Charles Lu & Ian Faison 40 min

Time Kills All Deals


On this episode, Charles Lu, VP of Operations at LexCheck. Charles explains how he uses RevOps as a strategic tool for not only tracking revenue, but assessing performance and identifying areas for improvement.



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[MUSIC PLAYING]

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Welcome to Rise of RevOps.

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Today's episode features an interview with Charles Lou,

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VP of Operations at LexCheck.

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LexCheck accelerates contract review and streamlines

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negotiations by delivering red lines and issues lists in minutes.

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Today, Charles will explain how he uses RevOps

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as a strategic tool not only for tracking revenue,

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but assessing performance and identifying areas

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for improvement.

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He'll also describe the biggest challenge

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in modern sales leadership, balancing creativity and process.

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Welcome to Rise of RevOps.

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I'm Ian Faizan, CEO of Cast me in Studios.

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And today, we are joined by special guest Charles.

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How are you?

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I'm doing great.

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And thanks for having me.

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I'm excited to have you on the show.

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We'll be talking rev-ups and all the cool operational stuff

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you're doing at LexCheck.

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So first, let's get into it.

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I know you're not technically a diet in the world,

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rev-ops person.

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And yet, here you are.

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How did you come to be someone who is leading operations?

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Yeah, yeah.

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Definitely don't fit, at least what I know of as the typical persona

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for operations.

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Originally, I was trained as a mechanical engineer.

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And then I practiced corporate law, actually,

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at a large firm in New York City after I went to law school.

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So I actually came to LexCheck originally

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as a refugee from Big Law and then

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into a product and a business analyst role, actually.

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And so my path to now leading operations of the company

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actually went through product and business development,

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if you will, initially building out features of the tool,

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like very technical stuff, and then from there

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into more dealing with our clients,

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figuring out how to maximize value for them.

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And from there, really taking charge

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of a lot of the operational aspects of the business.

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And at this point, that mandate includes sales and revenue.

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So my title now really reflects that not only

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is the operations of the company in terms of delivering

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and just day to day, making sure employees are taken care of,

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but also our sellers and how they're going to go out

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and help people solve their problems, get LexCheck,

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and for us at least close those sales and then get them going.

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So yeah, that's a little bit of the history.

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And what's your definition of revenue operations?

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It's a structure that my sales team needs to fit themselves

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into so I can help them be better at what they do.

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That in a nutshell is the way that I look at it.

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It's a tool, right?

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It's a tool for me to, one, get information

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about how the revenue acquisition aspect of the business

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is working, right, evaluate whether it's doing well,

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whether it needs to be improved in certain areas.

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But also it's a tool to help me experiment, right?

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With different tactics, different ideas,

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to be able to kind of implement those things

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in an efficient way and get learnings out of them

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that I can implement and deploy and kind of get value out of.

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Obviously coming into a role where you didn't have

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like a dad in the law, operational background,

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or operations background and now leading rev ops

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and seeing the business holistically, obviously,

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you are, if you have a background in law,

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so you know the product intimately from that perspective,

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do you think that sort of gives you an advantage

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in like the rev ops lane because you understand

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the product so well?

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I think it definitely does and I think it does in two ways,

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right?

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So first coming from more of a product operations

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and just general kind of operations pathway

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through the company to rev ops, I think I'm a little bit more

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in tune with the kinds of problems that we're actually

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trying to solve for our clients first and foremost.

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Some of them might actually solve with our internal tools,

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right?

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It's great to be able to eat our own dog food,

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be able to kind of take these tools that we spend so much time

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developing and get some real value out of them.

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And in that process, that gives me even more insight,

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right into the kinds of things that go into an implementation

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cycle or even a buying cycle and things from those,

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from essentially those being able to take things

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from the act of implementing or setting up the tool

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and actually using it in practice that are going to translate

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or need to be reflected and measured at different parts

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of our sales cycle.

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So I think it definitely adds a layer of a perspective

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that wouldn't otherwise be there and I'm really glad to have it.

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Yeah, you know, so often on the show,

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there's sort of the more strategic level revenue,

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life cycle decisions that get made.

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And then you have the like underlying technical sort of ability

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and the team that can sort of build that stuff out

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and bring information back to sales and marketing

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and customer success.

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Yeah, yeah, I think particularly for us,

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because now revenue operations and our product

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are very intimately linked not only through myself

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but also some of our other sellers, right?

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Who we brought in over actually from our implementation side

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since I kind of took over.

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We're closing that gap even more, right?

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We really want that gap to be as small as possible.

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What the client experience is and how to maximize that

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should be front and center in the minds of all of our sellers.

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Yeah, zoom in out.

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So tell us a little bit more about LexCheck

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and who are your customers?

5:36

Yeah, sure.

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So LexCheck is an automated AI powered contract review solution,

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right?

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So in a nutshell, we can actually make edits

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to foreign documents.

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So documents that are coming across the desk of your sales

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team or your procurement team contracts

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that your business is entering into.

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LexCheck can actually read those even if it's not your document,

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even if it's coming from somebody else,

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it can actually go in and make automated changes

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to the language, right?

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So it's actually taken a first cut

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and marking up that document, something

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that typically you would have to wait for legal to be able to get to.

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I mean, we all know legal departments are strapped everywhere,

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right?

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And I've never heard of a legal department that

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isn't short of short on bandwidth.

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But to be able to do that first pass

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and be able to take some of that lift off of legal's plate,

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what we're really doing is helping

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legal kind of serve our business teams a little better.

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And then obviously, you're not just out of operations here.

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Maybe you've observed also the council, the announced council,

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how involved are you in the actual deals?

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You're seeing things from the one inch view

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and from the 30,000th of you.

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Yep, no, that's exactly right.

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I do serve the role of in-house council

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when it comes to any agreement that we're signing.

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So I'm essentially a team of one.

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And we're serving all of our customers, all of the entire sales

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team, our procurement team, our product team,

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when they're looking at new tools,

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all that kind of has to run through me.

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So let's just say I'm really, really grateful

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that I have a great tool internally that I can use to help me do that

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and help me make sure that nobody's waiting too long for help from legal.

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OK, let's get to our first segment.

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Rev obstacles.

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Let me talk about the tough parts of RevOps.

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Would have been some of the hardest problems

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that you faced leading a team that includes RevOps?

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Yeah, I think when I came in and kind of took over

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the mandate, one thing that I noticed immediately

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was our sellers had some friction with the infrastructure

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that we had put around them.

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So exit criteria for stages in our pipeline,

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requirements for escalating issues, all of those kinds of things.

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Do we have a product sheet?

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What am I selling?

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And how do I sell different things?

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Do we have the right collateral?

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We had a very comprehensive infrastructure set up,

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but it actually became a bit of an obstacle

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because it prevented folks from getting creative.

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We've been around for a while, and we've been fairly successful

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in a lot of ways.

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But I think that we are still, as far as I'm concerned,

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always experimenting to be able to do things better.

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In the space where we're at, especially as one

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of the first movers in the AI space,

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in order to stay ahead, right, and stay ahead of the competition,

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not only do we need to be creative from a product perspective

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and a delivery perspective, but also from a sales perspective.

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And so the biggest obstacle that I've had to face in this role

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so far has been creating an infrastructure or process

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points around our sellers that is flexible enough to let them

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be creative and let them do what they do well, which

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is help our customers identify pain points

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and get them on a tool that's going to provide them value.

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But at the same time, I still need

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to be able to get that insight around how they're doing their jobs

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and how well they're doing their jobs.

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So being able to take that really complicated infrastructure

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and turning it into something powerful but manageable

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was probably the biggest overall challenge.

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I love this stuff because it's totally

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where the road meets the road.

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And it's like, obviously, in a smaller work,

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it's like you can see it all if you're running,

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if you're running Ramos for a 20,000 person company,

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it's completely different.

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I want to talk about the stages.

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Yeah.

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It's like, what was it about exiting the stages that was creating

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the challenge?

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So I'll give you a real easy example.

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So our pipeline for sales opportunities that are qualified

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starts with discovery.

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But the exit criteria from discovery

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into the later stage in the pipeline,

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at that point it was evaluation or proposal,

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something like that.

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The exit, there were something like 12 or 14 different exit

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criteria that needed to be filled in around what the customer

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was doing, what kinds of documents

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were they looking at, what kind of throughput

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or in the workflow were those clients seeing, right?

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Estimated time savings, all of that kind of stuff.

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And don't get me wrong, those things

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are super, super important for us to know, right?

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To be able to get maximum value for our clients.

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And so I understand why they would have been there

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to begin with.

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That being said, though, as we--

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I mean, one of the monitors that I live by--

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and this actually comes from our CEO

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is the time kills all deals, right?

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Inactivity kills all deals.

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Open decision points will kill a deal.

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Yeah, right.

10:39

And so what the challenge that we saw coming in

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was taking those exit criteria and boiling them down

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to, can you write a proposal for this client, right?

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Not a proposal that they need necessarily to sign, right?

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But can you write a proposal that will basically

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set out something that we can provide them

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that will provide them value, right?

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At a price point, that makes sense

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to solve a problem that exists.

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And if you have that information,

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you can move it into proposal, right?

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So that's super, super concrete example of kind of one thing

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that we did.

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Another example, actually, is taking that proposal document

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and moving it way further up in the process, right?

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And this is a little bit counterintuitive,

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I think, for our sellers when we first did it,

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maybe not for your listeners, right,

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who have kind of thought about this problem a little bit

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more broadly.

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But for our sellers, I think, they, in bless their hearts,

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they really want to get it right.

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So they want to know the information.

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They want to be able to serve our clients

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in the best possible way.

11:38

They want to get all this information,

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get it down, basically down the line,

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know everything that they possibly can

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before they put a very detailed proposal in front of the client.

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And one thing we changed was we took that proposal

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and actually moved it right after discovery, right?

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And what that helped us do was one,

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create a tangible, achievable goal for our sellers

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as to what they're discovering it to accomplish.

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And two, give us a measurement point very early on about,

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is this a deal that makes sense for us

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to continue spending time on, right?

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Our clients at this point know because we've,

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we've kind of optimized the way that we communicate this stuff,

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that this proposal document isn't a final,

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it's not meant to be signed right now, right?

12:19

Nobody's saying that you need to take this proposal,

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take it to, you know, your investment committee

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or your procurement committee

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and have them sign off on it right now.

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It's just meant to be a vehicle

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to make sure that we're on the same page, right?

12:33

Is this a need for you?

12:35

Is this a product that you're interested in?

12:37

Is the price point in the right ballpark?

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And getting that out very early in the process gives us

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some certainty in terms of, you know,

12:44

this is worth making additional investment, right?

12:47

Working with the client to kind of get this

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across the finish line,

12:50

but also it's really, really beneficial to the client.

12:54

'Cause then they have a piece of paper

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that they can use to have internal discussions, right?

12:57

They have a piece of paper that they can ever refer back to

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or show people and it helps them solidify in their minds

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that this is a sales process.

13:03

It's not just, you know, we're up in the air talking

13:05

about interesting problems to be solved by novel technology.

13:09

It's a really tangible, okay, we can,

13:12

if we sign this up next week,

13:13

we can get started within, you know, two weeks

13:15

and my problem is gonna go away, right?

13:18

That's the kind of, that's essentially

13:19

what we're trying to achieve.

13:20

- That was a great answer.

13:22

So obviously, you know, you're a growing company,

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how do you balance managing sales,

13:28

which we talked about, a bunch, marketing

13:31

and customer success?

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- I mean, the short answer is there's not much

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balancing, right?

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It's just three different firehouses, right, if we're honest.

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- Right, flops.

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- And ideally, they're all kind of,

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you can point them all in the general direction

13:45

of success of the company, right?

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Which is really for us, success of our clients.

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So, whether it's, you know, marketing and sales,

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it's really about finding a way for our clients

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to understand that they have pain points

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that can be solved with our software, right?

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They can be better off using our tool than otherwise.

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And then our customer success,

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it's really about the practical nitty gritty

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of helping them get there.

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Making sure that once things are implemented,

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they can find that value.

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I guess where the balancing comes in, right,

14:15

is the better job we're doing from a marketing

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and a sales perspective, the easier a job

14:19

our customer success department has, right?

14:22

So being able to kind of create some process

14:24

around, you know, marketing and sales, right?

14:28

What kinds of points we're pushing

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in terms of highlighting value and pain points

14:34

to how those things can be solved

14:37

when we really get into the sales process.

14:39

What are the must-haves when you're doing the demo, right?

14:41

In terms of being able to communicate that

14:43

with the client and being able to show them

14:45

what the value looks like.

14:46

If you can map those things on

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to how customer success is also doing their jobs

14:51

and bring it all back, right?

14:52

You get past that, the biggest problem,

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which is always that loss and translation piece, right?

14:59

We're experts in our tool, the client is not.

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The more we can hit consistent,

15:03

the same consistent points over and over again

15:06

from top of funnel, right, in marketing

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to, you know, the real heart of the funnel

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with our sales team and then kind of post-sale activity,

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the more we can be consistent

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and be hitting the same things,

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the more success we have.

15:19

- Obviously, legal review is incredibly hard to scale.

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This is something that like every single company deals with,

15:30

like no matter who you are, you deal with,

15:32

legal problems you deal with legal review.

15:34

It's incredibly expensive and time-consuming,

15:38

but you also have to deal with this too.

15:40

And so, yeah, just curious how do you,

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how do you make the legal stuff easier for a customer

15:45

and then how do you deal with it sort of internally?

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- It's interesting, right, because, you know,

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Lex check is really on the cutting edge

15:51

if you're using AI to solve a lot of these problems,

15:53

but the fundamental principle of what we do

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is actually very simple, right?

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And it's not, you know, we're not a company

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that's rooted in LLM, even though we use it.

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We're not a company that's rooted in NLP,

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even though we use it, right?

16:06

We're a company that's rooted in just simplifying

16:09

and scaling legal.

16:11

And that starts with a word that everybody has heard,

16:14

not a lot of people actually do this,

16:16

but it starts with playbooking, right,

16:17

the way that you actually conduct the legal review.

16:20

And that's easier said than done, right?

16:21

If it was easy, everybody would already,

16:23

like they'd already have it done,

16:25

everyone would have a super easy to understand,

16:26

super easy to follow, you know, call it a Bible, right,

16:29

for how you review legal documents.

16:32

But because it's such a difficult thing

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for a lot of people to wrap their heads around,

16:37

the alternative is let's rely on lawyers

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to just exercise their own judgment, let's basically

16:43

bring in expensive resources to be able

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to do this job for us.

16:45

And that's where we get into the problem

16:46

that we were describing, right?

16:48

Which is, it's really difficult to scale

16:49

because all you're doing then is you're stacking body

16:51

on body on body, each of those bodies are super expensive

16:55

and the only return that you're getting on them is linear,

16:58

right?

16:59

So you're not really setting yourself up for good growth,

17:02

right, especially if, you know, your revenue takes off.

17:06

By playbooking things gives you two advantages.

17:10

First, it actually makes the on-the-ground task

17:12

a lot simpler, right?

17:14

You take out a lot of the discretion,

17:15

you make it so, you know, somebody with less experience,

17:18

right, somebody with, you know, somebody with less

17:21

of a proven track record on judgment,

17:23

you're more comfortable having them take the wheel, right?

17:25

Because they have guardrails from that playbook.

17:28

The second thing you can do is actually take a look

17:31

at the playbook holistically and think,

17:33

does this actually, does this playbook make sense

17:35

for our organization, right?

17:37

Are the things that we're doing,

17:38

do they actually make sense for a company our size?

17:41

Now, those are things that you can do without LexCheck, right?

17:45

If you're really disciplined and you take an eye

17:47

on all these things and you kind of see it all holistically,

17:50

you can do that kind of stuff without LexCheck.

17:52

But with LexCheck, we are able to actually, you know,

17:56

with LexCheck, I'm able to support all the departments

17:58

of the company by myself, right?

18:00

I don't have any help.

18:01

I can do it all by myself.

18:03

And that's because instead of delegating to another person

18:05

that I need to train up, instead of, you know,

18:08

delegating the analysis of the playbook to somebody

18:10

that I need to train up, what I can do is actually delegate

18:12

this to our own software.

18:14

So I have a playbook.

18:16

I know how I like to mark up NDAs, right?

18:18

I know the, you know, three or four things in NDAs

18:21

that I really care about that make,

18:23

that are important to the company to LexCheck.

18:25

And now I have a piece of software that whenever one

18:27

of our sellers has an NDA, they need to enter in two.

18:30

Instead of coming to me with it,

18:31

they can run it through the software.

18:32

And if the software says, you know,

18:33

I don't see any big issues here,

18:34

I'm not making any big changes, they can sign it then.

18:37

Yeah.

18:38

They don't have to come to me anymore, which is great.

18:41

For stuff that's a little bit more complicated, right?

18:43

For stuff like when we're entering into sales agreements

18:45

with our clients, and they want us to use their form,

18:48

obviously, right?

18:49

Especially when you're dealing with Fortune 500 clients,

18:51

like, you know, we are, they're often saying,

18:54

no, we're not using your paper.

18:56

You gotta use ours, right?

18:57

Like we're, we're XYZ Fortune 1 company, right?

19:00

Like, we're not using your paper, come on.

19:03

They're sending it to us.

19:04

And at that point, what I can do is I can look at, you know,

19:08

running it through our tool, I can see, okay,

19:10

here are the points that I actually need to push back on.

19:12

And it helps me out a little bit, right?

19:13

'Cause it makes it so that review process

19:15

is actually quicker on me,

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and I can get it back around to myself

19:18

rather quickly.

19:19

But in addition to that, when you start running more

19:22

and more of these documents or more and more

19:24

of our clients through the tool,

19:26

what I can see is essentially a heat map, right?

19:29

What are the things that are sticking points, right?

19:31

Having the software be a layer on top of the playbook,

19:34

having it actually apply the playbook

19:36

gives me a ton of information about

19:38

what are the sticking points of legal review?

19:40

What are the things that are holding back

19:42

our performance from a RevOps perspective, right?

19:45

And then, you know, because these two functions

19:47

are consolidated here, I can make a judgment call.

19:49

I can say, okay, well, you know,

19:51

and if I had a colleague who was representing legal,

19:53

you know, apart from me, I would go to that person,

19:56

I would say, these things are, on average,

19:59

taking us, you know, they're adding a week or two weeks

20:02

to our sales cycle, right?

20:04

We think that that's projecting out

20:06

to killing X percent of our revenue, right?

20:09

If we get rid of this, we think we can see the benefit.

20:12

Do you want to keep that, right?

20:14

Is that something that you really want to keep?

20:15

And we can have that conversation

20:17

because we have the data, because we're measuring it.

20:19

Specifically on the legal documents,

20:21

because anybody, I think, who sells, you know,

20:24

especially enterprise stuff, right?

20:26

It's gotten to that point where legal is doing their best,

20:30

but ultimately, you know,

20:33

frustrating a lot of the other stakeholders

20:35

because they have a job that's so hard to understand, right?

20:38

And being able to take that job,

20:40

codify it, simplify it, and be able to optimize on it,

20:43

one increases transparency,

20:44

so everybody's on the same page, right?

20:45

This is not because legal wants to slow anything up.

20:47

It's because legal has a mandate, right?

20:50

But then we can have a conversation about that mandate.

20:52

And then form a conversation, you know,

20:54

that is based on actual facts and actual documents,

20:58

and we can have a conversation about smoothing things out

21:01

and making things easier for everybody.

21:02

- Gosh, I cannot even tell you how many deals

21:05

I feel like I've lost in my life

21:07

because the legal review is so slow.

21:10

And so it's like those sort of things

21:12

that every single sales leader, you know,

21:16

loath the wait time of that legal review,

21:19

forget the deal getting killed, but just like the actual time

21:22

time kills all deals.

21:24

And like, obviously you must see that all day, every day.

21:27

Like, would you have any like data about that?

21:29

About like, how much time things go into legal review?

21:32

How much time is wasted there?

21:34

- Yeah, for sure.

21:36

So, and I'm gonna speak for us at this point,

21:39

just on kind of data that we have internally, right?

21:42

I think before we started using our product internally

21:45

to help us review our sales agreements, they were taking,

21:49

and this is my time, right?

21:51

This is just actually my time.

21:53

They were taking me on average between six and 10 hours, right?

21:57

And typically that would be spaced out

21:59

over a couple of days.

22:00

And these are fairly robust agreements.

22:04

I like to think I was already taking

22:06

a pretty commercial approach, pretty middle of the road,

22:09

not trying to hold up the sales team.

22:10

At that point, you know, I was working with the sales leader

22:12

and the sales team, I really need them to succeed.

22:14

I'm an early employee at the company, right?

22:16

And ultimately my goal here is growth, right?

22:19

But since we've implemented that software,

22:21

that time has shrunk down to less than half.

22:24

And, you know, it's actually shrunk down probably more,

22:27

but I'm gonna say half 'cause I don't wanna create

22:29

just like an unbelievable situation, right?

22:33

I think a lot of people, they might not necessarily

22:35

understand exactly how much time you can save

22:37

when you have something you can go in

22:39

and make some changes for you,

22:40

and actually streamline your review process.

22:43

The real benefit though, is that instead of having

22:46

to sit down like two or three times with that doc, right?

22:49

Like open it up, you know, after I have my coffee

22:51

in the morning, if I don't have other meetings, right?

22:53

Like what kind of day is that?

22:55

Being able to come back to it, you know,

22:56

having to come back to it the next day

22:58

because my afternoon got totally destroyed

23:00

by a bunch of fire drills, right?

23:03

That, you know, that right there,

23:04

that's another 24 hours in the cycle.

23:07

If I can do this thing in half the time

23:09

or a quarter of the time, I can do it in, you know,

23:11

maybe a third or a fourth as many days, right?

23:15

So that review time actually gets magnified

23:19

when it comes to how much you can save in a sales cycle, right?

23:22

Saving four hours of review time can equate

23:24

to way more than four hours in a sales cycle

23:27

because of all the handoffs.

23:28

So-- - Oh, it's like a week, right?

23:29

- Yeah, it's amazing. - Because the thing is,

23:32

I mean, you know this way better than I do,

23:34

but I have from a sales perspective,

23:36

the problem is that they have a review time too.

23:39

So it's like you have two rounds back and forth

23:42

of red lines. - Yeah.

23:43

- And plus there might be another call in there

23:47

where the lawyers have to get on the phone

23:48

and hash some stuff out. - Yeah.

23:51

- And that's a negotiation in of itself.

23:53

So it's like, yes, let's say it's like, you know, 10 hours,

23:58

but it's also that 10 hours ends up getting broken up again

24:03

by each of those different iterations.

24:06

And like, those are much shorter,

24:07

but still you have to work all those in.

24:09

And it's always a week. - So if I can't--

24:10

- Yeah, at least a week.

24:12

I think, let me, so ideally where we wanna get

24:16

is where we currently are with NDAs, right?

24:19

The MSA problem is always gonna be bigger,

24:21

it's always gonna be more complicated,

24:22

it's always gonna be a little bit more specific

24:24

to each of our clients, which is why our focus right now,

24:26

especially for our commercial clients,

24:29

is down to the NDA, right?

24:32

The big problem with the NDA is not necessarily

24:35

that the review itself takes in anordinate amount of time.

24:38

The docs are short, people kind of get them, right?

24:42

But really to your point, the problem is all the handoffs.

24:46

Comes in from the business, it's gotta go to legal.

24:49

Legal's gotta pick it up, it's at the bottom of a stack.

24:53

You're not getting it, even if it's the easiest thing

24:54

in the world, even if it only takes 20 minutes to do,

24:57

to your point, it's not coming back in less than a week, right?

25:01

- Yeah. - 'Cause they got a 20 page MSA,

25:04

they gotta go through.

25:06

- Yeah, or they're reviewing, you know,

25:08

chat, GBT, or open AI, it's like fair use policies

25:10

or whatever, right?

25:11

Like they're looking at other things,

25:13

they're helping everybody else out in the company.

25:15

And so that, who knows how long it's gonna take

25:16

to even get to that NDA, right?

25:18

So for us, right, being able to have our sellers

25:21

and our technical sales guys,

25:23

be able to just use the software, run it through,

25:25

get an answer back.

25:26

And if there's nothing in there that, you know,

25:27

jumps out at them as, or if there's nothing in there

25:29

that the software has flagged as needing escalation,

25:33

they can just go ahead.

25:35

And that right there, that's the real value, right?

25:37

Being able to get into these simpler documents

25:39

and getting rid of that,

25:41

getting rid of that hand-up altogether.

25:42

- You know, when we look at sort of like operational challenges,

25:45

like one of the ones that was identified

25:47

for a lot of organizations is like,

25:51

does the rep actually have approval authority

25:53

to do XYZ, right?

25:55

Do they have approval authority to give a discount?

25:57

They have approval authority, like,

25:59

what is the back and forth between that stuff?

26:00

Like all that, right?

26:01

Like we've identified that's a huge sticking point

26:04

for many reasons, and we try to optimize that.

26:06

And then on the legal side, like we never did that, right?

26:10

- Yeah.

26:10

- It's like, even though it's just as time consuming,

26:12

just as painful, like giving the power of the rep

26:13

is like generally speaking, as long as they have guidance,

26:16

like, it saves us way more time than money.

26:20

- Yeah, and I think the added benefit of having some,

26:23

like having the software as a check on that

26:26

is that we have an audit trail.

26:30

- Right.

26:32

- Right, we have an audit trail about what's acceptable

26:33

and what's not.

26:34

The software's already made a call.

26:35

And so it's way more conducive to building trust

26:40

because we know that there's gonna be an audit trail.

26:44

We know that the rep is seeing the issue, right?

26:47

And then we can trust that they actually saw it

26:49

considered it and made a call.

26:51

So being able to have that has been really, really helpful.

26:54

- Any rev oops moments that you've made since you took the role?

26:59

- Ah, rev oops moments.

27:00

I mean, I'm sure there are plenty, right?

27:02

And I think we run a lot of experiments and some of them don't pan out.

27:06

I think early on for us was, again, this is maybe a,

27:11

maybe vestigial of kind of where we started before I took over.

27:14

But I think, you know, we were a little bit too specific

27:18

with some of the experiments that we were running early on.

27:21

And that was sort of a miscalculation on my part.

27:23

I think I think, you know, obviously you come in

27:25

and you wanna make impact, right?

27:27

You wanna make some changes,

27:27

you wanna be able to kind of show improvement.

27:29

And so you have, you know, really specific ideas

27:31

about things you wanna do.

27:33

And so we tried a couple of these things

27:35

and luckily, you know, it didn't burn too much time for us,

27:38

but the results were just not what we wanted.

27:40

- And either thoughts on sort of coming into the role

27:45

new to rev oops, any other things

27:49

that sort of lessons would take place there?

27:51

- I mean, I think I knew generally kind of what

27:54

the mandate was gonna be,

27:55

but I don't think I really appreciated coming in,

27:57

just gonna have broad, right?

27:59

How complicated, how many moving parts there were.

28:02

One thing I've definitely learned is, you know,

28:07

I'm not here necessarily to reinvent the macro wheel, right?

28:11

There's a lot of great thinkers out there.

28:13

There's a lot of great literature.

28:14

People have, you know, published a lot of really great stuff

28:17

about how to kind of think about this stuff

28:19

from like a high level, where the rubber meets the road

28:24

is being able to actually execute on those things.

28:26

And so that's where I focus most of my time now.

28:28

I can really leverage that my background

28:30

as a lawyer and an engineer, right?

28:31

To kind of break things apart.

28:32

I think in a lot of ways lawyers and engineers

28:34

are have a lot more in common than you might think,

28:37

'cause both of them are just taking something

28:39

that's more complicated, breaking it up

28:40

into its constituent parts

28:41

and fixing it to be able to achieve a goal, right?

28:43

And that's now what I'm doing here.

28:45

So the takeaway is,

28:47

be able to leverage some of the really good thinking

28:52

that other people have done, and be creative and applying

28:55

into kind of actually getting it to our sales reps,

28:58

to our marketing guys, right?

28:59

To our customer success team.

29:01

Be able to kind of compartmentalize,

29:03

a little like compartmentalize things

29:05

so that they can run their experiments.

29:06

And then so as they're running their experiments,

29:09

you get real-time feedback, right?

29:12

With our sellers, it's okay.

29:13

You're trying some very specific outreach

29:15

into five specific organizations, right?

29:18

You need to, like every two weeks,

29:19

you're gonna have to report back

29:20

what are the things you tried that have worked,

29:21

what are the things you tried that haven't worked?

29:23

We're gonna dig into those things.

29:24

It's gonna influence how we do our marketing.

29:26

It's gonna influence how we do our customer success stuff,

29:28

right? That kind of thing.

29:30

- Let's get into our next segment, the tool shed.

29:32

We're talking tools, spreadsheets, metrics,

29:34

just like everyone's favorite tool.

29:36

Qualified, you can go to Qualified.com.

29:39

To learn how no B2B tool shed is complete without Qualified,

29:43

head to Qualified.com right now and check them out.

29:46

They're our best friends in the whole world,

29:47

and they've been with us since the very beginning

29:50

of Rise of RobOps.

29:51

So go check them out at Qualified.com.

29:53

Charles Woodson, your tool shed.

29:55

- Right, tool shed.

29:56

So we're a HubSpot shop.

29:58

So we're using it from a CRM perspective,

30:00

but beyond that, I'm actually trying to keep it

30:03

as simple as possible.

30:05

Right?

30:06

And that gives me as much flexibility as possible.

30:07

So we, I mean, like, I'm sure like a lot of other people

30:10

in this space and in this role,

30:11

I just live in spreadsheets.

30:13

Love them, love pivot tables.

30:15

If I can pivot in, it makes me happy, right?

30:17

I would say that right now,

30:21

like the most important stuff to me right now

30:24

are spreadsheets that help me track two things.

30:25

So first is essentially a product sheet, right?

30:30

Of what's going on in proposals and what's coming back.

30:33

So we keep track now of every proposal that goes out there

30:36

and the response that we get from it.

30:38

Right?

30:38

So we've centralized all that information.

30:39

So we can kind of see in as close to real time as possible

30:43

what the trends are in terms of what people are,

30:46

what people think is makes sense for our tool, right?

30:48

Actual feedback from the space in terms of our proposals

30:52

going out.

30:54

The second thing, again, and this goes back to, you know,

30:56

time-killing all deals is being able to track

30:59

how many of our deals are stale, right?

31:03

That's something that very early on,

31:05

because we had a very complicated sales pipeline

31:08

when I came in and took over the role,

31:11

was really, really hard to figure out, right?

31:13

Because you just have all these deals

31:14

and they're all in the same stage

31:15

and some of them have been there for a long, long time.

31:17

I mean, if they're not actively engaged,

31:20

there's a couple of reasons why that couldn't be, right?

31:21

But all of them are bad for us, right?

31:24

The customer doesn't have a pain point.

31:25

We might not be able to help them.

31:26

Our customer just doesn't treat it as a big priority.

31:29

You know, either way something needs to happen.

31:32

And so being able to kind of track that in real time,

31:34

see how long things have been in which stages

31:36

of the pipeline, right?

31:38

And have that rolling on a day-by-day basis

31:40

of when things are crossing a certain threshold,

31:42

gives us a process point for folks to go in and say,

31:44

okay, well, this deal has actually kind of been stale for,

31:47

you know, I've sent three emails out in two weeks,

31:50

I haven't gotten a single response, right?

31:52

Maybe I keep an eye on it.

31:54

Keep going.

31:55

You know, people are busy, they might not get to it.

31:57

Once we cross that six, eight-week boundary, right?

31:59

Maybe it's time to try a different tack.

32:01

Maybe it's time to try to, you know,

32:03

shake something loose.

32:04

Maybe, you know, it should be special.

32:06

You'll find a way to get special promotional pricing

32:09

out to this particular client based on what they do

32:11

or, you know, what other things

32:13

that they could bring to the table.

32:14

Or maybe it's, you know, maybe it's giving them a bit more

32:17

of a, you know, maybe something like a light breakup email,

32:21

right, really kind of moving the needle a little bit.

32:23

But having that process point is really, really important

32:25

because it creates some accountability again

32:27

for the sellers, right?

32:28

So that they come back and, you know, they're forced to,

32:31

'cause a lot of sellers are optimistic as they should be.

32:33

And so they always think it's gonna come back.

32:35

They always think, hey, my next hour

32:36

to my next email is gonna be the thing, right?

32:38

It's gonna shake it loose.

32:39

It always is, but being able to kind of track that,

32:43

you know, as close as real time as possible

32:46

and having, you know, that trigger be there

32:48

so that the seller can think, oh, yeah,

32:50

this is crossing that threshold where, you know,

32:52

after eight weeks, like our win rate drops precipitously.

32:55

I gotta figure out whether or not this is worth

32:57

to keep, you know, in my pipeline, right?

32:59

And then, you know, they can take that

33:01

as a process point and go get some answers.

33:03

One way or another, 'cause either way,

33:06

either they can help the client out

33:07

or if there's really, you know,

33:08

at this point it doesn't make sense for that client,

33:10

then let's focus on someone where it does make sense, right?

33:13

Someone who can get some more value out of our tool.

33:15

What are your favorite spreadsheets?

33:16

- Oh, God.

33:17

I really do love, I love our proposal spreadsheet,

33:20

which basically just has like every line item

33:22

that we've ever proposed.

33:23

Being able to kind of see that in the pivot table,

33:24

like what was the reason, how much one's progressed,

33:27

been super, super, super helpful.

33:29

And then also just being able to kind of track activity

33:32

at a really granular level, right?

33:35

Being able to see, okay, you know,

33:38

these are three or four different initiatives

33:40

that our sellers are running, right?

33:42

In terms of like being able to kind of generate

33:44

their own outbound meaning for themselves a little bit, right?

33:46

They're looking at these targets here

33:48

are how many people that they've been able to contact,

33:51

these are the kind of strategies that they're running

33:53

and what the results have been.

33:54

And, you know, if you have your seller's report

33:56

and like a relatively simple but consistent format,

33:58

you can roll that stuff up

34:00

and you can start seeing kind of trends across, you know,

34:03

which verticals make sense, which titles make sense, right?

34:07

That stuff has been really, really fun for us.

34:09

So those would be the two for me.

34:11

- Any blind spots that you wish you'd measure better?

34:14

- The biggest blind spot is probably,

34:19

what are our customers actually sending upstairs, right?

34:27

When they're talking to their bosses for approval.

34:31

And you can try to include like tags and documents, right?

34:36

You can try to include, you know, links and PDFs

34:39

that will get you, you know, get the data that you need

34:41

to see like who's opening what?

34:43

But oftentimes it's just someone's writing a summary

34:47

of that information and it's going.

34:49

So it's a problem that we're trying to tackle first

34:52

with the proposal.

34:53

It's a problem that we think like if the proposal

34:55

is moving its way upstairs and it's being like,

34:57

we want to create a document that is a no brainer

35:00

to include when it goes upstairs.

35:02

- Right.

35:03

- Right?

35:04

And if we can do that, then we have some more confidence

35:06

and we can try to optimize around, okay,

35:07

how do we get that satellite out there

35:10

in the universe that is, you know, the client's atmosphere,

35:13

like they're Jupiter, like you know, it's going in

35:15

and it's making a pass or the atmosphere

35:16

and it's going to send some signal back, right?

35:18

That's what we want to kind of create.

35:20

But I'm sure it's not unique to us,

35:23

but like being able to know like what they're actually

35:25

valuing and trying to get more of that.

35:27

We try to do it a little bit with like surveys

35:29

and just asking folks, but it's still a big blind spot

35:32

for us in terms of, you know, what ultimately

35:34

is moving the needle upstairs.

35:36

- I love that.

35:37

So true.

35:37

Like are you using the tools that we're making you?

35:41

Are you using the ROI calculator?

35:42

Like are you like, is that making the slide?

35:45

- Exactly.

35:46

- Who's on the slide with us?

35:48

- Right, right.

35:49

Which, yeah, and if you have like a deck, yeah, sure.

35:51

The deck goes out there, but like which slides

35:53

like actually matter, right?

35:55

Which slides are people actually looking at it?

35:56

Like all that kind of stuff.

35:58

So for us again, like we're going to try to keep it simple.

36:01

Definitely, you know, obviously we try to do

36:03

with case studies now, but like those things get, you know,

36:05

pass around so much, it's difficult to separate the noise,

36:09

right?

36:09

Okay, if like an executive assistant's printing

36:12

something out, like does that mean that it went

36:15

to the executive?

36:16

Does it not?

36:17

You know, which executive did it go to?

36:18

Who does that person work for?

36:20

Yeah, a lot of interesting stuff that we,

36:23

a lot of really, really interesting wood

36:25

that we still let the child for us.

36:27

- All right, let's get to our final segment, quick hits.

36:29

These are quick questions and quick answers.

36:32

Number one, what is your favorite thing to watch,

36:37

read or listen that you've been checking out recently?

36:41

- In terms of industry publications,

36:43

I'm still in above the law sucker, right?

36:45

I like to see kind of, you know, what the trends are

36:48

in terms of hiring, right?

36:50

What the trends are in terms of like tech use, obviously.

36:53

I think a lot of the macro sort of forces

36:58

that are affecting, especially in house council,

37:00

a lot of them will start in private practice.

37:03

And so it's like a bit of an early warning signal,

37:06

which has been really, really helpful.

37:09

Outside of the office, you know,

37:11

there's all sorts of stuff,

37:13

but I've really gotten into just like, you know,

37:16

I've always loved Anthony Bourdain stuff,

37:18

but his publications, his writing is just so great.

37:20

I really just love it.

37:22

And it's a great way to kind of take a step back,

37:25

do a little bit of meditation almost, right?

37:28

When you can kind of take a look at that kind of material.

37:30

- If you could make any animal any size,

37:32

what animal would it be and what size?

37:37

- Let's see.

37:39

I think what I'd want to do is

37:43

make a corgi the size of a horse so I could ride it.

37:48

- Who doesn't want a huge corgi?

37:52

What advice do you have for someone

37:54

who's newly leading a rev-ops?

37:56

I'm going to mark a team.

37:58

- Two things.

37:59

So first, I would say,

38:02

do your research on the landscape of best practices.

38:06

There's a lot of really good stuff out there.

38:08

Don't feel like you need to reinvent the wheel, right?

38:10

Especially on a high level.

38:12

The second thing is,

38:14

try to be as specific as possible.

38:19

Try to be as specific as possible

38:21

with the problems that you start with solving, right?

38:24

So it shouldn't, don't bite off more

38:26

than you can chew all at once.

38:27

Run your experiments in tangible, practical pieces,

38:31

because otherwise you're not going to be able

38:32

to get a signal back.

38:34

And at that point your experiments are the next to useless.

38:37

- Charles, awesome having you on the show for listeners.

38:41

You can go check out LexCheck.

38:44

Clearly, there's gaps in the legal review process.

38:49

So check that out from your rev-ops perspective.

38:52

Charles, any final thoughts, anything to plug?

38:54

- No, I think anybody who's having trouble

38:57

with getting things back from legal, right?

38:59

You should definitely hit us up.

39:01

We're probably going to be able to help you.

39:04

The last thing I probably will leave for folks,

39:06

and this is something that we hear from our clients

39:08

all the time and are really successful,

39:10

is that there isn't a problem that's too small

39:12

to start with.

39:13

I think a lot of people will generally feel like,

39:15

okay, I have some contract bottlenecks,

39:17

but I don't know if they're a big enough problem

39:20

to do like an IT procurement exercise for.

39:24

The solutions in this space,

39:26

and especially ours, are really, really lightweight

39:28

from an implementation IT perspective,

39:31

and they're not super, super expensive, right?

39:34

Being able to start with something small

39:37

also gives you the ability to get a quick win.

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And that is instrumental, especially for our clients

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and building up the capital that they need internally

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to be able to affect even more change.

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So don't be shy about reaching out

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if you have something that you think is,

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this is something that LexCheck could help out with.

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It probably can, and our guys are always,

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always ready to spend some time just breaking it down, right?

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At the end of the day, our priority is helping

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our clients solve problems, right?

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So if you have something that we can help you solve,

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we're more than happy to help you break it down.

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- Charles, it's awesome.

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Thanks so much, and we'll talk soon.

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- Yeah, absolutely.

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Thanks so much for having me.

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