Back to jobs
New

Head of Generative AI Technology

Remote, USA

About Stitch Fix, Inc.

Stitch Fix (NASDAQ: SFIX) is the leading online personal styling service that helps people discover the styles they will love that fit perfectly so they always look - and feel - their best. Few things are more personal than getting dressed, but finding clothing that fits and looks great can be a challenge. Stitch Fix solves that problem. By pairing expert stylists with best-in-class AI and recommendation algorithms, the company leverages its assortment of exclusive and national brands to meet each client's individual tastes and needs, making it convenient for clients to express their personal style without having to spend hours in stores or sifting through endless choices online. Stitch Fix, which was founded in 2011, is headquartered in San Francisco.

About the Role

We’re seeking a Head of Generative AI to lead Stitch Fix’s strategy and execution for applied GenAI technologies. This person will be responsible for identifying and unlocking opportunities to drive business value through generative AI — from enhancing our client experience to transforming internal productivity.

This is a highly cross-functional leadership role that requires deep technical expertise, strong product instincts, and excellent soft skills. You’ll partner with executive stakeholders, build and lead a team of subject matter experts, and play a key role in shaping Stitch Fix’s future through innovative applications of AI.

You're excited about this opportunity because you will…

  • Define and drive the generative AI strategy across Stitch Fix, ensuring alignment with business goals and priorities.
  • Serve as the internal expert on GenAI technologies — from foundational models to practical use cases across content generation, personalization, automation, and more.
  • Build, lead, and mentor a high-performing team of AI practitioners with a consultative, impact-oriented approach.
  • Partner cross-functionally with product, engineering, data science, styling, marketing, and operations to surface use cases and develop scalable solutions.
  • Stay ahead of the curve on the fast-moving GenAI landscape — continuously evaluating emerging technologies, vendors, and open-source tools.
  • Ensure responsible, ethical, and secure use of generative AI across all applications.
  • Translate complex technical concepts into accessible language to influence decision-makers at all levels.
  • Overcoming obstacles of adoption and scaling of Artificial Intelligence across multiple industries and geographies and ensuring client success

We’re excited about you because…

  • You have 10+ years of experience in AI, machine learning, or related technical domains.
  • You have  at least 3 years of hands-on experience with software engineering and at least one year specifically with modern LLMs (e.g., Claude, GPT-4, Llama 3) OR 3+ years working more generally in AI/ML.
  • You possess strong knowledge of Python, TensorFlow, PyTorch, LangChain, and AI/ML cloud services.
  • You have a deep understanding of RAGExperience with multi-modal AI systems (text, numerical data, and structured documents)
  • You possess expertise in modern prompting techniques (e.g., Tree of Thoughts, Constitutional AI, Agent protocols) architectures and experience optimizing retrieval pipelines.
  • You have a proven track record of developing and deploying GenAI solutions in a business setting.
  • You have strong product intuition and a user-centered mindset — you’re as passionate about the "why" as you are about the "how."
  • You are an experienced people leader, able to attract top talent and create a strong team culture of curiosity, collaboration, and delivery.
  • You are adept at communicating across technical and non-technical audiences; able to influence at all levels, including executive leadership.
  • You have an entrepreneurial spirit with the ability to think like an owner and operate in ambiguity.
  • Strong preference for candidates with experience applying AI in consumer-facing tech or retail environments.
  • Above all else, you are bright, kind and motivated by challenge.

Why you'll love working at Stitch Fix...

  • We are a group of bright, kind people who are motivated by challenge. We value integrity, innovation and trust. You’ll bring these characteristics to life in everything you do at Stitch Fix.
  • We cultivate a community of diverse perspectives— all voices are heard and valued.
  • We are an innovative company and leverage our strengths in fashion and tech to disrupt the future of retail. 
  • We win as a team, commit to our work, and celebrate grit together because we value strong relationships.
  • We boldly create the future while keeping equity and sustainability at the center of all that we do. 
  • We are the owners of our work and are energized by solving problems through a growth mindset lens. We think broadly and creatively through every situation to create meaningful impact.
  • We offer comprehensive compensation packages and inclusive health and wellness benefits.

Compensation and Benefits

This role will receive a competitive salary, benefits, and equity. The salary for US-based employees hired into this role will be aligned with the range below, which includes our three geographic areas. A variety of factors are considered when determining someone’s compensation–including a candidate’s professional background, experience, location, and performance. This position is eligible for an annual bonus, and new hire and ongoing grants of restricted stock units, depending on employee and company performance. In addition, the position is eligible for medical, dental, vision, and other benefits. Applicants should apply via our internal or external careers site.

Salary Range

$219,600 - $323,000 USD

This link leads to the machine readable files that are made available in response to the federal Transparency in Coverage Rule and includes negotiated service rates and out-of-network allowed amounts between health plans and healthcare providers. The machine-readable files are formatted to allow researchers, regulators, and application developers to more easily access and analyze data.

Please review Stitch Fix's US Applicant Privacy Policy and Notice at Collection here: https://stitchfix.com/careers/workforce-applicant-privacy-policy

Apply for this job

*

indicates a required field

Resume/CV*

Accepted file types: pdf, doc, docx, txt, rtf

Cover Letter

Accepted file types: pdf, doc, docx, txt, rtf

Have you previously been employed by Stitch Fix in any capacity? *
Select...
Select...

US Demographic Questionnaire

Voluntary Self-Identification

Stitch Fix is committed to equal employment regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, gender identity, age, citizenship, marital status, disability or Veteran status. Disclosure is voluntary, and this information will be kept confidential in compliance with Stitch Fix's Recruiting Privacy Notice.

Protected Veteran Qualification

Stitch Fix's hiring practices comply with federal and state laws regarding veteran hiring preferences, and we recognize veterans of all categories, including disabled veterans, recently separated veterans, active-duty wartime or campaign badge veterans, Armed Forces service medal veterans, and other protected veterans.

If you believe you are a member of any of the categories of protected veterans listed above, please indicate by checking the appropriate box below. Your decision to provide the relevant information is purely voluntary on your part, and refusal to provide such information will not subject you to any adverse treatment. The information will not be used in a manner inconsistent with VEVRAA, as amended.

Voluntary Self-identification of disability

Why are you being asked to complete this form?

Identifying yourself as an individual with a disability is voluntary, and we hope that you will choose to do so. Your answer will be maintained confidentially and not be seen by selecting officials or anyone else involved in making personnel decisions. Completing the form will not negatively impact you in any way, regardless of whether you have self-identified in the past. 

How do you know if you have a disability?

You are considered to have a disability if you have a physical or mental impairment or medical condition that substantially limits a major life activity, or if you have a history or record of such an impairment or medical condition.

Disabilities include, but are not limited to:

  • Autism
  • Autoimmune disorder, for example, lupus, fibromyalgia, rheumatoid arthritis, or HIV/AIDS
  • Blind or low vision
  • Cancer
  • Cardiovascular or heart disease
  • Celiac disease
  • Cerebral palsy
  • Deaf or hard of hearing
  • Depression or anxiety
  • Diabetes
  • Epilepsy
  • Gastrointestinal disorders, for example, Crohn's Disease, or irritable bowel syndrome
  • Intellectual disability
  • Missing limbs or partially missing limbs
  • Nervous system condition for example, migraine headaches, Parkinson’s disease, or Multiple sclerosis (MS)
  • Psychiatric condition, for example, bipolar disorder, schizophrenia, PTSD, or major depression
Select...
Select...
Select...
Select...