Robotic process automation has taken the enterprise world by storm by providing a set of tools for those doing repetitive, volume-based tasks to use software to remove some of that labor to let those people focus on more complicated tasks. Today a startup that’s taken some of that ethos and is applying it to more individualized work — that of salespeople — is announcing some funding.

Dooly, a Vancouver, Canada-based startup that has built a set of AI-based tools that automate the busywork that goes into updating data in their sales software, and namely Salesforce, has picked up $20 million in funding to build out its business, which to date has picked up a number of customers among the sales teams of enterprise-focused software companies. They include Airtable, Asana, Intercom, Contentful, Vidyard, BigCommerce, Liftoff and CrowdRiff.

Its aim is to make sales software more useful for salespeople by eliminating the work that goes into inputting data into those systems.

“Really they’ve just created a mountain of virtual filing cabinets,” Kris Hartvigsen, Dooly’s founder and CEO, said in an emailed interview with me. “Filing cabinets just wait for drawers to be opened — or in the case of enterprise software, reports to be pulled and data to be input. We know people are capturing information across the business and our job is to make sure that the people and systems across the business have a better, faster, more far-reaching way of staying informed.”

The funding is being announced today, but it was actually raised in two tranches that had not previously been disclosed. A $3.3 million seed round was led by Boldstart Ventures and also included BoxGroup. Its $17 million Series A, meanwhile, was led by Addition, with Boldstart and BoxGroup again participating, along with Battery Ventures, Mantis (representing musicians The Chainsmokers) and SV Angel.

Alongside the VCs, there are a number of interesting strategic individual investors, too. Daniel Dines and Brandon Deer of UiPath (the RPA connection clearly is not one that I’m imagining!); Allison Pickens, the ex-COO of Gainsight; Zander Lurie of SurveyMonkey); Jay Simons, ex-CEO of Atlassian); Harry Stebbings; and other unnamed investors are all also involved. Ed Sim of Boldstart is joining Dooly’s board of directors with this announcement.

The challenge that Dooly has been built to solve is that while there are a lot of tools out there now to help salespeople source leads, manage the progress of their sales, give them advice and other helpful material to supplement their charm and the basic strength of a product, manage customers once they’ve signed on, and so on, all of them still require something important to work: a time commitment from salespeople to keep them updated with information. Ironically, the more tools to help them that are built, the more time salespeople need to spend feeding them data.

Even more ironically, one of the big daddies of the problem — the somewhat overweight Salesforce — has published figures (cited by Dooly) that say salespeople spend just 34% of their time selling. The rest (minus trips to get coffee to stay caffeinated) seems to be about data entry.

The idea with Dooly is that you turn it on, connect it to what you are using — starting with Salesforce — and Dooly lets you make notes which it then organises and puts into the right places in the rest of your apps.

“When a salesperson starts using Dooly, the ‘aha moment’ is pretty immediate,” Hartvigsen said. “Whether they want to do quick pipeline edits or push their notes to Salesforce, we don’t ask the user to learn any new patterns they aren’t familiar with, we just automate a bunch of things they hate doing, often comparing those traditional chores to clerical work.” For example, he notes, when they sync a note, Dooly automatically updates any Salesforce with any contacts found in the meeting, updates fields, adds to-dos, logs activities, and pushes messages to the appropriate internal stakeholders on Slack, all in the same motion.

The product currently also integrates with Slack, G-Cal and G-Drive, because, Hartvigsen said, “we see this as an area where there is the most immediate friction and an area that was in need of disruption.” He added that the plan is to add more integrations over time. “We see need to expand the solutions that anchor to our connected workspace, with our near-term focus being the systems that touch revenue teams,” he said.

The design of Dooly seems to be about investing a little in order to save more. On average people are using Dooly between 2.5 and 5 hours each day, but Hartvigsen claims that right now the system helps people make up for more hours each week in lost productivity. Its pricing starts at $25 per user per month, going up depending on features and use.

There are quite literally thousands of products out in the market today, and among them hundreds of strong ones, being built to help salespeople with different aspects of getting their jobs done. I’ve written about quite a few of them, and I’ve actually asked companies about whether they are tackling the very issue that Dooly has identified and is trying to fix.

They weren’t, but that doesn’t mean that they won’t. Chief among them are companies like UiPath and Salesforce, which sit on different sides of this problem and could well move into it as they keep growing. (Having UiPath as a backer by way of its founder and a senior executive points to a relationship there, which is interesting.)

In the meantime, there have been some other interesting innovations using AI to improve the sales process, with companies like Pipedrive, Clari, Seismic, Chorus.ai and Gong all using natural language, machine learning and big data analytics (itself helped by AI) to improve how sales get done.

“The first thing we noticed when we met the Dooly team was the thoughtful design-first approach to product that engendered tons of customer love. This love was inherent not only on popular ratings sites like G2 Crowd but also in the individual usage and viral adoption throughout companies with only one initial user,” said Ed Sim, founder and managing partner at Boldstart Ventures in a statement. “Dooly is revolutionizing the note-taking experience for customer facing end users from sales to customer success to product.”

“Dooly is relentlessly focused on building a user-first experience for its customers to seamlessly create workflows and unlock new revenue opportunities,” said Lee Fixel, founder of Addition, added. “We are thrilled to support Dooly as it continues to scale and enhance the sales function for more businesses.”

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Early Stage is the premier “how-to” event for startup entrepreneurs and investors. You’ll hear firsthand how some of the most successful founders and VCs build their businesses, raise money and manage their portfolios. We’ll cover every aspect of company building: Fundraising, recruiting, sales, legal, PR, marketing and brand building. Each session also has audience participation built-in — there’s ample time included in each for audience questions and discussion.

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Box could be facing troubled times if a Reuters story from last week is accurate. Activist investor Starboard Value took a 7.9% stake in the storage company in September 2019, and a year ago took three board seats as its involvement in the cloud company deepened. It seemed only a matter of time before another shoe dropped.

That thunk you just heard could be said shoe as Starboard is reportedly after three additional board seats. Those include current CEO Aaron Levie’s and two independent board members, all of whom have their seats coming up for election in June. If the firm were to obtain three additional seats, it would control six of nine votes and could have its way with Box.

What could the future hold for the company given this development (assuming it’s true)? It seems changes are coming for Box.

Below, we’ll explore how Box got to this point. And if an acquisition is in Box’s future, just who might be in the market for a cloud-native content management company built to scale in the enterprise? There would very likely be multiple suitors.

Box’s fickle financial fate

Starboard may have reason to be frustrated by Box’s performance. The cloud company’s stock price and market cap remain stubbornly low. Its share price is mired around $18 a share, not much higher than the price it went public at in 2015 when it was valued at $14 per share. Its market cap today is $3 billion, which is lacking in comparison to fellow cloud stalwarts like Dropbox at $9 billion, Slack at $23 billion or Okta at $34 billion.

Remember back in March 2014 when Box announced it was going public? It then did something highly unusual, delaying the deed 10 months until January 2015. One thing or another kept the company from pulling the trigger and just doing it. Perhaps it was a sign.

Instead, Box raised $150 million more after its S-1 filing received a lackluster response from the market. Looking back, you could argue that the SaaS model was simply less well known in 2014 than it is today. Certainly public investors are more sympathetic to software companies that run deficits in the name of growth than they were back then.

But when Box did file again, finally pricing at $14 per share in 2015, it received a strong welcome. The company had priced above its $11 to $13 per-share IPO range as TechCrunch reported at the time and instantly shot higher. We wrote on its IPO day that the cloud company quickly “surged to over $20 a share and [was then] trading at $23.67.”

A year later, our continuing coverage had flipped with the share price stuck at $10 in January 2016.

When growth won’t come

It’s (virtual) Microsoft Ignite this week, Microsoft’s annual IT-centric conference and its largest, with more than 26,000 people attending the last in-person event in 2019. Given its focus, it’s no surprise that Microsoft Teams is taking center stage in the announcements this year. Teams, after all, is now core to Microsoft’s productivity suite. Today’s announcements span the gamut from new meeting features to conference room hardware.

At the core of Teams — or its competitors like Slack for that matter — is the ability to collaborate across teams, but increasingly, that also includes collaboration with others outside of your organization. Today, Microsoft is announcing the preview of Teams Connect to allow users to share channels with anyone, internal or external. These channels will appear alongside other teams and channels and allow for all of the standard Teams use cases. Admins will keep full control over these channels to ensure that external users only get access to the data they need, for example. This feature will roll out widely later this year.

What’s maybe more important to individual users, though, is that Teams will get a new PowerPoint Live feature that will allow presenters to present as usual — but with the added benefit of seeing all their notes, slides and meeting chats in a single view. And for those suffering through yet another PowerPoint presentation while trying to look engaged, PowerPoint Live lets them scroll through the presentation at will — or use a screen reader to make the content more accessible. This new feature is now available in Teams.

Also new on the presentation side is a set of presentation modes that use some visual wizardry to make presentations more engaging. “Standout mode” shows the speaker’s video feed in front of the content, for example, while “Reporter mode” shows the content above the speaker’s shoulder, just like in your local news show. And side-by-side view — well, you can guess it. This feature will launch in March, but it will only feature the Standout mode first. Reporter mode and side-by-side will launch “soon.”

Another new view meant to visually spice up your meetings is the “Dynamic view.” With this, Teams will try to arrange all of the elements of a meeting “for an optimal viewing experience,” personalized for each viewer. “As people join, turn on video, start to speak, or begin to present in a meeting, Teams automatically adjusts and personalizes your layout,” Microsoft says. What’s maybe more useful, though, is that Teams will put a gallery of participants at the top of the screen to help you maintain a natural eye gaze (without any AI trickery).

As for large-scale meetings, Teams users can now hold interactive webinars with up to 1,000 people inside and outside of their organization. And for all of those occasions where your CEO just has to give a presentation to everybody, Teams supports broadcast-only meetings with up to 20,000 viewers. That’ll go down to 10,000 attendees after June 30, 2021, based on the idea that the pandemic will be mostly over then and the heightened demand for visual events will subside around that time. Good luck to us all.

For that time when we’ll go back to an office, Microsoft is building intelligent speakers for conference rooms that are able to differentiate between the voices of up to 10 speakers to provide more accurate transcripts. It’s also teaming up with Dell and others to launch new conference room monitors and speaker bars.

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Early Stage is the premier “how-to” event for startup entrepreneurs and investors. You’ll hear firsthand how some of the most successful founders and VCs build their businesses, raise money and manage their portfolios. We’ll cover every aspect of company building: Fundraising, recruiting, sales, legal, PR, marketing and brand building. Each session also has audience participation built-in — there’s ample time included in each for audience questions and discussion.

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At its Ignite conference today, Microsoft announced the launch of Azure Managed Instance for Apache Cassandra, its latest NoSQL database offering and a competitor to Cassandra-centric companies like Datastax. Microsoft describes the new service as a “semi-managed offering that will help companies bring more of their Cassandra-based workloads into its cloud.”

“Customers can easily take on-prem Cassandra workloads and add limitless cloud scale while maintaining full compatibility with the latest version of Apache Cassandra,” Microsoft explains in its press materials. “Their deployments gain improved performance and availability, while benefiting from Azure’s security and compliance capabilities.”

Like its counterpart, Azure SQL Manages Instance, the idea here is to give users access to a scalable, cloud-based database service. To use Cassandra in Azure before, businesses had to either move to Cosmos DB, its highly scalable database service that supports the Cassandra, MongoDB, SQL and Gremlin APIs, or manage their own fleet of virtual machines or on-premises infrastructure.

Cassandra was originally developed at Facebook and then open-sourced in 2008. A year later, it joined the Apache Foundation and today it’s used widely across the industry, with companies like Apple and Netflix betting on it for some of their core services, for example. AWS launched a managed Cassandra-compatible service at its re:Invent conference in 2019 (it’s called Amazon Keyspaces today), Microsoft launched the Cassandra API for Cosmos DB in September 2018. With today’s announcement, though, the company can now offer a full range of Cassandra-based servicer for enterprises that want to move these workloads to its cloud.

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Early Stage is the premiere “how-to” event for startup entrepreneurs and investors. You’ll hear firsthand how some of the most successful founders and VCs build their businesses, raise money and manage their portfolios. We’ll cover every aspect of company-building: Fundraising, recruiting, sales, legal, PR, marketing and brand building. Each session also has audience participation built-in — there’s ample time included in each for audience questions and discussion.

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As the pandemic drags on and we learn about the requirements of working from home with distributed teams, users could be craving more integration across their tools to help reduce the clicks required to complete a set of tasks. Today at the Ignite Conference, Microsoft announced tighter integration between its business suite Dynamics 365 and its collaboration tool Teams to help with that issue.

Alysa Taylor, corporate VP for business applications and global industry at Microsoft, pointed out that one of the advantages of this native integration approach is that it helps reduce context switching across different applications. “We are committed to really bringing together the collaboration platform and the business process layer to enable salespeople, service representatives, operations managers [and other similar roles] to really have a unified platform in which they both collaborate and have their everyday business functions,” Taylor explained.

This could manifest itself in a number of different ways across marketing, sales and service. For instance, a marketer can create a webinar, which they set up and track in Dynamics 365 Marketing tools and run in Teams as a streaming event with the Teams streaming setup integrated directly into the Dynamics 365 console.

In a sales example Taylor says, “We’re enabling sellers to be able to track the career movements of their contacts using the LinkedIn Sales Navigator, as well as connect very specific sales records within Microsoft Teams without ever having to leave Dynamics 365 Sales. So you can be in the Sales application and you have the ability to deeply understand a contact and any contact changes that occur in Teams, and that’s automatically updated in Sales.”

If your company is not an all-Microsoft shop and wants to use different tools as part of these workflows, Taylor says that you can use Microsoft cross-cloud connectors to connect to another service, and this is true regardless of the tasks involved (so long as the connector to the desired application is available).

Salesforce, a primary rival of Microsoft in the business software space, spent over $27 billion to buy Slack at the end of last year to bring this kind of integration to its platform. Taylor sees the acquisition as a reaction to the integration Microsoft already has and continues to build.

“I think that Salesforce had to acquire Slack to be able to have that collaboration [we have], so we are years ahead of what they’re going to be able to provide because they will not have these native integrations. So I actually see the Salesforce acquisition as a response to what we’re doing with Dynamics 365 and Teams,” Taylor told me.

It’s worth pointing out that Salesforce is far ahead of Microsoft when it comes market share in the CRM space, with over 19% versus under 3% for Microsoft, according to Gartner numbers from 2019. While it’s possible these numbers have shifted some since then, probably not significantly.

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Early Stage is the premier “how-to” event for startup entrepreneurs and investors. You’ll hear firsthand how some of the most successful founders and VCs build their businesses, raise money and manage their portfolios. We’ll cover every aspect of company building: Fundraising, recruiting, sales, legal, PR, marketing and brand building. Each session also has audience participation built-in — there’s ample time included in each for audience questions and discussion.

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