3+ years leading B2B software sales teams (small teams acceptable) and remote regional leadership, including hiring and coaching.
Experience scaling high-performing teams from proven product-market fit to predictable growth, with an outbound-led sales culture.
Proven track record building and scaling outbound systems to consistently deliver against quota, with strong CRM and data-driven processes (HubSpot preferred).
Experience selling into complex/enterprise GTM environments; ability to develop territories, ICP focus, and adaptable sales playbooks; comfortable with AI/automation adoption.
Requirements:
Own US new ARR, expansion revenue and forecast accuracy, with full accountability for regional performance against quarterly and annual targets.
Lead and coach US Account Executives and drive the outbound-led GTM motion with pipeline discipline.
Build foundations for scale: define territories, ICP focus, outbound playbooks tailored to the US market and pipeline coverage targets.
Establish a predictable operating cadence including forecasting, deal reviews, pipeline hygiene, performance management, hire/onboard the next wave of GTM roles, and optimize sales operations and tech stack; collaborate with product and marketing.
Job description
About Draftable Draftable is building the next generation of document drafting tools for lawyers. Since launching our first legal product in 2023, 1,000+ law firms and legal teams globally have adopted our product.
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 wins head-to-head against incumbents, and it's the foundation for a broader product suite we're building.
Our ambition is tobecome the leading provider of document drafting solutions for lawyers, and the most loved software in a lawyer's toolkit.
We’re part of Affinda Group, a founder-led global AI company focused on helping organizations create value from AI. Headquartered in Melbourne, Australia, Affinda Group supports customers in more than 85 countries, with a team of ~100 people across Asia Pacific, North America and Europe.
The role We're looking for a Sales Director to lead Draftable’s sales function in the US, with the opportunity to take on broader Americas responsibility as we grow.
This is a sales leadership role focussing on building out our regional presence. Reporting to our Australia-based Head of Sales, you will grow the US team from its current size of 3. You will succeed by implementing global standards and regional structure to increase sales and impact: outbound motion, territory design, pipeline discipline, hiring and coaching, and a clean handoff model as we scale our prospecting function and build out customer success.
You will operate within a defined global sales operating rhythm, including weekly forecasting, monthly pipeline and delivery reviews and quarterly strategic planning cycles.
Growth in the US is a strategic priority for Draftable, and you will be supported by our product, marketing, sales and support teams, who are all motivated to help Draftable achieve its growth objectives in your region.
What makes this role compelling
Real traction: You're scaling a motion that already works – repeatability is the mission.
Direct impact: You will design, build and own the US go-to-market function: structure, territories, hiring plan, and operating rhythm.
Clear story: Challenger product, strong win rates, and a customer base that actively switches from incumbents.
Resourced to win: 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, and retention is best in class.
The US is already our largest and fastest-growing region – and we’ve done it with a lean team. This is the moment to put senior leadership in place and build a repeatable growth engine. For a proven B2B software sales leader, this is a rare opportunity: strong tailwinds, a clear challenger story and a product customers love.
You will:
Own US new ARR, expansion revenue and forecast accuracy, with full accountability for regional performance against quarterly and annual targets
Lead and coach our US Account Executives
Execute within a globally standardised GTM and customer success framework, with the ability to apply localised nuance and jurisdiction-specific adaptation to maximise new customer acquisition and expansion revenue
Build the foundations for scale: territories, ICP focus, outbound playbooks adapted to the US market and pipeline coverage targets
Establish a predictable operating cadence: forecasting, deal reviews, pipeline hygiene and performance management
Hire and onboard the next wave of US GTM roles (SDRs, AEs, customer success)
Optimise our sales operation and tech stack (currently Hubspot, Gong, Apollo, Dealhub and internally built AI agents)
Partner closely with product and marketing as we launch and sell new products
What you'll bring Essential:
3+ years leading B2B software sales teams (small teams are fine, but you must have managed and hired)
Experience scaling high-performing teams from proven product-market fit to predictable growth
Experience building an outbound-led sales culture where teams proactively source, qualify and convert their own opportunities
Proven track record in building and scaling outbound systems to consistently deliver against quota
Strong coaching, hiring and performance management skills
Comfort managing team delivery across lead indicators (pipeline strength, activity quality, conversation ratios) and lag indicators (ARR, retention, expansion outcomes).
Experience driving sales outcomes across segmented GTM systems, i.e. complex / enterprise purchasing cycles and higher velocity small – mid market environments
Systematic, data-driven approach to sales processes and operations, with strong CRM and reporting fluency (ideally HubSpot) - comfortable in the detail
Comfortable building in stages: hands-on early, then progressively adding structure and people
High accountability, and comfort in working as a remote regional leader
Comfort adopting AI and automation to improve productivity
Nice to have:
Experience selling into law firms or other professional services organisations
Experience selling a challenger brand
Who this won’t suit:
Leaders who need a large company support machine (sales engineers, sales ops, enablement teams) to be effective
Anyone looking for a player-coach role with personal quota as the primary focus
People who prefer short-cycle, inbound-led, high-velocity sales motions
Variable compensation linked to US net new ARR, with meaningful upside
Benefits include health insurance, 401(k) matching and generous paid time off
Location:
Fully remote within the US with flexible working arrangements
Occasional travel for customer meetings, industry events and conferences
How to apply Submit in PDF format:
A short cover letter that includes why this role and why now for you
Your CV
The interview process is typically completed in 1 to 3 weeks.
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.
