Open to opportunities

Blair Boylan

@blairboylan

Message

I build business operating systems and AI-enabled workflows that turn strategy into coordinated execution.

United States

Message

What I'm looking for

I'm focused on building business operating systems, enterprise architectures, and AI-enabled execution models that make strategy, ownership, workflows, decisions, and accountability explicit across organizations.

I've built operating systems at Nymbl and Gloo that connect strategy, priorities, ownership, workflows, financial models, meeting cadences, and accountability. At Nymbl, I partnered directly with the CEO and executive team while helping scale annual services revenue from $1.5M to $9.2M.

I lead executive operations, organizational design, portfolio prioritization, resource planning, and enterprise architecture. I managed six direct reports at Nymbl, led SOC 2 Type II readiness, created executive and board materials, and assembled a cross-functional team to define the company's AI offering.

Through Oso Group, I design business operating systems, enterprise architectures, and AI-enabled execution models, starting with operating structure and building the workflows, data models, integrations, and software needed to run it.

Experience

Work history, roles, and key accomplishments

Current

Founder & Principal

Current

Oso Group

Mar 2026 - Present (5 months)

Founded an independent advisory practice focused on designing business operating systems, enterprise architectures, and AI-enabled execution models. Created a productized enterprise architecture offering and integrated AI-assisted reasoning and agentic development tools to accelerate implementation.

Enterprise Architecture Agentic Development Change Management TypeScript SQL Python API Design

Chief Strategy Officer

Nymbl

Feb 2022 - Mar 2026 (4 years 1 month)

Executive leader reporting to the CEO at an approximately 100-person company, owning departments spanning strategy, advisory professional services, solutions engineering, and corporate operations. Built the company's Business Operating System, partnered with the CEO on strategic decisions, and led cross-functional initiatives including AI offering definition and SOC 2 readiness.

Business Operating System Design Strategic Planning OKRs Organizational Effectiveness Cross Functional Execution Workforce Planning Resource Allocation KPI Tracking SOC Agentic Development TypeScript SQL Python API Design

Senior Solutions Architect

Freelance / Independent Practice

Jan 2020 - Jan 2022 (2 years)

Advised clients on solution architecture, operating workflows, and reusable application patterns. Designed a reusable TypeScript/Node.js application framework and a hierarchical knowledge and integration hub.

Solution Design TypeScript Node Knowledge Management

Enterprise Architect

Gloo

Jan 2017 - Aug 2020 (3 years 7 months)

Progressed from software engineering into enterprise architecture at an approximately 200-person platform company, with scope extending into organizational effectiveness, portfolio delivery, resource allocation, budgets, and executive operating structures. Built the Alignment Management System and created board decks and financial models for the CEO.

Enterprise Architecture Strategic Planning Portfolio Management Resource Allocation Budgeting SAFe Financial Modeling

Full Stack Developer

Gloo

Jan 2015 - Jan 2017 (2 years)

Hands-on software engineering role at a platform company, contributing to development efforts before transitioning into enterprise architecture.

Software Engineering

Designer & Full-Stack Developer

Starkmedia Digital Agency

Jan 2012 - Dec 2014 (2 years 11 months)

Designed and delivered custom web and enterprise CMS solutions across multiple industries, combining client discovery, design, implementation, and hands-on software development.

Web Design CMS Customer Discovery Implementation