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.
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.
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.
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.
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.
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.
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.
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.