Contract Heroes

Streamlining Contracts for Business Success with Courtney Irelan

Episode Summary

Have you ever found yourself drowning in a sea of boring contract templates, or struggling to make sense of confusing legal jargon? If you have, you're definitely not alone. It can be incredibly frustrating and overwhelming to deal with all the complicated language and vague terms in legal documents. It's like being lost in a maze without a map.

Episode Notes

In this episode of the Contract Heroes Podcast, we are delighted to speak with Courtney Irelan. Courtney is a corporate attorney and possesses extensive expertise in various contract types, primarily specializing in commercial transactions and procurement. Prior to her legal career, she climbed the ranks in sales and marketing and eventually assumed the role of overseeing business operations for multiple retail stores. Courtney harbors a strong enthusiasm for contracts.

During our conversation, we talk about the Contracts Con event and the importance of practical contract management education in law schools. Courtney emphasizes the need to define the scope of services and terms clearly, as well as to avoid vagueness and ambiguity in contracts. She also stresses the importance of using plain language instead of legalese, which can be difficult for non-lawyers to understand. We also touch on tips for successful contract management implementation and highlight the benefits of having standardized templates in a CLM system, which can empower sales and procurement teams to turn around contracts quickly and efficiently. 

Listen to this episode to learn more about the importance of practical contract management education and the benefits of streamlining contracts for all parties involved.





Episode Transcription

Audio V1 - Courtney Irelan - Contract Heroes


Intro [00:00:05] You're listening to the Contract Heroes podcast. Your one-stop shop for all things contract management. And now here are your hosts, Marc and Pepe.


Marc Doucette [00:00:14] Hello, everyone, and welcome back to another episode of Contract Heroes, today joining us is Courtney Irelan. Courtney is a corporate attorney with experience in a wide array of contracts, with a primary focus in commercial transactions and procurement. Before she was an attorney, she worked her way up in sales and marketing to manage business operations for multiple retail storefronts. She has a very big passion for contracts. She loves hanging out on TikTok. So we're going to go ahead and jump in. But thanks for joining us and we hope you enjoy this one.


Courtney Irelan [00:00:42] Hey, Marc, thanks for having me. So I did go to Contracts con was the first in-person event put on by a law insider, spearheaded by Laura Frederick of How to Contract. It was an amazing event. It was really, really great. I've been to a few in-person events in my life. That was one of the best events I've ever been to It really felt like a bunch of friends coming together, particularly because, you know, if you are familiar with Laura Fredericks had a contract and some of the other presenters, there are people that you've read a lot of their content, you've seen their content maybe on TikTok, LinkedIn, etc., being there and integrate into a massive room full of people who all are geeking out over contracts, which was really cool. A couple takeaways from it, If there's ever a time that a lawyer or a contract professional is wondering, am I doing things right? What are these best practices? Am I doing the right thing? Is what I'm saying, supported by other people's best practices? Questions like that we often ask ourselves. Contracts Con really helped me  for example, say, Hey, this is something that I'm doing right. I feel really good about this. All these impressive people are saying these things and I'm just nodding my head yes. Oh, great. I do can do this. And then four things on the flip side that I'm I should maybe approach in a different way. I'm like, hey, this is a great new way to look at things. Let me look at the way that I currently do that and reassess. I think that they had a great lineup of speakers and of information and topics that even the most seasoned contract, professional or lawyer could benefit from it. There were some things that could seem very introductory, and then there were some things that were more advanced when it comes to data privacy, data security, intellectual property, indemnification, limitation of liability clauses, those a little bit more complex things with contracting. Those were the areas that I found to be the most helpful for me, but there was something for everybody. So throughout the process there might have been a couple presentations where it was mostly just validation that what I'm currently doing is in line with that presenter's perspective of what our best practices. And then in addition, having people in the room that were asking questions and getting clarification, hearing those different perspectives. It was all just a really lovely event, and I left there feeling very confident and walked away with more tools in my tool belt as well. And, you know, 17 hours of sleep was a big win.


Pepe Toriello [00:03:45] That's great Courtney we had a chance to meet with Laura twice in just a couple of months.  First time in Phoenix at the World CC event and last time last week at the C LM Academy, you can see like the passion, the heat that she has on all this community that she's been building for the past couple of years. It gives me a lot of FOMO that I saw,  like a lot of the contracts and legal tech celebrities going to Miami. But well, hopefully next next year we are going to be there. And I totally agree with you. I mean, there's like a different thing regarding contracts, more focus into the negotiation. You know, like all the types of processes and frameworks you didn't get from law school. I mean, maybe at law school, you get, you know, how to understand there what things that you have to take into consideration with contract law, but nothing like very practical like these types of events. So I totally agree with you that this can be something that will be like super useful for maybe a student going to law school or just to see some lawyer that is handling contracts in the day to day. And Right. If they're out of the law firm or working in-house, Right?


Courtney Irelan [00:04:52]  Absolutely and you know, to take that a step further, you know, I've been following Laura. I kind of stumbled upon one of her posts before she even started adding cool little cartoons back in 2021. I want to say like early 2021 or mid 2021 I stumbled upon. So I was kind of her original fans, I guess. So it was really kind of also emotional to meet her in person, got a nice hug and all that because she really helped me in the early stages of my career as an attorney. And I've only ever done contracts and corporate law. So I've read both of her books, and I am a member of her  Contract Community online. And I've been reviewing her posts every single day and reading all the contracts and things that other people in the community that she's built contribute to each one of her posts. So meeting her in person and then everybody else as well, many people who I am connected with on LinkedIn already and just getting to know them, it was really great. And I think that I genuinely think that her had a contract like, especially her latest book It should be its own class. It definitely should in every law school. I know that had I taken a class that taught with her book, it would have completely solidified my decision to go into in-house and contracting roles, but it would have prepared me as well as I didn't. I might have not felt like I was thrown in the fire, so to speak, as much as I was when I first started and just tried to scramble to learn from her information and from people, you know, who I referred to who were training me at the same time. So it's something that I'm hoping I'm starting to see in some law schools, including my own, but they are starting to introduce more of this type of curriculum. So I'm hopeful that law students in the future will start to actually get more of this hands on real world application learning.


Marc Doucette [00:07:06] Like you said, I think we're starting to see those classes pop up more. And I totally agree with you. When you know, you talk about Laura or you know, who we're going to be talking about next, which is, you know, Nada and contract nerds. But a lot of these people have built up such a reputation for themselves over the past couple of years. And, you know, we've we've all been virtual. I agree that, you know, you do get maybe a little star struck when you see all these people that are always posting all the time on LinkedIn and have a such a big following, you know, you finally get to meet them in person. And I think it's a really exciting experience. And it's great that we are seeing law schools that are starting to add these to their curriculum. You know, I can equate this to, you know, I wish that there were more sales oriented classes when I was going to college and, you know, in business school. And we're starting to see more of that, too, which I think is really solidifying it as a legitimate career. And more younger folks are getting excited to say, hey, you know, I do want to go into sales. And it's not just, you know, an afterthought where they don't know what they want to do and they take that path. But it definitely helps to have more courses out there that actually are things that you can apply to either work or your personal life. So that's that's great to see. And, you know, talking about Nada, you actually just wrote an article for for contract nerds. And I think this is going to play a role in kind of the rest of the conversation. So maybe we could start by you giving us a, an overview of what the article was about, and then we'll dive in from there.


Courtney Irelan [00:08:26] Sure. Yes. So whenever I started working with Nada at Contract Nerds, she asked me to come up with some kind of article. And the first thing that I thought about is what I have done, the most of which is and I've done this for companies where there's one, you know, a solo entrepreneur all the way to companies that are publicly traded. I've done this as a, you know, a legal consultant, business consultant and as counsel, and that is to take their preexisting contract templates and completely redo them. And I have this perspective of how contracts should be, and it's developed through my own personal experiences throughout my first career in sales and marketing and business operations, and then throughout my second career now as an attorney working in-house, and then also doing these various consultant roles for companies. And I've seen the same thing repeated no matter how large or small the organization is, and it's that they'll have like file folders of various contract templates. And it can even I mean, it can be so granular to the point where if they have their if it's a, you know, like a vendor of like a SAS vendor, they might offer, you know, 20 different kinds of options. They could have 50 different contracts, you know, for those. And it can get really overwhelming because as you know, the lawyers are individuals red line things and go back and forth with different companies. It starts to mess up the various templates. So when you end up looking at all of these templates and comparing the language, the language actually ends up being different. So you'll have conflicting language and different, you know, limitation of liability clauses, indemnity clause, merchant obligations and just name a clause and it's different from template to template. And so what I do is I try to consolidate all of that and then make sure that there is a master to the master template that could apply for all services. And also from there, you know, it really applies in every major department. So if there's a procurement department having their master service agreement that they would send out in lieu of using a counterparties paper or if they're dealing with like a smaller business that may not have their own paper to produce that. And then the same thing for H.R. employment agreements in many areas, MBA's, even finance department, if they're discussing any M&A work, you know, investments, things like that. So just ensuring that everything is really streamlined. So I wrote the article based on how to craft your contracts with confidence and providing ten tips to level up these contract templates. And I really tried to condense it to the top important features. So you really want to initially define the scope of services and really understand what are the services that are being provided, who is providing the services and what are the terms. And then that leads into defined terms because as you're talking about what services are being provided, there's going to be certain terms that are used throughout a contract and they'll be used repetitively throughout the contract. So it's really important to make sure that the definition there's a definition section, whether that's at the beginning, at the front or an appendix, it's much clearer to do it, to have an actual section versus having defined terms throughout the contract. It can get a little messy. I've seen it sometimes where they'll be defined term and then in parentheses it says defined later on like, Oh, well, now I got to go search and find the paragraph where it's defined later on. Whereas if you just have a defined terms section, you have that to refer to. And then from there stating the obligations from merchant and client or whoever the two counterparties are, or to individuals entering into a business transaction and really understanding what each party is bringing to the table, what is required of them. And with this, I would like to say that I've seen a lot of contracts that are super heavy with legalese and coming from sales myself, I remember before being an attorney and reading contracts that I was dealing with and not having a clue what was being said and so.


Pepe Toriello [00:13:36] Different language.


Courtney Irelan [00:13:37]  Yes, it absolutely is a different language. I mean, that's part of  law school teaches you from reading thousands of cases over the course of years is how to speak and write in legalese. So I use that skill and that new language that I learned, and I try to distill my legalese, language and contracts to as close to layman terms as possible. So in that way, anybody should be able to read it and. Understand, at least generally what it's saying, this reduces red lines dramatically. I've seen it firsthand so many times, countless times, where, you know, you start off sending out contract templates that are rife with legalese. And this often does occur whenever companies in particular outsource some of their contracts written by outside counsel. A lot of law firms are so used to writing with legalese that even when they're writing a contract, the law lawyers of law firms will often write contracts very heavy and old school legalese. And that's also where I think that, you know, Laura's book, How to Contract, really can help any lawyer that might be working in business or corporate law learn this same kind of skill, because she talks about this as well, just making sure that, you know, a salesperson can understand and talk with, because most of the time it's not it's not lawyers that are reading these contracts. It's the salespeople and the people they're selling to, which are usually various leaders of business departments.


Pepe Toriello [00:15:20] So write that. And what you need to have there is that the commercial side of the business understand the contracts, because most of the time they're the ones doing the negotiation process. Right. And, you know, the legal team does not need to be involved in every deal. Otherwise, they will just become overwhelmed. And especially where you see a like huge corporation with small legal teams and they just can't find the time to be, you know, being involved in the deals and negotiation process and also into the other, you know, issues, legal issues inside their company, talking about labor law, taxes and so on. Right. So I think that having very good pre-built templates, I mean, a well-designed, you know, legal design because that's something that also law firms, at least when I used to work at a law firm, nobody explained that to us. And you get a think about how you can make it easier for the commercial side to close the deal, to make a sale or to, you know, hire a new vendor. And that's very important. But one of the things that we've seen in and we really will like to get your opinion on this is that of course, a lot of the times this is going to be something that you should start working with the legal team. However, I would say that the departments that are most benefited by this type of work, working with their templates or they can stream are the processes and reduce that red redlining process with a third party are either a procurement or either a sales team or finance team, because now they can understand what's what the hell is inside of the classes, inside that contract. But what type of companies have you seen that are interested in these type of services? Like how does this look on your site? Like, do you usually approach to somebody inside the legal team or this is something that you need to bring all their stakeholders or buy into like procurement, for example?


Courtney Irelan [00:17:19] So by and large, my experience has been that having a contract lifecycle management software of some kind is a desired tool by every department, and that is that I've not I have never run across a scenario where anybody within a business says, Oh, we don't want that. Typically, it is a matter of prioritization and cost and a disconnect between knowing why it's so important to have a CLM. In fact, in my very last role, that was what I did within my first 90 days, I ran a procurement bidding process, the whole RFP process to get a CLM, because I, you know, once I finished revamping those contract templates, that was the very first thing that I did after that. And the way that I started with that is kind of getting a pulse check from everybody. So initially in my last role, for example, there was no real training when I was hired, so I was kind of given my laptop, my office, access to the legal inbox and told, Hey, all right, get started drafting contracts. So after I created a master to the master contracts, I immediately started organizing meetings. First, I worked at a software check company, a Fintech company, and so I met with the lead developer first and actually went through certain areas of the contract that were technical and broke down that legalese into layman's terms for him. And then asked him to do the same for me in the technical side of things that I didn't understand, to ensure that the things that were saying in the contract that we're providing are still accurate. Some of those contracts might have not been updated for many years and the services have changed drastically since then. And so that also required adding in new things, especially for obligations if you're a service provider, to ensure that the services you're providing are reflected in the contract and that those are updated. And what was great about meeting with the lead developer is he also happened to know for the questions that I had that he couldn't answer the expert or head of the department that I should speak with. So by the end of it, I ended up meeting with about ten plus different individuals and really got a great understanding of the business because I was meeting with all of these different business unit leaders within their specialized verticals, and I was able to fully have a well-rounded understanding of what the business does, how it does things, and how the contracts contributes to that process and whether certain services require more PII, for example. And so that helped with regard to whenever I was putting in different language that would conditionally format and move into a contract if that service was selected for example, if a salesperson sold a certain service and that service required a higher level API from the end user. Then certain protective language would come into play and then maybe that's when we need to deploy our data processing agreement, things like that.


Marc Doucette [00:20:59] You know, in these organizations that you worked with, are you seeing is there a common trend around, you know, the specific contract types? Are there certain contract types that you always see that they really need help with? Or does it is it very wide and large by, you know, the vertical that they're in or the type of companies that they work with? Things like that.


Courtney Irelan [00:21:18] I've mostly worked with fintech and tech companies. I have also worked with consumer finance and related industries. But most of the time what I see is master service agreements, master service agreements and SAS agreements. They are the ones that tend to have been outsourced or completely written by a lawyer that maybe came from a law firm and may not have that training in contracts, or the history and background and knowledge from a sales person perspective to know like, Hey, maybe we shouldn't make contracts so difficult to read It requires a lawyer to help their commercial team or the procurement team understand what's being said here. Maybe if we write it in a simpler way where most people can understand what's going on, we're going to be able to remove a lot of burden from the legal department. A lot of bottleneck gets removed. So everything's not just coming to legal just because it's nobody understands what the contract says. So I try to make sure that the message is that that's your key agreement messages and SAS agreements, that those are the two key contracts I've seen and messages of all kinds, right, Because that's pretty wide across the board and it's always kind of the same deal that they're just not spelling out the necessary information in a way that is accessible to everybody. And by streamlining that and making it really, well, kind of broken out and follow a logical order, it really helps to keep things simple and reduce the amount of legalese, keep things in a plain language, and then a huge, huge key thing. There's two, two big key things. One, avoid vagueness and ambiguity. I know there are a ton of business leaders who feel deep within themselves that the more they have vagueness and ambiguity in their contract, the more they feel protected. Right, because like, oh, this could be interpreted so many different ways. This protects us more because it's vague and it's actually the opposite. You know, traditionally contracts are construed against the drafter. So you have this whether it's an employment in employment or whether it's with a vendor or whoever drafted the contract, you're going to have to answer for what does this phrase mean, What does this clause mean? And if you really can't say that and it doesn't say it and it could be interpreted multiple ways that goes against the person who drafted it or the company that it's coming from. So I believe it's extremely important to make sure that we don't shy away from trying to spell out as many risks as possible, even though it's very tempting because I understand the desire to have it be vague and ambiguous. But yeah, it's just that's not going to work. And then the second thing is to use examples to your advantage. Make a really clear statement that this is an example, especially if the business model is of a more technical nature. Providing an example within the contract helps contextualize why certain things may or may not be needed. So if if you know, procurement departments or legal departments or even business were on the sales side, they're receiving a lot of pushback in certain sections. That may be a good indicator that either it's two things either the section needs to be rewritten, but also maybe include an example for that that helps people understand how this might interact with them.


Marc Doucette [00:25:14] Yeah, And I think, you know, obviously a big trend lately and some of the things you just touched on are revolving around making these these contracts more simplified so that other people can understand them. You know, the first time I heard the phrase legalese is I had to look it up because I had no idea what anybody was even talking about. So we've come a long way. And in eight years, I think these are all awesome points. And, you know, I think something else that we wanted to touch on was how does having these better built templates and using a CLM system, how do those two things come together to strengthen organizations and make everybody really better at their jobs?


Courtney Irelan [00:25:51] That's a huge and wonderful question. I mentioned earlier that in my experience it's been that every team wants a CLM. And one of the biggest problems that teams seem to have is getting executive leadership buy in. And what I have seen over and over and over again is that CLMs, not only do the streamline the efficiency of getting deals done, it's a wonderful process, efficiency, but it standardizes things, reduces red lines. And I mean, so I'll give an example. My most recent position when lawyers were being tasked with having to draft all the sales contracts and then send them back to sales and sells them out, we could do, depending on how complex it was, whether it was an enterprise or smaller business between. 5 to 20 in a week. 20 like if it's smaller stuff, easier stuff by having multiple standardized templates inside a column and it empowers your procurement and your sales department. So they could be at a trade show, right? If they're selling something and trade shows, part of what they do. They could be at a trade show, pull out their iPad, open up a CLM platform, and immediately start drafting a contract using pre-approved legal language. And that could be over weekend. So then by the time Monday morning rolls around, there are 15 contracts that are ready for review and signature. And the first week that we have the entire sales team up and rolling with the CLM, we had close to 50 contracts completed in the first week, completed both sides signature. That was a massive increase. And I think that it's really important for executive leadership buy in to understand that part. But the sales turnaround part sales always wants the deal done yesterday. Right. And having that part there, too, where you're empowering your sales team to have the contracts and they already know that everything is approved by sales, or maybe you have some fallback language. If there's any pushback on certain areas, you can have pre-approved fallback language and stuff like that, They can turn those contracts around themselves and their business leaders can approve certain commercial terms so it may never even need to come to legal unless it touches specific legal realms. Right. Certain legal clauses like limitation of liability clause, for example, the most common one. So if that's not touched, pretty much you can just give full control to procurement and sales.


Marc Doucette [00:28:43] And, you know, the last thing that I wanted to touch on here, Courtney, is, you know, when we're talking about user adoption and training folks to leverage these CLM tools, how much easier do you think it makes it when everybody can understand the templates? Maybe the sales team is actually filling out, you know, how much easier and faster does that make it to get adopted to a CLM tool that an organization has just implemented?


Courtney Irelan [00:29:06] Super fast. I just did this. I just rolled out a film to a pretty large sales team of international folks, like people located all over the world. And we did different rounds and we created two different profiles. One was a salesperson for the business and one was a potential client. I had one of my fellow corporate counsel. We both played one or the other role and we did a Zoom meeting and we just would switch sharing screens and show them how to give a demo of how the process works. And then before we gave them access to it, we required that they went through the CLM, provided training and provide us with a completion like some kind of screenshot that they actually completed the training so that we knew that they were invested in it. And if they didn't do it, we said, Well, it's available for your use. So as soon as you complete that, you can get your contract done. So it really incentivized sales and their business leaders to learn how to use software.


Marc Doucette [00:30:19] And I like that. Yeah, I like that a lot. I think we might start doing that.


Courtney Irelan [00:30:23] Yeah, it's a good incentive. And then next thing you know, I mean, like I said, the first week, 50 turned around just like that. And I think that seeing that for themselves, just how many more contracts can get turned around when you have the CLM in place and everybody knows how to use it, everybody's familiar with it, of course is going to be growing pains, of course, is going to be questions, but that's fine. I mean, once it's up and running, you have a well-oiled machine and then, you know, legal is then free to be able to periodically, you know, every 3 to 6 months, quarterly, whatever you're comfortable with, review the different templates because you have that free time now. So now you can have those meetings and touch base with various department heads and say, all right, you know, are there other any changes to the services or obligations of the way that we're doing things or, you know, integrations, APIs? Is there anything that we need to know that's that's changing or will change and then updating those various and relevant sections and clauses within the contract.


Pepe Toriello [00:31:32] Right. And now they have data, you know, what things have been improved then where are like new bottlenecks? Maybe because this is like an ongoing process that you can just keep improving and that's also part doing CLM implementation is, is not just like one time. And then that said, this is something that you need to be continuing working. So I really love this, and I just want to have to ask you one more question. And this is like having all your experience doing this implementation like for folks that are starting to do a kickoff call, maybe for a CLM implementation of what would be like the number one tip on what not to do during this implementation.


Courtney Irelan [00:32:15] It depends on who's talking. If it's the legal team talking or a business team in there, I feel like I'm going to give you a lawyer's answer. It depends. Because if you don't have sufficient buy in, some sales people may look at CLM's like, Oh, great, now I've got more work to do on my end. They may not realize initially just how much power it gives them. So I think that really emphasizing to sales teams, executive teams and business leaders that this empowers your team. You're not having to wait on legal anymore. You're not even having to wait on procurement a lot of times anymore. CLM's gives so much power to the sales and business unit leaders, and that is something that I would really focus on kind of drilling in one is saying, Hey, this is handing you back the power. Instead of sending in an email or request form to legal asking for this contract and having to wait depending upon the pressures that are on legal or procurement, you can do it yourself right now, which is what every salesperson and business leader wants. They want that turnaround. I would say, you know, don't focus on what it's going to do for legal, focus on what is it going to do for the business? What is it going to do for sales?


Marc Doucette [00:33:35] Yeah, I mean, that's what we always talk about, right? I think it used to be considered legal tech. You know, this was something for the legal team. But I think as the spaces evolved in, the solutions have evolved. Everyone is probably a little bit past realizing that this is really enterprise wide technology that multiple departments really need to take involvement in. And it's not something that legal should, should own. It's something that legal should definitely be a big part of. But the business units really this this puts the power in their hands and allows them to to really drive their contracting processes.


Courtney Irelan [00:34:06] Exactly. Yes.


Marc Doucette [00:34:08] Well, Courtney, this has been awesome. I think we went a little over in time here, so we're going to go ahead and wrap up. But awesome conversation. I think there are a bunch of takeaways here for, you know, organizations that are in all different parts of their journey, whether they're still using manual methods and I think things that they can focus on or, you know, harmonizing their templates, simplifying them and doing this alone will allow those organizations to cut down cycle times when it comes to negotiating with other parties. And if they are, you know, involved in the in CLM  process obviously, we talked about a bunch of good takeaways there as well. So thank you so much for joining us and good luck in your future roles, and we hope to chat again soon.


Courtney Irelan [00:34:45] Thank you so much. Thank you both for having me, I really did enjoy my time here.


Marc Doucette [00:34:48] Awesome. Well, thanks, everybody, for listening to another episode of Contract Heroes. We hope to have you back here real soon.


[00:34:54] This episode of the Contract Heroes is sponsored by Koho Consulting. Koho helps organizations of all shapes and sizes, find, implement and manage their chosen CRM tool. Whether your project is buy or sell side LED, Koho can help you navigate the waters of the clean space to make sure that you're getting a product that's going to fit like a glove year to come. If you'd like to learn more about Koho, visit their website at