Founding Technology Director (Pre-Series A)

Note: You don’t need to have led every aspect of technology delivery or product development before. We’re equally keen to hear from talent and senior managers who’ve driven strategic programmes or worked closely with a CTO/CIO in high-growth settings and now want to step into their first leadership role. If you’re excited by the idea of shaping technology strategy and execution in a pre-Series A company, this is your opportunity to make the role your own

Responsibilities:

• Strategically select and manage a network of Global Systems Integrators, Systems Integrators, and AI studios that align with S.AI.L's Legal-First AI Framework, ensuring each partner can deliver enterprise-grade solutions that integrate seamlessly with clients' existing cloud infrastructure while maintaining the highest standards of security and compliance

• Orchestrate complex multi-phase technology implementations across diverse jurisdictions and regulatory environments, managing external teams through constitutional mapping, executive dashboard development, and strategic legal enablement phases while ensuring deliverables meet S.AI.L's exacting standards for quality and business impact

• Develop and execute technology partnership strategies that enhance S.AI.L's competitive positioning and drive sales success, identifying emerging AI studios and technology partners who can extend our capabilities in areas such as agentic AI development, compliance automation, and cross-jurisdictional governance frameworks

• Collaborate closely with our Sales Director to create technology-enabled sales processes and competitive advantages, providing technical expertise during client engagements and developing joint go-to-market strategies with key technology partners that accelerate deal closure and client value realisation

• Build and maintain strategic relationships with senior technology leaders at major GSIs and emerging AI studios, negotiating partnership agreements, managing performance metrics, and ensuring continuous innovation in our service delivery capabilities while identifying new opportunities for collaboration and growth

• Oversee the technical architecture of S.AI.L's Legal-First AI implementations, ensuring that bespoke AI agents, real-time monitoring systems, and automated compliance frameworks are delivered on time, within budget, and exceed client expectations for operational impact and strategic value

• Drive continuous innovation in legal AI transformation methodologies by evaluating emerging technologies, piloting new approaches with trusted partners, and developing proprietary frameworks that maintain S.AI.L's position as the definitive leader in legal-first enterprise AI adoption

Qualifications:

• Communication skills: You excel at translating complex technical requirements into clear strategic objectives that resonate with both C-suite executives and external technology partners. Your ability to facilitate productive relationships between legal departments, technology teams, and external consultants sets you apart. You're equally comfortable presenting technical architecture decisions to a General Counsel as you are negotiating performance metrics with a Global Systems Integrator, and you understand how to communicate the strategic value of legal-first AI implementation to skeptical stakeholders across diverse organisational cultures.

• Growth mindset: You thrive in the dynamic intersection of legal technology, AI innovation, and enterprise transformation, seeing every implementation challenge as an opportunity to pioneer new approaches to legal-first AI adoption. You understand that we're building something entirely new – not just managing traditional technology projects, but creating a category where legal departments become the strategic catalyst for enterprise-wide AI transformation. Your curiosity about emerging technologies like agentic AI and your willingness to experiment with new partnership models make you an ideal fit for our rapidly evolving market and ambitious growth trajectory.

• Track record in AI, machine learning or data science: Strong experience in machine learning and data science, with a focus on integrating AI within cloud environments such as Azure, AWS and Google Cloud. You bring proven success in managing complex technology implementations with external partners, whether in AI platforms, regulatory technology, legal software, or enterprise transformation initiatives. Your experience might come from procurement roles where you managed technology vendors, consulting positions where you coordinated external teams, or technology leadership roles where you built strategic partnerships. What matters most is your demonstrated ability to select the right partners, manage their performance, and deliver measurable business outcomes through external collaboration in regulated or complex environments.

• Coaching and Mentoring: You're passionate about developing both internal capabilities and external partner relationships to achieve exceptional results. Your approach to managing GSIs, SIs, and AI studios goes beyond traditional vendor management – you create collaborative environments where external teams understand SAIL's vision and can contribute meaningfully to our clients' transformation journeys. You have experience building high-performing networks of external partners, providing guidance and feedback that elevates their capabilities, and creating processes that ensure consistent quality and innovation across all external collaborations.

Compensation

• Equity ownership: ~2% of fully diluted shares at grant

• Vesting schedule: 4-year vest, 1-year cliff, monthly thereafter

• Salary: Market-rate compensation effective upon Series A close (~12 months)

• Exit potential: c.US$7.5-15M based on conservative 5x revenue multiple at liquidity event

Ready to architect the future of legal-first AI transformation? Join S.AI.L and help us build the technology partnerships and implementation frameworks that will define how enterprise organisations approach AI adoption for the next decade. Be part of a team creating the future of enterprise-wide AI transformation

Disclaimer: Any reference to potential valuation figures for S.AI.L are purely illustrative and should not be interpreted as a promise or guarantee. These forward-looking estimates reflect our aspirations, not certainties. Like any early-stage company, outcomes may vary based on a range of factors beyond our control. We share this information to be transparent, not to mislead. Equity-based compensation will be governed by the final terms outlined in our formal agreements.

A Note to Our Valued Recruitment Partners

We deeply appreciate the incredible work that recruitment professionals do in connecting talent with opportunity. It's a relationship-driven business that requires genuine expertise and market insight. At this particular stage of S.AI.L's journey, we're taking a hands-on approach to building our founding team, working directly with candidates to ensure cultural alignment and shared vision around our legal-first AI methodology

This isn't about bypassing the recruitment community that we respect and value; it's about the unique requirements of early-stage team building where every conversation shapes not just who joins us, but how we grow together. As we scale and our needs become more specialised, we look forward to partnering with recruitment professionals who understand the nuances of AI transformation.

For now, we're asking candidates to apply directly so we can build those foundational relationships from the start. We're grateful for your understanding and look forward to collaborating as S.AI.L evolves.

The S.AI.L Careers Team