Digital Process Jobs in Chicago, IL (NOW HIRING)

Job Description

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 leaves@acrisure.com.

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.