Part-Time
Head of Personal Injury
Updated on 9/10/2026
Smokeball
51-200 employees
Legal practice management with automatic time-tracking
Compensation Overview
$300k/yr
Chicago, IL, USA
Hybrid
Two days on-site per week, Wednesdays and Thursdays, are required in the Chicago office.
Bachelor's
 Sales & Account Management (1) |
|---|
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- Personal injury market fluency, including understanding personal injury firm workflows, economics, and buying behavior.
- Experience owning a revenue line and delivering pipeline, expansion, adoption, or renewal outcomes.
- Experience sourcing, negotiating, and landing partnerships and channels, with credibility at trade shows and industry events.
- Ability to drive outcomes across Sales, Client Success, and Marketing through business cases, shared goals, and relationships.
- Ability to set direction and execute in ambiguous, fast-changing conditions while building cohesion across dotted-line reporting.
- Ability to connect commercial work to revenue and communicate status and impact clearly to executives.
- Ability to use company-approved artificial intelligence tools for rapid experimentation and team velocity.
- Bachelor's degree.
- At least 10 years of professional experience, including commercial or revenue leadership.
- Proven track record owning and delivering a revenue line through new business, expansion, or usage/transactional models.
- At least 4 years of experience in legal technology, or at least 5 years working closely with or selling to small-to-medium law firms, with strong familiarity with the operational and software needs of a personal injury practice.
- Experience building and managing partnerships and business development.
- Ability to operate effectively in a fast-paced environment with shifting priorities.
- Own the United States personal injury vertical revenue target and the commercial strategy to achieve it across new business, expansion, and renewal influence.
- Drive adoption of Smokeball's personal injury application as a revenue and retention lever by connecting product usage to a measurable revenue line.
- Translate personal injury market dynamics and firm economics into a focused commercial plan that defines where to play and how to win.
- Own personal injury monetization opportunities, pricing input, and packaging in partnership with Product and Finance.
- Identify, land, and grow partnerships with referral networks, bar associations, personal-injury-specific vendors, integrations, and co-marketing organizations.
- Work across Sales, Client Success, Product, and Marketing to drive personal injury outcomes without directly owning those teams.
- Align go-to-market motions, enablement, pipeline, campaigns, and retention initiatives behind shared personal injury targets.
- Direct the growth pod as a hands-on player-coach, initially including the Personal Injury Growth Manager.
- Set commercial priorities, connect pod execution to revenue and adoption outcomes, remove blockers, and hold the pod accountable for results.
- Maintain an operating rhythm across the pod and dotted-line partners in Product and Client Success.
- Travel regularly for trade shows, conferences, partner meetings, and industry events.
- Attend occasional after-hours meetings because of time-zone constraints across teams and partners.
Smokeball is legal practice management software for small law firms. It helps lawyers run their practice efficiently by tracking every minute spent on legal tasks automatically, which supports billing more hours per day and increasing revenue per fee earner. The platform includes robust document management with a library of over 17,000 public documents and tools to automate the creation of firm-specific documents, saving hundreds of hours annually. It also provides comprehensive case management and billing features, helping firms operate like a business. Revenue comes from subscription fees that include ongoing updates and support. Compared with competitors, Smokeball combines automatic time tracking, extensive document automation, and integrated productivity tools tailored to small firms, focusing on driving efficiency and profitability.
Company Size
51-200
Company Stage
Late Stage VC
Total Funding
$30M
Headquarters
Chicago, Illinois
Founded
2011
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Simplify's Take
What believers are saying
- Archie AI prompt volume rose 241% since January 2026, showing strong usage.
- Florida Bar launched Smokeball Bill free access on June 9, 2026.
- Smokeball added GPT-5.5 support and Outlook iOS integration in June 2026.
What critics are saying
- Clio, MyCase, and Referent attack Smokeball with cheaper, AI-native alternatives in 2026.
- Smokeball’s latest disclosed capital remains 2023’s $30 million, limiting war-chest depth.
- Free bar-distributed Bill risks customers staying on low-margin trust accounting instead of upgrading.
What makes Smokeball unique
- Smokeball’s AutoTime, document automation, and matter workflows are deeply embedded together.
- Twenty-eight state bars now distribute Smokeball Bill to 900,000 lawyers.
- Thomson Reuters partnership gives Smokeball integrated CoCounsel Legal research inside practice management.
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Benefits
Health Insurance
Dental Insurance
Vision Insurance
401(k) Company Match
Wellness Program
Parental Leave
Paid Vacation
Paid Sick Leave
Paid Holidays
Remote Work Options
Hybrid Work Options
Growth & Insights and Company News
6 month growth
↓ -3%1 year growth
↑ 0%2 year growth
↓ -1%Florida Bar expands free trust accounting offerings with Smokeball Bill. Smokeball Bill added as a free alternative to Nota. The Florida Bar now offers members free access to Smokeball Bill, a trust accounting and billing software solution built by legal practice management software platform Smokeball. The addition of Smokeball Bill as a Member Benefit gives Florida lawyers a second free option for trust accounting tools and aligns with the Bar's commitment to supporting members with accessible technology. "The Florida Bar has long been committed to equipping our members with practical tools that help them serve clients effectively and meet their professional responsibilities," said Terry Hill, director of the Bar's Programs Division. "By expanding our free trust accounting software offerings to include Smokeball Bill, we are providing attorneys with greater choice and flexibility in selecting the technology that best fits their practice. We're excited to make another valuable resource available to our members and to continue supporting firms of all sizes across Florida." The Bar adds Smokeball Bill as an alternative to. The main difference between the two platforms is that Smokeball Bill integrates with QuickBooks, while Nota integrates directly with the member's financial institutions. By offering multiple free tools, the Bar is helping reduce disparities in access to legal technology, ensuring that lawyers - regardless of firm size, budget, or location - have the resources they need to effectively manage client funds, says Hill. According to a 2023 News article, trust accounting was in the top 10 complaints filed against members annually from 2019 to 2023, and for good reason; trust accounting is one of the most complex and detail-intensive responsibilities attorneys handle. "From managing IOTA accounts to reconciling client funds tied to real estate closings, retainers, and settlements, the process can be time-consuming without the right systems in place," according to a Smokeball statement. Smokeball says Smokeball Bill "is designed to simplify these workflows with features like three-way reconciliation, detailed audit trails, and integrations with tools such as QuickBooks to support firm operations more broadly." The company adds that its flagship solution is used by 28 state bars representing more than 900,000 lawyers across the United States. Florida Bar members may upgrade from the free Smokeball Bill service to the full Smokeball practice management solution at a discounted rate. "Florida has long been a leader in improving access to legal technology for its members," said Jane Oxley, Smokeball COO and co-founder. "We're proud to collaborate with The Florida Bar to build on that foundation - giving attorneys more choice in how they manage trust accounting today, along with the flexibility to adopt additional tools as their practices grow."
The Florida Bar and smokeball expand free trust accounting and billing software offered to all members. Smokeball builds a new relationship with The Florida Bar by offering attorneys in the state more choice and access to modern tools. June 9, 2026 Table of Contents Explore Smokeball * Bill accurately with AutoTime * Integrate with Word & Outlook * Access 20,000 - prebuilt legal forms * Grow with smart reports & insights Smokeball, the industry-leading legal practice management software platform, today announced a new relationship with The Florida Bar to provide its more than 115,000 members with free access to Smokeball Bill, Smokeball's trust accounting and billing software solution. This offering expands The Florida Bar's longstanding commitment to supporting attorneys with accessible technology, giving members an additional option for trust accounting tools. The Florida Bar was the first state bar in the nation to provide its members with free trust accounting software, setting a precedent for improving access to legal technology across firms of all sizes. With the addition of Smokeball Bill, Florida attorneys now have greater flexibility and choice in how they manage trust accounting and billing, with solutions that fit the unique needs of their practices. This initiative reflects The Florida Bar's continued focus on increasing access to technology for all attorneys - whether they are part of firms in larger cities like Miami and Tampa, or running solo practices in smaller communities across the state. By offering multiple free tools, the Bar is helping reduce disparities in access to legal technology, ensuring that attorneys - regardless of firm size, budget, or location - have the resources they need to effectively manage client funds. "The Florida Bar has long been committed to equipping our members with practical tools that help them serve clients effectively and meet their professional responsibilities," said Terry Hill, Division Director, Programs Division at The Florida Bar. "By expanding our free trust accounting software offerings to include Smokeball Bill, we are providing attorneys with greater choice and flexibility in selecting the technology that best fits their practice. We're excited to make another valuable resource available to our members and to continue supporting firms of all sizes across Florida." Smokeball and The Florida Bar recognize that trust accounting remains one of the most complex and detail-intensive responsibilities attorneys handle. From managing IOTA accounts to reconciling client funds tied to real estate closings, retainers, and settlements, the process can be time-consuming without the right systems in place. Smokeball Bill provides a modern, user-friendly solution designed to simplify these workflows, with features like three-way reconciliation, detailed audit trails, and integrations with tools such as QuickBooks to support firm operations more broadly. "Florida has long been a leader in improving access to legal technology for its members," said Jane Oxley, COO and co-founder of Smokeball. "We're proud to collaborate with The Florida Bar to build on that foundation - giving attorneys more choice in how they manage trust accounting today, along with the flexibility to adopt additional tools as their practices grow." Get tips, invites & updates - straight to your inbox! This marks Smokeball's 28th state bar relationship, extending access to its technology now to more than 900,000 lawyers across the United States. To learn more about Smokeball's free offering for The Florida Bar members or to sign up, please visit www.smokeball.com/floridabill. About Smokeball Smokeball is your partner to drive your law firm into the future. As the industry's leading cloud-based legal practice management software, Smokeball empowers you to run your firm specific to your area of law. Its platform gives you all the insights and tools you need to work smarter, not harder: automatic time tracking and invoicing, streamlined workflows for your specific practice area, a library of over 20,000 standard legal forms and documents, and actionable reports. Smokeball is a member benefit of over 20 U.S. bar associations. Learn how to run your best firm at smokeball.com. About The Florida Bar The Florida Bar, the state's guardian for the integrity of the legal profession, is the statewide organization of lawyers established by the Florida Supreme Court to regulate the legal profession. With more than 115,000 members, The Florida Bar is committed to protecting the public, improving the administration of justice, and supporting its members through education, resources, and innovation.
Smokeball, a cloud-based practice management platform for law firms, has launched "Archie AI: Next Generation", embedding agentic AI directly into lawyers' daily workflows. The AI assistant is now integrated into Microsoft Word, Outlook and matter pages, enabling document analysis, drafting and email management without switching tools. The upgraded Archie uses agentic reasoning to work through problems step-by-step, retrieving matter context and verifying responses before delivering answers. New features include proactive suggestions, voice dictation and customisable tone profiles for different audiences. Founded in 2012, Chicago-based Smokeball serves small to mid-size law firms across the US, Australia and UK. The company recently partnered with Thomson Reuters to integrate CoCounsel Legal for research and analysis, creating a unified platform connecting practice management with AI capabilities.
Mar 25, 2026 | partnerships. A partnership to build the premier legal technology ecosystem. Bringing together Smokeball's practice management platform and Thomson Reuters CoCounsel Legal to connect the business and practice of law Aaron Rademacher, general manager, Small Law Firms The legal industry is transforming at a pace we've never seen before. Law firms are being asked to do more - more research, faster client communication, sophisticated drafting with expertise, quicker turnaround - while clients arrive better informed and with higher expectations than ever before. AI has changed what clients believe is possible: they expect prompt responses, transparent pricing and work product that reflects genuine expertise, not hours billed on routine tasks. For small law firms, meeting that bar with lean teams and tight margins is the central challenge. They need enterprise-grade solutions without enterprise-level complexity. That's exactly what we're building together with Smokeball. Smokeball and Thomson Reuters announced a partnership to create a legal technology ecosystem that connects the business and the practice of law in a single, integrated experience. By bringing together Smokeball's industry-leading practice management platform with CoCounsel Legal, our agentic AI solution for authoritative legal research, document analysis, and drafting, we're giving legal professionals in small law firms something that simply hasn't existed in the market until now. Smokeball brings operational excellence to running a firm; Thomson Reuters brings two centuries of legal expertise - the driving force behind the power of CoCounsel Legal - purpose-built for the rigor the practice of law demands. Law firms finally have both in one place. Why this partnership matters for our customers. For too long, legal professionals have had to stitch together disconnected systems. They rely on one tool to manage matters, another to do research, another to draft documents, and another to bill. Every handoff between systems is a place where time is lost, errors creep in, and client service suffers. This partnership changes that. Smokeball's platform already handles the full operational layer of running a legal practice: case management, document automation, billing, time tracking, calendaring, and client communications. Right away, our joint customers in the U.S. will be able to connect matter documents directly to CoCounsel Legal in bulk, saving significant time, reducing the risk of errors, and streamlining workflow like never before. This is only the start of the journey, as additional exciting integration phases are in progress. The trajectory is to create a unified interface where legal professionals can effortlessly access Thomson Reuters legal content, AI, know-how tools, and current matter data - all in one seamless interface. Built on a foundation of trust and proven scale. This partnership does more than just create an ecosystem, it connects a shared commitment to serve legal professionals at the highest level and with solutions they trust. Thomson Reuters recently announced that one million professionals have chosen CoCounsel, the company's professional-grade AI technology, across 107 countries and territories. That milestone is a testament to something important: AI is moving from experimentation to production. Rather than standalone solutions, firms are embedding AI directly into daily workflows where accuracy, sourcing, and data protection are essential. Professionals are not deciding whether to use AI anymore. They are deciding which AI they trust when their reputation and their clients' data are on the line. CoCounsel is built for exactly that moment. The next generation of CoCounsel Legal, entering beta soon, is designed around conversational task execution, meaning the best is still ahead for our customers. Leading the industry forward. With Smokeball and CoCounsel Legal, no other combination of technology in the small law firm market brings together this depth of legal content and AI capability with this breadth of practice management functionality. This is what legal tech leadership looks like - not just building great individual products, but creating ecosystems that meet lawyers where they are and give them the resources they need to serve their clients at the highest level. The legal industry is moving fast. Thomson Reuters is committed to making sure our customers don't just keep up, but that they lead. Our partnership with Smokeball is a continued step in delivering on that, and we're just getting started. Aaron Rademacher is the general manager of Small Law Firms at Thomson Reuters.
Smokeball, a cloud-based practice management platform for small to mid-size law firms, has partnered with Thomson Reuters to create an integrated legal technology ecosystem. The partnership combines Smokeball's practice management tools and AI matter assistant with Thomson Reuters CoCounsel Legal, which provides legal research, document analysis and drafting capabilities. The collaboration will initially feature a real-time data connector allowing Smokeball users to sync legal documents across platforms in bulk, eliminating manual uploads. Further integration phases are planned to create a seamless interface combining Thomson Reuters' legal content and AI tools with matter-specific information. Founded in 2012, Smokeball serves firms across the US, Australia and UK, primarily those with 2–30 people. The partnership aims to help small firms compete at higher levels by connecting operational infrastructure with trusted legal content.