Josiah Surface

About Josiah Surface

As Director of Revenue Operations at Flywl since February 2026, I architect scalable revenue systems that drive growth and operational excellence. I\'ve built comprehensive benchable revenue systems that drive growth and operational excellence. I\'ve built comprehensive benchmarking platforms, AI-powered CPQ applications, and automated workflows that transform how enterprise buyers negotiate and manage cloud commitments. My work spans strategic product development, compensation design, and cross-functional collaboration with product, engineering, and sales teams to deliver data-driven solutions that enable intelligent decision-making.Previously, as Sales Strategy & Operations Manager at Google Cloud, I contributed to a 153.5% increase in bookings (~$1B) by leveraging advanced analytics, AI tools, and streamlined pricing operations. I developed AI-powered workflows that saved the GTM organization 28-84 weeks of effort, created Vertex AI chatbots for executive leadership, and built pricing calculators that reduced estimation processes from weeks to minutes.With deep expertise in revenue operations, AI/ML integration, and process automation, I specialize in building systems that scale. Whether developing tiered service models for enterprise commit management, designing compensation structures aligned to strategic objectives, or creating web applications that automate quote-to-cash processes, I focus on solutions that eliminate friction and unlock growth. My approach combines technical innovation with business acumen, enabling teams to move faster, decide smarter, and achieve ambitious revenue targets.I\'m passionate about using data, automation, and strategic thinking to solve complex operational challenges and create competitive advantages in rapidly evolving markets.

Experience

1. Director of Revenue Operations

   Flywl

   Feb 2026 — Present · Washington, DC, US

   Strategic Product Development: Led development of comprehensive benchmarking and pricing analytics platform, creating Google Stitch designs, Lovable prototypes, and web applications to enable data-driven deal structuring and commit management capabilities• Revenue Operations & Automation: Built CPQ web application in HubSpot using AI to automate quote generation process, reducing manual effort and enabling scalability. Implemented workflows to automatically populate CRM data and generate commission statements• Enterprise Commit Strategy: Conducted extensive research and developed tiered service model (Advisor, Manager, Autopilot) for managing cloud commits across AWS, GCP, and Azure, presenting findings to executive leadership• Sales Enablement & Compensation: Designed and implemented compensation plans for sales team, including tiered commission structure based on net revenue and strategic objectives• Cross-functional Collaboration: Partnered with product, engineering, and sales teams to integrate benchmarking data, usage tracking, and deal analytics into platform. Coordinated with ISV partners on pricing strategies and deal structures• GTM Tech Stack Optimization: Evaluated and recommended sales tools including Sybil for call intelligence, Clay for data enrichment, and Swarm for warm introductions, leading vendor selection and implementation• Data Analysis & Reporting: Created hero reports and deal scorecards to benchmark customer transactions across seven key dimensions, providing actionable insights for buyers and internal stakeholders• Process Improvement: Streamlined inventory data management, order form generation, and private offer workflows, reducing quote-to-cash timeline and improving data quality across systems

Education

• University of Washington

  Bachelor of Arts (B.A.)

• Virginia Tech MBA

  Master of Business Administration - MBA, Finance, General

  2018 — 2021