Checkbox’s Key Learnings and Takeaways from Running Legal Like a Business

October 31, 2023

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Checkbox dove right into the inaugural Conference, Running Legal Like a Business, this year! This event brought together a diverse group of attendees; from legal ops veterans to fresh faces, was a brilliant mix of small, medium and large companies to provide a well-balanced exchange of ideas and culture. We were privileged to attend and participate, continuing to witness the progression of the legal industry, especially with AI (Artificial Intelligence) taking center stage recently.  

In this blog, we recap some of the highlights from the event and delve into the transformative landscape of legal operations.

AI: The Shining Star of Legal Tech

The Conference revolved around various themes regarding technology, but the one that stole the spotlight was AI. Attendees had the unique opportunity to dive deep into the world of AI and receive practical advice on how to safely approach the use of Generative AI. These in-depth discussions highlighted the dramatic reduction in the time it takes to train AI compared to a few years ago, making it more accessible and applicable for legal operations.  

One of the key takeaways from the discussion of AI was the importance of safeguarding sensitive legal data while using AI. Speakers on this topic emphasized the need to wrap AI systems in an application layer to ensure that data remains protected and is not inadvertently used to inform or train the AI. This practical insight has opened new horizons for AI implementation in legal operations and showcased the potential for safer and more efficient workflows. Of the three main LLM's available today, conversations steered towards the safest way of being able to utilize them and protect your data is by wrapping in an application layer (like Checkbox) so that the data stays protected and is not used to inform or train the LLM.

At Checkbox, we understand the significance of these discussions and we are dedicated to making sure AI is implemented across our platform in a secure and efficient manner. The AI APIs we use have a zero-retention policy - meaning OpenAI cannot view any of that data, store it longer than required to process the request, use it for training, or use any of it to train the AI model. Data sent over to OpenAI is not exposed to any other parties, including publicly accessible models like ChatGPT.

We share the vision of making AI a driving force in your legal operations and, in turn, strengthening your partnership with the business, as we all work towards a more efficient and effective legal service delivery model.

Speed Dating for Workflow & An Unforgettable Checkbox Demo

One of the standout and favorite moments for us at the conference was the workflow workshop, where we got to showcase our platform to attendees. Session engagement was not only active but thoughtful, and there was even room for laughter. Checkbox showcased the next generation of AI-meets-intake-and-workflow, seamlessly integrating AI with collaboration tools like Slack, Teams, email and Salesforce. Attendees lauded the session and expressed how much they enjoyed it, making it one of the highlights of the event. We love showing what our platform is capable of and creating an electric atmosphere that features joy and laughter.  

In the session, we showcased our AI-powered front door that meets business users where they live in Slack, Teams, email, and more. To easily capture and manage requests from the business, we provide employees with an experience that allows them to ask for help in a way that comes naturally to them, using conversations and not just forms. Drawing from a source of knowledge unique to each company, the Checkbox chatbot assistant can answer FAQs and seamlessly link to automated workflows to collect approvals, submit disclosures, generate documents, and assign work to the appropriate person. It's been very exciting to showcase the kind of user experience achieved by synthesizing conversational intake, knowledge, and workflow automation, and it is only going to get better from here. The feedback was overwhelmingly positive, with attendees especially praising how seamlessly Checkbox's AI was integrated with collaboration tools and how they can see it strengthening and maintaining legal’s relationship with business. One attendee after the event also provided bonus points for Evan’s mesmerizing accent (our CEO & Co-Founder) that featured together with the presentation

If you missed the demo at the conference, book a call with us for a more personalized look.

Workflow Automation in the Limelight

One of the most noteworthy takeaways from the event was the dedicated focus on workflow automation where workflow automation had its own dedicated demo showcase and workshop. This visibility, championed by industry leaders and’s very own Connie Brenton and Jeffrey Franke, speaks to the growing importance of workflow automation in legal operations and how it should be the cornerstone for any legal tech stack.

In a recent webinar we hosted together with CEO, Jeffrey Franke states that workflow sits at the foundational level together with basic e-signature and e-billing, as the first set of technology to be adopted by Legal Ops professionals. “Workflow really is foundational; I would probably put it at the foundational level one.”

Workflow was also frequently mentioned to be the first tool implemented within a company’s infrastructure and internal processes, especially if starting from scratch as it will make the biggest difference in a team’s operation from the very start. While e-signature and e-billing are foundational tools, workflow automation is not considered enough as a fundamental tool that needs to be brought into the business.

Stay Connected

Part of our goal here at Checkbox is to inspire and enable legal ops professionals to make a real impact, and this event was a testament to that vision. We hope you were as inspired as we were by the experience, and that you leave with newfound energy and ideas to drive change within your organization.

The Conference was just the beginning, and we are excited to continue this journey of transformation with you. Stay connected with Checkbox for updates, insights and more opportunities to engage with our community.

Thank you for being a part of this exciting event, and we look forward to seeing you at future conferences and events.

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