Strategic AI transformation lead

About the role

WRITER is actively seeking a visionary and execution-oriented AI transformation lead to serve as a high-impact strategic partner for the world's most demanding Fortune 100 enterprises. In this pivotal role, you will be the primary architect of change, tasked with helping these organizations fundamentally rethink their operational models and move beyond incremental improvements to achieve transformative AI-driven value. You will operate at the critical intersection of business strategy and technology innovation, acting as the trusted advisor who translates the advanced capabilities of the WRITER platform into tangible, measurable P&L impact for executive leadership. This position represents a rare opportunity to build the playbook for enterprise AI transformation from the ground up, defining not just how the technology is used, but how it reshapes the very way these companies operate and compete. You will work hand-in-hand with C-suite leaders, guiding them through the journey from initial AI experimentation to full-scale, organization-wide value realization and operationalization. Your insights and strategic direction will directly influence WRITER's product evolution and establish new benchmarks for how the world's largest brands leverage superintelligence to expand human capacity and drive growth. This role is based in a hybrid capacity within our Chicago and Austin hubs, requiring collaboration with a distributed team dedicated to rapid innovation. You will report directly to the director of AI transformation and success, positioning you at the heart of our strategic initiatives.

This is more than a management position; it is a leadership mandate to own the end-to-end transformation journey for key accounts. You will be responsible for defining the vision, building the business case, and shepherding the implementation of AI strategies that deliver real, measurable outcomes. You will partner closely with customer success managers, aligning adoption strategies with value realization goals to ensure technology investments translate into business results. Your work will involve conducting deep-dive analyses, synthesizing complex information, and framing the P&L impact of AI initiatives in a language that resonates with boards and executive committees. You will be the driving force behind making AI a permanent strategic priority for these executives, securing their buy-in and commitment to long-term digital transformation. Furthermore, you will proactively identify and unlock new expansion opportunities, acting as the bridge between customer needs and WRITER's evolving platform capabilities. By documenting and scaling your methodologies, you will create reusable frameworks that empower the entire transformation team, ensuring best practices are replicated and success is not siloed. Ultimately, your success will be measured by the depth of transformation you enable and the sustained business value delivered to our most strategic partners.

Key facts

What you'll do

• Orchestrate end-to-end strategic transformation programs for a portfolio of Fortune 50-100 clients, managing complex cross-functional initiatives from initial scoping through full-scale deployment and value optimization.
• Serve as the primary transformation strategist and trusted advisor, developing and articulating a future-state vision that aligns with C-suite priorities and defines the journey to an AI-first operating model.
• Build and leverage deep C-suite relationships to elevate the strategic importance of AI initiatives, positioning WRITER as the indispensable partner for executive-level digital transformation.
• Lead the development and execution of ROI-focused business cases, utilizing surveys, interviews, and data analysis to quantify the P&L impact and strategic value of AI adoption for each key account.
• Translate the technical capabilities of the WRITER platform into clear, compelling narratives that demonstrate tangible business outcomes and drive executive sponsorship and adoption.
• Proactively identify, evaluate, and drive expansion opportunities by anticipating evolving customer needs and collaborating with sales teams on strategic cross-sell and upsell initiatives.
• Orchestrate complex stakeholder ecosystems, managing diverse customer teams, mitigating risks, resolving escalations, and providing timely, high-quality program updates to all relevant parties.
• Scale and institutionalize transformation best practices by creating reusable assets, including decks, frameworks, and communication templates, to accelerate success across the wider enterprise team.
• Partner with the customer success team to refine adoption strategies, ensuring seamless integration of the WRITER platform and maximizing long-term value realization and retention.
• Analyze program performance and derive actionable insights to continuously optimize transformation methodologies and enhance the strategic impact of the AI initiatives.

Requirements

• Possess over 10 years of progressive experience in strategic account management or transformation consulting, with a demonstrated history of success managing Fortune 50-100 enterprise clients.
• Exhibit mastery of change management principles and strategic thinking, with the ability to define a clear vision, establish JTBD frameworks, and translate technical platform capabilities into measurable business outcomes and P&L impact.
• Demonstrate exceptional executive presence and communication skills, capable of delivering composed, high-stakes presentations to boards and C-suite audiences while orchestrating cross-functional teams and resolving complex conflicts.
• Cultivate a deeply curious mindset and an active listening style that builds trust and establishes you as a genuine leader whom clients want to follow and collaborate with closely.
• Bring a strong professional background in management consulting or strategy advisory, providing the necessary expertise to navigate complex business environments and enterprise sales cycles.
• Thrive in a fast-paced, mission-critical environment where you are comfortable with ambiguity and empowered to make high-impact decisions with incomplete information.
• Maintain a high degree of professionalism and integrity, aligning your work ethic and values with WRITER's core values to Connect, Challenge, and Own every initiative.
• Show a proven commitment to meticulous execution and ownership, ensuring that transformation programs are delivered on time, within scope, and with clear accountability for results.
• Embrace a collaborative work style that leverages diverse perspectives, actively partnering with internal stakeholders to drive consensus and achieve shared strategic objectives.
• Demonstrate the ability to manage multiple high-priority initiatives simultaneously while maintaining a sharp focus on quality, detail, and strategic alignment.

Nice to have

• Experience developing and presenting compelling executive-level narratives and business cases to C-suite stakeholders.
• Familiarity with AI platforms and enterprise-scale technology transformation programs.

Practical notes

This role is available as a hybrid position based out of our Chicago and Austin hubs. You will report to the director of AI transformation and success.