Legal Case Management Series - A Gravity Legal Interview of our CEO, Jonathon Fishman

Jonathon Fishman

LeanLaw CEO Jonathon Fishman was interviewed by Gravity Legal’s Dan Lear. Dan asked Jonathon about the history of LeanLaw, Jonathon’s background, and where LeanLaw is headed in the near future.

Jonathon spoke about his San Francisco beginnings, his love of creating order out of chaos, and why LeanLaw law firm accounting software is going to solve midsize law firm financial workflows with an intuitively elegant user-interface and crafty AI to give law firms insights into how they can create better businesses.

Watch below or read the transcript (edited and condensed for clarity).

Welcome to Financially Legal, the podcast that provides inspiration and tactical advice for small, mission-driven consumer-facing lawyers, brought to you by Gravity Legal. 

Case management has become the heart and operating system of modern law firms. While many firms recognize the need for case management, they struggle to choose from the numerous options available.

At Gravity Legal, we understand that lawyers frequently ask us for guidance on this issue. I’m Dan Lear, your host for Financially Legal, and in this limited podcast series, we aim to equip firms with the information and insights necessary to select the right case management system.

In the upcoming episodes, we’ll be speaking with several case management companies, asking them the same set of questions. Our goal is to enable listeners to compare their options effectively. Today, I’m joined by Jonathon Fishman, CEO of LeanLaw, established in 2015. LeanLaw serves as the financial operating system for small to medium-sized law firms. Their platform automates essential financial workflows, including time tracking, invoicing, and reporting.

I’m delighted to welcome Jonathon Fishman from LeanLaw to the Financial Legal Podcast. Jonathon, thank you for joining me.

Jonathon: Thanks for having me, Dan.

Dan: Jonathon, before we dive into our questions, let’s give our audience a brief introduction to you. Could you share some background information, including your role at LeanLaw and your experience?

Jonathon: Absolutely, Dan. I’m Jonathon Fishman, one of the founders and the CEO of LeanLaw. I’ve been involved with early-stage companies since the beginning of my career. Starting in San Francisco, I found myself immersed in the tech community, which was merging with the creative community of Marin. This experience provided me with valuable insights into the world of startups.

I joined LeanLaw through an introduction to Gary Allen, the original founder and a lawyer turned entrepreneur. We connected over our shared pragmatism and my talent for organizing chaos. Our focus was on addressing the needs of the legal community. While I had knowledge about small businesses, I was relatively unfamiliar with law firms’ operations. However, through numerous conversations with law firm administrators and managers, I gained a deep understanding of how these firms operate.

Gary, a practicing attorney for 35 years, brought the perspective of an end-user to the company. My expertise is in translating customer needs into actionable insights for the organization. With this foundation, LeanLaw was established in 2015, and we launched our product in 2016. I took charge of customer interactions from the early days, engaging with law firms’ administrators and managers. Now, I have had over 4,000 conversations, which have made me well-versed in law firm operations.

In 2021, I assumed the role of CEO with the intention of scaling the organization. LeanLaw had already built a product, achieved product-market fit, and cultivated a loyal customer base. My transition to CEO felt natural, given my previous experience with early-stage companies and my affinity for conversing with lawyers and firm administrators about their businesses.

Dan: That’s fascinating, Jonathon. It’s not often you hear someone express pure joy in talking to lawyers, but it’s great that you’ve found that connection. I’m glad you were able to build trust with your constituents. It’s crucial to understand lawyers’ intellectual curiosity and their direct approach to problem-solving. Once that trust is established, lawyers are willing to follow guidance, especially when it comes to financial matters.

Jonathon: Absolutely, Dan. Initially, I was a bit intimidated when I started talking to lawyers. There’s a perception that they can be tough and difficult to work with. However, I soon realized that their tough questions and directness were simply reflections of their problem-solving approach. Once I understood that mindset, it became easier to communicate effectively and establish trust. Lawyers are intellectually curious and smart, and they appreciate receiving clear directions, particularly regarding financials. Building trust with our clientele has been essential for LeanLaw.

Dan: That’s fantastic to hear, Jonathon. Let’s delve into my first question. As a co-founder and CEO of LeanLaw, what problem did you aim to solve with the development of this software? Additionally, has your vision for solving this problem evolved over time?

Jonathon: Our mission at LeanLaw has always been to help law firms run better businesses, and we’ve remained steadfast in pursuing that goal. Initially, our focus was on modernizing law firms’ financial workflows. We observed that the industry had numerous all-in-one practice management tools, but we believed a customizable financially-focused solution was necessary. We recognized that to run a successful business, law firms needed to streamline their financial management processes. Regardless of how well lawyers performed in other areas, such as depositions or drafting memorandums, if they struggled with billing, payments, and cash flow, their business would eventually suffer.

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Our aim was to refine our tool around financial management workflows, rather than becoming an all-encompassing practice management tool. We also embraced a best-of-breed approach, understanding that we didn’t need to create every feature or aspect ourselves. From the beginning, we focused on automation, integration, and data opportunities to enhance financial management.

The first important realization we had was that in order to successfully manage finances, we had to be adept at bookkeeping and accounting. But we didn’t want to develop an accounting tool ourselves. As a result, we decided to create an app integration with QuickBooks Online, a decision which turned out to be very beneficial for us early on. We didn’t want to handle accounting ourselves, we wanted to integrate, automate, and utilize data. We have always maintained this approach. 

As our understanding of our customers and their needs evolved, so too did our product and business model. We’ve incorporated financial technology into our product, recognizing it as both a revenue opportunity for our company and a workflow enhancement for our law firm clients. 

This evolution hasn’t always been straightforward. For instance, in 2015, integrating payments and payment workflows wasn’t part of our business model. But as the industry evolved, it became crucial. We needed to understand and improve the financial relationship between law firms and their clients. 

Our business continues to evolve, with our most recent focus being artificial intelligence. We began discussing machine learning and AI in 2018, but it wasn’t until recently that we found practical applications for these technologies. 

Overall, our mission remains the same – to help law firms run better businesses. But the specifics of how we achieve this mission evolve as we learn more about our customers and the challenges they face.

Our ideal client is financially focused, entrepreneurial, and has a deep understanding of their firm’s financial operations. They value a platform that is both sophisticated and easy to use, and is tailored to their specific needs. They also appreciate the data transparency our product provides, which allows them to monitor the health of their firm, their clients, and their workforce. 

Our clients range in size, but we find our sweet spot is with firms of 10 to 50 people. We also work with many smaller firms, as well as a few larger ones. 

At this time, our product does not integrate with systems that handle case management or matter tracking. However, this is part of our long-term strategy and we expect to make significant progress on this front in the upcoming quarters. 

We currently integrate with SharePoint and the Microsoft 365 platform for document management and storage, and we are planning to integrate with Net Documents and iManage by the end of the year. 

Time tracking and billing are key features of our product, and we believe we excel in these areas. As such, we don’t integrate with other time tracking or billing software. 

For calendar and schedule management capabilities, we integrate with Microsoft 365 and Outlook. However, we see this as a function of time tracking rather than case management. In terms of docketing tools, we are working on this as part of our broader integration strategy.

Dan: Does the system offer built-in CRM features, or is it more of a CRM and marketing tool that you integrate with or consider?

Jonathon: When it comes to CRM, we have some functionality in our platform. We can add clients and create custom form fields for various purposes. These custom form fields allow users to report on different aspects of their clients. However, we are not aiming to be a complete marketing and CRM tool. Currently, we are working on integrating with Lawmatics, a tool that could be perfect for businesses with a B2C focus, such as law practices. We have a great relationship with the Lawmatics team.

Dan: And another question related to integration. Does your system offer financial and balance sheet reporting?

Jonathon: Our reporting can be categorized into two areas. First, we have robust financial reporting for the firm, including profit and loss statements, balance sheets, and cash flow statements. We treat QuickBooks as the source of truth for financial data, so our integration with QuickBooks provides comprehensive financial reporting. 

Second, LeanLaw excels in client, matter, and attorney reporting. We provide insights into metrics like work in progress, billed hours, collected revenue, and productivity. These reports help law firms assess their performance and understand various aspects of their operations, beyond just profitability. Another important feature is our compensation tracking, which is highly dynamic and automated, based on the “finder, minder, grinder” model. We offer extensive customization options at the firm, user, and matter levels to track compensation in real-time based on collected revenue.

Dan: That’s impressive. Now, let’s talk about data security, privacy, and continuity. How does your system ensure these aspects?

Jonathon: Our approach to data security follows both a top-down and bottom-up strategy. As a young company, we are working towards obtaining a full SOC audit, adhering to industry standards for privacy, data security, risk management, etc. We have implemented policies and best practices to ensure data security is ingrained in our company culture. From a technical perspective, our environment is hosted on the Microsoft Azure network, with co-location in two environments. We backup our data to Amazon S3, ensuring a secure architecture. We prioritize PCI compliance and partner with Gravity for secure credit card handling. We have contingency plans and strong best practices in place to address any unforeseen issues. Additionally, our product has a comprehensive permissions architecture to control access to data within a firm, allowing for fine-grained control over who can access specific matters and information.

Dan: That’s reassuring to know. Finally, what customer support options do you offer, and when are they available?

Jonathon: At LeanLaw, we provide both chat and phone support. We usually start with chat and then escalate to Zoom calls if needed, as screen sharing can be more effective. When clients onboard with LeanLaw, they have access to a free Quickstart Coaching session, where our QuickBooks ProAdvisor helps them get started and ensures a smooth integration. 

For mid-market clients, we offer a white-glove onboarding service, which includes a more extensive onboarding process divided into three phases. Our support is available during standard business hours, and customers can reach out to us whenever they need assistance. We also provide additional resources such as knowledge bases and instructional videos to support our users.

Jonathon: Customers can expect prompt support from us. When they reach out to our support team, they usually have questions or need assistance with specific tasks. We’ve made it a part of our onboarding process to ensure that customers are well equipped with the necessary knowledge to navigate our system effectively. Onboarding plays a critical role, and we take it seriously. 

Our support team comprises individuals with a mix of skills. They possess deep product knowledge as well as accounting expertise. We’re also in the process of adding engineers to our support team, so we have subject matter experts readily available. What’s essential for us is to always have an accounting professional on our support team because we understand that accounting-related questions often arise, and we want to provide the necessary support without taking on the role of an accountant.

Dan: That sounds great. Now, let’s talk about pricing. How is LeanLaw priced, and can you explain it simply for someone who’s new to the system?

Jonathon: It’s quite straightforward. You determine the number of unique users you need for LeanLaw and multiply that by either our core version or our pro version. 

We offer two versions of our product. Most small firms use the Core version, which is priced at $40 per seat on an annualized basis or $50 on a month-to-month basis. For example, if you and I are part of a law firm along with one other person, the total cost would be three users multiplied by $40, resulting in $120 per month. It’s as simple as that. This price includes all services. 

Additionally, we offer onboarding options that you can choose from, such as our white-glove onboarding or a free Quickstart Coaching session. 

If you opt for our Pro version, it is priced at $55 per month per user on an annualized basis or $65 on a month-to-month basis. The Pro version offers more advanced accounting features, enhanced reporting capabilities, and improved user permissions management. Typically, mid-market clients, accounting-savvy users, prefer the Pro version due to its additional functionalities.

Dan: That’s clear and easy to understand. Now, let’s discuss integrations. Which integrations are most popular with LeanLaw?

Jonathon: Our primary integration is with QBO — we are a QuickBooks app in the QuickBooks app store — which is highly popular and widely used. Additionally, we receive considerable interest in our embedded integration with Microsoft 365. Customers are excited about the potential of leveraging artificial intelligence and integrating with Microsoft 365 to streamline time tracking throughout the day. Looking ahead, we aim to integrate with best-of-breed tools in the legal industry, such as NetDocuments and Law Toolbox, to provide users with a seamless experience. 

Our goal is not to integrate with every tool available but to carefully select and integrate with tools that are considered the best in their respective areas. QuickBooks and Gravity Legal are already strong integrations, and we are proud of the value they bring to our clients. We will continue to advance our integration with Gravity Legal, and our next major integration will focus on Microsoft 365. 

Additionally, Google integration is on our radar, considering its growing presence and appeal, particularly among millennial law firms.

Dan: What would be your best sales pitch to our ideal customers? Why should they choose LeanLaw?

Jonathon: Let me break it down simply. If you are a law firm that uses QuickBooks Online or plans to use QuickBooks and you want a tool that focuses on financial aspects, LeanLaw is the best choice in the legal industry. We address many pain points associated with QuickBooks integration and offer intelligent workflows for tasks like retainer management, time tracking, and invoice generation. 

For firm operators, LeanLaw ensures seamless integration with your QuickBooks Online account, which serves as the source of truth for financial data. 

If you are a firm manager, general partner, attorney, or anyone seeking an intuitive, cost-effective solution with a strong financial focus, LeanLaw is an excellent fit. Our user-friendly interface, lower costs compared to other solutions, and comprehensive reporting capabilities put valuable data forecasting and insights right at your fingertips. 

We don’t just provide basic reports; we empower you with actionable information to manage your firm effectively. LeanLaw is designed for modern law firms, accommodating the devices you prefer to work with. We are future-focused, dedicated to integrating and automating disconnected systems and providing a smooth user experience. Our philosophy revolves around best-of-breed tools and streamlined workflows. So, if you prioritize the best QuickBooks integration and seek a modern, financially-focused solution, LeanLaw is the ideal choice.

Dan: That’s a compelling pitch, Jonathon. Thank you so much for your insights. Where can our listeners or viewers find out more about LeanLaw?

Jonathon: It’s simple. Just visit our website at You’ll find plenty of information there. You can find our mobile app in the app stores (iOS or Android). You can reach out to me on LinkedIn. I’m very accessible, and I encourage anyone interested to ask me questions. LinkedIn is a great way to connect. Alternatively, you can email me at [email protected]. Feel free to reach out in whatever way is convenient for you. We’re here to assist.

Dan: Thank you, Jonathon. It’s been a pleasure having you, and we appreciate the collaboration we have with LeanLaw. We value our relationship with your company.

Jonathon: Thank you, Dan. It was my pleasure, and we are grateful for our partnership with Gravity Legal.