Resume · concise version
Blair Boylan
Solutions Engineering Leadership • Pre-Sales Operating Systems • AI-Enabled Solution Design • Enterprise Architecture
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
- Scaled the Nymbl organization from 5 to 75+ FTEs and contractors as a core member of the executive team
- 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).
- Scaled the Nymbl organization from 5 to 75+ FTEs and contractors as a core member of the executive team, establishing operating governance to support 6x services revenue growth.
- 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. 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.
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, 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).
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 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.
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
Architecture
Cloud & DevOps
Coaching
Community Engagement
Corporate Operations & IT
Customer Experience
Customer Success
Data
Data Architecture
Domain — LegalTech / GRC
Engineering
Enterprise Architecture
Financial Leadership
Go-To-Market
Integration
Leadership
Marketing
Operating System Design
Operations
Pre-Sales / Solutions Engineering
Pre-Sales / Technical Diligence
Product
Program Delivery
Security & Compliance
Solution Architecture
Solutions Engineering
Strategy
Education
Mechanical Engineering
Milwaukee School of Engineering · Milwaukee, WI · 2006–2010
Coursework (program not completed)
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