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About This Role
The AI Solutions Analyst will work directly with lawyers and business professionals to understand how they work, then build the prompts, instructions, and AI\-powered workflows that make Claude Cowork and ChatGPT Custom GPTs genuinely useful when working day\-to\-day tasks.
This role is part prompt architect, part workflow designer, part trainer. The analyst will craft sophisticated system prompts and multi\-step workflows tailored to specific legal tasks — contract review, research, drafting, matter summaries, and configure Custom GPTs and Cowork automations that connect to the firm’s documents and data. Equally important is the ability to coach users so they get the most from these tools independently.
- Design and maintain a library of complex, production\-grade system prompts for Claude Cowork and ChatGPT Custom GPTs tailored to legal tasks: contract review, clause extraction, due diligence checklists, legal research summaries, and matter intake.
- Build multi\-step prompt workflows that chain instructions, handle conditional logic, and produce structured outputs (tables, memos, checklists) formatted for attorney consumption.
- Configure and maintain Custom GPTs with firm\-specific instructions, knowledge file uploads (precedent packs, playbooks, style guides), and actions that connect to internal document stores and matter management systems.
- Set up and optimize Claude Cowork automations that route tasks, process uploaded documents, and deliver AI\-assisted outputs within existing team workflows.
- Conduct deep\-dive discovery sessions with practice groups to map current workflows, identify friction points, and translate attorney needs into precise AI task specifications.
- Run structured prompt testing and evaluation cycles — comparing outputs across model versions, prompt variants, and edge cases — to maintain quality and consistency standards.
- Deliver hands\-on training sessions and workshops for attorneys and staff; build self\-serve guides, prompt templates, and a firm\-wide prompt library they can adapt independently.
- Act as internal expert and escalation point for AI tool questions; troubleshoot underperforming prompts and continuously refine based on user feedback.
- Stay current on new capabilities in Claude, GPT\-4o, and emerging models; proactively identify and prototype features (deep research, file analysis, voice, computer use) that add value for legal users.
- Maintain responsible AI usage guidelines; flag prompt patterns that risk hallucination, data leakage, or outputs unsuitable for client\-facing use.
Education and Experience:
Required:
- Bachelor’s degree in Business, Information Systems, Computer Science, Engineering, or a related field.
- A minimum of 2 years of relevant professional experience.
- Experience with agile methodologies and familiarity with product management tools (e.g., Jira, Confluence, or similar).
Other Skills and Abilities:
The following will also be required of the successful candidate:
- Strong organizational skills
- Strong attention to detail
- Good judgment
- Strong interpersonal communication skills
- Strong analytical and problem\-solving skills
- Able to work harmoniously and effectively with others
- Able to preserve confidentiality and exercise discretion
- Able to work under pressure
- Able to manage multiple projects with competing deadlines and priorities
\#LI\-Hybrid
\#LI\-OE1
Applicants must be authorized to work in the United States without the need for employer sponsorship, now or in the future
The target salary range for this role is:
$85,000 \- $108,000 if located in Illinois.
Salaries vary by location and are based on numerous factors, including, but not limited to, the relevant market, skills, experience, and education of the selected candidate. Our compensation package also includes bonus eligibility and a comprehensive benefits program. Benefits information can be found at Sidley.com/Benefits .
To perform this job successfully, an individual must be able to perform the Duties and Responsibilities above satisfactorily and meet the requirements. The requirements listed above are representative of the minimum knowledge, skill, and/or ability required. Reasonable accommodations will be made to enable individuals with disabilities to perform the essential functions of the job. If you need such an accommodation, please email [email protected] (current employees should contact Human Resources).
Sidley Austin LLP is an Equal Opportunity Employer.
Salary Context
This $85K-$108K range is in the lower quartile for AI/ML Engineer roles in our dataset (median: $180K across 1937 roles with salary data).
View full AI/ML Engineer salary data →Role Details
About This Role
AI/ML Engineers build and deploy machine learning models in production. They work across the full ML lifecycle: data pipelines, model training, evaluation, and serving infrastructure. The role has evolved significantly over the past two years. Where ML Engineers once spent most of their time on model architecture, the job now tilts heavily toward inference optimization, cost management, and integrating LLM capabilities into existing systems. Companies want engineers who can ship production systems, and the experimenter-only role is fading fast.
Day-to-day, you're writing training pipelines, debugging data quality issues, setting up evaluation frameworks, and figuring out why your model performs differently in staging than it did on your dev set. The best ML engineers are obsessive about reproducibility and measurement. They instrument everything. They know that a model is only as good as the data feeding it and the infrastructure serving it.
Across the 3,823 AI roles we're tracking, AI/ML Engineer positions make up 69% of the market. At Sidley Austin, this role fits into their broader AI and engineering organization.
Demand for AI/ML Engineers has been strong and consistent. Unlike some AI roles that spike with hype cycles, ML engineering is a foundational need. Every company deploying AI models needs people who can keep them running, and the gap between research prototypes and production systems keeps growing.
What the Work Looks Like
A typical week might include: debugging a data pipeline that's silently dropping 3% of training examples, running A/B tests on a new model version, writing documentation for a feature flag system that lets you roll back model deployments, and reviewing a junior engineer's PR for a new evaluation metric. Meetings tend to be cross-functional since ML touches product, engineering, and data teams.
Demand for AI/ML Engineers has been strong and consistent. Unlike some AI roles that spike with hype cycles, ML engineering is a foundational need. Every company deploying AI models needs people who can keep them running, and the gap between research prototypes and production systems keeps growing.
Skills Required
Python and PyTorch dominate the requirements. Most roles expect experience with cloud platforms (AWS, GCP, or Azure) and familiarity with ML frameworks like TensorFlow or JAX. RAG (Retrieval-Augmented Generation) has become a top-3 skill requirement as companies integrate LLMs into their products. Docker and Kubernetes show up in about a third of postings, reflecting the production focus of the role.
Beyond the core stack, employers increasingly want experience with experiment tracking tools (MLflow, Weights & Biases), feature stores, and vector databases. Fine-tuning experience is valuable but less common than you'd think from reading Twitter. Most production LLM work is RAG and prompt engineering, not fine-tuning. If you have both, you're in a strong position.
Companies that are serious about AI/ML hiring tend to post specific infrastructure details in the job description: the frameworks they use, their model serving stack, their data pipeline tools. Vague postings that just say 'ML experience required' without specifics are often companies that haven't figured out what they need yet.
Compensation Benchmarks
AI/ML Engineer roles pay a median of $181,170 based on 12,692 positions with disclosed compensation. Mid-level AI roles across all categories have a median of $165,000. This role's midpoint ($96K) sits 47% below the category median. Disclosed range: $85K to $108K.
Across all AI roles, the market median is $200,100. Top-quartile compensation starts at $253,500. The 90th percentile reaches $307,500. For comparison, the highest-paying categories include AI Engineering Manager ($275,000) and AI Safety ($274,200). By seniority level: Entry: $97,880; Mid: $165,000; Senior: $227,400; Director: $247,800; VP: $250,000.
Sidley Austin AI Hiring
Sidley Austin has 1 open AI role right now. They're hiring across AI/ML Engineer. Based in Chicago, IL, US. Compensation range: $108K - $108K.
Location Context
AI roles in Chicago pay a median of $201,225 across 312 tracked positions.
Career Path
Common paths into AI/ML Engineer roles include Data Scientist, Software Engineer, Research Engineer.
From here, career progression typically leads toward ML Architect, AI Engineering Manager, Principal ML Engineer.
The fastest path into ML engineering is through software engineering with a self-directed ML education. A CS degree helps, but production engineering skills matter more than academic credentials. Build something that works, deploy it, and measure it. That portfolio project is worth more than a Coursera certificate. For career growth, the fork comes around the senior level: go deep on technical complexity (staff/principal track) or move into managing ML teams.
What to Expect in Interviews
Expect system design questions around ML pipelines: how you'd build a training pipeline for a specific use case, handle data drift, or design A/B testing infrastructure for model deployments. Coding rounds typically involve Python, with emphasis on data manipulation (pandas, numpy) and algorithm implementation. Take-home assignments often ask you to build an end-to-end ML pipeline from raw data to deployed model.
When evaluating opportunities: Companies that are serious about AI/ML hiring tend to post specific infrastructure details in the job description: the frameworks they use, their model serving stack, their data pipeline tools. Vague postings that just say 'ML experience required' without specifics are often companies that haven't figured out what they need yet.
AI Hiring Overview
The AI job market has 3,823 open positions tracked in our dataset. By seniority: 112 entry-level, 1,798 mid-level, 1,516 senior, and 397 leadership roles (Director, VP, C-Level). Remote roles make up 15% of the market (590 positions). The remaining 3,217 roles require on-site or hybrid attendance.
The market median for AI roles is $200,100. Top-quartile compensation starts at $253,500. The 90th percentile reaches $307,500. Highest-paying categories: AI Engineering Manager ($275,000 median, 41 roles); AI Safety ($274,200 median, 55 roles); Research Engineer ($260,000 median, 434 roles).
Demand for AI/ML Engineers has been strong and consistent. Unlike some AI roles that spike with hype cycles, ML engineering is a foundational need. Every company deploying AI models needs people who can keep them running, and the gap between research prototypes and production systems keeps growing.
The AI Job Market Today
The AI job market spans 3,823 open positions across 15 role categories. The largest categories by volume: AI/ML Engineer (2,629), Data Scientist (322), AI Software Engineer (279). These three account for the majority of open positions, though smaller categories often have higher per-role compensation because of specialized skill requirements.
The seniority mix tells a story about where AI teams are in their maturity. Entry-level roles (112) are outnumbered by mid-level (1,798) and senior (1,516) positions, reflecting that most companies are past the 'build a team from scratch' phase and need experienced engineers who can ship production systems. Leadership roles (Director, VP, C-Level) total 397 positions, representing the bottleneck between technical execution and organizational strategy.
Remote work availability sits at 15% of all AI roles (590 positions), with 3,217 requiring on-site or hybrid attendance. The remote share has stabilized after the post-pandemic correction. Senior and specialized roles (Research Scientist, ML Architect) are more likely to be remote-eligible than entry-level positions, partly because experienced hires have more negotiating power and partly because these roles require less hands-on mentorship.
AI compensation is structured in clear tiers. The market median sits at $200,100. Top-quartile roles start at $253,500, and the 90th percentile reaches $307,500. These figures include base salary with disclosed compensation. Total compensation (including equity, bonuses, and sign-on) runs 20-40% higher at companies that offer those components.
Category matters for compensation. AI Engineering Manager roles lead at $275,000 median, while Prompt Engineer roles sit at $140,000. The spread between highest and lowest-paying categories reflects the premium on specialized technical skills versus broader analytical roles.
The most in-demand skills across all AI postings: Python (1,979 postings), Aws (1,190 postings), Azure (899 postings), Rag (839 postings), Gcp (726 postings), Pytorch (595 postings), Prompt Engineering (595 postings), Claude (540 postings). Python dominates, appearing in the vast majority of role descriptions regardless of category. Cloud platform experience (AWS, GCP, Azure) is the second most common requirement. The newer entrants to the top skills list (RAG, vector databases, LLM APIs) reflect the shift from traditional ML toward generative AI applications.
Frequently Asked Questions
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