BBBlair Boylan
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Experience

A career building the layer between strategy and software.

My work spans strategy, solution architecture, technical pre-sales, AI-enabled delivery, and operating-model design, across healthcare, financial services, fintech, and SaaS. This page is the pattern underneath it, and the outcomes that came from putting it to work.

Explore the timeline →View resume

Career Highlights

AI orchestration

AI-enabled delivery workflows

Built AI workflows for intake synthesis, advisory engagement preparation, and compliance evidence generation. The same pattern now powers Oso Group's internal delivery system.

Operating model

Scaled services revenue 6x

Designed and operationalized PADRE (Pipeline, Acquire, Deliver, Run, Extend), the customer-centric GTM operating model that scaled Nymbl's services revenue 6x in three years.

Business Operating System

Designed advisory offerings around the model

Built Technology Assessments, Product-Market Fit assessments, and custom Analysis of Alternatives engagements that reduced decision ambiguity for clients before any code was written.

Through-line

The same pattern, across every role.

The roles, titles, and industries changed. The work underneath them did not. In every one, I was running some version of the same six moves:

01Break down the business value stream into its real flows of work.
02Define workflow and system boundaries that match how the work actually moves.
03Structure business objects and the data behind them.
04Design the execution interface the team uses to act on the work.
05Support human validation at the points where judgment, risk, or compliance require it.
06Translate ambiguity into implementation-ready architecture.

Timeline preview

Major career periods.

A structured view of the roles, systems, and operating models that shaped my work.

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.

StrategySolution ArchitectureAI Workflow DesignBusiness Operating Systems

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. Established the Solutions Engineering function and grew it from 1 (Blair himself) to 4 Solutions Engineers (titled Solution Consultants internally), designing and running the Pitch to Close pre-sales motion — built as an AI workflow that converts unstructured client calls, notes, and documents into structured, curated solution inputs — that drove growth from $1.5M to $9.2M in annual services revenue over three years. Nymbl operated at approximately 100 people, including roughly 60 FTEs. Blair directly owned his assigned departments while participating in broader company operating decisions, owned the Pitch to Close portion of the sales motion, formally owned Corporate Operations, and carried delivery-function responsibility early in Nymbl's growth before a dedicated leader was hired.

StrategySolution ArchitectureTechnical Pre-SalesAI Workflow DesignBusiness Operating Systems

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.

OperationsSecurity & ComplianceAI Workflow Design

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.

Solution ArchitectureTechnical Pre-SalesStrategyAI Workflow Design
Full timeline

Capability snapshot

The recurring patterns.

A capability map of the recurring patterns across the career.

Strategic Leadership & Business Architecture

Advanced

Defines vision, aligns executives and stakeholders, and translates business strategy into measurable revenue, operating, and delivery outcomes.

Top skills

  • OKR FacilitationExpert
  • Sales Process Design (PADRE)Expert
  • Executive WorkshopsAdvanced
  • Revenue Modeling & ForecastingAdvanced
  • Account PlanningAdvanced
  • Client Success ManagementAdvanced

Demonstrated in

Solution Architecture & Systems Design

Advanced

Designs scalable platforms, workflow systems, ERP patterns, and integration architectures that turn business intent into operational technology solutions.

Top skills

  • Low-Code PlatformsAdvanced
  • PostgreSQL Data ModelingAdvanced
  • Relational Data NormalizationAdvanced
  • Entity-Relationship Diagram (ERD) DesignAdvanced
  • Microservices ArchitectureAdvanced
  • Boomi IntegrationAdvanced

Demonstrated in

Security & Compliance Architecture

Advanced

Designs and operationalizes security, compliance, access governance, and policy programs that protect systems and support audit readiness.

Top skills

  • Program ManagementAdvanced
  • SOC 2 ComplianceAdvanced
  • Security Policy AuthoringAdvanced
  • Node.jsAdvanced
  • API DesignAdvanced
  • Identity & Access ManagementAdvanced

Demonstrated in

Full capability map

Roles

Selected roles.

Each role represents a different expression of the same through-line: turning ambiguity into structured execution.

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.

StrategySolution ArchitectureAI Workflow DesignBusiness Operating Systems

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. Established the Solutions Engineering function and grew it from 1 (Blair himself) to 4 Solutions Engineers (titled Solution Consultants internally), designing and running the Pitch to Close pre-sales motion — built as an AI workflow that converts unstructured client calls, notes, and documents into structured, curated solution inputs — that drove growth from $1.5M to $9.2M in annual services revenue over three years. Nymbl operated at approximately 100 people, including roughly 60 FTEs. Blair directly owned his assigned departments while participating in broader company operating decisions, owned the Pitch to Close portion of the sales motion, formally owned Corporate Operations, and carried delivery-function responsibility early in Nymbl's growth before a dedicated leader was hired.

StrategySolution ArchitectureTechnical Pre-SalesAI Workflow DesignBusiness Operating Systems

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.

OperationsSecurity & ComplianceAI Workflow Design

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.

Solution ArchitectureTechnical Pre-SalesStrategyAI Workflow Design

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, normalized relational data models, Entity-Relationship Diagrams (ERDs), 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). ERDs and supporting data models were standard architecture assets included in solution handoffs to engineering and delivery.

Solution ArchitectureEngineeringBusiness Operating Systems

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.

Solution ArchitectureEngineering

Jan 2015 — Jan 2020 · Boulder, CO

Enterprise Architect

Gloo

Led enterprise architecture modernization and portfolio delivery practices across a growing platform business while also participating in functional management across departments and teams. Responsibilities extended into resource allocation, budgets, functional planning, management accountability, organizational effectiveness, and the operating structures required to translate company strategy into coordinated execution. Gloo operated at approximately 200 employees during Blair's tenure.

Solution ArchitectureStrategy

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.

Engineering

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The writing explains how I think. This page is where that thinking came from. If you’re hiring for a strategy or architecture role, or building this kind of operating-system work inside your own business, the fastest next step is a conversation. If you’d rather start with the concise version, the resume has everything in one scroll.

Get in touch →View resume