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Established in 2019, Pinwheel is a B2B SaaS company that uses API integrations to connect employees' payroll accounts to various apps. In 2022, the company’s operations and commercial headcount were surging at an exponential rate, and this is when Ryan Nier joined Pinwheel as their General Counsel. 

“Pinwheel is a nascent early-stage startup building a B2B SaaS tool. I am the first non-commercial attorney here, and I aim to build legal functions and facilitate fast-paced growth by navigating legal risks.”

Ryan is unlike any other GC you would come across. He started his professional journey as a core software developer and then went on to become an attorney. It has been nearly two decades since Ryan took this plunge, and today, he has diverse experiences in both legal and tech. 

In an interesting conversation with SpotDraft, Ryan sheds light on the approach that GCs can take to identify the significant gaps in the legal function of a fast-paced company. He also talked about how his prior experiences have helped him prepare for his current role at Pinwheel. Read this blog to learn about:

  • Making the legal team approachable and transparent 
  • Showcasing the value of legal
  • Scaling the legal function
  • Quantifying the contribution of legal

Making the legal team approachable and transparent

Although Ryan had the experience of working extensively with cross-functional teams in his previous jobs, working at Pinwheel made him encounter new challenges. 

#1 Communicating in business terms, not legal

Legal team members must understand that business stakeholders might not be familiar with even the most straightforward legal jargon. When legal teams rely on legal jargon to communicate risks or get feedback on legal issues, there is a high possibility that business stakeholders will be frustrated or not follow. 

“Even though you’re from legal, you can't speak legal jargon in meetings. Translate your legal opinion to an easy-to-understand business rationale. And for this, legal counsel needs to learn relevant business terms and KPIs. Translate into their terms, not just yours.” 

#2 Reducing friction with stakeholders

“Sales takes precedence in commerce-driven companies.”

In commerce-driven companies, it is common for business units to see the legal team as a blocker. There might be instances where the sales and growth teams are looking to close a deal quickly, and the legal team takes time to run diligence or assess risk. That’s a natural tension – close the deal, but protect the company – usually healthy.  But it requires careful management of expectations and a true partnership where the business team understands you’re there to help and hence you should educate them on such risks and decisions.  

“If you’re in an advisory role like Legal, it is natural for you to have friction with business stakeholders. With B2C products, it will often be with the Product team but in a B2B setup, it will likely be with the Sales team. My advice is to understand which stakeholders you’ll have maximum friction with and then adjust and lean in. Try to align the legal roadmap with their goals. In case of conflicts, make sure you’re both seeing it as a partnership. Help them understand and navigate legal risks. Also, make sure they feel educated and comfortable in making decisions (or, if they’re not the decision maker, help them resolve and get to YES).”

Showcasing the value of legal 

Ryan suggests that, at fast-paced companies, GCs should actively engage in meetings with stakeholders to understand how the business works, identify the most prominent risks and try to find a few quick wins.

“Do an informal audit to identify legal risks or challenges. Push lightly to see where there’s resistance to change. Then see if you can find a solution on your own. These are the quick wins that will showcase the value that the legal department brings to the table.”  

In his first 60 days at Pinwheel, Ryan operationalised the contract pipeline. At the time, the company was neither leveraging a CLM tool nor having any dashboard/process to streamline contract management. He identified this problem and built a primary CLM tool that notifies people about contract updates on Slack, tracks approval and acceptances, allows prioritisation, and saves copies and drafts along with dates, versions etc. 

“I was a software engineer before, and thus I was uniquely positioned to build a CLM tool. Using, I built the tool in a couple of weeks. It was obviously janky at first (and if I were to do it again, I would have done a better job describing it and offering guidance on how exactly to use it as I rolled it out), but it’s now a pretty great tool that we rely on extensively. Presently, the contract pipeline at Pinwheel is operationalised, and every stakeholder uses this tool to manage contracts better.”  

By doing so, Ryan was able to streamline contract management at Pinwheel (with the help of his team), which resulted in two things:

  • Stakeholders saw someone from the legal department step up as a business enabler and invest in improving their processes.
  • Deals started closing faster and with better documentation, contributing positively to revenue growth. 
“By building the CLM tool, we brought added value. When you’re spending multiple hours a day on redundant tasks, it’s a good sign to see small improvements to that process yielding tremendous results. The CLM tool helped our legal team work more efficiently and the sales team to see what we were doing to enable them. Also, we got the bandwidth to prioritise commercial work and strategic thinking. It also helped us document the work and learn from it, and as a side benefit, it helped make a solid business case to scale the legal team at Pinwheel.”

Scaling the legal function in hypergrowth startups

“As a GC, you should have a clear understanding of all the legal functions that your team is responsible for or required to do. Then, you must acknowledge the fact that you specialise in a few fields and not all of them. Hire people and build functions accordingly.”

Ryan took on a role as GC and Chief Compliance Officer at a startup before Pinwheel. He mentioned recognising immediately that his strength is as a GC but not in the day-to-day functions of running Compliance. One of his first moves was to prioritise hiring compliance experts, including a Compliance Lead and a lawyer with deep experience in running a Registered Investment Advisor (RIA). 

“GCs should be aware of their weaknesses and ‘know what they don’t know’ - it is key to scaling the team. At the same time, you also need to keep in mind that your legal team should be lean and do your best to diversify talent while reducing redundancy.  Easier said than done, but that’s always the goal.” 

To keep the team lean, Ryan suggests GCs do not hire for all traditional roles from the get-go. Instead, hire folks for a specific role and give them to chance to grow. 

“While scaling a legal team from scratch, I don’t immediately hire for all functional areas. I look for what I call ‘Plus Ones’ or ‘Plus Twos’: people who are really good at something the business needs but have an interest or aptitude in one or two other things that I think we’ll need in the long term. For example, I hired an outstanding Regulatory lawyer with a history in Compliance. It’s both helpful for the business and great for the person’s development and career. People who want to spread their wings into other areas are also pretty motivated by those opportunities. It’s a win-win. Then, later depending on workload and bandwidth, you can promote some members and, if needed, make the next set of hires.” 

Quantifying the contribution of legal

​​Something lawyers are always super scared of is translating their turnaround times into quantifiable metrics. But whether it's a marketing review or a sales contract review, Ryan tracks the average times for those automatically through the tool he uses. 

“For example, my average for marketing review is around 1.8 days. Whenever someone's worried about the process and says something like, ‘Do I have to submit all marketing to Legal?’ — I try to stress the partnership again. Here’s why I need to review everything, here’s my experience in why that matters when you want to go public or get acquired, and here’s what standards I’m willing to hold myself to so that you don’t have to worry about turnaround times.  More often than not, they’re not upset that you need to be involved.  They probably just worry it will be slow, or you’ll have non-legal feedback disguised as legal. So don't be scared of the process, be scared of a flawed process.”

To gauge the contribution of legal, Ryan suggests GCs measure:

  1. The impact that every member of the legal team creates, and
  2. How happy each legal team member is in the role. 
”Happy people do great work, and sometimes we can lose sight of that when we stress output or hours or rely purely on KPIs.” 

For #1, he recommends soliciting feedback and conducting anonymous surveys, asking questions like:

“How was that meeting for you? What did we do well?  Where can we be better?”

Here’s his approach for #2:

“On the latter, I track engagement scores (based on anonymous, company-wide surveys meant to assess how happy someone is in a role and with their manager, etc.). Engagement scores represent how a team member engages or collaborates with cross-functional teams, how much they believe they can grow in the role, and how satisfied they are at work and with me. I hold myself to a high standard: I have a personal KPI of keeping engagement scores at 90%. That’s always a challenge.”

How to improve engagement scores:

“The easiest way I’ve found to up these scores is to ask my team on a bi-weekly basis to score 1-10 on things like how good I am at taking feedback, how happy are you in your job right now, what’s one thing I could have done this week to be better.  By asking for a score, you’ll get people to open up to you.  No one will ever give you a 10, and that gives you a great way to ask the follow-up question, ‘Ok, it’s an 8; what would need to change (about me, the role, etc.) to get you to 10?’’

While there is no one-size-fits-all approach to addressing the critical challenges that legal teams face, these solutions will definitely steer you in the right direction to help make a mark in your organisation as someone heading a legal team.

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