The Convergence Of Private & Public Valuations Is Good For Employees 

There’s been a lot of talk in the tech blogosphere over the last couple of weeks about the convergence of private and public valuations. One of the things that hasn’t been talked about all that much is how important this convergence is for employees at early-stage companies.

I was talking to a founder recently and he was telling me that he really struggles with the tradeoff between the importance of showing the world that his company has a unicorn-like valuation versus the importance of keeping his valuation low so that new employees can see lots of value in a follow-on round or an IPO.

On one hand, being a unicorn gets you lots of good press and attention and is for good sales and good for recruiting. On the other hand, a huge valuation makes it hard to deliver value to employees in the form of stock options — if you’re already a unicorn, it’s likely that future employees have missed the big uptick and equity becomes a lot less valuable from a compensation perspective. When you have a potential bubble in the private market and normalcy in the public market, lots of employees are going to find their options are deep underwater. Castlight Health learned this the hard way following their IPO last year (see image below).

Castlight IPOBecause of the emergence of crowdfunding, angel syndicates, private exchanges, and a lower regulatory bar to invest in early-stage startups, it’s likely that we’ll start to see much more consistency between private valuations and subsequent public valuations. Also, don’t underestimate tools like eShares that help founders manage complex cap tables. I can vividly remember being at a startup where we didn’t want to give out stock options to consultants for no other reason than it would’ve added too much complexity to our cap table. It’s a lot easier for a private company to manage thousands of investors than it used to be.

A founder’s desire to push for a massive valuation is perfectly understandable. It creates a buzz that helps recruit employees and close big deals. But when founders push too hard for a private valuation that won’t hold up when employees find liquidity, it’s bad for the team that built the company in the early years. It’s great to see private and public valuations beginning to converge.

Managing The Enterprise Deal (Panel Notes)

Enterpise Sales Meetup
Earlier this year I participated in a panel for the NYC Enterprise Sales Meetup. The topic of the panel was Managing the Enterprise Deal. It was a great discussion and I thank Mike and Mark for inviting me to participate. Prior to the panel, the moderator provided us with a list of questions that we should be prepared for. In preparation for the discussion I wrote down some rough answers to each of the questions and I thought I’d post my notes here. It’s great to see that Enterprise Sales Meetup has expanded to other cities over the last few months. I highly recommend attending one if they’re in your area.


How many deals do you think a high level business to business professional can manage?

This depends on the salesperson’s goal and the average deal size. Generally, salespeople should have a pipeline that is 3x their goal. So if your goal is $1MM and your average deal size is $250k, then you need to be working 12 deals.

What are the best tactics you find to manage a pipeline effectively?

To me it comes down to good stages and good tipping points. I recommend using 4 or 5 stages of a deal, and then for each stage assign actions or things you need to get done before you can move them to the next stage (tipping points). This ensures that there’s consistency across deals and ensures the salesperson isn’t kidding themselves when they say they have 3 deals ‘in contract’. The stages I use are generally something like, Lead, Decision Maker Engaged, Project Design, In Contract, Closed Won. The tipping points for each stage depend on what you’re selling, but it could be things like contract sent, legal work completed, technical review completed, etc.

Do you believe in mapping out a process for your company to manage deals?

Absolutely. You need consistency across stages and tipping points. And you need a funnel so you can determine where you’re getting stuck.

How do you qualify deals?

Typically I would come up with 3 or 4 elements that I’m looking for from a prospect. Size, revenue, technical setup, management structure, etc. Over time you can iterate on these as you discover what makes a good prospect that leads to good revenue.

How do you find your deal sponsor?

You have to nail down the one or two business metrics that your product impacts and then find the people who are responsible for those metrics.  If X metric goes up at the company you’re selling to, who is going to get a bonus at that company? That’s the person that should drive the deal for you.

Who else do you need besides a sponsor, what other personas do you see?

Project Managers. You want to push for a strong Project Manager that is totally sold on your product and can get it launched and can help you get the deal done. After the executives are sold, so much of enterprise sales is about simple project management and driving the deal through the prospect’s buying process. It’s really hard for big company’s to buy things. You need a partner at the company that can help you get it done.

How do you build a relationship with your sponsor?

One thing is frequency of communication. I always try to set up a weekly check-in. Those consistent check-ins force you to get to know one another. The other thing is I try to make their job really easy. Keep communications really short and simple and show them how to buy your product. Map out their own buying process and track them on it.

How do you determine the buying cycle and process?

You try to identify trends across organizations on how they buy. Who needs to be involved? Who needs to approve? What kinds of meetings need to happen to get to that approval? And then you start to map out the ideal buying process that works for you. If you don’t have one, make one up based on what you do know. And map to that.

How do you map out the decision-making team?

Again, another useful way of mapping out a decision-making team is to show one from another client and get them to react to it. Make sure you show legal, technical, compliance, procurement, business people, etc. so nothing gets missed.

How prevalent do you think consensus decision-making is?

It’s huge. I’ve never seen a large company buy without consensus. You have to tell everyone that is involved in the decision-making process your story. Everyone has to support the concept.

How do you use or overcome the startup stigma?

Use it as an advantage. By definition you’re disrupting the old way of doing things.. You’re doing something much bigger. Inspire them. I find most people want to get better and recognize that the status quo isn’t working. Tap into that. Challenge them. The way they are doing things now is not acceptable anymore. Get them to see that and get them on your side. The size and stage of your company is irrelevant compared to the problem you’re solving.

How do you establish an ROI, is it even that important?

It’s important, but it’s often not as important as you think. I think most businesses buy primarily for emotional reasons, rather than rational reasons (prospects buy with their heart and justify it with their mind). So when you come up with your story, it’s important that you focus on how your story makes people feel. Most buyers aren’t going to believe your ROI anyway.  It’s about emotion. And most big companies aren’t as metrics driven as salespeople would like them to be. Your focus should be on getting the team you’re selling to a bonus at the end of the year. And you need to understand what are the levers that will drive that bonus.

If you have a brand new offering how do you overcome the need for an ROI? 

The easy answer is a pilot. But the bigger answer is that you have to sell them on your vision and the thing you’re trying to disrupt. They have to believe in you, in your company, in your priorities and in your team. That’s the hard part. Then you can provide them with a rough ROI that gets them comfortable they’re going to make their money back. Use the “what you would have to believe” approach where they only have to believe that you will move the numbers a small amount and they’ll still make their money back. Be conservative.

How do you add value in your interactions dealing with other executives?

I like to use what I refer to as “insight selling”. Be interesting. Your pitch should be exciting and provocative and short. Like Peter Thiel says, “say things that others aren’t”. Be exciting. But also use the approach of not “always be closing” but “always be leaving”. Have one foot out the door. Look to disqualify opportunities. The prospect is looking to disqualify you and you should do the same thing. You’re both trying to figure out if there’s an opportunity to help one another. You’re total equals in that sense. Act like it. Also, I try to drip prospects quarterly with tidbits of information that might be interesting to them with absolutely no ask.  You’re not allowed to ask for something in these drips.  It could be an article, an insight you picked up from another prospect, etc. Stay on the radar but do not ask for anything. You need to preserve that level of trust and the power dynamic you’ve built.

A List Of Health Tech Startups

For a while now I’ve been keeping a running list of the health technology startups I come across sorted by the category they compete in. There are about 100 companies on the list. 

I’ve moved the list over to an open Hackpad that you can find here. Hopefully this list will help people better understand what’s happening in the industry, research competitors and even discover new investment and job opportunities.

I’ve left the Hackpad open so that anyone can add a company or category. Please add any that I’ve missed (I’m sure there are a lot).

As we move to the “Post-EHR” world where innovation is led by patient and provider needs as opposed to government mandates, I’m sure we’ll see even more startups and categories emerge — so I expect this list to get a lot longer.

Some Summer Reading – 2015

As this amazing summer comes to an end, I thought I’d capture some quick thoughts on some of the books I read over the past few months. I tried to read more history books than business books this year and I found a couple pretty good ones.

The list is in no particular order and you can find last summer’s post here.

wright kindle

The Wright Brothers by David McCullough.

A phenomenal book about two of America’s most accomplished entrepreneurs. It was incredibly eye-opening to read how hard it was for them to build their product and, once they had a successful prototype, how hard it was to actually sell it. It’s not clear which part was more difficult. Like most radical innovations, the masses thought their ideas were crazy. Their first planes were sold to clients in Europe because they couldn’t find any buyers in the U.S. that were interested in the product. I’m a big fan of McCullough and this is one of his best.

four hour work work

The 4-Hour Workweek by Tim Ferris.

I’m surprised it took me so long to get around to reading this one. This book is full of productivity tips and a really compelling perspective on how to get more from your energy. From only checking your email to once a day to outsourcing most of your personal life, a lot of the tactics he uses aren’t for everyone. But his perspective is great and there are a few good tips in here that will work for everyone.

king of cap

King of Capital by John E. Morris.

This is the biography of Stephen Schwarzman, the founder of the Blackstone Group — the massive private equity group. This is one of the best books I’ve read in a long time. The private equity business has always fascinated me and this is a deep dive into how it works and how the best of the best were able to sell it as an asset class. Buying a public company by borrowing money where the only collateral on the loan is the company that’s being bought is mind-boggling to me. And this is great deep dive into the personalities of the founders and early employees that gives great insight on how they got these deals done. A great read for deal makers.


Money Master the Game by Tony Robbins.

A colleague recommended this book to me and, given all that has been written about personal finance, I was shocked that I found this book so informative. Lots of solid and practical advice. Robbins spends a ton of time on mutual fund management fees and makes the case that everyone needs to immediately check the management fees that they’re paying on their retirement accounts. He points out that they’re a total waste of money because less than 1% of managed mutual funds will beat the S&P over a 10 year period. You must move your retirement to an index fund with lower management fees. Over time, these fees will have a compounding negative impact on our portfolio and can cost you literally millions of dollars. Most of us know a lot of the stuff in here but definitely worth reading if you need to brush up on personal finance.

johnstown real

The Johnstown Flood by David McCullough. This book details the tragedy that occurred after a dam that was holding water in a lake at the top of a small mountain broke and poured water into the small valley town of Johnstown, Pennsylvania. The water that poured into the small valley was the equivalent of the amount of water that flows down Niagra Falls for 36 minutes. An incredible tragedy. The writing is great but the story drags a bit and I wish he gave a bit more perspective on the larger impact of the flood.

dead wake

Dead Wake by Erik Larson.

Dead Wake is the story of the Lusitiania, the sister ship to the Titanic that was sunk by a torpedo fired by a German submarine as it traveled from New York to England. Many believe that this was the key event that brought the United States into World War I. This was hands down the best book I read this summer. It gives incredible detail on some of the individuals involved, including American, German and English political leadership and the captains of both the Lusitania and the submarine that fired the torpedo. It also gives great historical context on what was happening around the world at the time. Like most great non-fiction, this one feels like you’re reading fiction for most of the time. Highly recommended.

ready aim kindle

Ready, Fire, Aim by Michael Masterson. This is a book written by a self-made billionaire that details some of the basic lessons needed to build or grow a business. His message is basically that sales and marketing are the only things that matter at the beginning and gives tips on how to get started. There isn’t a ton in here that’s terribly new but for entrepreneurs or business-people that aren’t used to engaging in sales and marketing activities it might be worth skimming.

The Next Big Thing In Healthcare Technology Will Start Out Looking Really Small

Fred Wilson had a great post last week titled, Bootstrap Your Network With A High Value Use Case. He points out how Waze’s initial value proposition was to help drivers that like to speed identify speed traps. But it of course quickly expanded way beyond that and now provides lots more value to lots more drivers. It has become mainstream. Same thing with Snapchat — it started out as a “sexting” app and has now expanded to more applications and is used by the mainstream.

This is sometimes called the “bowling ball strategy” in new product development where you focus on knocking down the first pin by being very focused on one segment and one application and then you gradually knock down more pins (segments & applications) over time until your product works for the mainstream. The idea is to find a narrow niche that loves what you’re doing, refine the product and expand from there.

Related to healthcare, this blog has talked a lot about centralizing patient data with the patient, as opposed to multiple medical records across multiple healthcare providers. Most would agree we need to get to this place but the path to getting there isn’t terribly clear. Patients aren’t clamoring for it yet and there will likely be some resistance from software vendors and healthcare providers as it flies in the face of the strategy of owning the data and, by extension, the patient.

My guess is the way that we’re going to get there is similar to the way that Waze built a massive maps business and Snapchat built a massive photo sharing business — it’s going to start with a small niche.

I can see an application that has built a network of highly engaged users with a very specific and highly sensitive medical condition that shares important clinical information back and forth between provider and patient becoming the starting point for consumer-driven patient data. Big software vendors will likely ignore this application because it impacts a small niche and the patients will be highly engaged because their affliction is such an important part of their lives. Once the product is refined it can be extended to other patient segments with other medical conditions and it’ll grow from there.

As Chris Dixon likes to say, “the next big thing will start out looking like a toy”.

In this case, the next big thing in healthcare technology will start out looking really small: a simple tool that serves a very small, but highly engaged set of patients.

How Much Should A Startup Charge Its Early Customers?

Last week I had a conversation with a founder about how much they should charge their first few customers. Cost plus a fee? Slightly below the incumbent? The same as the incumbent? Some fraction of the estimated ROI?

My answer to this question is pretty simple: charge as much as you can get, charge whatever the market will bear.

At an early stage, a founder’s time and focus is the firm’s number one asset. Any compromises made in getting less than the absolute maximum amount that a client will pay creates an unrecoverable opportunity cost. Early-stage companies can’t afford to not charge what the market will bear.

Pushing for the max more has other benefits. It helps to determine the product’s real worth and the real challenges the client is having in buying the product. When pricing makes buying too easy you don’t get a good sense of the challenges you’ll encounter down the road, you don’t get the real story. It also generates a level of respect from the client (we’ve all heard the stories of people appreciating things more because they cost more regardless of the true value).

Finally, often a startup’s instinct will be to charge less because it’ll move the deal along faster. This is a myth. The opposite is true. The larger the deal the more attention it will get, the more senior people will need to be involved and it’ll move faster as a result.

This post isn’t meant to say that you shouldn’t negotiate, do a pilot and be flexible where and when it makes sense. You should do all of that. But in lieu of a defined market price, charge a simple one — the absolute most that you can get.

The Interface Layer & The New Economy

I’ve been thinking a lot about this notion of the “interface layer” in web services and how it’s changing the economy and the way money flows.

The concept of the “interface layer” is pretty simple. It says that the old economy was about building tangible infrastructure — cars, buildings, stores, etc. And the new economy is about building really slick and beautiful and easy to use web services (interfaces) on top of that infrastructure;AirBnB for lodging, Uber for ride sharing, OpenTable for restaurants, Expedia for planes, etc. These companies don’t own buildings, cars, restaurants or planes, but they make a lot of money by allowing consumers to easily access these things. It’s no longer about building infrastructure, it’s now about building beautiful, slick, mobile, easy to use ‘layers’.

One of the big complaints about these layers (or interfaces) is that many believe that they commodotize the underlying asset. Uber users don’t really care which cab company the driver is a part of, they just want the cheapest ride that gets them from point A to point B. This detachment from the brand drives down the cost of the ride and drives down the income that goes to the driver. Uber is commodotizing drivers. And drivers need to think really hard about how they’re going to separate themselves from the pack if they want to continue to charge a premium.

Uber’s layer is winning the taxi space.

But with the increasing use of mobile and the decreasing use of the desktop web, mobile is quickly becoming a platform on its own. And soon, instead of Uber being the ‘commoditizer’, Apple’s iPhone or Google’s Android could easily commodotize Uber.

Let me explain. Today, if I want a ride somewhere I go to Uber or Lyft or Sidecar or some other app to book a ride. This is a bit clunky in that it’s hard to know which of the services has the best option for me based on the time of day and where I want to go.  I have to download all of the ride sharing apps and scroll through them to find the best deal.

Of course I’m not the only one that’s annoyed by this. Very soon (if not already) we can expect that there will be services that will aggregate all of the top ride sharing apps into one so I can pick the best option for me (just like Kayak does for plane tickets).

This would be really bad for Uber. Now they’re the one getting commoditized. 

But when mobile is a platform, it gets much worse.

Apple and Google could easily add their own layer on top of these aggregation layers. At some point soon, instead of going to the Uber or Lyft app, I could just open up Siri and say, “give me a ride to SoHo”. And Apple will scan all of the ride sharing apps or ride sharing aggregators (even if I haven’t downloaded them from the App Store) and deliver the best result. This is absolutely what Siri wants to become — the entry point to the web.

In an extreme example, I could tell Siri, “take me to my friend’s apartment and let’s stop somewhere to pick up a bottle of wine that pairs well with Italian food.” Siri then decides which ride sharing app, which business directory app, and which wine app to use to bring me the best experience.

Apple could easily cut a deal with a ride sharing aggregator, Yelp and HelloVino (a wine discovery app) and take a fee from each of them. In this case, not only is the Uber driver getting commodotized, so is Uber and so is the ride sharing aggregator.

This is an important issue for any web based service to think about. The new economy might be less about the battle for the most beautiful interface and more about the service that can get closest to the user. And it’s beginning to look like platforms rather than interfaces might win the war.

How Mobile Is Impacting Facebook & Healthcare Strategy

Many people used to believe that Facebook was an extremely defensible business and that it would be almost impossible for another social network to compete.

It has grown to an enormous scale with massive troves of data and more than 1.5 billion monthly users. The thinking around their defensibility was that because all of your friends and photos and updates are already stored on Facebook, it would be tedious and unnecessary to switch to another social network. Everything you need is there. Why go somewhere else?

Facebook did have quite a bit of defensibility back when the predominant access point to the service was the desktop web. Moving your data to a new social network was painful and impractical. But now that the main access point to social is our mobile phone (more than half of Facebook’s traffic comes through mobile) things have changed dramatically.

We now carry around all of the key elements of a social network on our cell phones. Our phones carry our location, our photos and our address book and allow us to message anyone at no cost from anywhere in the world. With the click of the touchscreen we can view and connect with all of our friends on a new social network and instantly recreate our social graph. We can take a photo and instantly send it to a multiple social networks. We can easily join different social networks with different groups of friends focused around different needs. The friction of leaving Facebook and joining a new network has disappeared. This wasn’t possible with the desktop web, or it was at least much more difficult.

As a result of the increasing use of mobile, we’ve seen lots of new social networks emerge (there are now dozens of social networking apps with 1 million+ downloads in Apple’s app store, including Kik, WhatsApp, Tumblr, Google+, Instagram, Snapchat and many others).

This increased use of mobile has reduced the friction of launching a new social network to near zero and as a result has shifted ownership of data away from the network and back to the individual. Trying to own the data and lock-in the consumer is no longer a viable strategy.

Facebook is well aware of this and has adjusted by rapidly buying up many of these new networks. We’ll likely see more acquisitions like these in the months to come.


Over the last several years, large healthcare provider organizations and healthcare software vendors have been employing a similar strategy to that of Facebook. Health systems have been growing by buying up ambulatory, community-based sites and employing doctors to build out giant systems that can offer clinical services across the entire continuum of care giving the patient no reason to go anywhere else. In parallel, providers and software vendors have been creating a single patient record (including blood tests, physician notes, imaging and other data) that flows across the entire provider organization and can be easily shared with providers across the system. This avoids all of the classic frustration associated with having to fax your x-rays from one provider to another. Everything exists on the web in one single record. Providers then roll out a patient-facing portal that lays across the patient record where the patient can access all of their data (mostly through the desktop web).

The strategy is simple. Providers are telling the patient to 1.) stay with us because we do everything and you don’t need to go anywhere else and 2.) you can’t go anywhere else because we have all of your data.

But as we saw with Facebook, now that a consumer’s primary entry point to the web is their mobile phone, this strategy has some flaws.

Not only do our phones enable messaging and carry our location and address book and photos, they can also carry data on our movement, our sleep, our heart-rate, the prescriptions we’re taking, our body temperature and, with the use of implanted devices, much, much more. This real-time data that we carry on our phones is arguably more valuable than the data stored in our clinician’s patient record that only gets refreshed while we’re sitting in the examination room.

Increasingly, providers will own some patient data but the patient will own more data and better data.

Like Facebook, healthcare providers are trying lock in their customer by owning the data. But the increasing use of mobile has changed the game. Just like social network users can effortlessly syndicate their own data out to multiple social networks, a patient will be able to syndicate their real-time clinically relevant data out to multiple providers, regardless of which system they’re associated with.

Mobile has put patients in the driver’s seat.

Meanwhile, with the emergence of home care and tele-health and urgent care clinics and apps and implants that manage more serious and chronic conditions, in many ways healthcare has actually become more fragmented. The traditional providers may be consolidating, but new players are creating new channels for care and causing more fragmentation across the industry. Where and when and how care is delivered is being completely reshaped.

But unlike Facebook, large healthcare providers can’t buy their way out of this conundrum. First, because they don’t have enough cash (most are non-profits with microscopic profit margins) and second because healthcare is local. Health systems are no longer just competing with the hospital across the street, they’re competing with web services that are available to the global market.

As a result, large provider organizations are going to have to consider new ways of providing value and will have to select which segments of patients they want to serve.

In short, they can’t own the patient because they can’t own the data.

The idea of locking the patient into one network of providers was always a bit flimsy. But the strategy was somewhat understandable. A lot of this was driven by the trend towards value-based payments and the convenience of ‘owning’ a patient under that model.

But the lessons of Facebook are clear. Locking up the data is not a path to success.

Social networks and healthcare providers must focus on what they do best and focus on serving the consumer they want to serve and abandon their attempts to win by owning data that isn’t theirs to own.

The Importance Of Relationships In Enterprise Sales

One of my favorite questions to ask when interviewing a potential sales hire is: “given your experience in sales, if you had to write a book about sales, and you wanted to sell a lot of copies, what would be the theme or the thesis or the title of the book, what insight would you bring?”

Much to my dismay, the candidate will often sit back and say something like, “that one is easy, relationships, it’s all about relationships”.

This is a disappointing answer. And it also isn’t true. I don’t think it is all about relationships. Especially when selling innovation. People buy from a seller because they think they believe it’ll move their company forward or, more selfishly, they’ll get a raise or a promotion or a bonus at the end of the year after they roll out the product. They don’t buy from a company because they like playing golf with the salesperson.

That said, for some products it’s different. For some products, successful selling is driven by good relationships.

This got me thinking about which products are sold based on relationships and which aren’t.

I think a lot of it is driven by the life-cycle stage of the product and the level of competition in the product’s vertical.  For example, when when out to sell their first cloud-based CRM product to its first group of customers, it wasn’t about building a relationship. It was about convincing early adopters to completely rethink the way they manage their customer data. It was about getting big companies that were stuck in their ways to make a massive mind-shift. You can’t do that with a relationship. You do that with thought leadership and creating a vision and great communication. Of course, it probably didn’t hurt if they built a nice relationship along the way but there’s no way that was what was driving their deals at that stage.

On the other hand, when Benjamin Moore sales reps sell paint to a commercial real estate developer, it probably is very much about the relationship. The products are more of less the same, so it comes down to price, and how much the buyer likes the seller.

This chart illustrates my point:

Relationship Chart

When a product is brand new and innovative, relationships matters less than when the product is mature and commoditized by lots of competition.

Of course, the line is probably not this linear. For the first 1 or 2 customers, relationships typically matter a lot (often these are friendlies) and the importance of relationships probably levels out at some stage of product maturity. But I don’t want to over-think the simple point.

It’s worth salespeople taking some time to think about how they sell and whether or not the product they’re selling is at the right stage for their skill-set.

You might not want a relationship salesperson selling structural innovation and you might not want a disruptive salesperson selling paint.

The Death Of Enterprise Sales

A few weeks ago I was chatting with a guy that specializes in something called “disruption consulting”. Basically he goes into mature companies and works with their management teams to help them think through how they would disrupt their own business. This is a healthy exercise for large, successful organizations and something individuals ought to think about with regard to their own company and — more importantly — their own role in their own company.

This got me thinking about enterprise SaaS sales and the theory that salespeople have become less of a necessity in this new world. As I’ve written in the past I actually think the opposite is true. Sales is growing, not shrinking, in importance. That said, here are some of the trends that I’ve seen out there that are giving the skeptics some ammunition:

  1. Micro budgets. With the ‘consumerization’ of enterprise software, lots of companies are letting their employees directly buy and expense their own productivity tools circumventing the traditional buying process. 
  2. Pay-per-use contracts. Traditionally enterprise salespeople have sold large buckets of access to their software — e.g. Salesforce has negotiable pricing tiers based on the number of licenses purchased. Companies like Slack and others are getting away from this model and are pricing based on who actually uses the system. At the end of a month, they look at how many people logged-in and then send an invoice accordingly. This pushes the revenue responsibility pendulum far away from sales and much closer to product.
  3. Freemium enterprise software. This is a model where software can be accessed for free by an individual employee and an enterprise deal gets triggered at some critical mass of employee usage (e.g. B2E2B).
  4. Standardized contracts. More enterprise software companies are creating click-through agreements that can’t be negotiated by the buyer. And there does seem to be a very slow but steady move towards more consistency across companies in what they want a contract to look like. Corporate attorneys will make this really difficult, but the idea does seem to be gaining momentum. 
  5. Data in the cloud. The advent of the cloud has made the old-fashioned, big, CIO-based sale a bit less prominent. Cloud-based software programs require much less of an implementation burden and thus much less of the need to sell the bureaucratic IT department. That said, much of the work these teams do has moved towards integration into the cloud, which still requires a hefty sales process.

There’s no doubt that the landscape in enterprise sales has changed. And all of these trends are worth watching. But what the skeptics miss is that this is nothing new. Buyers and sellers always been trying to minimize the cost of their transactions. These are just new variations of that process. It simply means that to stay relevant enterprise salespeople must continue to shift their energy towards larger, more complex deals and higher value sales activity.

When real estate listings became available to everyone on the web, real estate brokers didn’t disappear (in fact, there are more of them now). They simply started focusing on higher value activity. Instead of their core asset being access to listings, their new asset is helping someone navigate the process of buying a home (over half of home buyers find their home online, but 90% still use a broker to make the purchase).

Similarly, when employees begin buying their own software, enterprise sales teams will just shift their activity towards more strategic, higher value deals. They’ll focus on the things that can’t be bought or implemented by a single employee.

In short, enterprise sales drives new and incremental growth. It’s the hard stuff. The easy stuff gets automated. And diffusion of the greatest innovations and the highest value deals can’t be automated.

Companies that aren’t growing their enterprise sales teams are likely either very early-stage and don’t have enough product to sell, or they’re later stage and aren’t trying hard enough.