BBBlair Boylan
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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

Narrative

What this role was actually about.

The CSO role at Nymbl is where the through-line crystallized. PADRE, Pitch to Close, SOC 2, AI-enabled intake, and the Solutions Engineering function were not separate programs. They were one operating system that scaled services revenue 6x in three years.

Initiatives & deliverables

What I built, shaped, designed, led, or translated.

Internal Operating System Architecture

Designed the internal operating system architecture used to connect strategy, advisory work, solution design, and delivery execution across the business.

  • Defined end-to-end workflows, core data structures, and integration patterns for internal operations spanning opportunity management, solution design, delivery coordination, and execution visibility.

    Impact: Created a shared operating model that improved alignment between strategic planning, solutioning, and delivery activities.

  • Validated implementation workflows that linked strategic initiatives, advisory outputs, and delivery artifacts to executable downstream work.

    Impact: Improved traceability from business objectives to implementation-ready deliverables and reduced ambiguity during project handoff.

AI-Driven Intake & Solution Automation

Introduced AI-assisted patterns that transformed unstructured client information into structured intake, requirements, and solution design inputs.

  • Designed AI workflow and orchestration logic that converts unstructured client notes, calls, and documents into structured solution inputs aligned to the Implementation Framework taxonomy.

    Impact: Accelerated early-stage solutioning and improved consistency of intake outputs across advisory and architecture engagements.

  • Created reusable prompt frameworks, schemas, and structured templates for automated intake, requirements decomposition, and solution mapping.

    Impact: Reduced manual synthesis effort and made solution design methods more repeatable across teams and engagements.

  • Architected the Pitch to Close pre-sales motion as an AI workflow that converts unstructured client calls, meeting notes, and documents into structured, curated solution inputs aligned to the Implementation Framework taxonomy — the same knowledge-curation and data-quality discipline that determines downstream AI feature output quality.

    Impact: Transformed the pre-sales motion from manual synthesis into a repeatable, AI-orchestrated intake and solution-design process, improving consistency and speed of early-stage solutioning across the Solutions Engineering team.

  • Used Postman throughout solution architecture and implementation work to validate APIs, inspect requests and responses, and troubleshoot integrations across custom applications and low-code platforms, including API validation while building AI agents in Moveworks and n8n.

    Impact: Establishes direct hands-on integration debugging experience alongside Blair's existing API architecture and Solutions Engineering evidence.

PADRE Sales & Delivery Process

Built and institutionalized a staged sales-to-delivery framework that standardized how the company moved from discovery through validated solutioning and implementation.

  • Designed and documented a structured sales and delivery guide spanning discovery, validation, architecture design, implementation planning, and enablement.

    Impact: Improved consistency across client engagements and supported the scaling of services delivery from founder-led work to a more repeatable operating model.

  • Packaged an end-to-end offering that connected strategy, design, build, and launch into a coherent service pathway.

    Impact: Improved offer clarity, supported account growth, and created a stronger bridge between business development and delivery teams.

  • After enterprise solutions were sold, remained engaged as the client Strategy Partner and strategic architecture stakeholder throughout implementation. Reviewed delivery-level requirements and user stories against the approved solution architecture, resolved architectural implications of scope or requirement changes, and maintained the architecture as a living document throughout the build.

    Impact: Preserved traceability between the solution sold and the solution delivered, reduced architectural drift during implementation, and provided continuity from technical pre-sales through production delivery.

Strategy Practice Development

Expanded the advisory and strategy practice by creating structured methods for market analysis, solution design, technology assessment, and capability-to-delivery translation.

  • Created a methodology to quantify markets, assess competition, and produce strategy recommendations with clear go-to-market implications.

    Impact: Enabled more rigorous strategy engagements and improved the quality of advisory outputs delivered to clients.

  • Built a standardized intake-to-contextualization-to-engineerable-requirements workflow that linked business objectives to implementation scope.

    Impact: Improved the transition from advisory work into architecture and delivery by reducing ambiguity and increasing requirements readiness.

  • Developed a data-driven vendor evaluation method that compared multiple systems against capability criteria and produced recommendation outputs.

    Impact: Improved the rigor and defensibility of technology assessment recommendations across client engagements.

  • Designed enterprise solution architectures around the customer's broader future-state system rather than only the initial project. Structured sales recommendations into three phases covering approximately 18 months, using the first implementation as the initial step in a larger modernization roadmap. Through advisory engagements, produced recommendations, future-state assets, and executive-facing materials that internal champions could use to secure approval for subsequent projects.

    Impact: Created a natural path from initial implementation to longer-term platform and systems modernization while helping customer champions build executive support for continued investment.

Achievements

Linked outcomes.

  • Internal Operating System Foundation

    Architecture

    Designed the internal workflow, data, and integration architecture that linked strategy, solution design, and delivery execution.

  • PADRE Framework Institutionalization

    Strategy & Delivery

    Built and operationalized a structured sales-to-delivery framework that improved consistency across client engagements.

  • Strategy Practice Expansion

    Strategy

    Built repeatable methods for market analysis, requirements contextualization, and technology evaluation.

  • AI-Driven Intake Patterns

    AI

    Designed AI-assisted methods for turning unstructured client information into structured solution inputs.

  • Pitch to Close as AI Workflow

    AI

    Architected the Pitch to Close pre-sales motion as an AI workflow converting unstructured client inputs into structured, curated solution inputs.

  • Post-Sale Architecture Stewardship Through Implementation

    Solutions Architecture / Customer Delivery

    After enterprise solutions were sold at Nymbl, remained engaged as Strategy Partner and strategic architecture stakeholder throughout implementation, validating delivery-level requirements and user stories against the approved solution architecture and evolving the living architecture as implementation requirements changed.

  • 18-Month Enterprise Expansion & Modernization Roadmapping

    Enterprise Architecture / Account Expansion

    At Nymbl, architected the broader future-state solution during pre-sales and structured customer recommendations into three-phase, approximately 18-month roadmaps. Ran advisory engagements that produced recommendations and executive-facing assets internal champions could use to secure approval for subsequent initiatives.

  • ClickUp Project Structure & Delivery Management

    Program & Delivery Management

    Used ClickUp extensively across Nymbl client delivery and designed the project organization structure used to manage project work, creating a consistent operating model for how teams organized and executed client engagements.

  • Hands-On API Validation & Integration Debugging

    Solutions Engineering / Integration Engineering

    Used Postman across freelance, Nymbl, and Oso Group to validate APIs and troubleshoot integrations in custom applications and low-code environments, including API work supporting Moveworks and n8n AI agents.

  • Global Distributed Technical Leadership

    Leadership / Global Delivery

    Worked across a distributed Nymbl organization with team members in Germany, Portugal, and India and supported customers in Australia and Europe.

  • Asset Management & Financial Services Workflow Architecture

    Financial Services / Solution Architecture

    Worked with several financial-services organizations on solutions centered on asset-management data, operational workflows, and supporting system architecture. For a banking client, conducted a deeper analysis of digital payments and how payment adoption was evolving in Canada to inform the client's solution context and technology direction.

  • Industry Conference Technical Representation

    Solutions Engineering / Industry Representation

    Represented Gloo at multiple education-technology conferences, demonstrating and explaining the platform to attendees. At Nymbl, attended a tolling-industry conference alongside a partner to support new-project discussions and represent the technical side of proposed tolling solutions.

  • Product & Partner Platform Knowledge Repository Architecture

    Knowledge Management / Solutions Engineering

    At Gloo, created a centralized knowledge center documenting platform functionality and connecting individual capabilities back to company strategy, creating a coherent repository for understanding how the platform fit together. At Nymbl, helped structure and maintain internal knowledge repositories for partner platforms so teams could understand partner capabilities and use them during solution design and customer engagements.

  • Quarterly KPI & Initiative Value Tracking

    Strategy & Operations

    At both Gloo and Nymbl, helped define KPIs for initiatives and departmental goals and participated in quarterly reviews evaluating performance, progress, and outcomes against those measures.

  • Annual & Quarterly Portfolio Prioritization

    Portfolio Management / Investment Governance

    At Nymbl, participated in annual executive portfolio-planning sessions where leadership decided which initiatives and offerings to invest in, scale, continue, pause, or retire, with lighter-weight reviews occurring quarterly. One example was discontinuing the Webflow offering after customer demand failed to materialize.

  • Enterprise AI Portfolio Visibility

    AI Governance / Portfolio Management

    At Nymbl, maintained visibility across multiple internal initiatives intended to advance the company's AI offerings, tracking project status, priorities, risks, and intended outcomes so leadership could understand the state of the AI portfolio and make prioritization decisions.

  • Cross-Functional Finance, Legal & Risk Governance

    Executive Governance / Risk

    As Nymbl Chief Strategy Officer, participated in executive governance and decision-making involving Finance and Legal, including annual planning and investment decisions, organizational structure and equity discussions, and SOC 2 implementation where financial, legal, security, and compliance considerations informed risk and investment choices.

  • Employee Engagement & People Partnership

    People Leadership / Organizational Effectiveness

    At Gloo and Nymbl, formally partnered with HR/People on employee engagement and organizational-health efforts, including employee surveys and pulse checks, team-health initiatives, organizational design, offsites, internal communications, retention, and culture programs.

  • 0→1 Delivery Function Ownership & Leadership Handoff — Nymbl

    Executive & Operational Leadership

    Early in Nymbl's growth, carried delivery-function responsibility before dedicated leadership existed, then intentionally transitioned that responsibility once a specialist leader was hired as the organization matured.

  • Founder/CEO Constructive Challenge & Governance — Nymbl

    Executive Leadership & Governance

    As a senior executive partner to Nymbl's CEO, advised and pushed back on consequential operating decisions including discretionary spending such as a proposed sports sponsorship, hiring decisions across departments, company equity structure, and employee evaluation practices.

  • Cross-Functional Executive Operating Scope — Nymbl

    Executive & Operational Leadership

    Directly owned assigned departments while participating in operating decisions across the broader organization, combining functional accountability with company-wide executive participation across adjacent functions.

  • Non-Engineering Domain Stakeholder Translation — Gloo & Nymbl

    Stakeholder Leadership & Solution Architecture

    Led discovery, architecture, and operating-model work primarily with non-engineering customer stakeholders, including stakeholders at a radiology organization at Nymbl and operators of in-person personal-growth programs at Gloo who needed to digitize their products and services.

  • Demand & Engineering Capacity Planning — Nymbl

    Operations & Capacity Planning

    Translated sold client solutions into engineering demand and delivery sequencing, balancing solution requirements, available engineering capacity, timing, and project dependencies to determine when work could be executed.