Draftable - Global Head of Sales

About DraftableDraftable is building the next generation of document drafting tools for lawyers. We're part of Affinda Group, a founder-led global AI company based in Melbourne, Australia.Since launching our first legal product in 2023, over 1,000 law firms and legal teams globally have adopted our product, including leading firms like Allens, King & Wood Mallesons and DLA Piper. We're growing ARR at well over 100% year-on-year, with very high win rates against incumbents and negligible churn. Our flagship document comparison product already matches or exceeds incumbent tools – and it's just the foundation for a broader product suite we're actively building.Our ambition is to become the leading provider of document drafting solutions for lawyers, and the most loved software in a lawyer's toolkit.What makes this role compellingReal traction: You're joining something that's already working – your job is to optimise and scale it, not prove it.Direct impact: Build and own the GTM function at a company where you're close enough to the product and customers to shape everything.Clear vision: Help build the drafting product suite the best lawyers in the world rely on every day. Comparison is just the starting point.Focus on long-term value: Work with leaders who care about long-term customer value and product excellence, not just quarterly numbers.Well-capitalised: Capital from Affinda Group is being allocated to Draftable specifically to scale the GTM function. You'll have the resources to scale properly.Why nowLegal drafting technology is going through a generational shift. Firms are moving away from aging, bundled platforms in favour of modern alternatives. We’re on the right side of that dynamic - customers are actively switching to us, we're winning head-to-head evaluations in all regions, and customer retention rates are best in class.For a proven B2B SaaS sales leader, this is a rare opportunity: strong tailwinds, a clear challenger story, a product customers love, and the chance to scale it globally.The roleWe're looking for a Global Head of Sales to take Draftable from $5-10 million ARR to $30+ million over the coming years.This is a senior, hands-on role for someone who has been on this journey before and wants to do it again – this time with a sharper product, clearer vision, and more ownership.You will:Report directly to Draftable’s General ManagerOwn global ARR targets and go-to-market strategyLead our global GTM organisation across sales and customer successOptimise our sales operation: playbooks, outbound engine, tech stack (currently Hubspot, Gong), deal desk, customer success and revenue opsPartner closely with product to shape our roadmapBuild and coach a high-performing global sales team to exceed quotasSupport recruitment efforts to grow our sales teams in the US and EMEAYou're building structure and scale around something that's already working.What you'll bringEssential:3+ years in senior B2B SaaS sales leadership roles, with direct experience scaling ARR from early traction to meaningful scaleSystematic, data-driven approach to sales processes and operationsComfortable building in stages: hands-on early, then progressively adding structure and peopleTrack record of building and leading high-performing sales teams across multiple regionsStrong coaching and talent development skills – you hire well, give clear feedback, and elevate performanceNice to have:Experience selling into law firms or complex professional services organisationsExperience taking market share from large incumbentsCompensation & locationCompensation:On-target earnings (OTE): A$500k–A$600kBase salary: A$280k (including superannuation)Variable commission linked to global ARR growth, with meaningful upsideLong-term equity incentive package in Affinda GroupLocation:Must be based in Melbourne, AustraliaFlexible working arrangements with regular in-person collaborationGlobal remit with regular collaboration across US and EMEA time zonesHow to applySubmit in PDF format:A short cover letter that includes: (1) why this role and why now for you, and (2) what you would prioritise in your first 90 days if you joined the teamYour CVWe're committed to fostering an inclusive workplace and welcome applications from all qualified individuals. We do not respond to unsolicited contact from recruitment agencies.