Why Sales and Engineering Professionals Gain from Building a Unified Vision of Business

In the world of technology products companies, one cannot say that opposites attract. Though business and engineering teams solve related problems, they often clash because they approach the business from diverse angles.

I often speak with sales professionals that see technology-myopic engineers as a source of disappointment for their customers.

I also regularly work with software engineers who complain that business demands force them to abandon good engineering practices in favor of quick fixes.

What both sales and engineering professionals can miss, however, is that both sides are focused on solving a problem for customers.

As a professional who has worked both sides of this picture, I appreciate companies that help both groups to see how their roles complement each other.

From the Business Side

The business side can see software engineering practices as dilatory, overly complex, cost prohibitive, and, most importantly, as risk from which they have to protect their prospects and customers.

Sometimes, they are correct. I worked with a team that spent years developing a product that went through multiple rewrites, several major technology changes, and ultimately never delivered.

Engineering’s obsession with creating the perfectly built product was partially responsible for causing the company not to deliver anything within the window during which the best business opportunity existed.

At the same time, sales had gone ahead and closed deals–in good faith, but by making promises to customers that the company ultimately could not keep.

Though the result was not pretty, I have also seen sales teams cause equally disappointing results.

From the Engineering Side

The engineering side can see business demands as evil, unempathic, lacking any serious future-oriented perspective, and, most importantly, as risk from which they have to protect their work and their people.

I have seen situations where this is the case. One sales team I worked with wanted to take advantage of a significant market opportunity.

They demanded quick solutions from their engineering team, who had to abandon test-driven development, refactoring, patterns, and basic coding principles.

The codebases quickly became brittle and error-prone. Though engineering delivered a product (albeit late), the company was unable to upgrade their product to reflect changing customer expectations over time.

The company gradually lost business as they found themselves increasingly less able to convey value. Eventually they were no longer in a position to compete at all.

A Unified View

For the most part, we all have the same vision. We want products that work exceedingly well, delight out customers, and make an enormous impact in the markets we care about.

It is true that some engineers, particularly junior-level ones, can get excited about technology in its own right, at the expense of delivering what the customer wants.

It is also true that some sales professionals, particularly those newer in their selling careers, can overpromise in order to close deals, putting pressure on developers to quickly fill gaps between customer expectations and product offerings.

In my experience, however, most engineers and sales professionals recognize each other’s role in making their own professional existence possible.

It is difficult to sell a product that doesn’t exist, just as it is challenging to thrive on technologies no one wants.

The right approach involves balancing concerns by exposing sales and engineering to each other on a regular basis.

Through fostering a culture where sales and engineering professionals have a unified view of the business, the two groups can reach a place of empathy.

When they learn to appreciate the demands they each face, they can do a better job balancing the interests of the company, and ultimately, the customers.

MassChallenge Doesn’t Really “Reject” Anyone: My Experience of the Application Process Through the Final Round

As someone who likes to build innovative products for underserved markets, I am not a stranger to rejection.

So, when I received an email last night informing me that my company, UnionConnect, did not advanced beyond the semifinals for MassChallenge in 2014, I was surprised that “rejection” was not a part of the experience.

MassChallenge, which is one of the most well-respected and largest startup accelerators in the world, had advanced UnionConnect from our initial application through to the semifinalist round, but declined to accept us as finalists into their four-month accelerator program. They promise to tell me why, in detail.

I look forward to that.

But I am not stressing over their decision. This post is about why.

Putting it in Perspective

I am used to rejection from all kinds of people. Since founding UnionConnect, however, one place I have never heard rejection is from the market. In the six months since we have been in the market, we have signed over a dozen large, organizational customers and we are just getting started.

Therefore, I know I am on the right track.

Additionally, we are well on our way to making back our initial investment out of profits, so my partner and I will soon own a profitable company outright. With zero dilution, we can have the full freedom to listen to our customers and build the products they truly want and need.

As such, I am feeling fantastically optimistic about where we are going.

That is not to say we do not have our challenges. We have many ahead of us, which I look forward to tackling at the appropriate times. There is no doubt in my mind that MassChallenge could have helped us to do so in their four-month program, and in that specific sense, I am disappointed.

But the fact is that MassChallenge has already helped us tremendously.

MassChallenge Only Provides Value

MassChallenge does a wonderful job of providing value at every stage of the process, from the moment they offer up their initial application.

For $99, any founder can get access to questions that not only help MassChallenge identify promising startups, but also serve as an incredible microscope under which every entrepreneur should place his or her business at least once.

The MassChallenge application process is not easy. They require that entrepreneurs distill very complex answers about critical business logic, often into 250-character slots. As a loquacious lawyer, that is particularly difficult for me.

But I love that I struggled with the MassChallenge application. It forced me to think about issues that will affect the success of UnionConnect.

Some questions were easy to answer in the sense that the business embodied a strategy that lent itself to a good answer. Other questions forced me to think strategically about how to address weaknesses.

When we advanced to the semifinals, we faced even more helpful scrutiny. The process of creating what is essentially an investor-oriented a pitch (in the sense that it differs from how I pitch to prospects) meant that I had a reason to assemble an astounding panel of experts for business advice.

Each one of them gave me at least some advice I now consider to be essential. I took that advice and composed a pitch I would be proud to deliver again-and-again.

Bringing the pitch before the seven MassChallenge judges we encountered only illuminated so many additional questions that are going to help us to think about. And, the judges were also very encouraging, which I appreciate.

All told, I had a hard time thinking of the application process as an application at all. Rather, at every turn of events, MassChallenge used the application process as an excuse to help every entrepreneur it possibly could. What’s more, their commitment to delivering detailed feedback is outstanding.


Going forward, I look forward to continuing to be involved in the MassChallenge community, not only because it can continue to help, but because I am thankful for what they have given me.

As I see it, any organization that would go out of its way to give what they gave for a mere $99 deserves my involvement.

And as far as not making it to the finals? Thanks to the way MassChallenge runs their organization, I feel like I already won.

Why I Closed the Boston Expert Witness Group: A Post-Mortem

I have closed a chapter in my business life, and it’s time I ensure that everyone who wants to know about it knows.

In January, I made the decision to close the Boston Expert Witness Group after over two years since I had my initial vision for the business.

Though I was making money and helping my clients with a genuine need, I ultimately realized that I was not creating the kind of business that I wanted to create.

Along the way, I learned (at least) six hugely important lessons about entrepreneurship, which I want to share with anyone who cares to read them. For each, I will explain how learning this lesson directly impacted my business and my decision to move on.

But before I get there, let me back up just a few meters in case you don’t know what I have been doing in this business.

About the Boston Expert Witness Group

The Boston Expert Witness Group offered the expertise of a premium group of high-integrity medical expert witnesses. We went to work on a variety of cases that all had a common thread of requiring medical expertise to explain material facts that were the subject of litigation.

We worked on personal injury cases, insurance defense cases, medical malpractice cases, and even some patent litigation. We gave expertise from both plaintiff and defendant standpoints. We worked on cases throughout the United States.

By the end of my running the business, we were revenue positive, and even a little profitable. We contributed essential expertise to our clients’ cases and in some situations were able to do so early enough to prevent litigation from happening in the first instance.

The Group worked with some of the leading boutique firms in Boston, as well as a handful of solo practitioners. We handled some very interesting cases and also some pretty typical ones.

Ultimately, we struggled with finding a product-market fit that could stand on the business’s core values: integrity, efficiency, and legal innovation. The lessons I learned explain why.

Lesson I: Put Markets First, not Ideas

I come up with a lot of interesting ideas. None but maybe two of them have ever been marketable… maybe. These are not good odds.

Contrast the process of starting with ideas to find markets with the process of starting with a market need to develop a business idea. When you start with market need, you know that as long as you can build a product or service that addresses it and connect with enough customers, you will have a business.

The Boston Expert Witness Group started as an idea in search of a market. Though I found the market late in the life of the business, it didn’t look anything like a market that would support a business built on our core values.

Most attorneys I worked with were not in the interest of using my business to find a vetted expert. Rather, they simply wanted a list of people who they could show to the firm’s partner handling the litigation.

The chance that a prospect was going to return to the business to hire our expert was minimal, yet we did not get paid until that happened.

Because our business put a lot of work into vetting experts before adding them to our database, we ended up doing a lot of work for free. That turned out not to be a good business model (obviously).

Catering to the market of attorneys who wanted lists to bring to their partners, we would have had to:

  1. lower our cost to build and maintain a database of expert witnesses;
  2. lower the quality of our referrals;
  3. charge for our lists; and/or
  4. support the business with another source of revenue.

These turned out to be approaches that were unmarketable, lacked innovative character, did not lead to improvements in the efficiency of law practice, and put our database at risk of containing experts who lacked integrity. These were not acceptable options.

Lesson II: Have a Sales Plan from the Beginning

Prior to starting the Boston Expert Witness Group, I had no sales experience. About a month after turning my idea into a full-time job, I began to realize I would have to learn to sell the services of medical experts or perish.

I embarked on a year of the best sales training I believe money can buy, which is Sandler Training. I got good at setting expectations, digging for pain, and talking about money and decision-making processes. But when I began to calculate just how much time I would have to spend selling our particular products to the prospects we were encountering, I realized I would have to spend most of my waking moments engaged in sales.

It left very little time for me to plan how my business was going to operate and to do what I had to do to support myself while the business still lacked sufficient revenue to pay me a decent salary.

Perhaps I could have hired others to fill either the sales or other functions, but when I thought of doing that, I ran into my next problem…

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