We’re looking for a Product Designer, AI to be the connective tissue between Product Design and Engineering. This role sits at the intersection of AI, UX, front‑end implementation, and systems thinking: you turn Figma into robust, reusable code, shape our design system in production, and lay the technical foundations that allow the Design organization to scale.

You’ll build interactive, high‑fidelity prototypes and production‑ready UI components, using AI‑assisted tools to accelerate exploration, prototyping, and iteration. You’ll partner closely with product designers, engineers, and product managers to bring ideas to life quickly, test them with users, and translate strong design intent into scalable implementation and a reliable design‑to‑code pipeline.

This role is onsite based at Shift4's location in Tampa, FL.

Responsibilities

Bridge design and engineering

• Translate design specs, components, and interaction patterns into high‑quality front‑end implementations that can be adopted by engineering teams.
• Work closely with designers to refine interaction details, states, and edge cases, then express them as code, stories, and clear usage guidelines.
• Collaborate with engineers to ensure prototypes align with technical constraints and can transition smoothly toward production.

Prototyping and AI‑assisted workflows

• Build high‑fidelity, interactive prototypes using a mix of design tools, AI prototyping tools (e.g., Claude‑style assistants, Replit, Figma AI), and code.
• Use AI‑assisted tools to rapidly explore ideas, generate UI logic, scaffold components, and iterate faster while maintaining implementation quality and consistency.
• Support UX research by preparing realistic prototypes for testing and iterating quickly based on user feedback and data.

Design System in Code

• Build and maintain the coded design system (components, tokens, utilities) in partnership with design system owners and front‑end leads.
• Ensure a tight mapping between Figma and code so components, variants, and tokens in Figma have clear, predictable equivalents in React/Vue and CSS/Tailwind.
• Establish standards for accessibility, performance, and theming within the component library, and ensure these standards are upheld across teams.

Foundations, tools, and workflows

• Set up and evolve tools, workflows, and repository structures that designers rely on for design‑to‑code (e.g., Storybook, design system sites, sandboxes, playgrounds).
• Define foundational conventions (naming, file structure, contribution guidelines, review processes) that make it easy for designers and engineers to extend the system.
• Partner with platform and DevEx teams to integrate design system components into product repos and CI/CD workflows.

Collaboration and enablement

• Pair with designers to upskill them on implementation realities and with engineers to deepen their understanding of design intent and UX quality.
• Support the adoption of AI prototyping tools and AI‑driven workflows within the design team, helping designers build confidence and fluency with new technologies.
• Create documentation, examples, and “how‑to” guides that help product teams use and extend the design system correctly.

Qualifications

• 8+ years of experience in product design engineering, UX engineering, design technology, UI engineering, or a similar hybrid role with strong knowledge
  of AI tools to accelerate design and development workflows, and interest in shaping how they’re used in design‑to‑code.
• Strong understanding of product design principles, UX patterns, and interaction design, with examples of complex product workflows.
• Strong proficiency in modern front‑end technologies: HTML, CSS, JavaScript/TypeScript, and a component framework such as React.
• Demonstrated experience implementing and maintaining a component library or design system in production.
• Comfortable working in Figma (or equivalent) and mapping design structures (components, variants, tokens) to code architectures.
• Experience building prototypes that go beyond click‑throughs (real data, logic, interactions, and edge cases).
• Experience collaborating closely with product designers, engineers, and product managers to ship user‑facing features in cross‑functional, Agile teams.
• Strong communication skills in English both written and verbal an with the ability to explain both design and technical decisions clearly to diverse stakeholders.
• Experience with design systems and component libraries, including contribution and governance.
•  

Nice‑to‑have

• Experience in a SaaS or payments/fintech environment with complex, data‑heavy interfaces.
• Familiarity with mobile platforms (Android; Kotlin a plus).
• Experience with documentation tools (Storybook, MDX, internal component galleries) and design system governance.
• Comfort with basic backend concepts and APIs sufficient to wire up realistic data into prototypes and component examples.
• Experience exploring and prototyping new interaction models, including AI‑assisted user flows, automated tasks, agent‑based experiences, voice interactions, or hardware‑connected interfaces.

#LI-BN1

Who You Are

You’re a quick learner and can deliver results in accordance with rules and regulations. You catch even the smallest of details and know what they mean for the bigger picture. You’re curious about working with a professional employer organization (PEO) and are confident in your ability to boost operations in this particular space.

As a Health Insurance Underwriting Assistant, you will assist the team of Underwriters with file review and data reconciliation needs, related to prospective customers’ insurance applications. You will be helping others solve problems and will be building something meaningful in an entrepreneurial environment.

Your Success Profile

What You Will Work On

• Review applications and related documentation for acceptability according to underwriting guidelines and determine tasks to be completed before moving forward
• Ensure all required customer documentation is accurate and collected in a timely manner 
• Act as liaison with vendors and internal sales teams through direction of leadership
• Apply principles of logical thinking to define problems, collect data, and create resolutions
• Communicate with company underwriters and internal teams to provide status or additional assistance as needed
• Perform other related duties as assigned

How You Will Do Your Work

As a Health Insurance Underwriting Assistant, how results are achieved is paramount for your success and ultimately result in our success as an organization. In this role, your foundational knowledge, skills, abilities and personal attributes are anchored in the following competencies:

• Detail-oriented - exercises extreme attention to detail; is thorough, accurate, organized, and productive and seeks to understand both the cause and effect of a situation.
• Ethical practice - the ability to integrate core values, integrity and accountability throughout all organizational and business practices.
• Clear communication - the ability to articulate thoughts and express ideas effectively using oral, written, visual and non-verbal communication skills, as well as listening skills to gain understanding.
• Analytical - uses a logical reasoning process to break down and work through a situation or problem to arrive at an outcome.
• Good judgement - the exercise of critical thinking, analyzing and assessing problems and implications, identifying patterns, making connections of underlying issues, understanding risks and developing mitigation strategies, and taking ownership of the outcome.

In addition, all Justworkers focus on aligning their behaviors to our core values known as COGIS. It stands for:

• Camaraderie - Day to day you can be seen working together toward a higher purpose. You like to have fun. You’re an active listener, treat people respectfully, and have a strong desire to know and help others.
• Openness - Your default is to be open. You're willing to share information, understand other perspectives, and consider new possibilities. You’re curious, ask open questions, and are receptive to thoughts and feedback from others.
• Grit - You demonstrate grit by having the courage to commit and persevere. You’re committed, earnest, and dive in to get the job done well with a positive attitude.
• Integrity - Simply put, do what you say and say what you'll do. You’re honest and forthright, have a strong moral compass, and strive to match your words with your actions while leading by example. 
• Simplicity - Be like Einstein: “Everything should be made as simple as possible, but no simpler.”

Qualifications

• Minimum 1 year of experience in a similar role; background in business, finance or economics preferred 
• Demonstrated ability to learn on the fly and apply new information/concepts into practice
• You like working with people and helping others solve problems
• You are flexible and open to changes in processes or teams
• You enjoy fast-paced entrepreneurial environments and want to help build something meaningful

The base wage range for this position based in our Tampa Office is targeted at $26.83 to $29.52 per hour.

#LI-Hybrid #LI-CD1

Who You Are

You are a natural leader with an eye for detail. You proactively seek out answers to improve processes instead of waiting for them to come to you. You know the ins and outs of underwriting health insurance. 

As Director of Health Underwriting, you will be responsible for supporting new business processes, renewal strategies, and year round book of business analysis and reporting for Medical Dental and Vision coverages with multiple carriers. This role will work cross-functionally, partnering with colleagues in Sales, Operations, Customer Success, and Finance.

Your Success Profile

What You Will Work On

• Assist in renewal strategies and reporting support for Medical Dental and Vision Insurance insurance across multiple national carriers.
• Serve as a subject matter expert and provide direction to underwriting staff, sales teams, and other departments on the principles and practices of new business underwriting and rating.
• Drive achievement of business goals through articulation and application of sophisticated underwriting policies, initiatives, and long-term vision.
• Architect and lead high-impact, cross-functional strategic projects, fostering robust partnerships across the organization. Drive innovation and deliver transformative, solution-oriented outcomes that directly advance Justworks’ overarching strategic goals."
• Proactively identify, analyze, and mitigate complex risks that could materially affect financial results, driving sound, unbiased, and strategically informed actions.
• Balance membership growth and profitability targets for specific groups, industries, and/or markets. Collaborates with other constituents on product and pricing strategies.
• Assists team members in handling difficult and/or complex sales/renewal situations.
• Builds strong cross-functional relationships with internal organizations and sales/account management.
• Innovate and champion next-generation underwriting methodologies and processes, continuously optimizing efficiency, accuracy, and profitability by leveraging advanced internal and external resources.
• Demonstrated success in communicating effectively with internal and external partners.
• Perform other related duties as assigned.
• Please note: This is an individual contributor position

How You Will Do Your Work

As a Director of Health Underwriting, how results are achieved is paramount for your success and ultimately result in our success as an organization. In this role, your foundational knowledge, skills, abilities and personal attributes are anchored in the following:

• Detail-oriented - exercises extreme attention to detail; is thorough, accurate, organized, and productive and seeks to understand both the cause and effect of a situation.
• Ethical practice - the ability to integrate core values, integrity and accountability throughout all organizational and business practices.
• Clear communication - the ability to articulate thoughts and express ideas effectively using oral, written, visual and non-verbal communication skills, as well as listening skills to gain understanding.
• Analytical - uses a logical reasoning process to break down and work through a situation or problem to arrive at an outcome.
• Good judgment - the exercise of critical thinking, analyzing and assessing problems and implications, identifying patterns, making connections of underlying issues, understanding risks and developing mitigation strategies, and taking ownership of the outcome.

In addition, all Justworkers focus on aligning their behaviors to our core values known as COGIS. It stands for:

• Camaraderie - Day to day you can be seen working together toward a higher purpose. You like to have fun. You’re an active listener, treat people respectfully, and have a strong desire to know and help others.
• Openness - Your default is to be open. You're willing to share information, understand other perspectives, and consider new possibilities. You’re curious, ask open questions, and are receptive to thoughts and feedback from others.
• Grit - You demonstrate grit by having the courage to commit and persevere. You’re committed, earnest, and dive in to get the job done well with a positive attitude.
• Integrity - Simply put, do what you say and say what you'll do. You’re honest and forthright, have a strong moral compass, and strive to match your words with your actions while leading by example. 
• Simplicity - Be like Einstein: “Everything should be made as simple as possible, but no simpler.”

Qualifications

• 8+ years of progressively responsible and strategic financial underwriting experience, demonstrating deep mastery and extensive insurance industry knowledge.
• Proven track record of successfully leading and influencing large-scale, strategic cross-functional projects with significant organizational impact.
• Skilling in generating and formatting accurate reporting, as well as experience in analyzing and interpreting data to support strategic decision-making. 
• Solid knowledge of other benefit programs (life, dental, medical, etc.) and pricing of related benefits is a plus. 
• Experience working with PEOs is preferred but not required

The base wage range for this position based in our Tampa Office is targeted at $144,615 to $166,307.25 per year.

#LI-Hybrid #LI-CD1

Who You Are

The Project Manager on the Risk & Insurance team is tasked with the end-to-end management of projects that impact our customers and overall team related to Risk & Insurance programs at Justworks. The person in this role will drive cross-functional projects that improve the customer experience on Justworks and keep Customer Success, Sales, and Operations informed on the project details.

The Project Manager is the conduit between the functional team and the rest of the organization: they are expected to understand what each department needs in order to execute initiatives, and to communicate those needs to other members of the project team. They are also expected to advocate for those needs to the project team, to set and manage expectations within each department, and to produce deliverables such as training materials, documentation, presentations, and project updates. Success in this role is not just about project completion - it is also about instilling confidence in the rest of the organization and in reflecting on a project’s outcome for future improvements. 

The person in this role will work closely with the other internal-facing teams within CS, Sales and Operations, as well as Enablement, Legal, Finance, and Product teams as appropriate for each project.

Your Success Profile

What You Will Work On

• Manage end-to-end projects: Own and lead cross-functional projects for Risk & Insurance, especially those with discreet timing, deadlines, and launch timeframes that affect customers and employees. Create and update project plans; conduct recurring status meetings and follow up on action items; drive successful completion of projects that align with the strategic objectives of the org.
• Work with stakeholders to determine necessary processes for internal teams and vendors to successfully execute projects - direct/motivate and manage the project team, delegate responsibilities and tasks, and ensure scope/requirements aligns with deliverables.
• Be the primary point of contact for other teams at Justworks during projects and looping in members of CSO, Sales, Operations, ProdEng, Revenue Operations, Marketing, and Legal as needed
• Keep the R&I team and related stakeholders up to date on the status of projects, key decisions, and any changes as they happen.
• Proactively surface risks to the timing and execution of a project, and propose contingency plans. 
• Lead post-mortems to celebrate wins, identify opportunities for future improvement, and learn from our experiences.
• Schedule and lead project team meetings, steering committee meetings and other ad hoc meetings as necessary to discuss the status of the project and proactively surface issues and risks that impact the timing and execution of a project. Know when to propose changing course or propose contingency plans.
• Perform other related duties as assigned

How You Will Do Your Work

As a Project Manager, how results are achieved is paramount for your success and ultimately results in our success as an organization. In this role, your foundational knowledge, skills, abilities and personal attributes are anchored in the following:

• Detail-oriented - exercises extreme attention to detail; is thorough, accurate, organized, and productive and seeks to understand both the cause and effect of a situation.
• Ethical practice - the ability to integrate core values, integrity and accountability throughout all organizational and business practices.
• Clear communication - the ability to articulate thoughts and express ideas effectively using oral, written, visual and non-verbal communication skills, as well as listening skills to gain understanding.
• Analytical - uses a logical reasoning process to break down and work through a situation or problem to arrive at an outcome.
• Good judgment - the exercise of critical thinking, analyzing and assessing problems and implications, identifying patterns, making connections of underlying issues, understanding risks and developing mitigation strategies, and taking ownership of the outcome.

In addition, all Justworkers focus on aligning their behaviors to our core values known as COGIS. It stands for:

• Camaraderie - Day to day you can be seen working together toward a higher purpose. You like to have fun. You’re an active listener, treat people respectfully, and have a strong desire to know and help others.
• Openness - Your default is to be open. You're willing to share information, understand other perspectives, and consider new possibilities. You’re curious, ask open questions, and are receptive to thoughts and feedback from others.
• Grit - You demonstrate grit by having the courage to commit and persevere. You’re committed, earnest, and dive in to get the job done well with a positive attitude.
• Integrity - Simply put, do what you say and say what you'll do. You’re honest and forthright, have a strong moral compass, and strive to match your words with your actions while leading by example. 
• Simplicity - Be like Einstein: “Everything should be made as simple as possible, but no simpler.”

Qualifications

• 3-5 years of professional experience in project management and/or operations role, preferably in the PEO or Insurance space and/or a tech-driven environment
• Strong Writing and Verbal Communication skills
• Experience in tech/SaaS a plus
• Basic Excel and/or SQL knowledge required
• Experience with Confluence, Jira, and/or other project management tools
• Agile, CAPM, or PMP certification preferred

The base wage range for this position based in our Tampa Office is targeted at $101,370.00 to $111,507.00 per year.

#LI-Hybrid #LI-CD1