Freelance Workflow Developer Jobs in Chicago, IL

About Smokeball
With offices in Australia, the US, and the UK, Smokeball is the leading provider of legal practice management software helping small and mid-sized legal practices run their best firm and live their best life. We're passionate about what we do, and our clients know it!
Culture plays a big part in our success, and our clear purpose and vision motivate us daily.
About the Job
Are you a paralegal or legal assistant who loves creating polished documents, solving tricky formatting challenges, and finding smarter ways to work? At Smokeball, you'll combine your legal expertise with technology to help law firms build better document automation and AI-powered drafting solutions.
As part of TemplateLab, one of Smokeball's premium document drafting solutions, you'll work directly with law firms to understand their document needs, transform those requirements into high-quality templates, and ensure every deliverable meets our exceptionally high standards. You'll also be the final quality checkpoint, reviewing and signing off on work configured by our freelance team before it reaches clients.
The best part? You'll set the standard, not just follow one. You'll shape how templates are built, delivered, and improved, and work closely with clients to determine whether traditional templates or AI-assisted drafting best serves their use case. As the technical expert your colleagues rely on, you'll partner with Legal Engineers, Product, and client-facing teams to surface client needs, shape decisions, and sharpen the tools behind the work.
One more thing... We're hiring two roles, one junior and one more experienced. So, if you're excited about the role but don't tick every box below, we'd still love to hear from you. We care just as much about curiosity, potential, and a willingness to learn as we do about experience.
This is a hybrid role based in our office in Chicago, IL. All Chicagoland employees are required to be in the office on Wednesdays and Thursdays.
Key Responsibilities
Document Templates, Quality & Delivery

• Consult with clients who purchase custom template packages, gathering their requirements, translating them into clear build instructions, uploading templates into clients' accounts and testing them, and owning improvements through the post-completion feedback period.

• Execute template building and template quality assurance based on standards set for all document template solutions (court & authority forms, starter templates, and custom templates).

• Troubleshoot complex technical issues and serve as the final decision-maker on template readiness before release to clients.

• Research, design, build, and maintain court captions across areas of law and jurisdictions using Smokeball's configuration application, including collaborating with clients to capture caption needs.

• Configure and deliver new-firm letterhead during onboarding, along with paid letterhead customizations, building reusable solutions that control formatting and behavior across templates.

• Work closely with the Legal Product Operations Manager to maintain and evolve Smokeball's library of 20,000+ court and agency forms, using client usage data and jurisdictional changes to prioritize what to add, update, or retire.

• Liase with our team of template-building contractors by answering questions, reviewing work, and providing feedback.

Collaboration, AI & Continuous Improvement

• Adopt emerging AI and automation tools to accelerate template development and help decide which documents are best kept as traditional templates versus AI-assisted drafting.

• Partner with Legal Engineers, Product, and Client Success to resolve issues, improve tooling and workflows, and reinforce quality standards.

• Define and evolve template quality standards, surfacing gaps and risks and driving process improvements that reduce rework and scale over time.

Skills & Experience

• 3+ years in a law firm (1-30 employees) in a legal support role (e.g. paralegal or legal assistant), with hands-on experience drafting legal documents and/or court forms.

• Experience with document templates, document automation tools, or form building/configuration - strongly preferred.

• Confident working directly with clients: gathering requirements, managing follow-up, and setting realistic expectations.

• Exceptional attention to detail and a track record of highly accurate work in a detail-oriented environment.

• Strong ownership and judgment - able to work independently, act with urgency, and hold a high bar for quality.

• Curious, adaptable, and excited to use AI tools to work more efficiently.

• Bachelor's degree, Associate's degree, or equivalent professional experience.

Nice to Have

• Experience with Smokeball or a similar legal practice management platform.

• Experience working with outsourcing teams or reviewing delegated work.

• Familiarity with multiple areas of law and their document workflows.

• Experience using AI in a work context, both for document drafting and to streamline day-to-day work.

Compensation
Jnr Template Specialist: $70-$80k
Template Specialist: $80- $90k
What's in it for you?
Competitive Salary
Work-Life Balance: 20 vacation days, 3 reboot days, birthday off, volunteer time, and more!
Benefits: Excellent medical, dental, vision coverage. 401(k) match, & monthly wellness stipend
Parental leave
Office lunch and loads of snacks
And of course...the SWAG!
Want to Know More?
Why do we do what we do? Where did the name 'Smokeball' come from? What are our values? Learn more here!
*Smokeball values diversity & inclusion and is proud to be an Equal Employment Opportunity employer. Smokeball considers all individuals seeking employment without regard to race, color, religion, national origin, age, sex, marital status, ancestry, physical or mental disability, veteran status, gender identity, sexual orientation, or any other legally protected characteristic.
If you're excited about this role, we encourage you to apply even if your experience doesn't check every box.