Director, AI Solution Sales & Delivery

Axiom
Chicago, IL

Remote (United States)

About Axiom:

Axiom is where legal teams go to find the right talent for everything from routine in-house tasks to complex outside counsel work. Too many legal departments are stuck having to choose between paying the high fees of their law firm, hiring full-time employees they don't need, or turning to a low-cost agency that can't meet their quality standards. At the same time, top lawyers want to work on challenging legal matters, but they want more control over how, when, and where they practice. Both are forced compromises that no one should have to make. Axiom shares and meets the higher standards of its clients and lawyers, with our "work smarter, adapt faster, go further" approach -- connecting growing mid-market and Fortune 500 companies with the world's deepest bench of experienced, specialized legal talent.

About the Team:

The AI Solutions and Delivery team sits at the forefront of legal industry transformation, pioneering the integration of artificial intelligence into legal operations. We work across the sales and technology organizations to identify opportunities where AI can drive efficiency, improve quality, and create new value for our clients. Our team combines deep legal industry expertise with cutting-edge technical knowledge to design, sell, and deliver AI-enabled solutions that fundamentally change how legal work gets done. We are evangelists for innovation, trusted advisors to our clients, and the bridge between transformative technology and practical legal application.

Our People:

  • Generate new, creative, and disruptive ideas to change the status quo in their fields
  • Possess an unbelievable work ethic and unwavering commitment to quality
  • Stretch beyond what's expected and prioritize ongoing learning and development
  • Assume best intentions and take a 'glass half full' approach to their work
  • Bring others together, creating strong relationships across lines of difference
  • Seek to understand and learn from perspectives counter to their own
  • Leave a lasting impression

About the Role:

  • We are seeking a Director of AI Solution Sales and Delivery to lead the charge in transforming legal operations through artificial intelligence. This role sits at the intersection of cutting-edge technology and legal expertise, requiring someone who can speak fluently to both General Counsels and technologists. You will be responsible for identifying opportunities where AI can impact legal workflows, crafting compelling value propositions, and ensuring successful delivery of these transformative solutions. This position requires a unique blend of sales acumen, technical understanding, and strategic oversight to achieve meaningful annual contract value while managing 10+ active opportunities simultaneously.
  • Specifically, you will spend your days:
  • Leading AI opportunity discovery and solution design: You will work directly with the Axiom sales team and clients to understand their pain points, identify use cases where AI can drive meaningful impact, and architect solutions that deliver measurable ROI. This includes conducting workshops, building business cases, and demonstrating how AI transforms legal operations.
  • Driving complex AI sales cycles: You will partner closely with Sales, from discovery through closing. This includes developing proposals, conducting product demonstrations, creating proof-of-concept implementations, and articulating the value of AI transformation to executive stakeholders. In some cases, you may also be the lead Legal talent for the client engagement, post-sale.
  • Engaging with C-level executives: You will serve as a trusted advisor to General Counsels and Legal Operations leaders at Fortune 100 companies, helping them navigate the complexities of AI adoption and develop strategic roadmaps for legal transformation.
  • Providing strategic delivery oversight: While day-to-day project management will be handled by dedicated delivery managers, you will maintain strategic oversight of implementations to ensure client success, manage escalations, and identify expansion opportunities. You will serve as the continuity between sales and delivery, ensuring promises made during the sales process are fulfilled.
  • Collaborating across teams: You will work closely with account executives, delivery managers, data scientists, and lawyers to ensure seamless client experiences. You will also contribute to the development of AI capabilities and go-to-market strategies based on client feedback and market insights.
  • Evangelizing AI transformation: You will represent Axiom at industry events, contribute to thought leadership content, and help position Axiom as the leader in AI-enabled legal services. This includes sharing best practices, case studies, and insights from successful implementations.

About You:

  • You have 7+ years of experience in B2B enterprise sales, professional services, or management consulting, with a proven track record of closing complex, high-value deals in the $250K-$1M+ range.
  • You bring deep understanding of artificial intelligence and its practical applications in business, with the ability to translate technical concepts into business value. You can confidently demonstrate AI platforms and articulate their impact on workflows and outcomes.
  • You have experience in the legal industry or legal technology, understanding the unique challenges, workflows, and stakeholder dynamics within corporate legal departments and law firms.
  • You excel at consultative selling, with the ability to uncover client needs, build compelling business cases, and navigate complex organizational dynamics to drive consensus among multiple stakeholders.
  • You are comfortable managing multiple opportunities simultaneously, with strong project management skills to keep 10+ active deals progressing through various stages of the sales cycle.
  • You demonstrate executive presence and can engage credibly with C-level executives, particularly General Counsels and Legal Operations leaders, serving as a strategic thought partner on transformation initiatives.
  • You have experience with AI platforms and tools in the legal space (Harvey, Legora, DraftPilot, or similar GenAI platforms) or can quickly develop expertise in new technologies.
  • You possess strong analytical and problem-solving skills, with the ability to understand complex legal workflows and identify opportunities for AI-driven optimization.
  • You are an exceptional communicator, both written and verbal, with experience creating executive-level presentations, proposals, and business cases. You're highly proficient in PowerPoint, Excel, and CRM systems like Salesforce.
  • You thrive in a fast-paced, entrepreneurial environment and are energized by the opportunity to build something new. You're comfortable with ambiguity and can create structure where none exists.
  • You are willing to travel up to 30% to meet with clients, attend industry events, and support key implementations.
  • You are legally eligible to work in the United States.

Preferred Qualifications:

  • MBA, JD, or advanced degree in a relevant field
  • Experience with contract lifecycle management, legal research platforms, or document automation technologies
  • Track record of thought leadership in legal technology or AI, including speaking engagements, publications, or industry recognition
  • Experience managing or overseeing the delivery of technology implementations or transformation projects
  • Existing relationships within the legal industry, particularly with Fortune 500 legal departments

Axiom's total rewards philosophy is to be transparent and equitable with all job candidates. The annual base salary for this role is $205,000 and you will be eligible to participate in our cash bonus plan which on target would be 25% of your base salary for a Director role in the IT team. You can also participate in our benefits programs that include healthcare, life and disability coverage, 401K with company match, paid sick and personal time off, paid parental leave and more. Please note that the final compensation is determined by several considerations, including the quality of your experience and expertise, your ability to immediately contribute to Axiom, your potential to move up to the next level, the market you are located in, and other business considerations.

Accommodation for Individuals with Disabilities:

Upon request and consistent with applicable laws, Axiom will attempt to provide reasonable accommodations for individuals with disabilities who require an accommodation to participate in the application process. To request an accommodation to complete the application form, please contact us at [email protected] and include "Applicant Accommodation" in the subject line.

Posted 2025-11-24

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