Senior AI transformation lead (Central)

WRITER•Chicago, IL
•$184,000 - $225,000•Hybrid

About The Position

WRITER is seeking a visionary, execution-oriented AI transformation lead to partner with strategic Fortune 100 accounts. The role goes beyond software implementation, helping large organizations rethink how they work and adopt AI-first operating models. It connects business strategy with technology, translating the WRITER platform into measurable P&L impact and guiding executives from AI experimentation to full-scale value realization. The role also contributes to WRITER’s product roadmap and helps establish its enterprise AI transformation playbook. This is a hybrid position based out of WRITER’s Chicago or Austin hubs. The position reports to the director of AI transformation and success.

Requirements

  • More than 10 years of experience in strategic account management or transformation consulting for Fortune 50–100 companies.
  • Proven track record of building C-suite relationships and leading large-scale transformations.
  • Expertise in change management and strategic thinking, including setting a vision, defining frameworks, and translating capabilities into measurable outcomes and P&L impact.
  • Exceptional executive presence and communication skills, including the ability to deliver composed presentations to boards.
  • Ability to proactively orchestrate cross-functional teams and resolve conflicts.
  • Curious mindset and active listening style.
  • Intrinsic motivation to do high-quality work while aligning with WRITER’s values to Connect, Challenge, and Own.

Nice To Haves

  • Professional background in management consulting or strategy advisory.

Responsibilities

  • Manage a customer portfolio and lead ROI and value initiatives in partnership with customer success managers focused on adoption strategy.
  • Act as a strategic transformation partner for Fortune 50–100 customers, setting a vision and defining the jobs-to-be-done (JTBD) framework with leadership teams to drive AI adoption.
  • Build C-suite relationships and serve as a trusted advisor who makes AI a priority for executives.
  • Lead value realization and ROI delivery, using surveys and interviews to analyze and frame the P&L impact of AI adoption in business reviews.
  • Orchestrate complex cross-functional programs involving multiple stakeholders, managing customer teams, escalations, risk mitigation, and program updates.
  • Identify and drive expansion opportunities by anticipating customer needs and partnering with sales on cross-sell and upsell initiatives.
  • Scale transformation best practices by creating and systematizing decks, frameworks, and communications for the wider team.

Benefits

  • Generous paid time off and company holidays.
  • Medical, dental, and vision coverage for employees and their families.
  • 16 weeks of paid parental leave for all parents.
  • Fertility and family planning support.
  • Early-detection cancer testing through Galleri.
  • Flexible spending account and dependent care FSA options.
  • Health savings account for eligible plans, with a company contribution.
  • Annual wellness stipend for expenses such as gym, massage or chiropractic care, and personal training.
  • Annual learning and development stipend.
  • Company-wide and team off-sites.
  • Competitive compensation.
  • Company stock options.
  • 401(k).
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