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Job Description
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About Acrisure
As a global fintech leader, Acrisure empowers millions of ambitious businesses and individuals with the right solutions to grow boldly forward. Bringing cutting\-edge technology and top\-tier human support together, we connect clients with customized solutions across a range of insurance, reinsurance, payroll, benefits, cybersecurity, mortgage services – and more.
In the last twelve years, Acrisure has grown in revenue from $38 million to almost $5 billion and employs over 19,000 colleagues in more than 20 countries. Acrisure was built on entrepreneurial spirit. Prioritizing leadership, accountability, and collaboration, we equip our teams to work at the highest levels possible.
Job Summary
Acrisure is seeking a Senior Director of Digital Experience \& AI to build and lead the organization's Digital Experience function. Reporting to the CMO, this leader will build the digital operating system for Acrisure Marketing, creating the capabilities, platforms, operating models, and ways of working that enable the organization to scale, measure impact, and compete in an AI\-driven future.
The role oversees website strategy and operations, analytics, AI enablement, digital discoverability (SEO/AEO), and customer experience optimization, ensuring marketing is increasingly data\-driven, AI\-enabled, and connected to business results. This leader will serve as the architect of Acrisure's Digital Experience pillar, building and leading a team that combines web strategy, analytics, AI enablement, and discoverability under a unified vision.
Responsibilities:
Digital Experience Strategy \& Transformation
- Define and execute Acrisure's enterprise digital experience vision, strategy, and roadmap across all digital channels.
- Lead customer journey optimization efforts, ensuring seamless experiences across the buyer and client lifecycle.
- Partner with executive leadership to align digital experience investments with enterprise growth objectives.
- Establish governance, processes, and best practices that enable consistent, measurable, and scalable digital experiences across the organization.
- Develop personalization and customer journey strategies that deliver relevant, connected experiences across web, content, campaigns, and emerging digital channels.
- Own digital performance across engagement, conversion, customer experience, and business impact, identifying opportunities to improve outcomes through digital innovation and AI.
Digital Platforms \& Experience
- Own Acrisure's web ecosystem, including strategy, governance, performance, optimization, and ongoing evolution.
- Partner with Product and Technology teams to improve platform capabilities, user experience, accessibility, and digital performance.
- Develop scalable operating models, workflows, and prioritization frameworks that improve execution across digital initiatives.
- Ensure digital properties support business objectives while delivering intuitive and engaging customer experiences.
- Oversee agency, technology, and vendor partnerships that support the digital experience roadmap.
- Drive conversion optimization initiatives that improve engagement, lead generation, customer self\-service, and business performance across digital properties.
AI Transformation \& Enablement
- Lead the transformation of Marketing through AI, identifying opportunities to improve productivity, scale expertise, accelerate execution, enhance customer experiences, and create competitive advantage.
- Partner with marketing teams to evaluate manual or inefficient workflows and determine where AI tools, automation, or process redesign can improve speed, quality, and scale.
- Translate business needs into clear use cases, success metrics, and implementation plans that drive measurable business value.
- Lead the development and adoption of AI powered tools, workflows, playbooks, and best practices that enable teams to work more efficiently while maintaining brand, legal, and operational standards.
- Champion AI literacy across the Marketing organization through enablement, training, education, and hands on partnership with teams and leaders.
- Partner with Technology, Data, Legal, and Compliance teams to ensure AI initiatives are secure, responsible, and aligned with enterprise governance standards.
- Drive organizational adoption of AI\-enabled ways of working through change management, enablement, governance, and executive partnership.
Digital Discoverability, Insights \& Growth
- Lead Acrisure's enterprise SEO and AEO strategy to maximize visibility across traditional search engines, answer engines, and emerging AI powered discovery platforms.
- Develop content, technical optimization, and structured data strategies that strengthen Acrisure's authority, discoverability, and digital presence at both the brand and local level.
- Establish measurement frameworks for organic growth, search performance, AI visibility, engagement, and customer acquisition.
- Monitor evolving search, AI, and content consumption trends to ensure Acrisure remains well positioned across digital ecosystems.
- Partner with content, brand, and business stakeholders to ensure Acrisure's expertise, solutions, and thought leadership are effectively surfaced across search and AI driven experiences.
Build \& Lead the Digital Experience Organization
- Serve as Acrisure's digital experience champion, raising the bar for innovation, customer experience, and operational excellence.
- Establish scalable processes, operating rhythms, and performance metrics that support growth and continuous improvement.
- Partner with the CMO and executive leadership team to connect digital experience initiatives directly to customer engagement, business growth, and brand performance.
- Accountable for the impact of digital experience initiatives on engagement, conversion, discoverability, operational efficiency, and revenue growth.
- Recruit, develop, and retain specialized talent while creating a culture of innovation, experimentation, accountability, and continuous learning.
Required Qualifications:
- 15\+ years of experience in digital experience, digital strategy, customer experience, digital product, or digital marketing leadership roles.
- Proven track record of building and scaling enterprise digital programs and high performing teams.
- Experience leading large scale website transformations, digital platforms, and customer journey optimization initiatives.
- Demonstrated success building and leading teams across digital experience, analytics, digital platforms, customer experience optimization, and digital discoverability.
- Strong understanding of digital discoverability, including SEO, content optimization, structured data, and emerging AI\-driven search environments.
- Strong understanding of AI technologies, large language models, and emerging digital engagement trends.
- Experience leveraging analytics, data, and customer insights to drive strategic decision making.
- Proven ability to influence executive stakeholders and lead cross functional initiatives in complex organizations.
- Experience managing agency, technology, and vendor ecosystems.
- Demonstrated success leading organizational change and driving adoption of new technologies, processes, and ways of working across large, matrixed organizations.
- Experience partnering closely with Product, Engineering, Data, Revenue, and Technology teams to deliver customer\-centric digital experiences and enterprise technology initiatives.
- Experience building new functions, teams, and operating models in high\-growth or transformational environments.
- Experience in fintech, financial services, insurance, or other complex regulated industries is preferred.
Why this Role Matters
Acrisure has built one of the most remarkable growth stories in fintech. Now it's time to build the digital experience that matches it. The Senior Director of Digital Experience \& AI will build the platforms, capabilities, and experiences that shape how customers discover and engage with Acrisure. This role will play a critical part in accelerating growth and positioning Acrisure to win in an AI\-driven future.
\#LI\-MF2
Pay Details:
The base compensation range for this position is $235,620 \- $318,780\. This range reflects Acrisure's good faith estimate at the time of this posting. Placement within the range will be based on a variety of factors, including but not limited to skills, experience, qualifications, location, and internal equity.Candidates should be comfortable with an on\-site presence to support collaboration, team leadership, and cross\-functional partnership.
Why Join Us:
At Acrisure, we’re building more than a business, we’re building a community where people can grow, thrive, and make an impact. Our benefits are designed to support every dimension of your life, from your health and finances to your family and future.
Making a lasting impact on the communities it serves, Acrisure has pledged more than $22 million through its partnerships with Corewell Health Helen DeVos Children's Hospital in Grand Rapids, Michigan, UPMC Children's Hospital in Pittsburgh, Pennsylvania and Blythedale Children's Hospital in Valhalla, New York.
Employee Benefits
We also offer our employees a comprehensive suite of benefits and perks, including:
- Physical Wellness: Comprehensive medical insurance, dental insurance, and vision insurance; life and disability insurance; fertility benefits; wellness resources; and paid sick time.
- Mental Wellness: Generous paid time off and holidays; Employee Assistance Program (EAP); and a complimentary Calm app subscription.
- Financial Wellness: Immediate vesting in a 401(k) plan; Health Savings Account (HSA) and Flexible Spending Account (FSA) options; commuter benefits; and employee discount programs.
- Family Care: Paid maternity leave and paid paternity leave (including for adoptive parents); legal plan options; and pet insurance coverage.
- … and so much more!
*This list is not exhaustive of all available benefits. Eligibility and waiting periods may apply to certain offerings. Benefits may vary based on subsidiary entity and geographic location.*
Acrisure is an Equal Opportunity Employer. We consider qualified applicants without regard to race, color, religion, sex, national origin, disability, or protected veteran status. Applicants may request reasonable accommodation by contacting *[email protected]*.
Final candidates will be required to complete post\-offer verification processes related to the role and in accordance with applicable laws.
California Residents: Learn more about our privacy practices for applicants by visiting the Acrisure California Applicant Privacy Policy.
Recruitment Fraud: Please visit here to learn more about our Recruitment Fraud Notice.
Welcome, your new opportunity awaits you.
Salary Context
This $235K-$318K range is above the 75th percentile for AI/ML Engineer roles in our dataset (median: $175K across 2162 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 4,317 AI roles we're tracking, AI/ML Engineer positions make up 70% of the market. At Acrisure LLC, 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 in Demand for This Role
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 $214,900 based on 6,420 positions with disclosed compensation. Director-level AI roles across all categories have a median of $274,554. This role's midpoint ($277K) sits 29% above the category median. Disclosed range: $235K to $318K.
Across all AI roles, the market median is $215,000. Top-quartile compensation starts at $266,300. The 90th percentile reaches $320,790. For comparison, the highest-paying categories include AI Safety ($287,500) and Research Engineer ($272,100). By seniority level: Entry: $110,000; Mid: $194,400; Senior: $227,400; Director: $274,554; VP: $241,000.
Acrisure LLC AI Hiring
Acrisure LLC has 1 open AI role right now. They're hiring across AI/ML Engineer. Based in Chicago, IL, US. Compensation range: $318K - $318K.
Location Context
AI roles in Chicago pay a median of $192,900 across 197 tracked positions. That's 10% below the national median.
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 4,317 open positions tracked in our dataset. By seniority: 138 entry-level, 2,071 mid-level, 1,655 senior, and 453 leadership roles (Director, VP, C-Level). Remote roles make up 15% of the market (635 positions). The remaining 3,657 roles require on-site or hybrid attendance.
The market median for AI roles is $215,000. Top-quartile compensation starts at $266,300. The 90th percentile reaches $320,790. Highest-paying categories: AI Safety ($287,500 median, 34 roles); Research Engineer ($272,100 median, 227 roles); AI Engineering Manager ($244,000 median, 23 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 4,317 open positions across 15 role categories. The largest categories by volume: AI/ML Engineer (3,004), Data Scientist (345), AI Software Engineer (309). 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 (138) are outnumbered by mid-level (2,071) and senior (1,655) 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 453 positions, representing the bottleneck between technical execution and organizational strategy.
Remote work availability sits at 15% of all AI roles (635 positions), with 3,657 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 $215,000. Top-quartile roles start at $266,300, and the 90th percentile reaches $320,790. 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 Safety roles lead at $287,500 median, while Prompt Engineer roles sit at $145,000. 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 (2,249 postings), Aws (1,224 postings), Azure (938 postings), Rag (915 postings), Gcp (660 postings), Pytorch (640 postings), Prompt Engineering (624 postings), Kubernetes (559 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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