Introducing DotAlign Cloud

DotAlign Cloud is a comprehensive cloud- based enterprise relationship solution that privately and securely analyzes mailbox data to automatically extract the people and companies your teams interact with, and assigns a score to each relationship. It also keeps contact information up to date, without requiring any manual input.

The solution is used by enterprises where relationships are key to open doors to new business and grow the top line, and helps those enterprises get the most out of their investments in outreach and customer relationship management efforts. Privacy and control over data at every level – enterprise, team, and the individual employee, are foundational principals of DotAlign Cloud.

DotAlign Cloud is available where users already are – whether inside Microsoft Outlook as an add-in, or inside Salesforce/LinkedIn as a Chrome extension or as a standalone desktop or mobile app.

Learn more by visiting


This blog has been quiet for the past couple years, as we’ve been heads-down developing and working with early clients & pilots. As we are now emerging to show the world what we’ve built, it’s time to bring the blog back online and provide an update on our transformation.

For the best summary of DotAlign today, please check out our product demo and company overview presentation delivered by our CEO at To catch up on the path that led from our last blog post to today, please read on…

2013 – Strategic Crossroads

In that last post we described a shift to productivity within Microsoft Outlook. Certainly given the overload of emails we all receive, this is a problem worth solving. As we delved into the problem and spoke with prospective clients about their pain points, we discovered that inbox productivity is closely related to relationship management. After all, emails contain the true record of correspondence across the web of one’s relationships. They contain data embedded in signature blocks and headers, not to mention related data such as calendar appointments and contact cards. Manually typed CRM notes should just be a supplement to these data sources.

Our client prospects also maintained quite strongly that customer relationship management (CRM), though an $18B growing to $36B industry, does a generally poor job in delighting end-users. They illustrated how CRM software requires tedious administration and data input. In their candid moments, professionals also explained that traditional CRM generates a high degree of anxiety, as end-users worry that their hard-earned relationships will be misappropriated by other colleagues. They also cited slow and cumbersome workflows. Together we identified that email would be a great source of Big Data to a CRM, but only if it could be done in a way that addressed the anxieties of end-users and compliance professionals. As long as we were planning to look at email, and do it in a unique way that allayed those concerns, they encouraged us to look at CRM.

At this point we faced a cross-roads. We could create a set of productivity tools within Outlook, or explore email as a source of Big Data to drive strategic relationship insights. Some inbox productivity tools would require very little knowledge of data and content. For example, we envisioned hot keys for quick filing to folders. (We later learned that Outlook Quick Steps allow this.) Perhaps we could quickly get a product out to market that bundled a set of productivity widgets. However, the tools that resonated the most with prospective users were the ones that require an understanding of data and content, such as “Who owes me a reply?”.  Asking questions of Outlook on-demand simply couldn’t power such tools. That led us to realize that a truly valuable inbox companion should leverage a locally cached database of data and related insights.

We decided during 2013 to “go big” and create a system for relationship intelligence as well as inbox productivity.  By the end of the year we had a working prototype and were holding sales meetings. (We lost a few months building a prototype against a red herring spec provided by a prospect, but that’s another story.) One firm, a boutique investment bank, liked our approach but had some specific requirements: they wanted to be able to replace a competitor’s system that centrally indexed Exchange Server. Although we would have preferred to do Exchange as phase two (e.g. as a supplement to Outlook-based indexing), earning a paying client and unseating a competitor was impossible to pass up. It would also give us the chance to learn how to work with truly large volumes of data in a real-world environment.

2014 – Big Data Indeed

In early 2014 we signed that first client. We were now three people coding two separate projects that would eventually converge: DotAlign for Outlook and DotAlign for Exchange. Of course, since we had a paying client for the Exchange product, it took top priority. As we had hoped, we learned a tremendous amount by working with terabyte-level data volumes in the real world via Exchange. The client also asked us to integrate with Salesforce, which we knew would be an important experience to have under our belts. A particular challenge that we had to solve was how to push to Salesforce the addition, deletion, merging, or splitting of Person or Company records. That said, we were pleased to power the client’s Salesforce implementation with relationship “scores” (who-knows-who well) powered by DotAlign.

The three of us spent 2014 incorporating lessons into the Exchange and Outlook products. We also ran demos for a wide range of enterprise prospects and received a resounding reception. Our pipeline of interest included decision-makers from several each of investment banks, private equity firms, Fortune 500 corporations, law firms, and accounting firms. Our message resonated particularly well at companies with secure corporate environments. This was due to our unique approach to sensitive data, e.g. keeping it all behind the firewall and allaying the anxieties of the individual professional.

As we worked to coordinate pilots with the firms in the pipeline, a key requirement became clear. We would need to find a way to enable collaboration without IT setup requirements. Clients wanted the data to stay behind the firewall, but they also didn’t want to incur the IT burden of setting up a SQL Server database until after a successful pilot. Enterprise sales cycles are already notoriously long, and so we took this problem seriously. Eventually we conceived of a unique approach for turn-key collaboration that met these requirements; a patent is pending on it.

Just after year-end we closed an investment round from existing investors, including material amounts from the management team. 2015 promised to be the year of go-to-market and closing a lot of contracts.

2015 – Learned from Pilots

We expected remaining work in 2015 toward the patent-pending architecture that allows turn-key collaboration. This seemed like something that could happen in parallel with driving the sales funnel, as it primarily impacted the length of sales cycle rather than the end-user experience. However, we also encountered the unhappy realization during early 2015 that entity management (tying together people and companies), an already hard problem, is even more difficult in a decentralized system. Whereas v1 of our Exchange product allowed for a single central database, our Outlook product (and our future direction) did not have the luxury of this requirement. A smooth end-user experience had to recognize and de-dupe People and Companies even when offline or when analyzing an un-shared data store.

When a pilot firm called saying that two people with the same name had been auto-merged and now needed to be split, our first instinct was to port over the code from our Exchange product. (We knew this feature would be important for a full-scale roll-out, but wanted to get feedback on an MVP.) However, it soon became apparent that certain assumptions, such as a “master Id” for person and company records, could not port over. The already difficult challenge of merging and splitting entity records turns out to be much more complicated in a decentralized model.

Without delving too deeply into the details, suffice to say that certain assumptions at the heart of the data model had to be revisited. This took quite a long time, but our unique approach now serves as a barrier to entry and a source of competitive advantage. Most provider have enough trouble managing duplicate entities, and rely on manual administration. Our system now allows for “n” sources of information on people, companies, and relationships that can automatically and seamlessly fit together.

2016 – Turn-Key and Mobile; Back-to-Market

Here now in early 2016, we are in the enviable position of having the only system for rich collaboration (be it social or CRM in nature) that avoids IT database setup requirements, yet keeps data behind the firewall. Once testing is complete, we will be excited to circle back to early prospects where database setup was an obstacle. Meanwhile, the application itself is in use as part of a strategic relationship with a late-stage VC firm. And our mobile application is at long last nearing completion.

We are excited to be back out in the marketplace, as this problem needs solving just as much as ever. Sensitive sources of data such as email are by far the most important source of Network Relationship Intelligence. Today, that treasure trove of valuable content is untapped due to concerns about security and privacy. We are pleased to offer a solution that allays the concerns of the individual as well as those of compliance. To learn more, check out the videos at and/or contact us for a demonstration.

Back to Our Roots: Productivity in Microsoft Outlook

It is with great emotion and excitement that we are announcing a major shift in our business.  The DotAlign social web application will soon be shut down.  We are grateful to our beta users and deeply regret that we cannot support the application going forward. Instead, we will focus on productivity and relationship intelligence within Microsoft Outlook. If you are familiar with the Microsoft Office tools built by my prior startup, DealMaven, our plan is to deliver similarly valuable tools for Outlook. Here is the story behind our transition, along with lessons learned.

B2C Social Challenges

Per my recent TED talk, I believe fervently that social networks have tremendous untapped potential value for professionals. Over the past couple years, I’ve/we’ve tried a couple different approaches to unlock this value but encountered key obstacles:

  1. Chicken & Egg: OpSpark, the predecessor to DotAlign, was an invite-only social network for highly credentialed professionals. In a world of social network fatigue, creating a new network proved incredibly difficult. We pivoted to DotAlign as a tool that gets value from existing networks rather than creating a new one. However, DotAlign encountered the next two challenges.
  2. Competing Social CRMs: Many startups have emerged, including some with serious funding, to bring together contacts from across different networks. It has been hard enough to cut through the noise when pitching VCs and we saw that as a sign that marketing the finished product (even a free one) to customers would be equally difficult.
  3. Email is Here to Stay: For me, Social CRM was always just the first step toward a meaningful sharing of information among related professionals. My LinkedIn social stream is of limited value today, mostly filled with commodity information that my contacts feel comfortable sharing publicly. The goal of DotAlign (and OpSpark) was to enable private conversations among smaller sets of relevant people. No matter what its advantages, however, the fact is that we were requiring a behavior change in moving these conversations out of email. This got us thinking further about use of email as an opportunity.

B2B – Meanwhile, Clients Need Our Help

My last startup, DealMaven, provided productivity tools for PowerPoint and Excel. Former clients and others have told us their firms desperately need similar tools for Microsoft Outlook. Considering that our CTO even worked on the Outlook team at Microsoft, we see this as a natural direction for DotAlign.

We understand Gmail and mobile are important to email too, and we may build solutions there in the future. However, for the customers we are targeting, it all begins with Outlook. Bankers, lawyers, and other high-end professionals don’t just sell, they manage relationships.  They use Outlook, and there are gaps in existing tools and traditional cloud-based CRM relative to their needs (including regulatory compliance issues).

If you find managing your inbox and your contact relationships to be a tedious, stressful experience, we plan to delight you. If your firm is exploring solutions in this area, let us tell you about the features we are building (and soon you can try them). Just reach out to team(at) We also welcome your ideas for features, and will give a free copy of the app to the most helpful contributors.

Lessons for Fellow Entrepreneurs

I understand why I made the mistakes I did. DealMaven improved quality of life and productivity for 10,000 professionals working in PowerPoint and Excel. It was a solid success for investors, employees, and stakeholders. But this time, I wanted to build a business with a greater societal impact. The goal with DotAlign wasn’t just to organize social contacts, it was to set up ways that professionals could help each other “connect the dots” toward opportunities (deals, investments, jobs, clients, etc.).

I still dream of changing the world and boosting overall economic productivity, and I still believe that DotAlign, Inc. will have that impact. But rather than starting with a free B2C web application and later finding ways to monetize it, we will instead delight paying customers and then find ways to create an impact beyond our initial base. If there is unlimited financing, I suppose either route can work. But I’m no longer interested in courting VCs. From now on, we’re courting customers.

My TED Talk – Helping Each Other Succeed

It was truly an honor to speak at TEDx Columbia Engineering this past week.

This economy needs your help. Many of us are pinning our hopes on the election, and assuming that someone else will figure it out for us. I’m here to share my belief that it is up to us as individual professionals and entrepreneurs. And if you each do well, then we do well as an economy. So I want to share some ideas toward that goal.

First, I think it’s important to get to the root cause of our economic problem. This isn’t just a classic business cycle that started a few years ago. The median worker, the guy in the middle, is in a 40 year slump. We’re talking about a period that transcends Republicans and Democrats. That’s not a story of handouts interfering with the American work ethic. The average American isn’t lazy.

And our debt is a huge concern for the future, but it isn’t the cause of today’s problems. Rates remain low and the dollar is still the world’s reserve currency. Let’s look deeper.

When Henry Ford made cars that his workers could afford, that created demand. His workers bought the cars. We built highways, moved to the suburbs, and began a 70 year path of prosperity led by mass-production, mass-consumption, and mass-media. This was our industrial era.  As output increased, corporations and domestic workers negotiated to share productivity gains, and the fortunes of both improved together.

Then starting in the 1970s, demographics and technology combined to “flatten our world”, to paraphrase Thomas Friedman. Since 1980, the number of non-farm workers in the world rose by 1.1 billion. That’s a demographic tidal wave of competing workers, and they inevitably dented the bargaining position of workers in developed countries.

Meanwhile, connective technologies allowed more and more work to move offshore — not just manufacturing jobs, but also clerical and support functions. Even high end jobs like investment banking analysis. Technology automated much of the rest. And so, in the negotiation that plays out between corporations and domestic workers, workers have inevitably seen their bargaining position erode.

From 1973 to 2011 labor productivity increased 80% but real median hourly wage only increased 4%.

Please don’t misinterpret this data, as so many do. Our standard of living has increased dramatically throughout this time. We can video chat with friends. We have safer cars with better fuel mileage. Life expectancy has increased by seven years. All of this is made possible by global competition and technology which are, in any event, inexorable.

Instead, my key point is this. Banking on big companies to give us steady raises and promotions? That’s now a risky bet.

And so, I believe we need to look less to our employers for our professional identity and start looking at ourselves as the center – as the center of a web of relationships that help us get things done.



Of course, many of those relationships are with colleagues, and of course our primary productive outlet is on behalf of our employer. But the most relevant business enterprise over the long term? It’s you! You and your most important relationships.

Let’s extend the analogy. A corporation takes a set of people, its employees and stakeholders, and sets up ways they can work together to create economic value.  And how about us as individuals, running the enterprise that Reid Hoffman calls the Startup of You?  What economic value are we creating within our social graph?

Not nearly enough. See, I think we are so dazzled by what social already does for us, that we don’t realize what it should do for us. What it does do already, and brilliantly, is to help us spread ideas.

Originally, the spread of ideas was limited to oral tradition and personal contact along trade routes. Then Johan Guttenberg invented the printing press, and suddenly the elite could reach a broad audience. Then with the rise of mass media, corporations could broadcast their marketing messages. The rest of us remained silent.

Today, as we know, an individual can use social media to broadcast their message. I’m using the word broadcast intentionally. A fully-formed idea is ready for broadcast to a wide audience. But great ideas don’t come to the world fully formed.

In his book, Where Good Ideas Come From, Steven Johnson talks about how shockingly few innovations arose from a lone genius with a Eureka moment. For the most part, ideas need to mix amongst people with different viewpoints and backgrounds. He tracked ideas through history, and proved that it’s always been that way. We went a step further and found the lost footage.

Have we been able to restore it? Great!

Here is rare film of one of the most important inventions in history. Here two people made a wheel. What do they do next? Do they sit on top of it? Roll it? Ooph. OK, now when someone else has a different perspective, like this woman who has been dragging a heavy cart, well, that’s when breakthroughs happen. A wheel becomes a wheelbarrow.

If you already have a fully formed idea or product (like this wheelbarrow) then blogging and tweeting can help spread the word. But if you’ve got a wheel, a heavy load, and a few people with a hunch that there ought to be a better way — that’s a different sort of problem.

And so I’m especially interested in the brainstorming and aligning resources with skills that creates economic breakthroughs in the first place. I want to look at how that process has evolved to date, and look at the untapped opportunity.

Back to Johnson.

During the Enlightenment, as Johnson points out, so many of the important innovations were originally hatched in a coffee house. There is something about what he calls “the architecture of the space” that makes a coffee house work.

To me, it comes down to three factors: informal networks, conversation, and selective sharing.

Informal networks include people who represent different backgrounds, skills, and business interests. And so they help us think about a problem differently.

The second aspect of the architecture is conversation. A blog or book publishes a fully formed idea. But it is conversations that help build those ideas and create those breakthroughs in the first place.

The third aspect of the architecture is selective sharing. In the business world, we don’t just cooperate; we compete. And a lot of information is sensitive. Even basic information like what you’re working, what you’re thinking about, who you’re trying to meet with– things you’d share with friends at lunch or over coffee — aren’t appropriate for a status update broadcast to your entire network. And yet, that’s the type of information that, once shared, can lead to a business breakthrough — a new job, a new product, or a new client.

So coffee house is mostly about private conversations with relevant people from your informal networks.

Email doesn’t really do the trick. Compare email to Facebook.

Thank heaven I don’t get an email every time my cousin posts a new picture or eats a delicious breakfast. Before Facebook, we didn’t share as much. When information sharing moves out of the inbox into a Facebook-style format, then we can share more freely and keep others in the loop in a much better, more polite way than email-all/reply-to-all. Imagine if more valuable nuggets of business information were shared among business friends each day (in an unobtrusive way), the way pictures and breakfast updates are shared among Facebook friends.

Too few of us are taking advantage of the fact that coffee house architecture is now available – and scalable – through social technologies.

McKinsey did a study showing about $700 billion of economic value in four industries alone from private social collaboration within and among enterprises. Only 3% of businesses are fully leveraging social.

But private business conversations shouldn’t just be defined by the walls of the enterprise. Remember, the enterprise is you! It is you and your social graph. Your greatest asset is your networks and relationships. And I wonder if even 3% of us are individually getting the most out of social to find ways to help each other succeed.

Out of the hundreds, or even thousands, of people you know, spread across LinkedIn, Facebook, and email, think about the most relevant sets of people. How can you share information about what you’re working on and what you’re thinking about? Which people in your network should all know each other?

On the micro level, if you can facilitate conversations and introductions like this within what Seth Godin calls your “tribe”, if you help each other connect the dots, then you and your friends will succeed. On a macro level, this is part of a larger narrative. So I want to frame today’s social era in the context of economic history.

Ever wonder how humans came to dominate the Earth?  Matt Ridley, in his book The Rational Optimist, determines that it wasn’t brain size or use of tools. We beat out 17 forms of hominid because humans are the only species on Earth, now or ever, where unrelated individuals will exchange one thing of value for another. Moving beyond mutual back-scratching to barter (the most basic form of economics) is what kicked off human progress. Matching up needs with resources is how progress happens.

The next major economic innovation was money, which opened up new forms of trade. A fisherman could buy bread even if the baker doesn’t like fish, because money would allow further trade.

But even with money involved, once the fish are consumed, they are not available for further trade. The Information Age removed this constraint with digital goods. I don’t run out of copies of software to sell. I can simply run off more copies at zero marginal cost. This is the economics of unlimited supply.

The Social Economy opens up another major evolution of economics through its own currency, reputation. Actually, I’ll go a step further and call it professional karma. I’m talking about something people who actively seek to help the good people in their networks. The payback is not immediate, and rarely even requested, but it is inevitable. After all, if you help people who I know and respect, I’m going to want to help you. This has always been true, of course. But innovations in social networks and our hyper-connectedness make it more tangible than ever. And any time economics moves beyond contemporaneous exchange, it opens up new forms of value creation.

We really do need your leadership. No politician is going to create this value for you and your friends. So think of yourself as the enterprise. Find ways to facilitate the private business conversations that help each other connect the dots, creating value for each other.
In the industrial era, the boss did this. He hired the right people and assembled them in conference rooms and factories. In the Information Age, the CIO put in place systems for this. Well, today you are the enterprise. And collectively we are the economy. We share a responsibility to lift this economy, and the best way to do it is also the most rewarding. Let’s help each other succeed. Thank you.

Getting Started with DotAlign

Update: This social functionality is being sunsetted. Read about our new direction

Hello! The DotAlign private beta is now open to a few early invitees. If you have your invite link already, here are a few highlights to check out:

  • Link your networks
  • Explore your connections
  • Post to start a private conversation
  • Create lists of relevant people

Link your networks

Connect to your LinkedIn or Facebook networks using this icon. Gmail is coming very soon. Then we’ll work on Twitter and Outlook. Don’t worry, this step does not message your contacts in any way.

Explore your connections (People tab)

When the process completes, click this icon at the top.

Then choose My People via the universe picker at the left to focus just on your contacts. You can also try clicking Everyone (includes fellow beta users).

Great! now you can search and group your contacts by Company, School, and Industry, sorted by number of people. We still have some tweaks to make in this area, but it should give the idea of where we’re heading.

Start a private conversation (Posts tab)

Alright, now let’s make a post to a few people from your network. If you linked your network(s), the people will appear in type-ahead. (We will soon be building support for adding additional people based on email address.) By posting to them, you are giving them access to our beta. Thanks!

Your contacts don’t have to join yet another network in order to comment on your post. They will get a link via a private LinkedIn or Facebook message (or soon email) and they can use it to reply.

Please note: We carefully limit the number of messages that go out, and instead rely on periodic digests. The default for non-members is a limit of one alert per week.

Guests and members alike can comment on posts to create conversations. Much better than clogging inboxes with reply-to-all chains, isn’t it?

Create lists of relevant people

Now that you’ve seen the basics, you might want to organize the contacts who matter most to you. Once your lists are set up, it’s even easier to share relevant content with exactly the right set of people. You can also use lists to filter posts, people, and messages.

Coming soon: Quickly adding people to lists via their picture.

Well, that’s it for now. We look forward to your feedback. And please spread the word!

OpSpark Is Now DotAlign

Update: This social functionality is being sunsetted. Read about our new direction

Dear friends, supporters, and beta users of OpSpark,

We built OpSpark for you, the business professional, as a place where the usual noise of social media is replaced by relevant and actionable content based on your needs. That portion of our mission remains the same.  However, DotAlign delivers that value in a different way, incorporating experience and feedback from the OpSpark beta.

DotAlign helps you leverage your networks to meet professional goals.

That one little word, “your”, makes all the difference.  OpSpark was set up as our network, a marketplace of opportunities posted mainly by strangers to you.  There was naturally a high bar to joining a new network, submitting credentials for verification, and then sharing high-value opportunities with strangers.  A few months in to the beta, we realized we either had to double down as a marketplace, charging hefty subscription fees to pay for member recruitment costs like our competitors, or find an even more compelling way to create value for you.  Well, we found it. And built it. And named it DotAlign.  DotAlign is way for you and your contacts to help each other connect the dots.

DotAlign is your network.  More accurately, it is a way to tap the value of your existing networks – LinkedIn, Facebook, Gmail, and Twitter.  Depending on what you’re working on, the relevant subset of your hundreds of connections will differ.  Rarely is it everyone, and rarely is it one person, and yet social status updates and email are optimized for those scenarios, respectively.

If you could meet up for coffee with all the relevant contacts, you would inevitably share what you’re working on and find ways to connect the dots for each other.

  • “Have any of you worked with Gallant Creative?  How’s their reputation?”
    (shared with selected industry colleagues)
  • “A friend is looking at doing a roll-up of supply chain management firms. Any ideas who he should talk to?”
    (shared with deal-oriented friends)
  • “I’ve got a startup idea that I’d like to run by you…”
    (shared with trusted confidantes)

Unfortunately, no one can drink that much coffee.  We set out to create a scalable way to deliver new insights about your relationships and connect on a new level.  Here were our most important design requirements:

  • Allow collaboration without having to send friend requests for yet another network; use existing channels of communication (Gmail, LinkedIn, Facebook, etc.).
  • Implement smart “no-nuisance” settings so that you can make information available to your contacts without ever bothering them (i.e. smart default limits on when they see an activity digest).
  • Design a business model where you, the individual professional, are the client, not the product being sold.  We have revenue models planned, of course, but none of them involve selling your personal information.
  • Let each individual define (privately) for herself which people are relevant, instead of having to join (and monitor) the same discussion group in order to derive value. (I hope to someday dedicate an entire post to this subtle, but important point about the value of asymmetric networks).
  • Build a business that our API partners (the big social firms) will love.  The more connected you are on their network, the more value you can gain via the DotAlign meta-network!

We’ve done our best to meet those requirements and deliver a fantastic user experience for professionals like you.  As always, we appreciate your feedback and work hard to incorporate it! Thanks again for your support.

You can sign up for the DotAlign beta here!

PS – Be sure to follow @dotalign and subscribe to this blog via the “follow” button at the top-left of our blog. If you’re looking for older articles written under the OpSpark banner, click here.