Draftable - Global Head of Sales

About Draftable

Draftable 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 Compelling

Real 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 now Legal 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 role We'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 Manager

Own global ARR targets and go-to-market strategy

Lead our global GTM organisation across sales and customer success

Optimise our sales operation: playbooks, outbound engine, tech stack (currently Hubspot, Gong), deal desk, customer success and revenue ops

Partner closely with product to shape our roadmap

Build and coach a high-performing global sales team to exceed quotas

Support recruitment efforts to grow our sales teams in the US and EMEA

You're building structure and scale around something that's already working.

What You'll Bring Essential:

3+ years in senior B2B SaaS sales leadership roles, with direct experience scaling ARR from early traction to meaningful scale

Systematic, data-driven approach to sales processes and operations

Comfortable building in stages: hands-on early, then progressively adding structure and people

Track record of building and leading high-performing sales teams across multiple regions

Strong coaching and talent development skills – you hire well, give clear feedback, and elevate performance

Nice to have:

Experience selling into law firms or complex professional services organisations

Experience taking market share from large incumbents

Compensation & location Compensation:

On-target earnings (OTE): A$500k–A$600k

Base salary: A$280k (including superannuation)

Variable commission linked to global ARR growth, with meaningful upside

Long-term equity incentive package in Affinda Group

Location:

Must be based in Melbourne, Australia

Flexible working arrangements with regular in-person collaboration

Global remit with regular collaboration across US and EMEA time zones

How To Apply Submit in PDF format:

A cover letter

Your CV

We're committed to fostering an inclusive workplace and welcome applications from all qualified individuals. We do not respond to unsolicited contact from recruitment agencies.

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