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Directly, which taps experts to train chatbots, raises $11M, closes out Series B at $51M

Directly, a startup whose mission is to help build better customer service chatbots by using experts in specific areas to train them, has raised more funding as it opens up a new front to grow its business: APIs and a partner ecosystem that can now also tap into its expert network. Today Directly is announcing that it has added $11 million to close out its Series B at $51 million (it raised $20 million back in January of this year, and another $20 million as part of the Series B back in 2018).

The funding is coming from Triangle Peak Partners and Toba Capital, while its previous investors in the round included strategic backers Samsung NEXT and Microsoft’s M12 Ventures (who are both customers, alongside companies like Airbnb), as well as Industry Ventures, True Ventures, Costanoa Ventures and Northgate. (As we reported when covering the initial close, Directly’s valuation at that time was at $110 million post-money, and so this would likely put it at $120 million or higher, given how the business has expanded.)

While chatbots have now been around for years, a key focus in the tech world has been how to help them work better, after initial efforts saw so many disappointing results that it was fair to ask whether they were even worth the trouble.

Directly’s premise is that the most important part of getting a chatbot to work well is to make sure that it’s trained correctly, and its approach to that is very practical: find experts both to troubleshoot questions and provide answers.

As we’ve described before, its platform helps businesses identify and reach out to “experts” in the business or product in question, collect knowledge from them, and then fold that into a company’s AI to help train it and answer questions more accurately. It also looks at data input and output into those AI systems to figure out what is working, and what is not, and how to fix that, too.

The information is typically collected by way of question-and-answer sessions. Directly compensates experts both for submitting information as well as to pay out royalties when their knowledge has been put to use, “just as you would in traditional copyright licensing in music,” its co-founder Antony Brydon explained to me earlier this year.

It can take as little as 100 experts, but potentially many more, to train a system, depending on how much the information needs to be updated over time. (Directly’s work for Xbox, for example, used 1,000 experts but has to date answered millions of questions.)

Directly’s pitch to customers is that building a better chatbot can help deflect more questions from actual live agents (and subsequently cut operational costs for a business). It claims that customer contacts can be reduced by up to 80%, with customer satisfaction by up to 20%, as a result.

What’s interesting is that now Directly sees an opportunity in expanding that expert ecosystem to a wider group of partners, some of which might have previously been seen as competitors. (Not unlike Amazon’s AI powering a multitude of other businesses, some of which might also be in the market of selling the same services that Amazon does).

The partner ecosystem, as Directly calls it, use APIs to link into Directly’s platform. Meya, Percept.ai, and SmartAction — which themselves provide a range of customer service automation tools — are three of the first users.

“The team at Directly have quickly proven to be trusted and invaluable partners,” said Erik Kalviainen, CEO at Meya, in a statement. “As a result of our collaboration, Meya is now able to take advantage of a whole new set of capabilities that will enable us to deliver automated solutions both faster and with higher resolution rates, without customers needing to deploy significant internal resources. That’s a powerful advantage at a time when scale and efficiency are key to any successful customer support operation.”

The prospect of a bigger business funnel beyond even what Directly was pulling in itself is likely what attracted the most recent investment.

“Directly has established itself as a true leader in helping customers thrive during these turbulent economic times,” said Tyler Peterson, Partner at Triangle Peak Partners, in a statement. “There is little doubt that automation will play a tremendous role in the future of customer support, but Directly is realizing that potential today. Their platform enables businesses to strike just the right balance between automation and human support, helping them adopt AI-powered solutions in a way that is practical, accessible, and demonstrably effective.”

In January, Mike de la Cruz, who took over as CEO at the time of the funding announcement, said the company was gearing up for a larger Series C in 2021. It’s not clear how and if that will be impacted by the current state of the world. But in the meantime, as more organizations are looking for ways to connect with customers outside of channels that might require people to physically visit stores, or for employees to sit in call centres, it presents a huge opportunity for companies like this one.

“At its core, our business is about helping customer support leaders resolve customer issues with the right mix of automation and human support,” said de la Cruz in a statement. “It’s one thing to deliver a great product today, but we’re committed to ensuring that our customers have the solutions they need over the long term. That means constantly investing in our platform and expanding our capabilities, so that we can keep up with the rapid pace of technological change and an unpredictable economic landscape. These new partnerships and this latest expansion of our recent funding round have positioned us to do just that. We’re excited to be collaborating with our new partners, and very thankful to all of our investors for their support.”

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UPDATE: Los Angeles-based CREXi raises $30 million for its online real estate marketplace

Los Angeles is one of the most desirable locations for commercial real estate in the United States, so it’s little wonder that there’s something of a boom in investments in technology companies servicing the market coming from the region.

It’s one of the reasons that CREXi, the commercial real estate marketplace, was able to establish a strong presence for its digital marketplace and toolkit for buyers, sellers and investors.

Since the company raised its last institutional round in 2018, it has added more than 300,000 properties for sale or lease across the U.S. and increased its user base to 6 million customers, according to a statement.

It has now raised $30 million in new financing from new investors, including Mitsubishi Estate Company (“MEC”), Industry Ventures and Prudence Holdings . Previous investors Lerer Hippeau Ventures and Jackson Square Ventures also participated in the financing.

CREXi makes money three ways. There’s a subscription service for brokers looking to sell or lease property; an auction service where CREXi will earn a fee upon the close of a transaction; and a data and analytics service that allows users to get a view into the latest trends in commercial real estate based on the vast collection of properties on offer through the company’s services.

The company touts its service as the only technology offering that can take a property from marketing to the close of a sale or lease without having to leave the platform.

According to chief executive Mike DeGiorgio, the company is also recession-proof thanks to its auction services. “As more distressed properties hit the market, the best way to sell them is through an online auction,” DeGiorgio says.

So far, the company has seen $700 billion of transactions flow through the platform, and roughly 40% of those deals were exclusive to the company.

“The CRE industry is evolving, and market players, especially younger, digitally native generations are seeking out platforms that provide free and open access to information,” said Gavin Myers, general partner at Prudence Holdings, in a statement. “CREXi directly addresses this market need, providing fair access to a range of CRE information. As CREXi continues to build out its stable of services, features, and functionality, we’re thrilled to partner with them and support the company’s continued momentum.”

CREXi joins the ranks of startups based in Los Angeles that have raised money to reshape the real estate industry. Estimates from Built in LA count roughly 127 companies, which have raised in excess of $2.4 billion, active in the real estate industry in Los Angeles. These companies range from providers of short-term commercial office space, like Knotel, or co-working companies like WeWork, to companies focused on servicing the real estate industry like Luxury Presence, which raised a $5 million round earlier in the year.

Due to inaccurate information provided by the company, an initial version of this story indicated that CREXi had raised $29 million in its Series B round. The correct number is $30 million.

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Luxury consignment e-tailer The RealReal to enter the unicorn club with new funding

The RealReal, an online retailer for authenticated luxury consignment, has authorized the sale of up to $70 million in new shares, per a Delaware stock authorization filing discovered by the Prime Unicorn Index. If the company raises the entire amount, it would reach a valuation of $1.06 billion, cementing its status as the newest e-commerce unicorn.

The filing doesn’t guarantee The RealReal will sell the full amount of authorized shares. The company declined to comment on its fundraising plans.

The RealReal is led by founder and chief executive officer Julie Wainwright (pictured), the former CEO of Pets.com, a company now synonymous with the dot-com bust. It has raised quite a bit of capital to date — a total of $288 million from venture capital and private equity backers, including Great Hill Partners, Sandbridge Capital, PWP Growth Equity, Industry Ventures, Greycroft Partners and Canaan Partners. Most recently, The RealReal closed a Series G financing of $115 million in July 2018 that valued the business at $745 million, per PitchBook.

The RealReal has recently expanded its brick-and-mortar footprint and added additional e-commerce fulfillment centers as demand increased for its supply of second-hand luxury items. Founded in 2011, the company operates eight luxury consignment offices, where customers can receive free valuations of their luxury items. The RealReal is headquartered in San Francisco.

In a conversation with TechCrunch in 2017, Wainwright confirmed the company’s intent to go public at some point. With this upcoming round, The RealReal would be well placed for a 2020 initial public offering.

“That’s the goal,” Wainwright said during the interview. “We really aren’t in the mood to sell the business, we’re in the mood to go public at some point in the future.”

The RealReal competes with fellow second-hand e-tailers ThredUp and Poshmark . The latter is gearing up for a fall IPO, according to The Wall Street Journal. The online marketplace has tapped Morgan Stanley and Goldman Sachs to lead its offering after closing in on $150 million in revenue in 2018. ThredUp, another major player in the fashion retail market, hasn’t raised capital since 2015, but did begin opening physical stores in 2017 as part of its greater effort to compete with fellow venture-backed second-hand e-tailers.

The RealReal would also be the latest in a series of high-profile female-founded companies to gain unicorn status. Glossier tripled its valuation to $1.2 billion with a $100 million round earlier this year, followed by Rent the Runway, which attracted a $125 million investment at a $1 billion valuation, to name a few.

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Appen acquires Figure Eight for up to $300M, bringing two data annotation companies together

Appen just announced that it’s acquiring Figure Eight in an all-cash deal that sees Appen paying $175 million upfront, with an additional payment of up to $125 million based on Figure Eight’s performance this year.

Both companies focus on using crowdsourced labor pools to annotate data, which in turn is used to train artificial intelligence and machine learning — for example, Figure Eight (formerly known as CrowdFlower and Dolores Labs) says its technology has been for everything from mapping to stock photography to scanning receipts for expense reports.

Appen, meanwhile, is a publicly-traded company headquartered in Sydney. CEO Mark Brayan described its technology — and its “crowd” of more than 1 million remote workers — as “highly complementary” to Figure Eight, which he praised for its data annotation and self-serve capabilities.

“We know that to compete and to be able to deliver even higher volumes, we need a richer set of technologies,” Brayan said. “That’s where Figure Eight comes in. They are, in our view, the leader in the market of the platform providers.”

As for what this means for the Figure Eight team, he said, “Everybody stays in place,” and that Appen plans to continue investing in the product.

Brayan also noted that Appen previously acquired another data annotation company called Leapforce in 2017, a move that he said provided the company with greater scale.

“The Figure Eight acquisition is the next step of our evolution,” he said. “Step one was to get bigger, step two is to become much more tech forward, which is what we get with Figure Eight.”

San Francisco-based Figure Eight has raised a total of $58 million in funding, according to Crunchbase, from investors including Trinity Ventures, Industry Ventures, Canvas Ventures and Salesforce Ventures. As CrowdFlower, it launched on-stage at the TechCrunch50 conference nearly a decade ago.

“I’m extremely proud of the team,” said Figure Eight co-founder Lukas Biewald in a statement. “This is a genuine validation of everything we’ve achieved and a great platform for our teams to combine and continue to do amazing things in AI.”

Biewald (a college friend of mine), along with his co-founder Chris Van Pelt, has moved on to a new startup called Weights and Biases, but he remains involved in Figure Eight as chairman. You can watch their TC50 presentation here.

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