Giles Thompson

Chief Revenue Officer

London, England, United Kingdom

About

Former lawyer building the future of legal drafting. Wish me luck.

Experience

  • Chief Revenue Officer (CRO) at Avvoka
    2020 - Present · 6 yrs 7 mos

    Context: Bootstrapped enterprise SaaS business selling to in-house and private practice lawyers (AI-enhanced Document Automation / CLM). No external investment beyond £500,000 at seed stage. Took a >66% pay cut from my salary as a lawyer (Herbert Smith Freehills & Kirkland and Ellis) to take the opportunity. Revenue Function: • First sales hire; built, trained, and now manage a 15-person global team (Pre-sales Engineers, Outbound/Inbound BDRs, Enterprise AEs) across the UK, North America, Australia, Singapore and Nigeria. • Scaled ARR by ~100% YoY for 4 years, with no advertising or marketing spend. • Grew from ~£250,000 ARR in 2020 (with <10 employees) to ~£5,000,000 ARR in 2024 (with >65 employees). • Achieved a 200% increase in median deal value. Sales Operations: • Designed the revenue KPI model and reporting structure. • Developed account mapping, ICPs, and pricing and targeting strategies. • Implemented MEDDPIC qualification, demo scripts, and playbooks for objection management, upselling, and negotiation. • Created sales campaigns, and collateral such an ROI calculator, and a model RFI. • Launched a pilot program, including materials and case studies. Distribution & Demand Generation: • Established new distribution channels through reseller and implementer partnerships (e.g., PwC). • Engaged in industry accelerators and government trade missions (e.g., AO Shearman Fuse, Legal Innovation Zone, Santander X). • Utilised social selling through podcasts, interviews and media features. Contract Negotiation: • Designed a standard SaaS contract and a negotiation playbook to speed up deal velocity. • Collaborated with the first General Counsel to optimize contract processes. Tools & Systems: • Procured and implemented essential tools: HubSpot, Brevo, Sales Navigator, Phantom Buster, Hunter.io, Apollo, Dux-Soup and Klenty.

  • Investor at Valerie
    Mar 2025 - Present · 1 yr 5 mos

  • Investor at WineFi 🍷
    Mar 2025 - Present · 1 yr 5 mos

  • Executive Member at Pavilion
    Sep 2024 - Present · 1 yr 11 mos

    Enrolled in Chief Revenue Officer School, and Revenue Operations courses.

  • Investor at Allora (drinks)
    Apr 2023 - Present · 3 yrs 4 mos