First, the caveats and safe harbor statements.

I’m no lawyer, and this is most certainly not an exhaustive review of the players in the space. This is simply a guy who sold CLM and became a student of the space sharing his take. I’m sharp-tongued, incredibly opinionated, and for those who’ll take issue with my synopsis… I’m blessed to be one of those sociopaths who couldn’t care less what you think. But sincere apologies if my take offends you.

With that, we look at the 2 top players in the SMB space for CLM:

PandaDoc and Ironclad.

So how are we going to structure this piece?

First… We’ll start with a vendor agnostic view of CLM, the “why” behind the growth of this goofy little idea. Why you should care and what it should deliver.

Second… The past. Spending time learning where the org started and how it has grown is unbelievably valuable in any SaaS evaluation. Those early years, those early ideas, are fundamental to an orgs growth and typically leave a distinct mark in the DNA of a company — the DNA used to build every subsequent product or release.

Third… The present. Where do they position themselves? What do they pride about their products or org? How do they address the space today?

Fourth… The future. It’s my belief that, worst case scenario, CLM should be a once-a-decade decision. With that in mind, how do the previous 2 points paint the picture of each vendors future? What have they done recently to hint at the companies guiding light?

Fifth… If it were my money, who would I give it to and then closing thoughts.

Part 1 — So why CLM?

For decades, businesses have had to decide between exorbitantly expensive Outside Counsel or an In House Counsel which tended to act in the same autonomous nature as their outside brethren. There was no effort to entrench counsel into the daily operations of the org. Counsels office would operate in a vacuum while the agreements outlining the organizations vast set of obligations sat idle in a filing cabinet. When technology came to the rescue, the cure became nothing more than a migration from physical to cloud filing cabinets… that’s the extent of the space’s disruption. “CLM” as a term, Contract Lifecycle Management, is a muddy pond to jump in blind. Dozens of vendors, with new entrants arising on the regular, and no clear or cohesive definition of the tool across the space. Some providers offer a solution offering no more than a productivity tool for the legal team, while the other end of the spectrum offers what I term “full-cycle” CLM… everything from request, generation, negotiation, through execution to where I feel the big value lies — post execution reporting and management across the lifecycle of the agreement.

Great, but say I’m a small business under 50–100ish employees. What about me, what should I do?

Hang with me, one of these vendors could be a solid win for you.

And how should I think about CLM?

At its core, think about your first CLM as acquiring your own personal legal team, and fully entrenching that team into the day to day operations of every functional unit within your organization. If the tool continues to segregate legal operations from the rest of the team, it’s not checking the CLM box and that juice probably isn’t worth the squeeze. The solution should streamline every step in the contracting process while offering a path towards managing and reporting on all obligations across the enterprise. No team within the org should see any additional steps compared to the old way, no team should see any cumbersome click paths to engage with the tool.

And your CLM should do more than simply run the contractural workflow, there should be peripheral wins — I call them the extracurriculars of the solution.

The players… I don’t believe it’s prudent to only evaluate one tool. Thus, we’ll review two, PandaDoc and Ironclad, simply to follow process. If it feels at times like this is a hit piece against Ironclad, that wasn’t the intent but I can see it giving that impression.

Part 2 — The Past

I place a considerable amount of weight on an organizations history while evaluating their solutions. I want to know how they landed on this particular space and how they’ve grown. I want to know where their leadership came from. These pieces are exceedingly valuable when judging how seriously to take product roadmaps and how to determine whether the solution set can grow alongside your org.

PandaDoc came around the old school way. In 2011 the founder, and current CEO… alright, lets pause here for a second. This is a modern SaaS org that’s a decade old and still founder led, that’s a good sign. Back to it… this founder personally had an issue building a proposal. Like any baller nerd, he decided to solve the problem himself and launched the first pass via Quote Roller. Over the past decade they’ve obv changed the name to PandaDoc, but they’ve also grown the suite from the initial proposal tool to what today is a robust platform capable of housing the typical CPQ workload in addition to the contract creation, execution, and renewal mgmt. They’ve taken on a laughably small $51M in funding across very few rounds, still only a Series B company.

Ironclad launched in 2014 by a Fenwick & West attorney to “combat barriers to legal work”. Since founding they’ve raised a breathtaking $184M, most recently at the pace of a crack addict tapping the payday loan shop for more cash — Ironclad can’t seem to spend money fast enough. The troubling aspect of their business is the customer volume. While PandaDoc quickly marched to thousands of customers, Ironclad has struggled to break 4 figures — seemingly doing so last year via acquisition of PactSafe.

Let’s call this round decisively for PandaDoc

Part 3 — The Present

PandaDoc is one of those remarkable SaaS orgs who bucks the trend of inflationary vanity and is very comfortable in its own skin. They don’t call themselves a true CLM, they’re a sales efficiency tool — part of that efficiency just happens to involve contracts and renewal management. They play well as a standalone platform for smaller shops without a robust stack, and they also integrate well with a wide range of tools. CRMs such as SFDC, Zoho, Zoom, and a multitude more. They offer a quick time to value and have a product that can be used sparingly or implemented as a full suite solution. They recently released a cool feature for transactional businesses that allows, through the Zoom integration, sellers to close deals while still on the meeting. That’s pretty cool.

PandaDoc is currently building a community push towards sellers of all makes via a thoroughly entertaining podcast and stellar marketing content.

Ironclad is a bit different. While they don’t necessarily tout themselves as a “CLM”, opting for the term “Digital Contracting Tool”… which by they way has to be the lamest tagline ever… in an attempt to reposition the org back towards its roots as a “tool for legal”. Ironclad offers a very slick UI that demo’s beautifully. What the product doesn’t do is offer much, if any, efficiency gains for non-legal personas. It’s a tool for legal, by legal. While touting a seamless integration with SFDC, the connection is neither seamless nor truly integrated. Don’t believe me, hunt down the demo conducted by their VP of Sales floating around Youtube. It’s less than a year old and, honestly, it’s clunky as hell.

Currently Ironclad is focused on building a community for the LegalOps function, which don’t get me wrong is needed and I had plenty of customers get some real solid benefit from the community, but a robust community does not a solid SaaS tool make.

Round 2? PD takes the win again, can’t argue with sincerity in product and market positioning.

Part 4 — The Future

THIS SECTION IS PURELY SPECULATION. I have no inside knowledge of either orgs roadmap. That said, this is precisely why I place so much importance on the past within any organization. Let’s take each orgs past and extrapolate that to assume future growth…

PandaDoc obviously has a history of organic, sustainable growth addressing 1 large pain point then migrating to peripheral pains within the business process… all while adhering to a platform model. I see future development expanding the quoting use case and possibly becoming a minor player in the SMB CPQ space. I can also see some logical development of their repository architecture leading to a new rich data set upon which to create a true full-scale CLM post-execution. I’d be surprised if PandaDoc becomes money hungry and tries to quickly cobble together a massive growth phase, as they didn’t take that route over the past 10 years it seems out of character to start now.

Ironclad is in a real pickle. $100M for an org still in early stage, without a robust customer roster, and who refuses to develop a product that addresses more than a modicum of the TAM within the CLM space is not a scenario I’d like to be in as an operator. I look at their past and worry about their ability to pivot and address the non-legal stakeholders within the CLM workflow.

Point goes to PandaDoc.

Part 5 — If it were my money, and closing thoughts

I’m sure this is apparent by now, but if it were my money… if I were leading a small organization and wanted the most bang for my buck and a vendor who will seemingly grow alongside me I can’t justify giving my money to anyone but PandaDoc.

Now, let’s have that sincere talk about Ironclad. There were a few major problems with the org from the outset that should be addressed.

First, they position themselves alongside the CLM space. This is at best naive, at worst downright disingenuous. I always started every CLM evaluation with a frank discussion around “Who have you spoken with in the space? Who are you most familiar with? And what is your view on what a CLM should do?” Over the past 18 months it’s become exceedingly obvious that Ironclad absolutely OWNS the messaging within CLM. Everyone has heard of Ironclad, and everyone has learned about CLM from Ironclad. Yet, Ironclad is resoundingly NOT a CLM tool. Again, it’s a tool developed to “combat barriers to legal work” not to expand the legal team into the rest of the organization. Because of this, I feel Ironclad itself has become the most dangerous impediment to advancement within LegalOps as a blossoming function. Ironclad is the caffeine stunting the growth of our LegalOps child.

Second, I philosophically don’t believe they are even capable of big advancements in the space. Renowned economist Clayton Christensen was keen to point out that disruption rarely, if ever, comes from the seat of incumbency. Rather, the change delivered by incumbents typically feels like small incremental advancements, minor efficiency gains. It’s a play on “Solomon’s Paradox” where as humans we tend to be way more adept at reasoning wisely about other people’s problems than we do our own. The lawyer can’t disrupt the space because they’re too entrenched. They simply can’t see the forest past the trees.

I heard it once said in the CLM space that, “I’d sooner let a pilot build my plane than I’d let a lawyer build my CLM.” There’s a lot of truth in that line. Big Law attorney’s aren’t LegalOps, they don’t play a role in a larger organization. They don’t have metrics to report on (aside from that whole billable hour thing… which again leads to the “why would they make this process faster” argument) and rely on an army of paralegals to draft, store, and retrieve agreements.

Third and finally, how on earth do you plan on justifying such stratospheric funding amounts without some criminal discount recapture levels and some drastic increases in list pricing? That’s just a chance I’m not willing to take with my orgs money.

Sorry for the knock, Ironclad. I was sincere, however, in just how beautiful your UI and demos are. Also, your State of Digital Contracting events have delivered some really top quality production value. You’re absolutely doing some things astoundingly well, it’s a shame none of those things are your actual product.

If you’re a larger SMB org, an org planning a hypergrowth scale push soon, or an org ranging from MidMarket through Enterprise…

Check back in a couple days when I’ll cover the “full-scale” CLM players: DocuSign, iCertis, and Conga Contracts for Salesforce.

And if you’re a CLM seller who lost a deal to Ironclad, do like I did with the 3 deals I lost… throw a calendar reminder up 9–10 months post go-live, that’s typically the right time to start the rip/replace evaluation (you’re welcome).




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Ryan Fiorenza

Ryan Fiorenza

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