Inc. (3 yrs 7 mos)
    • Team Lead / Sr Solutions Engineer - Partner Alliances NA
      Apr 2021 - Apr 2024 · 3 yrs 1 mo

      Served as both Team Lead and individual contributor for Okta’s Partner Alliances Solutions Engineering team. Acted as a servant leader for fourteen Senior Identity Solutions Engineers, supporting daily team operations, escalations, resource tracking, performance enablement, and employee upskilling. As an IC, enabled GSI, Big 4, MSP, and national scale partners through technical sales enablement, partner-led business development, solution design, RFP/SOW support, and customer-facing troubleshooting. Partner ecosystem efforts contributed to over $30M in ARR, and I was selected as SE of the Quarter in Q3 2021, my first full sales quarter at Okta. • Led team operations for Partner Alliances Solutions Engineers, including escalations, resource tracking, performance support, and employee development. • Enabled partners on Okta solutions including SSO, Adaptive MFA, LCM, IGA, PAM, SIEM integrations, Zero Trust strategies, and cloud identity use cases. • Partnered with sales teams on account mapping, joint pipeline generation, business development motions, and customer alignment. • Supported GSI, Big 4, MSP, and national scale partners, including Optiv, through technical enablement and solution positioning. • Developed partner-facing presentations, technical training, data sheets, and sales collateral across the Okta platform. • Assisted partners with RFP responses, SOW scoping, and implementation planning for Okta, IGA, PAM, and cloud identity services. • Led customer and partner troubleshooting sessions across Okta, AWS, GCP, and Azure environments. • Selected as Okta’s first global Managed Service Provider Solutions Engineer. • Served as technical lead for the Okta MSP Partner Program and route-to-market strategy, helping define how SSO, MFA, PAM, and IGA could support partner-managed services. • Engaged global enterprise MSP leadership to support onboarding, platform adoption, and managed services growth.

    • Customer Advisory Board Member (Infrastucture Access (ASA))
      Oct 2020 - Oct 2021 · 1 yr 1 mo

      Advisory Board meets with okta internal teams to assist in guiding the long term roadmap of the ASA product