Affinda Group

About Draftable Draftable is building the next generation of document drafting tools for lawyers. We're part of Affinda, 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 products. US ARR is growing rapidly 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 ambition is to become the leading provider of document drafting solutions for lawyers, and the most loved technology in a lawyer's toolkit. The role We're hiring a Sales Development Representative to grow our pipeline of US law firms and legal teams. You will be part of our growing US sales team – you’ll have autonomy, uncapped earnings, and products that customers genuinely love. If you’re looking for a role where you can build a sales career inside a global AI company that is scaling rapidly in the US, this is it. What makes this role compelling - Career growth: Gain hands-on experience and develop skills to grow your career in sales, with a clear pathway to become an Account Executive. - AI-native sales skills: You will use AI daily in your prospecting workflows – the skills you build here will compound for the rest of your career. - Product market fit: You’ll generate leads for products that customers are actively switching to, with best-in-class win rates and customer retention. - Uncapped earnings: Your success directly determines your compensation, with meaningful upside for high performers. - Well-capitalised: Capital from Affinda is being allocated to Draftable specifically to scale the go-to-market function. Why now The salespeople who learn to sell with AI will have a massive edge over the coming years. This role puts you inside a company where AI is its foundation, and every employee is expected to adopt AI in their day-to-day workflows. You’ll build prospecting skills, commercial instincts and AI fluency that compound over the next decade. High performers will create significant leverage for themselves and rapidly progress their careers. You will: - Build and manage a pipeline of outbound prospects across US law firms and legal teams - Book qualified discovery calls and product demos for AEs – this is your core metric - Run multi-channel outreach campaigns across cold calling, email, and LinkedIn - Partner with AEs to sharpen account targeting and ensure smooth handoffs - Use AI powered prospecting tools to work smarter and faster - Represent Draftable at industry events to build brand awareness and generate leads What you'll bring - 1-3 years in sales, business development or a customer-facing role - A true hunter mentality – you thrive on outbound prospecting, take pride in creating pipeline, and don’t wait for opportunities to come to you - Highly goal-driven with a history of meeting or exceeding KPIs (calls, emails, meetings booked, pipeline generated) - Resilience and self-discipline – you can handle rejection, stay organised and hit activity targets without someone watching over your shoulder - Sharp written and verbal communication skills - A track record of following through on commitments - Genuine curiosity about legal technology and AI Compensation & benefits - On-target earnings (OTE): US$80-90k, inclusive of a base salary of US$50-60k and variable commissions - Uncapped commission structure - Health insurance, 401(k) matching and generous paid time off - Remote work flexibility – work remotely from anywhere in the US How to apply To apply for the role, please submit the following in PDF format: - A brief cover letter detailing why this role interests you - Your resume Please note we do not respond to unsolicited emails or calls from recruitment agencies. Thank you for your understanding.

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 to become 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 Compensation & location Compensation: - Base salary: US$160-200k - On-target earnings (OTE): US$270-330k (60/40 base/variable split) - 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.