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Jesimin Berman is the Director of Legal Operations and Compliance at Papaya Global, a company that specializes in global workforce management. Initially, she wanted to be a comedy writer, and sought to achieve that in parallel to a career in law. Today, Jesimin is happy to have landed in law and apply her writing skills in other ways.

Before she transitioned into a technology consumer-centered legal role at a disrupter fintech company, her career was rooted in Intellectual Property and Entertainment from her time in animation. Her shift wasn't driven by whim or circumstance but by a keen interest in how technology can influence legal operations for better and allow her to work across cross-functional departments for the best consumer and business outcomes.

"I wanted to be on the technology side because I believe legal needs to work alongside the product and technology teams in real time as a business partner to ensure top outcomes for all sides: the business, the client, the regulators, and the technology product itself. Legal has invaluable insight that can support the end goal of other internal teams, because we hear directly from opposing legal and executive teams on what their pain points and concerns are.

I also wanted to know what was up and coming with technology, because it is so adaptive, and changes your life for the better, not the worse."

Papaya Global began its operations in Tel Aviv, Israel, and has since moved its headquarters to New York City. In her role, Jesimin is responsible for all U.S. legal operations and global compliance in the payments space, an area where she combines her in-depth legal expertise with technological insights.

Jesimin career trajectory

Jesimin’s career journey shows how she combined her legal acumen with tech-savvy insight. In this article, we explore Jesimin's advice on how to establish processes in legal ops practice and its broader implications for business success.

Navigating the transition from Head of Legal to Director of Legal Ops & Compliance

Jesimin's work in the legal operations field began when she took on the role of Head of Legal at a fintech company. Her motivation for stepping into this unique role was grounded in a belief that lawyers possess valuable business and technological insights.

“You don't have to restrict yourself to being one type of legal advisor. The skills inherent to being an attorney, such as issue spotting and analysis, prepare you to weigh in on the business elements as well, such as pricing, project management, or vendor selection. And if you're not the best person to give advice, help the customer or end client by flagging an issue and getting them to the right person or team to resolve it. The underlying objective is to make your client’s life easier and find ways to make their business more profitable.”

As Director of Legal Operations and Compliance at Papaya Global, Jesimin oversees the entire US market.

“It's really exciting to have the opportunity to build new processes from scratch on top of a technology that you hope will make your colleagues’ lives smoother. The user-friendly improvements we implemented increased internal team satisfaction, enhanced our KPIs on deal closings, and ultimately improved the experience for our clients. My mantra is “Small changes can have large impacts.” — Being able to remove a bottleneck, like having too many intermediary steps to address a customer need, benefits all teams.”

The decision to shift from a traditional legal role to legal operations may raise eyebrows. However, Jesimin's motivation was rooted in the needs of the company she joined and her desire to break free from the confines of the legal silos.

"I had always been very heavily involved in legal, but at the same time, I found that I didn't want to just stay in the “legal box”. I love the interpersonal interactions; seeing how other teams operate, and being able to solve a problem.  I wanted to be a part of, and lead, the strategic decisions that impact the company as a whole.

Generally, no one comes to the legal department because they’re having a good day. They’re seeking legal feedback because they have an active issue or a worry. Getting this type of all-encompassing view of the raw insight of each department and management allows you to be a key strategic partner. You can step in and direct the correct parties to connect and resolve open items, just as you can create and strengthen the processes to avoid it going forward.”

Jesimin explained how proving the value of legal ops and in-house legal roles can be challenging, especially when compared to more easily quantifiable departments like sales.

“While some companies view the legal and legal ops teams as cost centers without a financial benefit, legal actually provides a cost avoidance benefit — such as regulatory fines, compliance errors, lawsuits, etc. — that should be measured as a goodwill component and value-add. Legal has to evolve just like any other team.

Certain departments, like sales, have straightforward KPIs and a strong case for investment in tech tools, such as the latest lead generator, ZoomInfo, Hubspot, etc. But for roles like legal, it can be difficult to show a KPI or payoff for a business team to want to invest in it, or recognize that legal has a lot of knowledge and experience that assists and underpins the successful performance of all other teams and the end client.

Streamlining legal ops for business success 

Jesimin emphasized that legal, like any other team, must evolve and adapt to remain competitive in the business world, especially in the case where the company aimed to expand its footprint from Europe and the Middle East to the US market.

“By eliminating complex legal language and redundancies, we were able to streamline our contract documents as well as the negotiation process. Tracking the provisions that get the most pushback allows legal to adapt and cut back on the pain points in the negotiating time with the client, leading to more “signed as-is” wins. The goal is to respect your legal team’s time, and that of the client.

For example, if it’s industry standard to make a specific provision mutual, such as confidentiality, do it. Don’t make every client request it and divert your team’s time from other tasks. I’m in a unique position where I’m legal ops, but I still handle enterprise deals and run the payments lines. I interact with the contracts on a daily basis, and experience first-hand our client’s attorney’s redlines, as well as how the rest of my team answers.”

She explains how it’s important to have processes and templates in place that outline how the legal department will address issues to ensure consistency in their work.

“For MSAs, I implemented a playbook on the red lines our company accepts, and the explanations for redlines we cannot accept.  Similarly, I applied this system for our acquired payment entities and trained the team on these types of payment service contracts to ensure consistency in our answers to clients. Ensuring uniformity and consistency in answers impacts cross-functional teams especially. We don't want people on the team giving different answers because it can impact operations.”

When operating within a business, Jesimin emphasizes the importance of aligning yourself with business goals and ensuring customer satisfaction above all.

“Our aim is to meet our client’s needs and provide best-in-class service, from the contracting process to the product experience itself. This allows us as a team to adjust the MSA in real time and flex the process to the client’s and internal teams’ needs. That being said, it is still very difficult on the legal side to quantify your work because even if you show how many deals you close, deal wins are awarded to sales, even where legal is truly responsible.”

Papaya's legal ops evolution: From processes to performance metrics

During Jesimin’s tenure as Director of Legal Operations and Compliance at Papaya Global, she implemented significant structural and process changes that had a substantial impact on the organization's efficiency and effectiveness.

#1 Establishing Key Performance Indicators (KPIs) and subcategories

One of the first changes Jesimin initiated was a comprehensive analysis of KPIs relevant to legal operations.

“KPI’s need to be adaptive. They give insights to our board, who are not sitting with us day in and day out, as well as the management team that oversees the business regularly. I’m always looking to finetune the parameters, especially since legal and legal ops wins can be difficult to quantify and separate from another department. For example, I look for legal conferences and other legal-only access points to funnel deals to Papaya and add to our specific KPIs.”

#2 Building collaborative processes with sales and payments teams

Another change Jesimin introduced was the development of collaborative processes, particularly in partnership with the sales and payments teams.

“One of the best things at Papaya is the strong relationship between the sales team and legal, which we’ve only improved. New sales hires attend sales/legal process training seminars, where we explain the substance of the contracts and the deal management process with the other departments involved, such as finance, information security, etc. Employees at Papaya have immense access to the legal department, which is not something I’ve experienced elsewhere.

We also have routine refresher courses. Since our service allows companies to hire in over 140 countries, meaning someone’s livelihood is on the line, I want to do all I can to make sure we’re effective as a team to meet this very human need.”

Measuring legal excellence with KPIs

Jesimin sheds light on several crucial legal KPIs that can be tracked to showcase the legal department’s efficiency and impact.

#1 Deal closing times, broken down by subcategories

Jesimin emphasizes the importance of not just looking at this metric in a general sense but breaking it down into subcategories. 

“Subcategories give texture to the Board. For example, breaking deal size into tailored categories and showing their respective deal closing timeline is important. An enterprise deal for six-figures will likely take weeks to close, but if you absorb its closing time with a deal valued $50,000 and under, it will give an inaccurate picture of your team’s effectiveness. Approach the KPI details from the Board’s perspective: What data or metrics are most important for them to see?”

#2 Quantifying redlines with legal ops tools

Quantifying the success of changes to a process or redlines is another essential KPI that Jesimin recommends. Utilizing legal operations tools can be instrumental in achieving this.

“The Board is being bombarded with so much information from multiple teams, that how you present it is equally important. Your presentation to the Board and Management needs to be clear and concise, because they don’t have time to guess at the information or points you are trying to present. If you have a legal ops tool that will give contract provision data, such as how often you’re able to keep your limitation of liability clause as-is, that’s great. If not, find another way to track it, even if it’s an excel sheet.”

Tailoring KPIs to your unique business

Jesimin stresses that every legal department is unique, influenced by the specific needs and dynamics of the business it serves. Therefore, legal operations professionals should leverage their deep understanding of the organization.

“Your crucial knowledge of the business is built from your day-to-day experience, but without tangible data, you cannot show your team’s value to the business. Your presentation should inform management about the project status, key issues to resolve (if applicable), money or resource needs, and an overall summary of future initiatives to grow the business from your department’s perspective.. If you can implement legal ops tools to assist with these metrics, all the better.”

When it comes to implementing tools, Jesimin's perspective is clear: Processes should precede the implementation of legal operations tools.

“The tool is not going to help you if you do not have the buy-in of the individual on the other team. It has to be collaborative, even if you're working with challenging circumstances or personalities. Realize that the process has to exist before adding technology tools.”

While these tools can greatly streamline operations and provide valuable insights, they are most effective when integrated into well-defined workflows.

Cultivating advocates by building bridges beyond legal

Jesimin underscores the importance of building relationships not only within the legal department but also with the board and company leadership.

#1 Investing time and effort

Jesimin emphasizes that success in legal operations is a long-term endeavor. It's essential to recognize that meaningful change and impact do not happen overnight.

“When you join a company, you're extremely motivated. Especially if it's your first time in a leadership role.  There are a lot of thoughts, particularly the need to prove oneself. However, I would encourage everyone to realize that big changes cannot happen immediately. Before you stepped in, they had an entire way of working and they have their own view of legal. So, your job is to understand the needs of the company and those of each department and how you can foster the relationship.”

Trust is built over time, and key individuals see tangible results before they become advocates for the legal department.

“You have to invest time to get to know each individual C-suite leader or VP or whoever it is that has a voice and is seen as a contributor. For them to know and trust you, they need to see results from your strategies and tasks, while working collaboratively for the company as a whole.

As a new leader, don’t have expectations that you're going to implement massive changes in a week or even a quarter. Because just like with relationships, stakeholders come with baggage from their prior work experiences with your department or role. You have to show that stakeholder how what's happening in your team benefits theirs. If you can find a dual KPI, that's even better.”

It's a long process, though, building the trust and credibility for your team, says Jesimin.

“It's a marathon because even the best and most respected legal teams at a company don’t always get automatic approval of funding for operational innovation.”

#2 Building relationships with teams like sales

Effective collaboration with other departments, such as sales, is vital for legal operations. Jesimin draws parallels between professional relationships and group projects in school.

“It reminds me of being in school where you have a group project, and the person who presents it isn't the one who came up with the idea or implemented it, but the teacher hears that person say it, so they get credit, when it was actually a group effort. Or perhaps an assigned group is not working well together, and the teacher has informed them that they have to resolve their issues themselves.

When working with cross-functional groups, building a personal relationship can greatly improve team collaboration and performance, but the change has to come from within the group, and in collaboration with all members. This has allowed our legal and sales teams to flourish.”

In building relationships and showcasing the value of the legal team, it's crucial to lead by example. Jesimin highlights the importance of actively listening to the concerns and needs of other departments. Just as you want others to understand and support your initiatives, be attentive to their priorities and challenges.

“I have always believed that the happier people are in the world, the more good there will be in the world. Life is hard enough, so I just act the way I would want people to act with me. If I'm on a deal and I see a salesperson who’s doing a great job as a POC (they're assigning all the open items, taking charge, and making my life easier), you better believe I'm going to write to their manager say, ‘Hey, just wanted to let you know this person is being a rock star on X, Y, and Z.’ Because it's nice for somebody to recognize what you do.”

Embracing resilience, adaptability, and claiming credit

Jesimin shares invaluable advice for lawyers at all stages of their careers, emphasizing the significance of resilience, adaptability, and recognizing one's contributions.

#1 Resilience and adaptability

Jesimin acknowledges that pursuing a legal career, especially in highly competitive fields like entertainment, can be challenging. 

“Have the resilience and adaptability to take on new challenges. Even if you don't think it's a role that you want to have forever, if the colleagues appear strong, if the subject matter is something that you see has a future, you can study it. You can go to conferences and find ways to make yourself what the company needs, while unlocking new areas of interest for yourself.”

#2 Claiming credit and self-recognition

Jesimin acknowledges that many women in the workplace, herself included, sometimes struggle with openly taking credit for their accomplishments. This is a tendency that she's actively working to change.

“Women should not be afraid to take credit for their work, which is something I struggle with and hear my female peers say is an issue for them as well. We need more women mentors to coach other women in leadership skills.

When announcing the completion of a project to management, make sure to specify the benefit to the company, such as increased sales, cost savings, etc. Network with your coworkers and do job shadowing to build on current skills and learn new skills. Speaking at conferences or volunteering is a great way to demonstrate your competencies and to build new relationships. By advocating for yourself, you will gain new perspectives on work to advance your career. ”

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