Draftable, Head of Product - Affinda Group

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 1,300 law firms and legal teams globally have adopted our product, including leading firms like Allens, 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 exceeds incumbent tools, and it's just the foundation for a broader product suite we're actively building (our second legal-focused product Draftable Clean launched in March 2026).

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

• Own the product strategy: As AI makes building software ever easier, any product strategy requires evolution. Driving those decisions across our portfolio is the heart of this role.

• Build the product operation: lead and coach our product managers, mentor the team on product craft, and shape the roles and hires that come next as the portfolio expands.

• Own a multi-product portfolio: balance investment between our flagship comparison product and the new categories we're launching and incubate what comes next.

• Rearchitect how product management works: this isn't about adopting a few AI tools - you'll own the redesign of our product processes so humans working alongside AI agents define what we build.

• Hands on: Continue to adapt to a fast-changing AI landscape by remaining hands on with AI while maintaining a leadership position

• A warm culture with trust and autonomy: join a team with high trust and no politics - you'll be judged on outputs, working with people who care about the work and each other.

• A real seat at the table: you'll be part of the Draftable leadership team, reporting directly to the General Manager, with a strong engineering partnership beside you.

Why now

Legal technology is going through a generational shift. Law firms are moving away from aging, bundled platforms in favour of modern, best-of-breed alternatives, and Draftable is on the right side of that shift. At the same time, AI is fundamentally changing how product teams work: how requirements are written, how software is built, and how fast teams can ship. For a product leader, this is a rare moment: you can ship faster than ever before, and the decisions you make, on both strategy and process, carry more weight than they have in years.

It's also a pivotal time for Draftable itself. We've proven the model with our flagship product and established our position; now we're moving deliberately into multi-product territory. And while we have a view on product strategy, there are real, unresolved decisions: what we build next, how we sequence it, how we resource it. Stepping into this role means shaping those decisions from the outset rather than inheriting a settled roadmap.

The role

We're looking for a Head of Product to lead our product function through its next stage: growing the team, evolving the product strategy, expanding the portfolio, and rearchitecting how we do product management as AI changes what's possible.

Each of our products has a named product owner who is accountable for its commercial success - a model we hold to as products head to market. You'll develop those owners and hold them accountable, set commercial targets with them, and share in the outcomes: the portfolio's overall trajectory is yours. Earlier-stage concepts may sit with you directly until they earn a dedicated owner.

You'll also own how we do product management. As AI reshapes how software gets defined and built, you'll design the processes, standards, and tooling for the whole team - and you'll drive the decisions about what we build next, working closely with the General Manager, who holds the final call.

This is a hands-on leadership role in a lean team: beyond setting direction, expect to run discovery on early-stage concepts, join customer calls, and build some of the process tooling you ask the team to use.

You will

• Own the product portfolio: balance investment between maturing our flagship comparison product and launching new categories, and drive the what-we-build-next decisions with the General Manager

• Build out and lead the product team: coach and develop our product managers, raise the bar for product craft, and shape the team's structure as the portfolio grows

• Make each product owner successful: set commercial targets together, review adoption, retention and revenue trajectories, and share accountability for the outcomes

• Incubate new product concepts: run early discovery and validation yourself, handing each product to its dedicated owner as it heads to market

• Own our discovery, definition, and launch standards across products

• Rearchitect our product processes to be AI-native, structuring product definition so AI coding agents (not just human engineers) can build from it - working with tools like Cursor, Claude Cowork, Miro, Lovable and custom internal tools

• Partner with Engineering on technical feasibility, architecture decisions, and delivery planning

• Partner with Sales and Marketing on go-to-market strategy, product positioning, and customer feedback loops

• Analyse adoption, retention and usage data across the portfolio to surface opportunities, and set, track and communicate product KPIs with the General Manager

What you'll bring

Essential:

• 10+ years in product management, most of it in B2B SaaS, including leading and managing product managers

• Experience taking a new product from zero to launch and first customers - personally or through a team you led - you know what has to be true before launch for a product to land commercially

• A commercial approach to product: you run products against adoption, retention and revenue targets, and build that discipline in the teams you lead

• Strong product judgment, including the ability to discern between good and bad ideas, designs, and trade-offs

• Cross-functional leadership: a proven ability to align engineering, sales, marketing, and support behind a roadmap

• Excellent written communication across product requirements, strategy documentation and go-to-market enablement

• A data-driven approach to decision-making: comfortable analysing customer and usage data, setting KPIs, and using evidence to prioritise

• Active use of AI tools in your product work (including agentic tools like Claude Code, Cursor or Codex), with a vision for how AI changes product management

Nice to have:

• Experience in legal technology or selling to law firms and professional services organisations

• Product design education or hands-on design experience

• Experience in challenger brands taking market share from larger incumbents

Location & travel

• Melbourne-based hybrid role with office in Cremorne (next to the CBD).

• Flexible working arrangements with regular in-person collaboration and periodic travel for customer meetings, conferences, and events

Compensation

• AUD $240,000 (including super) and remunerate based on merit

How to apply

• CV and a short cover letter (PDF format) explaining your product leadership experience and why this role excites you

We run a structured, concise process and will walk you through the steps on our first call. 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.