Stephen Hilton

VP Operations @ Archie | Building the ops backbone AI startups scale on | RevOps · Compliance · GTM Systems · AI Infrastructure

Sacramento, California, United States

About

Operations leader with 10+ years building the systems venture-backed SaaS companies actually run on. I've been the embedded operator for high-growth startups since 2014. Today I'm VP of Operations at Archie, an AI-native accounting-automation startup, where I joined early and built the operational backbone while the product was still taking shape. My career started in the back office, running payroll, AP/AR, tax, and compliance for 25+ startups at once, so I genuinely know accounting, not just the software around it. That grew into revenue operations and go-to-market at Karbon, then product and technical leadership at Waverley and Archie. Finance, GTM, and product, across three functions most operators only touch one of. The through-line holds wherever I land. I walk into companies that have a vision and a technical team but no operational infrastructure, build it from scratch, and make it repeatable enough to run without me. Strategy and execution, connected at every level. What separates me from most operators is the technical depth. I architect CRM systems at the data-model level, design AI agent workflows, optimize LLM API spend, and ship production-grade automation with AI-assisted development. I'm not an engineer by training. I'm an ops leader who got curious enough to work at the infrastructure layer, and now I do it without needing a translator. On the side, I tinker and ship AI-native mobile apps end-to-end, currently a parenting app in TestFlight beta. Highlights: · Secured $400K in cloud credits (Google for Startups + Microsoft for Startups) for Archie · Drove SOC 2 Type II to completion at Archie · Architected a custom CRM, with native HubSpot/Nylas integrations · Designed multi-stage AI agent workflows (MCP + Claude code) and per-PR API cost attribution · Scaled RevOps across the Americas, APAC & EMEA · Cut sales ramp from 3 months to 1 · Supported operations for 25+ venture-backed startups — including Sourcegraph, Mode, & PlushCare

Experience

  • Vice President Operations at Archie
    Jan 2025 - Present · 1 yr 7 mos

    Founding team member when Archie spun out of Waverley Studios, serving as the operational backbone for an AI-native accounting-automation platform. AI Infrastructure & Cost Governance - Built an end-to-end Claude Code observability pipeline enabling per-PR, per-session, and per-repo token attribution for board-level AI ROI reporting - Cut Anthropic API spend ~$20K/mo (~67%, ~$240K/yr) via four levers: prompt-cache audit (missing cache_control + invalidated prefixes), org-wide system-prompt reduction, a model-blend KPI (plan-on Opus, execute-on-Sonnet), and Claude Skills for recurring workflows Partnerships & Credits - Secured $400K in cloud credits ($250K Google for Startups + $150K Microsoft for Startups) Technical Builds - Built the custom CRM integration layer full HubSpot custom schema data-parity mapping, plus a Google Calendar + Gmail integration via Nylas with a CRM-to-activity data model - Architected and shipped a production AI/ML video-to-SOP pipeline — a 4-stage LangGraph workflow combining Claude Vision (multimodal) and Whisper/Deepgram speech-to-text, served as an async FastAPI service with PostgreSQL, Redis, and FFmpeg/OpenCV, containerized on Docker + Kubernetes. Built end-to-end with AI-assisted development - Shipped an automated direct-mail pipeline: triggered leads into fulfillment, logged each shipment as a custom HubSpot object, and fired personalized outbound sequences off delivery events Finance, Accounting & Tax - Owned the monthly close cycle and prepared the board reporting pack, Payroll and benefits across US, UK, and Spain including manual HMRC and Nest pension filings for the UK, and owned the 409A valuation - Stood up the Spain office, including local employment, payroll, and compliance setup - Established multi-entity US/UK structure including UK Companies House establishment registration (OS IN01) for the Delaware C-Corp parent (EIS investment) Compliance & Trust - Drove SOC 2 Type II, GDPR, ISO-27001 to completion

  • Vice President Operations at Waverley Studios
    Jun 2024 - Dec 2024 · 7 mos

    Product and operations leadership at the venture studio that incubated multiple AI-native software products including the one that spun out as Archie, where I moved full-time with the founding team. - Structured core data entities for integrity; authored system documentation including entity relationships and data-flow diagrams - Drove feature prioritization across the studio's portfolio, translating user stories into MVP scope alongside engineering and design - Helped shape the early product direction for what became Archie (AI-native accounting automation) - Coordinated across engineering, design, product team - Owned the monthly close cycle and prepared the board reporting pack

  • Karbon (Full-time · 2 yrs 9 mos)
    • Revenue Operations Manager
      Apr 2023 - Apr 2024 · 1 yr 1 mo

      - Built and implemented an order-form policy within contract management, ensuring regulatory compliance and minimizing revenue leakage by 10% - Led evaluation, selection, and rollout of quote-to-cash tooling, including team training and adoption - Developed GTM KPIs and built out Gong deal boards and smart trackers to surface revenue-growth opportunities across CS and Sales organizations - Administered global compensation and commission for a 30-person sales team and executive leadership across multiple currencies

    • Revenue Operations Lead
      Jul 2022 - Apr 2023 · 10 mos

      - Led the end-to-end implementation of Gong from the ground up owning evaluation, vendor negotiation, and rollout, standing up the company's first conversation-intelligence and forecasting capability - Ran revenue operations across the Americas, APAC, and EMEA, building data-driven forecasting models for precise sales projections - Streamlined the sales process end-to-end via Salesforce customization: intent-data triggers, field/validation logic, DocuSign merges, and reporting/dashboards accelerating deal closures - Automated commission calculations, reducing errors and improving payout transparency - Implemented data-hygiene protocols and CRM best practices; built customer segmentation for targeted GTM

    • Sales Enablement Lead
      Aug 2021 - Nov 2022 · 1 yr 4 mos

      Karbon is the premium work management platform for the accounting industry and has become indispensable for firms around the world to support their team and navigate the sudden shift to remote work. Karbon brings planning, clients, work, and communication together in one place where it belongs. Founded in San Francisco, grown into a globally distributed team with people in the United States, Australia, New Zealand, and the United Kingdom. We are well-funded, have a fantastic team culture, and are making a global impact. - Restructured sales training and coaching, reducing rep ramp time by a full month - Became the org's go-to expert across the sales stack: Salesforce, Outreach, Vitally, Gong, Apollo, Bombora, DocuSign, G2 -Delivered market and competitor research to sharpen prospecting and closing

  • Officengine (7 yrs 4 mos)
    • Director Of Operations
      May 2019 - Aug 2021 · 2 yrs 4 mos

      - Key strategic advisor to the CEO; ran bi-weekly strategy sessions on project profitability, competitive pricing, partner-channel strategy, and operational metrics - Led stakeholders across US and Philippines teams, driving skills development and organizational alignment - Owned invoicing, payroll, and dynamic billing across diverse revenue streams; untangled fragmented data to recover visibility into a 15% revenue oversight

    • Onboarding Manager
      Jul 2016 - Aug 2021 · 5 yrs 2 mos

      - Led scoping meetings with C-suite executives implementation scope, tooling, growth projections, financial history ensuring documentation integrity and full tax/regulatory compliance - Translated strategic corporate audit roadmaps into executable plans in Asana, aligning service teams to stakeholder priorities - Primary liaison for client-side process overhauls: accounting month-end close processes, revenue tech stacks, CRM reporting, sales checklists, and commission/revenue recognition

    • Senior Client Success Manager
      May 2015 - Jun 2016 · 1 yr 2 mos