Timeline · Work — Blair Boylan

Timeline

The work, in order.

One pattern, repeating across every role: turning business intent into the workflows, data, interfaces, and validation points that make an operating system real. This is that progression, in order.

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Mar 2026 — Present·Telluride, CO
Founder & Principal · Oso Group
Independent enterprise architecture and AI-enabled delivery advisory work. Productizing solution design, AI-orchestrated delivery workflows, and custom business operating systems. Currently doing focused advisory engagements while exploring senior leadership roles at companies building in the AI orchestration and enterprise platform space.
Key initiatives
- Enterprise Architecture Design Offering
- GTM & Delivery Operating System
- AI-Enhanced Delivery Workflows
StrategySolution ArchitectureAI Workflow DesignBusiness Operating Systems
Capabilities: Strategic Leadership & Business Architecture · Solution Architecture & Systems Design · Enterprise Architecture & Portfolio Delivery · Business Operating System Design
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Feb 2022 — Mar 2026·Remote
Chief Strategy Officer · Nymbl
Executive leader reporting to the CEO at Nymbl, a Custom Enterprise Software & AI Services Platform Development firm engineering intelligent Business Operating Systems for enterprises across financial services, healthcare, life sciences, manufacturing, and ESG. Served as Head of Advisory Professional Services — owning the scoping, estimating, and delivery oversight of professional services engagements, advisory services, solutions engineering, solutions architecture, and technical pre-sales. Was Head of Advisory Services with full PS scoping and estimating ownership; did not run a separate solution delivery org but owned the delivery of solutions end-to-end as part of the PS motion. Scaled the Nymbl organization from 5 to 75+ FTEs and contractors as a core member of the executive team, designing and running the operating and delivery governance (including the Pitch to Close motion and AI workflows) that supported growth from $1.5M to $9.2M in annual services revenue over three years.
Key initiatives
- Internal Operating System Architecture
- AI-Driven Intake & Solution Automation
- PADRE Sales & Delivery Process
StrategySolution ArchitectureTechnical Pre-SalesAI Workflow DesignBusiness Operating Systems
Capabilities: Solution Architecture & Systems Design · Enterprise Architecture & Portfolio Delivery · Business Operating System Design · Full-Stack & Application Engineering
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Jan 2024 — Mar 2026·Remote
IT Manager · Nymbl
Owned Nymbl's internal IT stack, governance posture, access controls, and Corporate Operations while leading SOC 2 readiness and audit coordination. Ran the Corporate Operations department: architected the company's use cases and data objects, led the Google Workspace to Microsoft SharePoint change management migration, answered IT support questions, and owned SaaS-tool onboarding for all staff — genuine IT Service Management (ITSM) work. Built security policies, system administration routines, asset tracking practices, and automation for provisioning and compliance workflows. The SOC 2 Type II program was the foundation that unlocked Nymbl's ability to sell into banks, credit unions, and other highly regulated enterprise customers.
Key initiatives
- SOC 2 Readiness & Audit Program
- System Integration & Admin Automation
- IT Asset & Access Management
OperationsSecurity & ComplianceAI Workflow Design
Capabilities: Program & Product Leadership · Security & Compliance Architecture · Full-Stack & Application Engineering · AI & Intelligent Automation
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Jan 2022 — Mar 2026·Remote
Solution Consultant — Advisory Services · Nymbl
Ran all advisory engagements for Nymbl's enterprise clients using structured playbooks. Built and owned three named advisory offerings: Technology Assessments, Product-Market Fit assessments, and custom Analysis of Alternatives for the value streams of client organizations. Helped clients understand strategic options, business requirements, process gaps, and solution pathways that could be translated into executable delivery work for Nymbl's custom Business Operating System engagements.
Key initiatives
- Market Analysis Engagements
- Solution Design Workshops
- Technology Assessment & Analysis of Alternatives Engagements
Solution ArchitectureTechnical Pre-SalesStrategyAI Workflow Design
Capabilities: Strategic Leadership & Business Architecture · Financial & Organizational Leadership · Solution Architecture & Systems Design · Business Operating System Design
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Jan 2022 — Dec 2024·Remote
Solution Architect · Nymbl
Architected and delivered client solutions for Nymbl, a custom enterprise software development and AI services firm. Turned business objectives into scalable workflows, data models, integration patterns, and application structures across healthcare, financial services, fintech, logistics, and internal operations use cases using Nymbl's custom development plus AppGen approach (custom code combined with Retool, Mendix, Replit, and other low-code/AI-assisted platforms).
Key initiatives
- Course Review System
- Cashflow Management App
- Group Purchasing Organization OS
Solution ArchitectureEngineeringBusiness Operating Systems
Capabilities: Solution Architecture & Systems Design · Full-Stack & Application Engineering · Financial & Organizational Leadership · Enterprise Architecture & Portfolio Delivery
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Jan 2020 — Jan 2022·Remote
Senior Solutions Architect · Freelancer
Advised clients on solution architecture, operating workflows, and reusable application patterns. Designed practical frameworks and technical foundations that connected configurable application behavior, integrations, and long-term maintainability.
Key initiatives
- Reusable TypeScript MVC Framework
- Hierarchical Knowledge Center & Integrations
Solution ArchitectureEngineering
Capabilities: Full-Stack & Application Engineering · Cloud Infrastructure & DevOps · Business Operating System Design · Solution Architecture & Systems Design
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Jan 2015 — Jan 2020·Boulder, CO
Enterprise Architect · Gloo
Led enterprise architecture modernization efforts and supported portfolio delivery practices across a growing platform business. Focused on domain design, services architecture, integration patterns, and the operating structures needed to scale delivery across teams.
Key initiatives
- Microservices Platform Architecture
- SAFe Portfolio Implementation
Solution ArchitectureStrategy
Capabilities: Solution Architecture & Systems Design · Enterprise Architecture & Portfolio Delivery · Program & Product Leadership
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Jan 2012 — Dec 2014·Milwaukee, WI
Designer & Full-Stack Developer · Starkmedia Digital Agency
Designed and built custom client websites and digital solutions across industries. Combined design sensibility with front-end and back-end development to deliver complete web experiences on agency timelines.
Key initiatives
- High-Volume Web Delivery
Engineering
Capabilities: Full-Stack & Application Engineering
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The work, in order.

Founder & Principal · Oso Group

Chief Strategy Officer · Nymbl

IT Manager · Nymbl

Solution Consultant — Advisory Services · Nymbl

Solution Architect · Nymbl

Senior Solutions Architect · Freelancer

Enterprise Architect · Gloo

Designer & Full-Stack Developer · Starkmedia Digital Agency