Ironclad

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Ironclad’s Jason Boehmig: The objective of pricing is to become less wrong over time

In 2017, Ironclad founder and CEO Jason Boehmig was looking to raise a Series A. As a former lawyer, Boehmig had a specific process for fundraising and an ultimate goal of finding the right investors for his company.

Part of Boehmig’s process was to ask people in the San Francisco Bay Area about their favorite place to work. Many praised RelateIQ, a company founded by Steve Loughlin who had sold it to Salesforce for $390 million and was brand new to venture at the time.

“I wanted to meet Steve and had kind of put two and two together,” said Boehmig. “I was like, ‘There’s this founder I’ve been meaning to connect with anyways, just to pick his brain, about how to build a great company, and he also just became an investor.’”

On this week’s Extra Crunch Live, the duo discussed how the Ironclad pitch excited Loughlin about leading the round. (So excited, in fact, he signed paperwork in the hospital on the same day his child was born.) They also discussed how they’ve managed to build trust by working through disagreements and the challenges of pricing and packaging enterprise products.

As with every episode of Extra Crunch Live, they also gave feedback on pitch decks submitted by the audience. (If you’d like to see your deck featured on a future episode, send it to us using this form.)

We record Extra Crunch Live every Wednesday at 12 p.m. PST/3 p.m. EST/8 p.m. GMT. You can see our past episodes here and check out the March slate right here.

Episode breakdown:

  • The pitch — 2:30
  • How they operate — 23:00
  • The problem of pricing — 29:00
  • Pitch deck teardown — 35:00

The pitch

When Boehmig came in to pitch Accel, Loughlin remembers feeling ambivalent. He had heard about the company and knew a former lawyer was coming in to pitch a legal tech company. He also trusted the reference who had introduced him to Boehmig, and thought, “I’ll take the meeting.”

Then, Boehmig dove into the pitch. The company had about a dozen customers that were excited about the product, and a few who were expanding use of the product across the organization, but it wasn’t until the ultimate vision of Ironclad was teased that Loughlin perked up.

Loughlin realized that the contract can be seen as a core object that could be used to collaborate horizontally across the enterprise.

“That was when the lightbulb went off and I realized this is actually much bigger,” said Loughlin. “This is not a legal tech company. This is core horizontal enterprise collaboration in one of the areas that has not been solved yet, where there is no great software yet for legal departments to collaborate with their counterparts.”

He listed all the software that those same counterparts had to let them collaborate: Salesforce, Marketo, Zendesk. Any investor would be excited to hear that a potential portfolio company could match the likes of those behemoths. Loughlin was hooked.

“There was a slide that I’m guessing Jason didn’t think much of, as it was just the data around the business, but I got pretty excited about it,” said Loughlin. “It said, for every legal user Ironclad added, they added nine other users from departments like sales, marketing, customer service, etc. It was evidence that this theory of collaboration could be true at scale.”

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The Series A deal that launched a near unicorn: Meet Accel’s Steve Loughlin and Ironclad’s Jason Boehmig

The only people who truly understand a relationship are the ones who are in it. Luckily for us, we’re going to have a candid conversation with both parties in the relationship between Ironclad CEO and cofounder Jason Boehmig and his investor and board member Accel partner Steve Loughlin.

Loughlin led Ironclad’s Series A deal back in 2017, making it one of his first Series A deals after returning to Accel.

This episode of Extra Crunch Live goes down on Wednesday at 3pm ET/12pm PT, just like usual.

We’ll talk to the duo about how they met, what made them ‘choose’ each other, and how they’ve operated as a duo since. How they built trust, maintain honesty, and talk strategy are also on the table as part of the discussion.

Loughlin was an entrepreneur before he was an investor, founding RelateIQ (an Accel-backed company) in 2011. The company was acquired by Salesforce in 2014 for $390 million and later became Salesforce IQ. Loughlin then “came back home” to Accel in 2016, and has led investments in companies like Airkit, Ascend.io, Clockwise, Ironclad, Monte Carlo, Nines, Productiv, Split.io, and Vivun.

Not entirely unsurprising for a man who has dominated the legal tech sphere, Jason Boehmig is a California barred attorney who practiced law at Fenwick & West and was also an adjunct professor of law at Notre Dame Law School. Ironclad launched in 2014 and today the company has raised more than $180 million and, according to reports, is valued just under $1 billion.

Not only will we peel back the curtain on how this investor/founder relationship works, but we’ll also hear from these two tech leaders on their thoughts around bigger enterprise trends in the ecosystem.

Then, it’s time for the Pitch Deck Teardown. On each episode of Extra Crunch Live, we take a look at pitch decks submitted by the audience and our experienced guests give their live feedback. If you want to throw your hat pitch deck in the ring, you can hit this link to submit your deck for a future episode.

As with just about everything we do here at TechCrunch, audience members can also ask their own questions to our guests.

Extra Crunch Live has left room for you to network (you gotta network to get work, amirite?). Networking is open starting at 2:30pm ET/11:30am PT and stays open a half hour after the episode ends. Make a friend!

As a reminder, Extra Crunch Live is a members-only series that aims to give founders and tech operators actionable advice and insights from leaders across the tech industry. If you’re not an Extra Crunch member yet, what are you waiting for?

Loughlin and Boehmig join a stellar cast of speakers on Extra Crunch Live, including Lightspeed’s Gaurav Gupta and Grafana’s Raj Dutt, as well as Felicis’ Aydin Senkut and Guideline’s Kevin Busque. Extra Crunch members can catch every episode of Extra Crunch Live on demand right here.

You can find details for this episode (and upcoming episodes) after the jump below.

See you on Wednesday!

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As 2020 ends, new unicorn formation continues to impress

Here in the final few working days of 2020, a surprising number of new unicorns have come to light. The mad scramble that investors are seeing in seed-stage startups appears to be reflected across the later stages as well.

That deal-making is still alive is not a surprise, but the cadence at which the market is crowning new unicorns is slightly startling, given the time of year. I’ve given up expecting a slowdown in venture capital, but I did anticipate some deceleration in huge rounds and resulting unicorn valuations this close to Christmas.


The Exchange explores startups, markets and money. Read it every morning on Extra Crunch, or get The Exchange newsletter every Saturday.


This morning after contrasting a PitchBook-derived $500 million, post-money valuation for Bolt’s Series C that its CEO had said was roughly doubled in its Series C1, TechCrunch discovered that the online checkout software company likely landed a new valuation right around the unicorn mark. Bolt’s PR team declined to share a new valuation or grade our math, saying that its framing was “fine.”

One new unicorn — or near-unicorn, perhaps — was not enough for the day. The Information broke news this afternoon that Ironclad, which sells contract management software, put together a round worth “at least $100 million,” valuing the company at “more than $950 million.” Akin to Bolt, this unicorn-or-just-under valuation is also a doubling or better from its last private round.

In fact, two new unicorns were insufficient: a third company also made the mark today, namely Qualia, which trumpeted the valuation achievement in a release. Qualia builds real estate software.

Three unicorns in one day is busy. To see three come to light on December 21st is a little bonkers.

And they are hardly the only startups we’ve seen sprout horns and race about on four legs in recent days. There’s Boom, Zenoti and BigID also in the last week or so. That’s at least six new unicorns since roughly the mid-point of December. Wild!

Let’s talk about the rounds and see what we can learn from them.

Hello, new unicorns

Starting with Bolt, there are a few lessons for us to take away. First: not every company that secures a unicorn (or a near-unicorn valuation) wants to make noise about it. We’ve known this, but the company’s currently coy attitude underscores the point. Second from Bolt is that inside investors are more than willing to crown unicorns in their own portfolio.

According to CEO Ryan Breslow, after his company raised its Series C, the round’s lead investor offered the company another term sheet. But WestCap was not its only lead. General Atlantic came in as well, giving the $75 million investment two leads. Bolt had already decided to call its new round a Series C1 before General Atlantic entered the deal, the addition of which brought $15 million to what was previously a $60 million investment.

Bolt’s round fits neatly into a number of trends that we’ve been watching: inside rounds being bullish not bearish in 2020, the fastest-growing companies raising two rounds this year and the incredible focus by venture investors into startups that were not merely surviving COVID-19, but benefiting from how it shook up the market.

Turning to Ironclad, around $100 million at around a $950 million valuation is about as basic as a unicorn round can get. And because it has been more than a year since its last round, you might think that there is not that much to learn in its case.

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YC-Backed Ironclad Is An Automated Legal Assistant For Companies

DSCN5814-L Launching out of the latest YC class, Ironclad is an automated service to help companies draft, organize and execute common legal paperwork.
Expensive legal bills are often an unwelcome reality for young startups. Lawyers charge hundreds of dollars an hour, but are often a company’s only option for correctly preparing things like financial documents and sales contracts. Read More

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