Learn to sell

From time to time, I get asked for career advice. Sometimes it’s folks looking to get into product management, and others just curious about working in technology generally. I’ve thought a lot about what type of advice I can give that would actually be useful.

A big problem with an awful lot of career advice you hear, particularly in tech circles, is that it’s hopelessly tainted by survivorship bias. Almost all life/career advice from famous rich people is usually useless for this very reason. Beyond that, it seems like the most popular advice you see is “learn to code.” I think this is a mistake, and not very useful for most people. Learning to write code and develop web applications has definitely been a positive in my life, but it’s probably only been marginally advantageous career-wise. I’d certainly encourage anyone to learn, but mostly for personal enrichment, not career advancement.

Instead, here’s my pitch: go do a stint in Sales. If I were early in my career and looking to boost my long-term trajectory, I think is where I would try to start. Even in mid-career, where I am now, it’s something I think about often. More tech professionals should consider it. Hear me out.

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Paying for the Class of 2039

When we found out that Penny was on the way, among the first things I did as a soon-to-be dad was open a 529 college savings account.* I don’t know much, but I know that 18+ years is a lot of time for compounding to do its magic, and that sending her to college is not going to be cheap. We are determined for Penny to graduate in the Class of 2039 debt-free, as both Laura and I were able to do. I now pitch a few hundred dollars into her 529 every month.

Planning for something as far-out as college in 18 years obviously involves a ton of unknowns, like: will people even go to college as a matter of course then? My guess is that they will, so we have to plan for it, but I have my doubts. American higher education is in deep trouble and on a path whose costs alone are clearly unsustainable. (And as we know, the thing about unsustainable things is that, eventually, they always stop.) As a future buyer of educational services for our (nearly) 3-month-old, I don’t know that I’ll be on the universities’ side when the time comes to save them.

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Why SaaS will stay independent

A while back, the estimable Villi Iltchev published this outstanding piece on “Why SaaS consolidation is not happening.” It’s almost a year and a half old now, but has held up wonderfully. Villi points out a bunch of reasons why the SaaS market has not followed the same M&A path that on-premise software did in the 2000-2008-ish tech cycle, with a special emphasis on the importance of Customer Success in enterprise SaaS. I have some thoughts on enterprise SaaS that take it a step further, but as we close out 2017, his basic point has been proven correct. The Great SaaS Consolidation that many VCs were gambling on isn’t coming. Instead, we have something even better: a broad, burgeoning landscape of SaaS businesses whose need for outside investment is diminishing, whose customer bases are diversified, and whose destinies are bright as growing, independent companies.

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News on our book

There’s news on the book!

Refresher: a few months ago, O’Reilly asked to publish the book that Ben Gaines and I co-wrote this year on product management in enterprise software. We’ve been in editing cycles since then, getting feedback and some really awesome reviews from some big names. I’m super excited for y’all to see the final product.

Based on the feedback we received, we’ve decided to change the name – Make It So is no more. Our new title is Building for Business: Product Management in Enterprise Software. While I loved the Trek reference, I have to concede that it’s a little niche. “Building for Business” is catchier, I think (I mean, for product management – let’s not get carried away), and more germane.

You can learn all about the book at the (new) website: BuildingForBusiness.com. The old site will now redirect there, too. At the site, you can also read a sample chapter and get a heads-up when the book is released. Signups, I’m happy to say, have been brisk.

The book is also now up on O’Reilly’s website, though not available for preorders yet. I’m told that pre-orders will be available prior to publication. Go check it out!

How highly productive companies and nations are alike

I’ve been thinking a lot lately about the origins of productivity. Specifically, how many of the factors that contribute to it are similar between nations and companies.

The big governance factors behind national productivity are pretty well-understood: the rule of law, contract enforcement, private & intellectual property, investment in human capital, political stability. Big-D Democracy is not necessarily on that list (though hugely important for other reasons), but there are certain cultural factors that are often related as well: social trust, egalitarianism, the free flow of information, and openness to new ideas. More generally, there is a sense that as an individual, it’s in my interest to “follow the rules,” because that’s how I will get ahead.

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The Distributed Company

I’ve said before that distributed working models – which I prefer to the term “remote working” but whatever – are a disruptive organizational technology cycle that is already well underway. The number of salaried, professional workers who work remotely at least part-time has been growing slowly, but steadily, for two decades.

 

In some professions, this trend is more pronounced than in others. Even in tech, I personally find that remote working is actually much more common than many people seem to think. Remote arrangements, whether just working from home or from another city/state, are frequently granted on the basis of political weight (eg. longtime employees or executives) and/or without labeling them as such. So-and-so employee simply lives elsewhere, but isn’t called a “remote employee” per se.

Like any disruptive technology, distributed working has its critics who dismiss it as infeasible and unrealistic. And to be sure, it’s still improving (albeit steadily). But when I look at the broadening set of tools available to collapse the productive distance between professionals, as well as remote collaboration habits from other fields like gaming, the more convinced I am that this model is going to eat “the office.” One model of a high-productivity firm of the future will be a distributed one, where many or nearly all employees are based in separate towns, cities, states and even countries. This type of firm is able to use technology to most efficiently source talent regardless of location and route tasks throughout the organization, leaving geo-constrained firms at a permanent competitive disadvantage.

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Learning by doing

Recently, I took on a new challenge that has stretched my boundaries a bit. If you’re into product management, I recommend it to you, too. I opened a store.

Product management is one of those gigs where it just takes time and experience to build your skills. But like a lot of things in life, I’ve found that I’ve improved and gotten better not when times were easy and good, but rather when I’ve struggled. I’ve long said that the best training ground for becoming a product manager is not to hop right into working with a first-class, dominant product, but instead, to start in the bottom/middle of the pack, where you have to fight and scramble. My first PM gig was perfect in this way: we were fighting tooth and nail against a much larger, aggressive competitor on one end, and commoditizing, “free” solutions on the other. Interesting times.

Any product manager, but especially in enterprise software, has to try to build empathy with their users. We usually do this through tried-and-true methods like customer interviews, job shadowing, questionnaires, and many other forms of research. These are all effective when done well, but they’re really attempts to make up for the fact that most of us just don’t have the same experiential background that our users do. The career paths that lead into a software vendor’s product team and a retail brand’s digital marketing group are usually quite different. I’ve never run a digital analytics group for a major corporation, or a brand’s data science center, or a company’s digital marketing division, and nor have the vast majority of my peers. I know most of these folks’ pain points pretty well… but do I really get it? That’s been a nagging doubt that has always bugged me.

I was pondering this not long ago when an idea struck me. Why not open my own ecommerce store and give it a go myself?

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What I would do to fix Twitter

Twitter has had a spate of very bad press recently, mostly for good reasons that I don’t need to rehash here. Lots of ink has been spilled about what ails the company, but suffice to say, Twitter’s lack of high-quality, professional, and most importantly, full-time management is obviously its biggest single issue. Until that is fixed, nothing else probably matters.

Nevertheless, Twitter’s much-beleaguered product team has had a lot of turnover, and it shows in their paucity of product evolution. Twitter has crowed loudly about such new enhancements as 280 characters, Moments and “Twitter Lite,” among other things you probably don’t care about, as if small-ball like this actually matters, while ignoring the burning, revenue-stagnant ship they’re on.

So, as a product manager who works on products designed to make money, I have some suggestions. I’m not talking to Twitter’s product team here – they’re smart people, and I no doubt have had blueprints for many of these ideas ready for some time. Twitter’s executive management and board, on the other hand, need to listen, or get out of the way. Twitter’s window of opportunity for becoming a first-tier social platform has likely already closed – that race with Facebook was lost long ago.

Twitter can be something else entirely, though, which is still both valuable and inimitable, while its core network of high-value users contributing real-time content still exists. That network is undeniably slipping away, though. Battered by abuse, choked with spam and drowned out by bots, what makes Twitter great is dying. Here are some ways to save it.

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The three types of enterprise software

“Enterprise software” can obviously encompass a ton of different products and services, but I find it useful to break down our market into three broad categories that help inform product managers’ vision for their product:

  • Back-office products
  • Iterative products
  • Transformative solutions

One thing about enterprise software that makes it unique from consumer-facing is that its path to market and selling strategy is usually a fundamental part of the product itself. Businesses, especially in the “enterprise tier” (however you care to classify that), do not often buy, adopt or test out lots of software products on a whim; there are just too many legitimate concerns around risk, security, control, etc. Each of these categories has a meaningfully different path to market that product managers have to design for and build a product strategy around, even (or especially) if the ultimate goal is to go up-market (which – spoiler alert! – it usually is).

I’m going to talk a little about each category, how they’re interrelated, and how enterprise products can (sometimes) move between them.

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When lies aren’t lies

Note: this was originally a digression in my last post, Relevancy and Truth, but I decided it worked better as a standalone piece.


When someone asks your opinion about a topic, do you always answer with completely unvarnished honesty? Do you always give the answer you know or believe to be true?

The answer is no, of course you don’t. We all filter our self-expression through the lenses of what we believe others expect from us and how we think our responses will be received. This distorting effect is widely understood, from research psychology and behavioral economics to opinion polling. In short, people routinely voice opinions they know to be either false, or at least uncertain.

This is not exactly “lying.” It’s not deception; if anything, it’s more like self-deception. It gets to the core of how humans think and present themselves, and I think it’s more important than ever in understanding the mass psychology of the social web.

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