On the heels of acquiring sales tax specialist TaxJar in April, today Stripe is making another big move in the area of tax. The $95 billion payments behemoth is launching a new product called Stripe Tax, which will provide automatic, updated sales tax calculations (covering sales tax, VAT and GST) and related accounting services to Stripe payments customers initially in some 30 countries and across the U.S.

Stripe Tax is a separate service from TaxJar, but the two are not unconnected. As Stripe Tax was being built out of Stripe’s offices in Dublin over the last several months, Stripe’s business lead for EMEA Matt Henderson told me that the team had identified TaxJar as a strong company in the field. That ultimately led to M&A between them.

Sales tax — and specifically a more seamless way to deal with charging and tracking sales tax — is a painful issue for people doing business online.

Digital and physical goods are taxed in over 130 countries, Stripe said, and within that there can be a huge amount of variation and compliance complexity, since codes get updated all the time, too. Mishandled sales tax, meanwhile, can result in pretty hefty fines, sometimes up to 30% interest on past-due amounts.

Unsurprisingly, a sales tax tool has been the most-requested feature from Stripe’s customers, Henderson said, a call that presumably only got louder in the last year, as e-commerce and digital transactions went through the roof with COVID-19.

Arguably, that makes Stripe Tax one of the company’s more significant product launches, not to mention the first since announcing its monster funding round earlier this year.

Previously, Stripe customers would have resorted to using a third-party service (like TaxJar) to work out sales tax. Or, more typically, those Stripe customers would have opted to limit the number of places they sold goods and services, in order to minimize the pain of dealing with multiple, complex and usually quite localized tax codes.

“No one leaps out of bed in the morning excited to deal with taxes,” said John Collison, co-founder and president of Stripe in a statement. “For most businesses, managing tax compliance is a painful distraction. We simplify everything about calculating and collecting sales taxes, VAT, and GST, so our users can focus on building their businesses.”

Stripe said that a survey of its customers found that two-thirds of respondents said the challenge of implementing sales tax actually limited their growth.

TaxJar has built a strong system for handling that, but the company — based out of Massachusetts but with a remote team — is primarily focused on the U.S. market, which has sales tax that is complicated enough (there are 11,000 different tax jurisdictions in the country).

That leaves a lot on the table for building out sales tax tools for the rest of the world: The wider focus of Stripe Tax thus fills a particular geographical gap for the company, regardless of how well TaxJar and Stripe integrate over time.

There is another key difference worth noting between the two.

TaxJar came to Stripe’s attention with an established operation — 23,000 customers at the time of the announcement. Stripe (wisely) bolted that on as a standalone business, which means that new and existing customers that use TaxJar can continue to use it as is. That is to say, at least for now, they do not need to be Stripe payments customers in order to use TaxJar, even if the integration between the two platforms will only improve over time.

Stripe Tax, on the other hand, is being built from the ground up as a product aimed specifically at increasing touchpoints and stickiness with Stripe customers.

Stripe Tax provides real-time tax calculation based on customer location and product sold; transparent itemizing for customers; tax ID management in areas (like Europe) where business customers can provide their code and get a reverse charge on tax if they are under a certain turnover threshold themselves; and reconciliation and reporting across all transactions to make filing and remittance easier.

But there is for now no way to use Stripe Tax outside of Stripe payments.

This could pose some problems for some customers. These days, many of the strongest retailers will take an “omnichannel” approach that might cover selling through marketplaces, selling through websites, selling through social media and more — and not all of those experiences may be powered by Stripe. It will be worth watching whether future iterations of Stripe Tax can account for that.

Stripe’s most significant product launch prior to Stripe Tax — Stripe Treasury last December — underscores how the company is currently very focused on diversifying outside of its basic payments business and opening the platform to much wider, more scaled transactions.

Treasury, which is still in invite-only mode, saw Stripe partner with established banks to provide a business banking service, providing a way for its customers to handle money that they generate from their Stripe-powered businesses.

The full country list where Stripe Tax is launching is Australia, Austria, Belgium, Bulgaria, Croatia, Cyprus, Czech Republic, Denmark, Estonia, Finland, France, Germany, Greece, Hungary, Ireland, Italy, Latvia, Lithuania, Luxembourg, Malta, New Zealand, the Netherlands, Norway, Poland, Portugal, Romania, Slovakia, Slovenia, Spain, Sweden, Switzerland, the United States and the United Kingdom.

Updated to correct the number of customers TaxJar has to 23,000.

When companies are considering buying a particular software service, they typically want to test it in their own environments, a process that can be surprisingly challenging. TestBox, a new startup, wants to change that by providing a fully working package with pre-populated data to give the team a way to test and collaborate on the product before making a buying decision.

Today the company announced it was making the product widely available; they also announced a $2.7 million seed round from SignalFire and Firstminute Capital along with several other investors and industry angels.

Company co-founder Sam Senior says he and his co-founder Peter Holland recognized that it was challenging for companies buying software to test it in a realistic way. “So TestBox is the very first time that companies are going to be able to test drive multiple pieces of enterprise software with an insanely easy-to-use live environment that’s uniquely configured to them with guided walk-throughs to make it really easy for them to get up to speed,” Senior explained.

He says that until now, even with free versions or free testing periods, it was hard to test and collaborate in that kind of environment with key stakeholders in the company. TestBox comes pre-populated with data generated by GPT-3 OpenAI to test how the software behaves and lets participants grade different features on a simple star rating system and provide comments as needed. All the feedback is recorded in a “notebook,” giving the company a central place to gather all the data.

What’s more, it puts the company buying the software more in control of the process instead of being driven by the vendor, which is typically the case. “Actually, now [the customer gets to] be the one who defines the experience, making them lead the process, while making it collaborative, and giving them more confidence [in their decision],” he said.

For now, the company plans to concentrate on customer support software and is working with Zendesk, HubSpot and Freshdesk, but has plans to expand and add partners over time. It has been talking with Salesforce about adding Service Cloud and hopes to have them in some form on the platform later this year. It also plans to expand into other verticals over time, like CRM, martech and IT help desks.

Senior is a former Bain consultant who worked with companies buying enterprise software, and saw the issues firsthand that they faced when it came to testing software before buying. He quit his job last summer, and began by talking to 70 customers, vendors and experts to get a real sense of what they were looking for in a solution.

He then teamed up with Holland and built the first version of the software before raising their seed money last October. The company began hiring in February and has eight employees at this point, but he wants to keep it pretty lean through the early stage of the company’s development.

Even at this early stage, the company is already taking a diverse approach to hiring. “Already when we have been working with recruiting firms, we’ve been saying that they need to split the pipeline as much as they can, and that’s been something we have spent a long, long time on. […] We spent actually six months with an open role on the front end because we are looking to build more diversity in our team as quickly as possible,” he said.

He reports that the company has a fairly equitable gender and ethnic split to this point, and holds monthly events to raise awareness internally about different groups, letting employees lead the way when it makes sense.

At least for now, he’s planning on running the company in a distributed manner, but acknowledges that as it gets bigger, he may have to look at having a centralized office as a home base.

“Digital transformation” has been on the mind of many an organization in the last year: the pandemic and the shift it’s brought to how we work are speeding up investments in new apps, infrastructure and work practices to improve productivity regardless of where we sit all day. Now, it looks like we’re on to the next stage of that journey: actually figuring out how to adopt and run with all that new tech.

In a sign of the times, today a startup called Whatfix — which has built a platform that helps make better use of tech investments by giving chatbot-style guidance to users on how to use apps, with the option also to apply AI to understand what a person is doing to suggest what actions to take next — is announcing $90 million in funding. It will use the money to continue expanding its tech platform and hiring more talent to meet demand, said CEO Khadim Batti, who co-founded the company with Vara Kumar (CTO), in an interview this week.

Sources close to the company — co-headquartered in San Jose and Bangalore — confirmed that the Series D round was made at a valuation of around $600 million, triple Whatfix’s value in its Series C round last year.

That sharp rise is due in part to the state of the market today, but also the company’s growth within that bigger trend. Whatfix today has some 500 global customers on its books, The Netherlands Red Cross, Experian, Sentry Financial Services, Cardinal Health Canada, BMC Software Inc., and Bausch & Lomb among them. Some 75% of its business is coming out of the U.S., with another 18% from Europe. Revenues in the last six months have been growing at a rate of 100% quarter-on-quarter.

“This pandemic has proven an inflection point for adoption,” said Batti (pictured above, left with Kumar, right).

This latest tranche of equity funding is coming from a mix of financial and strategic investors.

SoftBank’s Vision Fund 2 is leading the round, with Eight Roads Ventures, Sequoia Capital India, Dragoneer Investment Group, F-Prime Capital and Cisco Investments also investing. The company has raised just under $140 million in total.

“Digital adoption solutions” — the general term describing what Whatfix has built — have become a popular solution for enterprises that have found themselves in an IT pickle, Batti said.

“We’ve seen more than $500 billion spent on enterprise software, with areas like SaaS growing very fast. There is so much there, and every employee has access to do better work. But most are not adopting or using that software. This means a lot [of inefficiency] in ‘digital transformation,’” said Batti. “We are focusing on fixing this problem.”

Digital adoption and digital experience overall can come in many forms these days.

They include assistants that are embedded directly into apps themselves (with some versions of this — such as Clippy on Word — nearly as old as software itself). The category also includes separate platforms that integrate at the back end with the apps that you use, providing not just a single ingestion point for data but intelligence on how best to use it, and what to use. (Dooly for sales teams is an example of that, although I don’t know if it would describe itself as a “digital adoption solution” per se.)

Others like Pendo are geared more at observing how your sites and apps are being adopted and used by others. And there are a number of others out there specifically looking at digital adoption by enterprises and competing directly with Whatfix: they include Apty, Userlane, Applearn.

One of the biggest — WalkMe — yesterday announced an IPO at an estimated $2.5 billion valuation.

Overall digital adoption and digital experience are big businesses: one analyst estimates that the market is growing currently at a rate of just under 11% annually and will be worth $15.8 billion by 2025.

Whatfix is built around the premise that it sits on top of whatever apps a company may choose to use, and will work with just about any piece of modern software, Batti said. That includes Whatfix being able to provide assistance on apps even when they have been customised for a particular workplace. It most commonly appears like a little chatbot on the user’s screen, like the one in this paragraph, which can expand with more details and information as needed, like this:

The company works with the most popular software packages — including Salesforce, MS Dynamics, Oracle’s CRM platform, ServiceNow, SuccessFactors, SharePoint, Workday — but, since it is used in the form of a browser extension or an overlay integrated by a company’s IT department, it can be used to help guide people with any application that’s available over the web. Batti said that one priority the startup has is to build deeper integrations with specific apps so that Whatfix can be used better across mobile and with local apps in future, not just via the web.

Many might think of “digital adoption” as training someone to use a particular software package, and while Whatfix is used for that, the company has also found a lot of traction as a tool beyond it, providing support on a more regular basis and across a wider variety of use cases, whether it’s to help guide people through app usage, or to monitor what they are doing in order to help suggest what to do next, and even populate relevant fields if “next” means using a different app.

The platform can be used to create usage guides, multilingual support, multi-device support, user tracking and more, and it comes with low-code options (it can be intergrated into an app with a single line of code, the company says).

The company claims its assistants can increase employee productivity by 35%, reduce training time and costs by 60%, reduce employee case tickets by 50% and increase application data accuracy by 20%.

While the field for digital adoption is very crowded today, it’s numbers like these, Whatfix’s own growth, and the fact that software is continuing to get more capable, but also more complex, that have interested investors.

“Digital Adoption Solutions are enhancing the growth and importance of SaaS products for enterprises globally,” said Munish Varma, Managing Partner, SoftBank Investment Advisers, in a statement. “Whatfix makes it easier for companies to use SaaS products, which increases productivity. Whatfix, with its roster of global clients, is well placed to become a DAS leader, and we are excited to be part of their journey.” Sumer Juneja, Partner, SoftBank Investment Advisers, added: “Enterprises spend billions on applications across multiple functions and yet employee adoption is low. Quick adoption ensures payback on software investments. Whatfix’s solutions will be a key driver for enterprises to achieve this goal, which is reflected in their growth.”

What will be interesting to watch is how platforms like Whatfix’s will evolve over time, and what further functions they might take on. For example, in enterprises, one of the biggest vulnerabilities in security has been how people mistakenly click on dodgy links in emails or otherwise inadvertently pass on information to malicious hackers. Could there be a role for digital adoption assistants to identify when this might happen and alert people before they click the wrong way? Regardless, the question and very existence of loopholes like that are signals for why we’ll probably why we’ll continue to see tools like Whatfix’s around for some time to come.

Sinch — the Swedish company that provides a suite of services for companies to build communications and specifically “customer engagement” into their services by way of APIs — has made yet another acquisition in its global march to scale up its business and compete more squarely with Twilio. The company today announced that it has acquired MessageMedia, a provider of SMS and other messaging services for businesses to manage customer relations, user authentication, alerts and more.

The acquisition is being made for $1.3 billion — comprised of $1.1 billion in cash and the rest in shares (or in Sweden’s currency, SEK10,745 million in total based on Sinch’s share price and yesterdays exchange rate). The deal is expected to close in the second half of this year.

The deal is notable not just for giving Sinch a major inroad into the world of business SMS, but also because of the timing. Less than a month ago, Sinch’s big rival Twilio announced that it would acquire ZipWhip, another big player in the same area of business SMS, for $850 million.

MessageMedia, based out of Melbourne, Australia, is currently operational also in New Zealand, the U.S. and Europe, and it focuses on providing services primarily to the SMB market with a self-service platform where customers can build and operate services, with the option of using a web portal provided by MessageMedia to handle the traffic.

It has some 60,000 customers and handles 5 billion+ messages annually, Sinch said. Growth is particularly strong in the U.S. market, where MessageMedia is adding 1,500 new customers each month. Alongside SMS, it also provides tech for companies to build MMS experiences and mobile landing pages, and it also provides them with tools to integrate other features as well as an API gateway.

Sinch itself says it handles some 150 billion mobile customer engagements for its customers annually, and it has eight of the 10 biggest tech companies as customers.

Sinch is publicly traded in Sweden and currently has a market cap of $13.6 billion, and the deal comes just weeks after the company announced that it would be raising $1.1 billion for more acquisitions, with a big chunk of the money coming from SoftBank, one of its major backers.

Given the size of this deal announced today, now we know which deal Sinch had in mind. It would be interesting to know whether Sinch’s move to buy MessageMedia predated Twilio’s for ZipWhip, which definitely does not feel like a coincidence.

“Sinch powers mobile customer engagement for some of the largest brands and technology platforms in the world. With the acquisition of MessageMedia, Sinch will now be able to bring the benefits of enhanced mobile customer engagement to every small business on the planet,” CEO Oscar Werner said to TechCrunch. “No longer will you need the deep pockets of an enterprise or the technical skills of an engineer to deliver first-class customer experiences.”

Sinch has been on a fast pace of buying up companies in recent times to scale up its existing business, tapping not just into the huge surge of people using phones and the internet to communicate in these pandemic-stricken times, but also to bulk up and have more economies of scale in the communications industry, essentially a business built on aggregating incremental revenues.

That fact has led to a lot of consolidation, with Twilio also buying up strategic, smaller businesses in quick order.

In this regard, MessageMedia is a strong buy for Sinch because it’s generating strong cash. MessageMedia is expected to make $151 million in profits for the year ending June 30, with gross profits of $94 million and EBITDA of $51 million, Sinch said. Sinch itself is also profitable.

Sinch’s other deals have included Inteliquent for $1.14 billion, ACL in India for $70 million and SAP’s digital interconnect business for $250 million.

For its part, MessageMedia very much plays into and is a product of the same API economy that has lifted the likes of Twilio, Stripe and many others built on the premise of knitting together very complex services, which customers can then use by way of simple lines of code that they integrate into their own digital operations, be it websites, apps, or internal systems.

Communications, and specifically messaging API-based systems are estimated to be a $9-13 billion market, Sinch said, with the U.S. accounting for 30% of that, and the global market projected to grow between 25-30% until 2024. SMBs, who might lack the resources to build such tools from the ground up, are a big part of that activity.

“Mobile messaging delivers tremendous ROI but smaller businesses often lack tools that cater to their specific needs,” said Paul Perrett, MessageMedia CEO, in a statement. “Serving these customers presents a tremendous opportunity, and with Sinch we can build a global leader in our field.”

Human resources is generally a salient cornerstone of any organization, but digitization has democratized a lot of the work that goes into HR, and that’s meant more people in businesses interested in, and using, the kind of data that HR people build and typically manage. Today, a startup called ChartHop that’s built a platform to cater to that trend is announcing $35 million in funding on the heels of strong growth.

The Series B is being led by Andreessen Horowitz, a past backer, with Elad Gil and previous investors Cowboy Ventures and SemperVirens also participating. We understand from sources close to the company that the round values ChartHop at between $300 million and $400 million.

ChartHop was founded in New York by Ian White, now the CEO, who first started building the tools to fill what he felt were gaps in his own knowledge when he founded, ran and eventually sold his previous company, Sailthru (which was acquired by CampaignMonitor).

He said he realized the company could build “all the tech we wanted,” but when it came down to thinking about how to run and scale the business, that was at its heart actually a people question, and also understanding how departments, and the entire organization, looked and worked as a whole.

Image Credits: ChartHop

“It was not as important as hiring, structuring a ‘single you’ of the organization,” he said. (Ian’s pictured here to the right.) Similar to the great analytics tools that have been built for developers, sales teams and others, “What I wanted was people analytics,” he said. “I wanted to understand my team.”

That’s actually a very multifaceted question. It’s not just a matter of an org chart — a big enough task in its own right that the very day that ChartHop came out of stealth in early 2020, another org chart startup, The Org, launched, too. It’s also retention strategy, employee satisfaction, turnover statistics, diversity statistics, predictive visualizations on finances if one area was compensated differently, or if hiring were frozen, etc. “All of those problems became mine and there was no great software out there to solve for it,” White said.

The ChartHop platform is built like all strong structures these days in the world of tech: tons of integrations to feed data into ChartHop to make it richer; tons of integrations also to export and use that data in more dedicated applications when needed; and an easy way for everyone to update data but also put in place easy and strong protections to keep confidential data as it should be.

And while HR still “owns” the platform, White said, it can be accessed and used by anyone in the organization, and it is.

It seems that others have found the talent management software market lacking for it, too. Since 2019 it went from a team of one — White himself — to 75, with 130 corporates now using its services. The list has a strong list of household company names with a heavy emphasis in tech, from what White showed me. Revenues in the last 12 months — a time when the spread-out nature of many of our workplaces has meant an even greater need for a platform to manage all the information has possibly reached a high water mark — have grown at a rate of 17% month-by-month.

“With HR and people functions so crucial to the growth and success of businesses, it’s unfortunate that most HR teams lack the critical people data to drive organizational decision making,” said David Ulevitch, general partner at Andreessen Horowitz, in a statement. “ChartHop is the solution to this all-too-common problem, and is built by company leaders who have felt this pain personally. ChartHop’s visual approach to people analytics allows leaders to make organizational planning and strategy decisions with confidence. We’re thrilled to lead ChartHop’s Series B because of their impressive growth, the company’s vision, and the terrific, mission-oriented team they’ve assembled.” He also led the company’s seed round in February 2020.

“Since implementing ChartHop earlier this year, we’ve seen significant improvement in our engagement with talent routines as they’re managed via ChartHop,” said Sara Howe, vice president human resources at ZoomInfo, a customer of ChartHop, in a statement. “Our employees have found the simple user interface and the centralized view of their data as the most helpful features. Leaders across ZoomInfo have also leveraged ChartHop to ensure that their organizations are well structured to support our continued rapid growth.”