Time for an update on Boston’s marketing tech cluster. It’s one of the real strengths of the local entrepreneurial ecosystem. And it looks like it’s getting stronger, with a couple of leaders making news this week. Here is a tale of two companies that have become competitors:

—Constant Contact (NASDAQ: CTCT), the Waltham, MA-based online marketing firm, has seen its stock price jump nearly 30 percent—from about $24 to just over $30—since Facebook filed for its IPO last week (coincidence?). Constant Contact has been positioning itself as a leader in digital marketing for small businesses across e-mail, social media, and Web platforms—especially social campaigns. The company also released some promising stats on its revenues and profits for 2011 and its most recent quarter.

—HubSpot, the Cambridge, MA-based marketing tech firm, said it has hired J.D. Sherman, Akamai’s former chief financial officer (also a former IBM exec). The company says Sherman is being brought in partly to help it prepare for a future IPO. HubSpot has been hiring aggressively and working on new products, while it pares away others (like Oneforty.com, which it acquired last summer). It remains to be seen whether the company will actually make it to an IPO before getting snapped up by Salesforce.com or some other suitor.

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The evolution of Constant Contact continues. The Waltham, MA-based online marketing firm (NASDAQ: CTCT) said today it has acquired Boston-based CardStar, a maker of a mobile app that lets people consolidate their loyalty and rewards cards. Terms of the acquisition weren’t given.

The deal represents Constant Contact’s first foray into mobile rewards technology aimed at helping small businesses stay connected to consumers. CardStar’s app lets people create a digital version of their physical membership cards (for retail stores, gyms, and so on) all in one place, on their smartphone. CardStar started in late 2008 and has four employees joining Constant Contact, including founders Andy Miller and Danny Espinoza. The startup says it has more than 2 million active users.

“I was a user before I was an acquirer,” says Constant Contact CEO Gail Goodman.

And acquiring CardStar makes a lot of sense for Constant Contact, which has been working to transform itself from an e-mail marketing firm into a one-stop shop for small businesses trying to reach customers through social media, online marketing, rewards programs, and other methods.

“This acquisition is at the intersection of everything we do,” Goodman says. “As we look at what small businesses are trying to do, they are trying to use every possible channel to reach customers—e-mail, social, mobile. At the core of that is a loyalty program. Andy and his team will help us weave those pieces into a really simple, really impactful application on the merchant side.”

Goodman declined to give specifics on any upcoming mobile products, but she emphasized that CardStar’s app will continue to run, and that more is on the way. “We are on a pretty aggressive product roadmap,” she says. “Much of what we’ve done has loyalty at its heart. Our customers have always wanted to take that a step further. But without mobile, it’s pretty hard.”

As for why Constant Contact chose CardStar over other companies in the mobile couponing and rewards sector, Goodman pointed to the startup’s traction with consumers and the culture fit with her team.

Constant Contact says it has more than 450,000 customers, mostly small businesses, nonprofits, and associations. Last summer, I spoke with the firm about its plans for innovating as a young public company (IPO in 2007), and about the biggest technology shift in its 13-year history (integrating Web software with existing database systems, among other things).

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We caught a fresh wave of tech startup financings, from companies working on improving e-mail, shopping, wellness, video surveillance, and enterprise computing. Here’s a quick rundown:

—Boston-based HelpScout, developers of software for managing group collaboration across a single e-mail address, announced the closing of its $435,000 equity round. The TechStars Boston graduate told me when we spoke this summer that it was in the process of closing a seed round, with funding from angels such as David Cancel, Dharmesh Shah, Joe Caruso, Chris Sheehan, and Brian Balfour.

—Ginger.io, another TechStars Boston alum, has amended an SEC filing to indicate it has raised $1.65 million of a targeted $1.7 million equity round, from 12 investors. The Cambridge, MA-based health and wellness tech company, which filed its regulatory papers under the company name Gingerd, presented in the startup Xpo at our XSITE conference in June.

—Boston-based fashion tech startup Snapette, a grad of the Mountain View, CA-based 500 Startups accelerator program, nabbed $1.1 million of a $1.275 million debt-based funding round, an SEC filing shows. Snapette, whose founder said last month that she had dropped out of Harvard’s MBA program to focus on the company, offers technology for enabling shoppers to share accessories available at local stores and for merchants to offer discounts.

—RemoteReality, a Westborough, MA-based developer of wide angle video camera systems for surveillance and navigation, has brought in $2 million of a potential $3.5 million equity-based financing round, coming from five investors, an SEC filing shows. The company’s website lists its previous investors as Chart Venture Partners and Connecticut Innovations.

—And Westborough-based Aternity, a maker of software for enterprise desktop monitoring, announced it had bagged $13 million in a Series D round led by Investor Growth Capital. The deal also included all of Aternity’s existing investors, Vertex Venture Capital, Genesis Partners, Intel Capital, and Clal Industries and Investments.

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When I heard the news of Steve Jobs’s death last night, even though I was hardly surprised, I felt like I had been kicked in the gut—as if the industry in which I’ve spent my career had lost its soul.

I’m rarely shy about criticizing the titans of our industry, but from the beginning Steve was different: a brilliant businessman whose primary motivation wasn’t money, a CEO who involved himself in every detail of product design, and a restless perfectionist who would change his plans in a heartbeat if he saw a better way to do things.

I saw this first-hand in the 1980s, when he visited my team at Carnegie Mellon. We introduced him to sending pictures, fonts, etc., through e-mail. He saw the value instantly, and tried to hire the whole team on the spot. When that failed, he quickly created the team that built NeXTMail, which eventually evolved into Mail.app on the Mac. Nobody ever “got it” faster than Steve—and when he got it, he made things happen in a hurry.

One of Steve’s least-mentioned talents was his mastery of e-mail. He was surely flooded with it, yet he answered more promptly than I can. I’ve spent my whole career working on e-mail, but if he had written a book on how to manage your e-mail, I would have bought it the day it was released.

I also admired Steve a great deal as a person. When he was the busy CEO of NeXT, my wife once put him on hold for over ten minutes while she hunted for me. He graciously uttered not a word of complaint. And when he famously called LSD “one of the two or three most important things I have done in my life,” he risked broad censure rather than betray the truth as he saw it—that LSD had helped open his mind to the insanely great possibilities of the coming digital age.

Steve left us too soon, when he still had much to teach us. But our world is incalculably better for the 56 years he gave us. May he rest in peace.

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Ladies and gentlemen, your attention please. Ahem.

[A giant “6x6” fills the screen.]

Macho narrator voice:
Star Wars had The Empire Strikes Back (Vader: “I am your father”)
The Godfather had The Godfather Part II (Pacino: “You broke my heart”)
Mad Max had The Road Warrior…well, you get the idea.

Now Xconomy presents 6×6, the long-awaited sequel to its riveting, change-the-world program from last December, 5×5. (It was “5×5” because we weren’t in New York City yet. Now we are.)

Yes, for the second straight year, Xconomy has canvassed its national network to find the most original, sensational, and transformative tech ideas out there—across software, hardware, digital media, social technologies, robotics, and more. We are inviting a select few speakers to Boston for an afternoon of mind-bending presentations and business networking.

It’s all taking place on the afternoon of Thursday, December 1, from 1:30-5:30 pm, at the Fidelity Center for Applied Technology in downtown Boston. One featured speaker will be on hand from each of our six cities: Boston, New York, Detroit, San Francisco, Seattle, and San Diego. We hope “6×6: Six Cities, Six Big Tech Ideas” will be a rallying point for the Boston tech community to get together and discuss the future of their fields with our out-of-town guests.

The concept is to highlight some of the BIGGEST tech ideas out there—as well as the nuts and bolts of how founders are building successful businesses around these ideas. This event is about truly changing the world, so we’ve asked everyone to please check their daily deals, social network plug-ins, and run-of-the-mill mobile apps at the door.

Who better to set the table than Stephen Wolfram? We’ve invited the renowned scientist, inventor, and business leader to give the opening keynote. Wolfram is the founder and CEO of Wolfram Research and the creator of Mathematica and Wolfram|Alpha. So he knows a little bit about changing the world from a software, computing, and business perspective. Oh, and he also spent 10-plus years working to reinvent the entire landscape of modern scientific thought with his book project, A New Kind of Science. I’ll stop there, but you can read an interview I did with Wolfram around the beginning of last year. (As for what he’ll talk about on Dec. 1, it’s safe to say I have no freaking idea—but I’ll keep you posted.)

Here’s a quick rundown on who’s representing our six cities at 6×6:

—From the hometown of Boston, we have Dave Icke, the CEO of Cambridge-based MC10, a pioneer in developing flexible electronics and sensors for consumer, healthcare, and energy markets.

—New York City is sending Jason Baptiste, the CEO of OnSwipe, a scrappy young startup that is trying to invent the future of media through a new tablet publishing platform.

—Representing Detroit is Nathaniel Borenstein, the Chief Scientist of Mimecast, an e-mail management company headquartered in the U.K. Borenstein, who’s based in Michigan, is one of the fathers of modern e-mail systems, and will talk about the future of communication in the cloud.

—From San Francisco comes Adam Goldstein, the CEO of Hipmunk, an online travel search company that’s been making waves with its novel visual interface for finding flights and hotels.

—Seattle will be repped by Kabir Shahani, the CEO of Appature, a fast-growing startup specializing in social and relationship marketing technologies for the healthcare industry.

—And from the sunny climes of San Diego comes Bill Walker, Chief of Global Hawk Business Development at Northrop Grumman, the aerospace and defense tech giant. Walker will talk about high-altitude unmanned aerial vehicles (UAVs).

We also have a few intriguing “burst” bonus talks to highlight, from some of the most exciting startups around Boston. They will include Affectiva (CEO Dave Berman), an MIT Media Lab spinout that’s commercializing software to make your computer or smartphone understand your emotional state (talk about a big idea); Krush (CEO Gina Ashe), an ambitious startup focused on social commerce and marketing for apparel and lifestyle brands; and GrabCAD (CEO Hardi Meybaum), a company that’s connecting engineers with people who need stuff built, via an online community and marketplace.

We are really looking forward to 6×6, and we hope to see you there on Dec. 1. You can register at the special super saver rate here.

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New York’s Sailthru plans to expand with its freshly minted $8 million Series A funding and nearly double its staff within 12 months, according to its CEO and founder Neil Capel.

The startup announced last week it completed the financing round, which was led by RRE Ventures with participation from AOL Ventures, DFJ Gotham Ventures, Lerer Ventures, Hatteras Funds, Thrive Capital, and Pilot Group. This latest funding, combined with a seed round in 2010, brings three-year-old Sailthru’s total financing to $9 million and positions the company for growth, Capel says.

Sailthru sends e-mails on behalf of clients such as The Huffington Post, Fab.com, Thrillist, and The New York Observer. Capel explains that his company curates flash deals, stories in newsletters, and other content that will be of interest to individual recipients. “We pick each piece of content for each user,” he says. “If there was a list of half a million, then half a million different e-mails would go out.”

On a macro level, Sailthru can be seen as a rival to e-mail service providers that handle distribution of bulk marketing, advertising, and other content for corporate clients. However, Sailthru says it offers individualized e-mails that it claims other providers do not.

Capel, a British transplant who confesses his accent skews more toward Australian these days, says his company wants to change the way … Next Page »

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Yesware, the Cambridge, MA-based developer of e-mail plug-ins for salespeople, announced today that its $1 million first-round funding came from Google Ventures, Foundry Group, Golden Venture Partners, and angel investors Geoffrey Hyatt, Colby Wood, Mike Baker, David Cohen, Mike Dornbrook, and Will Herman. The money will go toward developing Yesware’s technology for helping salespeople contact leads and helping sales managers track their workforce’s activities.

“Google and others can make better e-mail, but I really think if you want to hit it out of the park, this whole concept of vertically adapting e-mail for a specific vertical problem or task is just a brilliant space,” Google Ventures partner Rich Miner said on a phone call this morning.

Foundry Group’s Brad Feld has a track record of investing in e-mail-related startups, such as Email Publishing, Return Path, and SendGrid. “He was top of my list of people I wanted to work with because he has such deep e-mail investing experience,” Yesware founder and CEO Matthew Bellows told me today.

As Bellows explained when we met this summer, Yesware first raised the $1 million funding on the premise of building an entirely new e-mail platform for salespeople, but its board members suggested it change its model to work with existing e-mail systems (it now plugs into Gmail and Android phones and is in the works for Outlook). The software offers e-mail templates for helping sales people pitch and follow up with potential leads, and can copy those e-mails to salespeople’s accounts on customer relationship management (CRM) tools like Salesforce.com, Microsoft Dynamics, Oracle CRM, and Highrise. That information helps sales managers track their employees’ actual activity with potential customers, instead of requiring them to rely on what the salespeople enter themselves into their CRM accounts. “It saves time and provides better data,” says Bellows.

Yesware also provides reports to salespeople showing them how contacts are responding to e-mails and enabling them to prioritize who to follow up with first. Those reports can be viewed on a mobile browser for free. The Yesware e-mailing templates are also available via its Android mobile app, which costs $4.99. The Yesware software is available for free to individual salespeople, but starting in October, Yesware will charge sales managers who want to use the technology for their teams, at $20 per user per month.

The company, which has three full-timers and several contract and part-time employees, is “hiring like crazy,” particularly in the engineering department, says Bellows. “This funding and next round of funding is all about building up the team,” he says, noting that the company will soon start looking to raise its Series A round.

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Fresh from a three-month stint in California, Tawheed Kader, founder and CEO of New York’s ToutApp, is back home to build the ranks of his startup and pursue his next round of funding. Last Wednesday he and the other graduates from this summer’s 500 Startups business accelerator program in Mountain View, CA, showed off their products at demo day. Now Kader is on the hunt for new talent to help his company continue its efforts to make e-mail more efficient.

ToutApp has already secured early stage funding, thanks in part to the accelerator program. “It’s not just for first time entrepreneurs,” Kader says. “It’s for any company looking for that extra edge in connections and mentorship.” He says one-year-old ToutApp raised a seed round, under $1 million, with participation from Owen Davis, managing director of NYC Seed; Dave McClure, founder of 500 Startups; Esther Dyson; and Eric Ries. “We are already making money,” Kader says. “We don’t need to raise a tremendous amount at this point.”

From late May through last week, Kader fine-tuned his company’s plans with the help of McClure and other mentors 500 Startups. On August 31, he and others from the summer session will present their companies at another demo day in New York.

Finding early stage funding was initially difficult in New York, Kader says, because the local startup community is still growing. He demoed his product at such local groups as NY Tech Meetup in an effort to to connect with potential investors, but he found more customers than backers. “There aren’t enough entrepreneurs who ended up getting a huge exit and are now investors that understand what is like in the early stages,” he says.

Kader spread the word about ToutApp at March’s South by Southwest conference in Austin, TX, and met McClure, who invited him into the accelerator program.

ToutApp is a Web-based service that lets subscribers create form letters they can personalize and send to multiple recipients. Kader says ToutApp is not bulk mail software; rather the users create templates for reaching out to specific types of contacts. For example, if … Next Page »

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The West Coast might have all the big names in e-mail platforms, but Boston’s doing plenty when it comes to building technology on top of those existing foundations.

There are a number of established players that have been around and working on technology for things like managing e-mail outboxes (SMTP), bulk mailings (Constant Contact), and e-mail marketing and lead conversion (HubSpot).

But a new crop of companies has been developing technologies that aim to make life easier for businesses and consumers via the e-mail interface. So look out, Facebook and other social platforms: it looks like e-mail isn’t going away anytime soon. We’ve rounded up a mini cluster of e-mail app developers that have come out of Boston, so take a look. (Side note: a good chunk of them have TechStars roots.) Feel free to suggest any I missed.

—Yesware, working out of Cambridge, MA’s Dogpatch Labs, specializes in making sales people more efficient and effective. The company offers e-mail templates to help salespeople better approach, pitch to, and manage customers. It’s also looking to create a system for helping managers better understand their sales teams by observing e-mail communication with customers and its effectiveness. Yesware has $1 million in its funding pot from some notable names related to e-mail (none publicly named yet, though.)

—TechStars Boston 2011 graduate Help Scout is looking to aid businesses better use the inboxes run by multiple people, say, something like help@xconomy.com (not an actual e-mail address, but you get the picture). The big focus is on customer service applications for Web-based companies. Help Scout users can track customer e-mails, assign them a ticket number, and collaborate with other employees on the problem or question in a more organized fashion than shouting across the office. It runs in existing e-mail inboxes or through its own external app.

—Who’s got skills? Senexx wants to help organizations better understand who in their workforce is skilled at what, and connect them to the people who need help. As you might have guessed by now, they’re doing it through e-mail. The company came from Israel to TechStars Boston this year.

—U.K.-based Mimecast has a strong Boston presence. The company offers software for helping companies better keep track of where e-mails go and when. The idea is to help employees focus less on e-mail and more on their actual business, while making e-mail more efficient, manageable, and … Next Page »

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It’s probably reassuring for online shoppers and the like to know that the generic-sounding address they e-mail—-usually dubbed something like help, service, or contact @xyz.com—is actually manned by people and not robots. And TechStars Boston 2011 graduate Help Scout is looking to make life easier for the humans that are responding to those queries.

“We know that every business on the planet has some sort of catch-all inbox that typically goes to group of people,” says founder Nick Francis. “Anytime that account gets more than 10 emails a day, it becomes a bit unmanageable. Help Scout helps you manage the chaos.”

Without Help Scout, Francis says, employees are left to find alternate ways to inform each other on how a request or e-mail is being handled—like BCCing or sending separate e-mails to colleagues, and passing notes in person or shouting across a desk.

Help Scout’s platform sifts through the e-mails that come to those catch-all inboxes, and enables different users to collaborate on responses. There are features for assigning a customer e-mail to an employee, passing along notes before sending the e-mail, and creating a draft e-mail for review. (See screen shots below.) Help Scout’s big focus is on customer service applications, so incoming e-mails pushed through the system are assigned a ticket number to track how they are dealt with throughout the process.

The technology launched about seven weeks into this year’s TechStars program, and Help Scout scored some business with its TechStars mentor Jason Henrichs, COO of Boston Web-based banking startup PerkStreet Financial. “It’s really dangerous to think the target customer is always you, but halfway through a mentee session we realized we’re totally a customer,” says Heinrichs.

He says his firm was using the manual shouting and passing notes method of collaborating on customer e-mails. Help Scout technology helps them more efficiently scale as they grow customers for their Web-based, cash-back debit card account product.

“We add a collaborative layer on top of email,” Francis says. His startup is working on closing a $400,000 round from a group of 15 angels—including David Cancel, Dharmesh Shah, Joe Caruso, Chris Sheehan and Brian Balfour. It expects to

… Next Page »

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If you’re like most people, you do a lot of your personal communicating via Facebook and text messages, but you handle most of your business matters over e-mail. In fact, you probably spend far too much of your workday on e-mail (some estimates say 30 percent), and you wish you could be more efficient and productive with that time.

Well, what if you could do a lot more stuff directly from your inbox? Instead of clicking on e-mail links that take you somewhere else, for instance, what if you could watch videos, comment on people’s updates on Facebook and Twitter, and browse daily deals, all from the friendly confines of your e-mail account?

That’s the idea behind a young Cambridge, MA-based startup called PowerInbox. OK, maybe it won’t make you more productive at work or cut down on time spent in your inbox just yet. But the idea actually leads to something bigger, involving the future of e-mail as a unified platform for social apps.

First, some news. PowerInbox is rolling out its private beta platform today—you can try it out here using our access code. The free download works across Gmail, Hotmail, Yahoo Mail, and Outlook. Basically, it lets you do things like comment on Facebook, view photos, see and send tweets, and get information about local deals from Groupon (see screenshot below)—all without leaving your inbox.

The core idea behind PowerInbox, as founder Matt Thazhmon explains, is “let’s make e-mail interactive.” What he means, really, is adding social features to e-mail that will connect users more efficiently to the services they use every day.

PowerInbox was co-founded last year by three Electronic Arts veterans (including Thazhmon, who worked on Madden football and other games). The startup raised a $1 million seed round earlier this year from Atlas Venture, Longworth Venture Partners, Correlation Ventures, and angel investors. The four-person team, originally from Orlando, FL, by way of the San Francisco Bay Area, recently moved to the Boston area. The company has found office space for the coming year near Central Square in Cambridge.

There are plenty of e-mail-related companies out there, of course. They include—just to name a few—Baydin, Gist (now part of RIM), Help Scout, Mimecast, Rapportive, Taskforce, Senexx, SMTP, Sonian, and Yesware, to go along with Constant Contact, HubSpot, and a whole host of marketing tech companies. Some of these are trying to make your inbox more productive and efficient, while others use e-mail as a platform for other applications. And each e-mail system, like Gmail or Outlook, has its own add-ins and gadgets. But where PowerInbox is different is in its vision for the future.

The company’s long-term goal is for developers to create new apps on top of the PowerInbox e-mail platform. Anyone from Facebook to travel and deals sites (left) to video services (Netflix, anyone?) to recruiting, dating, or meeting-scheduling sites—indeed, any entity that interacts with customers by e-mail—could conceivably build an app that helps people interact with content through an inbox.

One emerging focus is on forming partnerships with gaming companies—such as social-network game giant Zynga, but also smaller developers—to let users play games within their e-mail, and make it that much easier to start playing. “We think this is going to be huge,” Thazhmon says.

But making big changes to e-mail tends to be hard because it’s an open platform, … Next Page »

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Maybe it’s because I’m hungry, but I’ve been thinking about the future of restaurants lately. Like a lot of people, I eat out far too often, and I have strong feelings about the way the experience should go—the food, the service, the ambience, and so on.

So does Josh Bob. OK, it’s his job (though maybe he’s hungry too). Bob is the founder and CEO of Boston-based Textaurant, a startup that runs a mobile service aimed at taking the hassle out of waiting for a table, and boosting customer loyalty through deals and offers. Using the service, restaurants can send text alerts to customers’ mobile phones telling them their table is almost ready. So Textaurant does away with buzzers and pagers and tries to reduce the workload on the host, while helping the restaurant win over customers who would otherwise leave and not come back.

In case you’re wondering if this causes restaurants to lose out on business from people waiting at the bar, Bob says surveys show more than 40 percent of people will leave (and not even consider going to the bar) if told there is a long wait. That’s the lost business Textaurant is trying to save—and not just by texting them, but also by opening up a channel whereby restaurants can offer special deals and rewards.

The three-person startup is backed by Massachusetts angel investors (and 500 Startups’ Twilio micro-fund) and counts among its dozen or so customers Finale Desserterie & Bakery, Fire + Ice, and Red Robin Gourmet Burgers. It is a finalist in the MassChallenge accelerator program. (You can expect a rebranding and name change along with a new website in the next month, Bob says.)

Textaurant is part of a thriving mini-cluster of food- and restaurant-related startups around Boston that also includes Plummelo, I Am Hungry, Text My Food, Good Eats For Me, and Objective Logistics (see profile here). To some extent, the technologies offered by these companies are a subset of the local-marketing, loyalty, and deals systems that have permeated small-business life as of late. But restaurants have their own quirks and challenges. They are not usually the most eager adopters of new technologies, which can be very polarizing among their managers and staff.

“The restaurant industry has to change,” Bob says. “Anyone who doesn’t use technology will get left behind.”

So here’s his vision of what going to a restaurant will be like five years from now. You’ll decide you want to go to a certain type of restaurant (Italian or Chinese, say) or a particular neighborhood, he says. You’ll use your mobile device to look at Textaurant, which will show you that there are five Italian places nearby, say, and what the wait time is at each of them. You’ll check yourself in at one of the restaurants—with or without setting foot in it—and customize how the table alert will come to you (via text, voice, Twitter, or e-mail). You can also pre-order drinks for the table so they’ll be waiting for you when you sit down.

What’s more, your phone will be connected to your bill so you can accrue loyalty points based on purchases and receive special offers (like a free appetizer at the bar), he says. And on your way out, you’ll pay through your Textaurant account or another mobile system connected to your credit card or payment account.

Groupon, by the way, will have morphed into something else that’s probably unrecognizable today, Bob says. (Presumably along with other daily deal sites.) Not that it’s a bad thing, of course.

“There will always be significant value in helping businesses survive,” he says.

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If there is anything constant about Constant Contact, it is change. The online marketing company (NASDAQ: CTCT), based in the Boston area, is announcing today it has opened a new office in New York City. That by itself isn’t big news, but it’s part of a larger strategic shift in the firm’s technology approach—what is being called the biggest evolution in its 13-year history.

Constant Contact’s New York office, a 2,850-square-foot space in Tribeca, is expected to house more than 10 employees within the next year. For now there is a small team of five, brought over in the firm’s $15 million acquisition of Bantam Live, announced in February. Bantam focused on “social CRM”—social media technologies for helping businesses do things like add new customers, retain them, and better understand what they want, especially in online communities. The New York office, which is currently hiring engineers, apparently will be the hub for integrating social CRM into all of Constant Contact’s marketing tools and services. (The company, with more than 800 employees, also has offices in California, Colorado, and Florida.)

Indeed, the firm’s newest space is symbolic of bigger changes happening under the covers. It’s all part of the broad innovation strategy that CEO Gail Goodman laid out for me last month, as Constant Contact transitions from being known mostly as an e-mail marketing company to being known as a more diversified software-as-a-service firm.

That sounds kind of abstract, but here’s one concrete aspect. Bantam Live uses Ruby on Rails, a popular Web programming framework, for its software development. Constant Contact uses mostly Java, which is older and more established (especially for large-scale backend stuff), for its software and database systems. It’s a challenge—albeit not a unique one—to integrate the two. The goal is to make it so that Bantam’s social software for managing sales contacts, for instance, can talk to Constant Contact’s account management, security, and e-mail and social media marketing systems. As newer social features permeate older technology stacks, this issue is bound to become more widespread.

For Constant Contact, the integration (and a lot more) falls under the domain of Stefan Piesche, the firm’s chief technology officer. Piesche, who joined the company two years ago from Cobalt, oversees an engineering team of about 150, roughly half of them software engineers. “The company is changing its tune vertically and horizontally,” he says. “This requires a different approach on the technology side. But we’re not rewriting everything.”

Rather, newer pieces of code written in Ruby are being embedded, rather cleverly, into existing Java applications so as to maintain a “very cohesive user experience” where “customers don’t see the difference,” he says. The end result: the user sees one unified product, even though it’s made up of multiple sets of products and new features.

Imagine performing this integration on the scale of 450,000 business customers and 8,000 partners (including hundreds in the New York area), and you start to get a feel for the … Next Page »

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Cambridge, MA-based Yesware kicked off late last year with the aim of building an entirely new e-mail system, one that would help salespeople close their deals and help enterprises actually understand their sales forces, says CEO and founder Matthew Bellows. It even raised $1 million on this premise. Then the company’s board spoke up. You see some of its investors knew the whole e-mail space pretty well, and told Yesware not to reinvent the wheel.

So Yesware scratched its plans for an e-mail reboot, and drew up new ones for a sales interface that would work with existing e-mail systems. Late last month the startup, which works out of Dogpatch Labs, opened up its beta version of an e-mail plug-in that offers customizable templates for salespeople. The objectives are still the same. At the individual user level, “we are down in the trenches with the salesperson trying to help them close that business,” says Bellows. And at the organizational level, “it extracts data that their enterprise needs from their activity, to learn from what they do and report on that.”

There are plenty of companies whose business is to generate and qualify sales leads (think Eloqua and HubSpot), and others aimed at managing sales account information (Salesforce), but few that provide tools for actually making the sale, Bellows says.

Yesware’s plug-in offers pre-set e-mail forms to help salespeople first connect with customers, and also to help them once they start getting objections from the customers they’re chasing. Say a salesperson keeps hearing from potential customers that the product costs too much, or that it can’t stack up to an existing offering from a big-name competitor. He or she can pull the appropriately template from Yesware addressing that concern.

“It’s a templates-on-steroids kind of thing,” Bellows says. “We help the salesperson with the right answers at their fingertips.”

The Yesware plug-in also has a button for automatically copying e-mails to a salesperson’s account on the customer relationship management system Salesforce. “It’s a very low cost way of having salesperson update Salesforce,” Bellows says.

Those updates are key to Yesware’s bigger mission of helping sales managers better track the work of their sales force—by actually looking at their communications with customers, rather than relying on the relatively cryptic notes salespeople often type into CRM systems, Bellows says.

“What a salesperson does from an action standpoint is going to be much more helpful than what they say that do,” says Bellows, who saw the frequent disconnect between the two firsthand while managing sales at companies like Vivox, Floodgate Entertainment, and WGR Media, the gaming media startup he sold to CNET in 2004. What’s more, “if we … Next Page »

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Constant Contact is a digital marketing company led by babes. I don’t mean women, though that is true, actually. And I don’t mean babies in the crying, needy, or naïve sense, but rather the youngest-in-the-family sense.

Let me start over. As it turns out, many of the senior management team of Waltham, MA-based Constant Contact (NASDAQ: CTCT) grew up as the baby of their family, and they had older siblings who influenced their worldview. And that has impacted the culture of the company in an important way.

That was one of the more interesting things I learned last week from speaking with Gail Goodman, the company’s CEO and chairman (and youngest of four). She has been CEO since 1999 and led the company’s $107 million IPO in 2007. For those who don’t know, Constant Contact started in the mid-1990s (originally called Roving Software) and rose to become a leader in e-mail marketing and online surveys for small businesses. Now 815 employees strong, it anchors a vibrant hub of marketing-tech-related firms in the Boston area.

Like most young public companies, though, Constant Contact faces challenges in continuing to innovate while staying focused on increasing its profits. The firm made $174.2 million in revenue in 2010—a 35 percent increase over the previous year—and a modest profit of $2.9 million. But its percentage growth has been slowing down over the past couple of years, and the company is investing in newer areas like social media and mobile marketing—to the tune of $24 million spent on R&D in 2010.

Earlier this month, Goodman presided over an annual “innovation day” at the company. Employees were encouraged to submit innovative new ideas for products and processes, and five finalists were selected out of a pool of 33 project ideas, she says. (The finalists weren’t revealed, but two had to do with mobile, and two had to do with “customer wow experiences,” she says.) There will be a final bakeoff in late August, with the overall winner to be implemented by the company by the end of the year.

But Goodman (see below) had a lot more to say about what’s happening at Constant Contact these days. Here’s an edited transcript of our chat:

Xconomy: It’s a perennial question, but how does a mid-size public company like Constant Contact continue to innovate?

Gail Goodman: It actually starts with making sure everyone knows they’re paid to think and to innovate. It all starts with an attitude: what else cool can we do? It helps that we innovate with context. Everyone here is really clear about who our target audience is—small businesses, small associations. We have more than 450,000 customers, and 70 percent of them have fewer than 10 employees. Our innovation needs to be highly usable cool technology. Everyone knows the problem set we’re trying to work on. We help [businesses] create and grow customer relationships. We talk about it a lot. And employees use 10 percent of their time to innovate.

X: So what are you doing that’s unique or special?

GG: We have a Labs organization, and we did that earlier than most companies. That’s where some larger companies get stuck. How do you invest in the future? We keep a running strategic roadmap, with a multi-year focus that has technology disrupters on it—here are things coming that could disrupt our market and customers. We continue to role play, we continue to do late-night pizza sessions.

One example: we have a fantastic “big data” problem. We have 450,000 customers, all of … Next Page »

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After maturing into a steady software company with a mammoth organizational chart, Microsoft is the source of plenty of eye-rolling in the world of tech upstarts—hometown fans included. But every so often, you see a glimpse of what the Redmond, WA-based tech titan could do if its energy was directed just right.

We’ve certainly seen that kind of promise with Microsoft’s big acquisition of Skype, and at the Microsoft NERD center in Cambridge, MA, folks were treated to a fascinating look at the future from Qi Lu, the company’s head of online services. As Xconomy’s Greg Huang details in this report, Lu’s talk touched on several areas—deals, social, mobile—where Microsoft wants to dominate. Also check out the transcript of our exclusive interview with Lu.

The rest of the past week’s tech news:

—Back out west, Microsoft scored a little coup right in Google’s back yard by landing a multimillion-dollar contract to handle cloud e-mail services for San Francisco’s city and county government. It’s not a big moneymaker for someone the size of Microsoft, but getting the city hall crowd in America’s tech capital to pick your service over the hometown offering is a big PR win.

—Google came north to do a little shopping, acquiring consumer electronics shopping startup Sparkbuy for undisclosed terms. Sparkbuy had barely taken the covers off its service, which used online travel-inspired customization tools to help shoppers find laptops and TVs—making this look pretty clearly like a talent acquisition. The Sparkbuy team will be joining Google’s Kirkland, WA office.

—Speaking of talent, we had two more entrants in what might be this year’s overarching story in tech: The lack of qualified hires to fuel growth. I’ve covered this story a few times already with reports on the overall job climate and individual California companies making aggressive hiring moves, but there’s more ground to cover. In this week’s roundup, we have a sharp analysis from guest columnist Ed Lazowska and a study from job-search site Dice, which took a national look at which states have big shortages of tech talent.

—Xconomy had another great event here in Seattle, bringing together leaders in the cleantech sector to talk about the future of alternative fuels in the U.S. The speakers on our main panel all have deep experience in the science and business of trying to disrupt oil’s dominance as the world’s primary fuel, and sparked some really interesting conversations. Also—a photo gallery!

—Clearwire (NASDAQ:CLWR) took another step away from its original business plan, handing over management of its 4G wireless network to Ericsson—the company that also manages the network of Sprint (NASDAQ:S), Clearwire’s majority shareholder. There’s been an enormous amount of change at the Kirkland, WA-based company in just the past six months or so. It’ll be really interesting to see what interim CEO John Stanton and crew have in store for the rest of 2011.

—Zaarly is technically based in San Francisco, but has strong Seattle connections: co-founder Eric Koester is based here. So naturally, Zaarly picked Seattle as one of the original cities for the crowd-buying service’s kickoff.

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On the day a Magnitude 9 earthquake and major Tsunami struck Japan, customers of MIR3 used the San Diego company’s automated notification system to transmit more than 650,000 real-time messages around the world.

“The minute it happened, I checked with engineering and our customers were using every modality of communications—SMS [text messaging], e-mail, phone calls,” CEO Amir Moussavian told me in a recent interview. MIR3 later determined its system had been used to deliver more than 346,000 e-mails; 167,000 automated phone messages; 137,000 text messages; 2,200 pager messages, 1,100 faxes, and even 291 BlackBerry PIN-to-PIN messages—sent mostly by U.S. companies to large numbers of their employees, customers, and partners.

Moussavian, who joined MIR3 in 2002, says it sometimes takes a tragedy for institutions to realize that how critically useful the Web-based messaging system can be. He says the company has been getting more inquiries about its blitz messaging service since the March 11 disaster in Japan—especially from companies and agencies in China.

Amir Moussavian

Likewise, scores of U.S. colleges and universities rushed to sign up for MIR3′s software-as-a-service following a shooting rampage that killed 32 people at Virginia Tech on April 16, 2007. Five months later, when a disturbed gunman was arrested on the Queens campus of St. John’s University, school officials used the new MIR3 system for the first time to transmit the warning: “From public safety. Male was found on campus with a rifle. Please stay in your buildings until further notice. He is in custody, but please wait until the all-clear.”

Moussavian says the company was … Next Page »

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Acquisitions and financing headlines were prominent this week for companies in the Web, mobile, and enterprise IT spaces.

—TA Associates and Summit Partners, growth equity firms with offices in Boston and Silicon Valley, nabbed a controlling share of the Germany-based online gaming company Bigpoint, by investing $350 million in recapitalization financing. Previous Bigpoint shareholder Comcast Interactive Capital’s Peacock Equity Fund sold its holdings. GMT Communications Partners and GE sold a majority of their Bigpoint stake.

—Wellesley Hills, MA-based AppNeta officially launched its cloud-based network management technology and announced it had raised $6.2 million in new funding, led by Bain Capital Ventures, Egan-Managed Capital, JMI Equity, and Business Development Bank of Canada. The company’s technology and staff come from Apparent Networks.

—Watertown, MA-based WiTricity, a developer of a wireless charging system for electric cars and plug-in hybrids, inked a technology partnership with Toyota Motor Corporation. The deal also includes a Toyota investment in WiTricity, in the single digit millions of dollars, according to a Boston Globe report.

—Dassault Systémes, a maker of product lifecycle management software with its U.S. headquarters in Lowell, MA, said it acquired Enginuity PLM of Milford, CT, which makes software for developing formula-based products like cosmetics and pharmaceuticals.

—Sedo, a Cambridge, MA-based company offering an online marketplace for domain names, said it brokered its third largest deal ever, with the sale of the “gambling.com” domain for $2.5 million to an unnamed British firm.

—Waltham, MA-based marketing research software maker Invoke Solutions nabbed $3.8 million in equity-based funding from two investors, a SEC filing showed.

—SMTP, a Cambridge-based emailing software firm, went public on the over-the-counter bulletin board (OTCBB: SMTP). Eighty-one shareholders paid … Next Page »

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An intriguing Boston-area tech company is going public after more than 10 years—and it’s not too late to shake things up in its market. I’m not talking about Zipcar (NASDAQ: ZIP), which had its long-awaited IPO a couple weeks ago. I’m talking about SMTP, a pioneering e-mail software firm based in Cambridge, MA.

Yes, the company with the famously boring name—it makes software for e-mail delivery management and marketing—is going public today. It’s not debuting on the Nasdaq or New York Stock Exchange; rather, trading of SMTP’s stock begins this morning on the over-the-counter bulletin board (OTCBB: SMTP). Companies that trade over the counter generally don’t have to meet the same SEC filing requirements as those that trade on the more regulated stock exchanges; it can also be harder for investors to trade OTC shares, partly because buyers and sellers must arrange their trades directly.

About two months ago, SMTP made an initial stock offering to 81 shareholders, who invested a total of $100,000 at 25 cents per share. The deal is different from a traditional, big-company IPO in that there is no investment bank involved as an underwriter—the offering went directly to a small pool of investors.

This isn’t your run-of-the-mill penny stock, though. SMTP says it doesn’t need the money, so it can afford to separate the process of going public from fundraising. The idea is that the firm could raise a few million in a secondary offering down the road—if its stock goes up—and in the meantime, it will keep growing and work towards becoming a much bigger player in e-mail tech. What’s more, its CEO has a contrarian’s sense of timing (and other important lessons to share), which we’ll get to in a minute.

SMTP, known as EMUmail until about a year ago, started in 1998 and first released its product for businesses in 2002. The company has grown a lot in the past year and has been making a small profit—just under $400,000 after tax in 2010, on $2.7 million in revenue. The firm had about 10,000 customers worldwide at the end of December. It says it competes with bigger companies like Constant Contact (NASDAQ: CTCT), JangoMail, MailChimp, and Amazon.com, which recently got into e-mail bulk delivery. SMTP currently employs 31 people, most of them in Ukraine; four are based in Cambridge.

“It’s small, but it’s solid, growing, and profitable,” says Semyon Dukach, SMTP’s chief executive (see photo, left). “Once we begin trading, we may very well go and raise a few million dollars in order to make acquisitions of related companies in our space.”

Indeed, anything seems possible when you have a guy like Dukach at the helm. While some might call him crazy (he wouldn’t deny it), Dukach has made a modest fortune thumbing his nose at the establishment. Most people know him as a swashbuckling master of disguise and leader of the MIT blackjack team, popularized in Ben Mezrich’s books Bringing Down the House and Busting Vegas. (He has the distinction of being the latter book’s main character.) But you might also say that Dukach, who is 42 and has five kids, has grown up a lot since then.

But we’re getting ahead of ourselves. Let’s go back to the beginning. Dukach is a Moscow native who came to the U.S. when he was 10, settling in Houston, TX, via Newark, NJ. He studied computer science at Columbia University and came to MIT in 1990 to do a master’s in electrical engineering and computer science. His thesis was on e-commerce and Internet money exchange (“way before it was cool,” he says).

Dukach got involved with the MIT blackjack team in the mid-1990s, and that story has been told. But it isn’t how he made his millions. That would be from his first software startup, … Next Page »

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E-mail is the great savior and scourge of our time. We couldn’t get much done without it. Yet as regular readers know, I have an ongoing feud with my inbox. I’ve declared e-mail bankruptcy (twice), I’ve adopted tools like Taskforce that help turn e-mails into to-do list items, and I’ve tried filtering options like Gmail’s Priority Inbox feature. Nothing seems to help with my fundamental problem, which is that I get at least 200 e-mail messages every day. If I gave just 60 seconds to each message, on average, I’d still be spending three to four hours a day doing nothing but battling my inbox.

I’m always on the lookout for ideas that might help, and I think I’ve found a new one. It’s a Web app called The Email Game, and it’s from Baydin, a Boston-born company that Xconomy has covered in the past. Specifically, my colleague Erin wrote a great piece last fall about Baydin founder Alex Moore’s $100,000 taxi ride. Moore, the story goes, responded to a tweet from legendary Silicon Valley angel investor Dave McClure, who wrote: “YO: need ride from Bucks/Woodside 2 Toyota/MtView @ 9:45am – will hear startup pitch in yr car; can a brother get a lift? Use #PitchVCtaxi.” Being nearby at the time, Moore obliged, and his pitch on the way to the Toyota dealership turned McClure into a Baydin investor.

Baydin, which was part of the 2009 class at the TechStars Boston venture incubator and is now based in Silicon Valley, is best known for a Gmail plugin called Boomerang. As the name implies, the plugin expels messages from your inbox with instructions to come back at a specified date in the future when you’ll presumably have more time to deal with them. I haven’t used Boomerang much, mainly because I feel like I’ll never really have more time—so sending an e-mail to myself in the future just delays the inevitable and increases my e-mail burden when the date comes.

But the Email Game is a different story. I’m really seeing the promise in this one, and it has already saved me a ton of time.

The idea behind the app is simple: it uses features borrowed from the video game world, including a countdown clock and a point system, to encourage you to plow through your Gmail inbox faster. For each e-mail, you might decide to respond to it, file it away, archive it, or delete it; the faster you make that decision, the more points you rack up. The goal is to get messages out of your inbox. So if you skip one—that is, if you just leave it in your inbox—points get taken away. After you’ve dispatched 30, 50, or 100 messages (you can set the number), the app stops and shows you your score.

How can such a simple, arguably frivolous game reduce your e-mail woes? It comes down to this: when there’s a clock ticking and points at stake, you’re less tempted to spend a lot of time crafting an e-mail reply or agonizing over whether to follow through on some sort of action request. The incentive is to swiftly delete or archive the unimportant messages and compose quick replies to the ones that merit a response. For messages that require a more time-consuming action, you can always pause the timer, skip them altogether (though this will cost you points), or boomerang them.

Just yesterday, I used the Email Game to get through 100 emails in about 17 minutes and 23 seconds, or about 10 seconds per email. It was a very intense 17 minutes, and I wouldn’t exactly say, as Baydin’s tag line puts it, that the app “Makes E-mail Fun Again.” But there’s no way I would have gotten through that many messages without the game. Now there are only 5,149 messages left in my inbox. I figure that if I can just play the game for 15 hours straight at the same pace, I’ll get through all of them.

Moore says he keeps his own inbox under control by playing the Email Game twice a day—once in the morning and once before knocking off work. Interestingly, he says he was never a big fan of the idea of inserting game mechanics into everyday activities, the way companies like Foursquare or SCVNGR have trying to do for the last few years. “I had a little bit of contempt for the whole gamification thing,” he says.

But he says he had an “aha” moment about game features last year after returning from a three-day trip to attend a friend’s wedding. “When I came back and had … Next Page »

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