Resume · concise version
Blair Boylan
Business Operating System Design • Enterprise Architecture • AI-Enabled Delivery • Executive Strategy
Telluride, CO (Remote) · Remote-first
A concise version for recruiters, hiring managers, and application systems. Fuller depth lives under Roles and Capabilities.
Professional Summary
Strategic and technical executive who connects business strategy, enterprise architecture, solutions design, and scalable delivery. 10+ years leading cross-functional teams across strategy, pre-sales engineering, solutions architecture, and engineering in healthcare, financial services, fintech, manufacturing, and SaaS. Established and grew the Solutions Engineering function and the Pitch to Close pre-sales motion that scaled the services revenue of a custom enterprise software and AI services firm from $1.5M to $9.2M in three years. Hands-on technical depth in Node.js, TypeScript, cloud infrastructure, and AI workflow orchestration. Effective working remotely with distributed teams and executive stakeholders.
Core Positioning
- 10+ years connecting business strategy, enterprise architecture, solutions engineering, and scalable delivery
- Established and grew the Solutions Engineering team at Nymbl from 1 (self) to 4 SEs; designed and ran the Pitch to Close pre-sales motion
- Scaled services revenue 6x ($1.5M → $9.2M in three years) through productized pre-sales-to-delivery operating model (PADRE)
- Owned SOC 2 Type II program end-to-end; unlocked enterprise sales motion into banks, credit unions, and other highly regulated industries
- Hands-on technical depth in Node.js / TypeScript, APIs, cloud infrastructure, and AI workflow orchestration
Selected Achievements
- Designed and operationalized PADRE — a customer-centric GTM operating model (Pipeline, Acquire, Deliver, Run, Extend) — and the embedded Pitch to Close pre-sales motion, scaling annual services revenue from $1.5M (2023) to $4.5M (2024) to $9.2M (2025).
- Established and grew the Solutions Engineering function at Nymbl from 1 (Blair himself) to a team of 4 Solutions Engineers, hiring, mentoring, and developing each through the Pitch to Close motion.
- Built automated pre-sales assets and standardized proposal workflows, reducing intake-to-proposal time from approximately 2 weeks to 3 days and significantly increasing sales velocity.
- Led the end-to-end SOC 2 Type II readiness and audit program, unlocking enterprise sales motion and contributing to $1.5M in new client revenue.
- Implemented an integrated operating framework connecting strategy, pre-sales, delivery, and billing, improving operational visibility and supporting the scale to $9.2M in annual services revenue.
Experience
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.
Capabilities
- Strategic Leadership & Business ArchitectureAdvanced
- Solution Architecture & Systems DesignAdvanced
- Enterprise Architecture & Portfolio DeliveryAdvanced
- Program & Product LeadershipAdvanced
- Full-Stack & Application EngineeringAdvanced
- Sports Program LeadershipAdvanced
- Retail Operations LeadershipAdvanced
- Customer Experience & Instructional ServicesAdvanced
- Security & Compliance ArchitectureAdvanced
- Financial & Organizational LeadershipAdvanced
- AI & Intelligent AutomationAdvanced
- Cloud Infrastructure & DevOpsEstablished
- Business Operating System DesignAdvanced
- Corporate Operations & IT Service ManagementAdvanced
Technical Skills
Advisory
AI
AI & Automation
AI Governance & Portfolio Management
Analytics & Marketing Operations
Architecture
Channel / Partnerships
Cloud & DevOps
Cloud Infrastructure
Coaching
Community Engagement
Corporate Operations & IT
CRM & Marketing
Customer Experience
Customer Success
Data
Data Architecture
Developer Tools
Domain — LegalTech / GRC
Engineering
Enterprise Architecture
Executive & Operational Leadership
Executive Leadership & Governance
Financial Leadership
Go-To-Market
Integration
Integration Architecture
Leadership
Low-Code / No-Code
Marketing
Operating System Design
Operations
Operations & Capacity Planning
Operations & Delivery
Operations & Governance
People Leadership
People Leadership & Organizational Effectiveness
Pre-Sales / Solutions Engineering
Pre-Sales / Technical Diligence
Product
Program & Delivery Management
Program Delivery
Revenue Leadership
Sales Methodology
Security & Compliance
Solution Architecture
Solutions Engineering
Strategy
Strategy & Executive Communication
Strategy & Leadership
Strategy & Operations
Strategy & Portfolio Management
Team Operations
Education
Mechanical Engineering
Milwaukee School of Engineering · Milwaukee, WI · 2006–2010
Coursework (program not completed)
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