Who have you upset lately?


Earlier in my career when I was selling to large companies in southern California, I had a customer become infuriated with me. I’ll spare you the details, but this executive didn’t like me at first and it culminated in him calling my manager to complain after a sales presentation. 

Luckily, I had an awesome manager at the time who taught me a very important lesson. When he received the call, he wasn’t disappointed in me. He actually said, “Ted, if your customers aren’t getting upset at you every once in a while, that means you’re not doing your job.” His mentality was that it was the job of account managers to challenge customers and ask the tough questions, because buying technology should be a mutual investment from both customers and vendors. Ultimately, the customer and I cleared up our differences, which lead to a very large and successful deployment for them, in addition to me hitting my quota. A true win win for both sides.

Similarly, as a product manager, if you’re not making uncomfortable decisions and upsetting the applecart, you’re probably not doing your enough. Customers may loudly disagree with changing functionality, even it’s beneficial for the long run. CEOs may question your product decisions and ask you to re-evaluate. Engineers may push back on feature requirements due to technical difficulty.

Whenever things seem too calm, I always re-evaluate if I’m pushing myself as a PM. So the question is…who have you upset lately?

BoxWorks 2014. What a great opportunity to talk about Box for Industries to thousands of awesome customers!

Highway to the Awesome Zone

If you haven’t already, I’d recommend reading Nicholas Zakas’s framework for thinking about work. If you don’t know him, Nicholas works at Box and is a thought leader in front-end engineering.

In short, he categorizes work into 4 quadrants:


Although this was written for the engineer’s point of view, it’s highly applicable to product managers as well. Whenever I look at stories or products I’m managing, I’m always on the hunt for projects in the Awesome zone. A great example recently was our launch of our advanced search API. Here’s how I knew it was in the awesome category:

  • Value: Many of our largest customers were asking us for this functionality to help with their eDiscovery use cases.
  • Effort: Most of the backend code was written already. All we had to do was write methods to expose it in our public API.

After convincing our engineering manager to load this story on his upcoming sprints, we were able to complete the new endpoint within one sprint with only one engineer. As an added bonus, we were even able to get a little help from our PR team to broadcast this to the public, resulting in a few great articles.

So as you plan out your next quarter, what are your stories you have loaded from the Awesome zone?

The Technology Value Pyramid

Learning from the Best
When I was at Cisco, I had the opportunity to help host a Telepresence sales call with John Chambers and the then-CEO of Northrop Grumman, Ron Sugar. I was 24 at the time (2008), playing host to two of the world’s top CEOs—so needless to say, I was pretty lucky to have the opportunity to learn from the best!

John Chambers has always been known for not being just a great operational CEO, but also, one of the best salesmen in tech. When he was talking with Ron, he didn’t talk about the speeds and feeds of his latest CRS-1000 routers. Nor was he talking about how Cisco stacked up against its best of breed competitors. What he talked about was joint vision—a vision that with the network as the platform, you could truly transform how you do business (in Ron’s case, it was how they could win more government programs). Hosting the call on Telepresence was a testament to this transformation: with Cisco’s technology, you could have two CEOs collaborate and accelerate decisions made across the world without losing a beat. 

By the end of the call, Ron Sugar was convinced that Cisco was a true partner and he was bought into the vision that John was proposing with the network as the platform. To say the least, he was more than happy to spend millions a year on Cisco equipment to power his network, in addition to using Cisco as his preferred vendor for the programs Northrop was bidding on. 

The Technology Value Pyramid: Vision > Solutions > Infrastructure
Cisco had a simple formula—it aligned on a customer’s vision and proposed solutions that sat on top of the network infrastructure. In Northrop’s case, Cisco’s technology value pyramid looked like this:


Once a customer was bought into this vision, it was really easy to justify a plan to purchase hundreds of switches, routers, access points, phones, and other networking hardware.

This strategy is not unique to only Cisco. Take Oracle for example—Larry Ellison always touted the many benefits of building applications on top of a shared database infrastructure. This was the strategy he carried in the 90s and 2000s; whereas in the 90s, he pushed best of breed applications on top of Oracle databases, then acquired and integrated applications like Siebel and Peoplesoft in the 2000s to fill in his solutions suite.  For example, their current value pyramid to a fortunre 500 CMO trying to optimize their marketing spend would look something like this: 


Building for the Technology Value Pyramid
When building out your next new product, it’s important to keep in mind how it will fit into the technology value pyramid. Think of it like test-driven development—you start with no production code and only failing tests, then work your way through your features until all your tests are green. Similarly, you should make sure all your technology value pyramid “tests” pass before building your products. These questions should help validate that your product is meeting customer requirements:

  1. What kind of customer vision/goals can I solve with my product?
  2. What type of solutions will my product enable?
  3. How will my product fit into my customer’s infrastructure strategy?

If you can easily answer these questions and convey your product’s value up and down the technology value pyramid, you’ll be able to align all vested parties — from customers, to management, to developers, and sales and marketing. If not, it may be a sign that you need to re-evaluate how your product is creating customer value and go back to the drawing board.

The Hello Kitty Effect

I was able to give my wife a hand-me-down Macbook Air about a year ago. This was a big upgrade from her stodgy Lenovo Thinkpad her employer provided her with, so I thought she’d be using it all the time. My hidden agenda was that this would also make her even more tech savvy, so that we could share my passion for geeking out. 

A few months passed with this new shiny laptop and her behavior remained unchanged. She rarely used the Air and it sat in our apartment collecting dust. Instead of pestering her or being passive aggressive in encouraging her to use it more, I had a brilliant idea. I went on Amazon, spent $5, and added a small improvement to her laptop:


Just as I predicted, she started using the laptop! Soon enough, I would come home from work and she’d be on the laptop; or before we went to sleep, she’d be sitting on the bed browsing the web reading her favorite blog. By marketing the laptop towards her with a small decal, I was able to turn her into a frequent user of a product that hadn’t fundamentally changed in functionality. 

The reason I share this story is to illustrate the power of marketing. In software particularly, no matter how good the code is that you write, the way you market a product can make or break its success. Take for example Marc Benioff—do you think he marketed Salesforce.com as a “way to store and retrieve customer information in the cloud”? No, he marketed Salesforce.com as the way to dramatically increase revenue through sales and marketing productivity. Similarly, did Larry Ellison build Oracle by touting its database performance alone? No—he talked about the importance of enterprise solutions that can transform your business and give you a competitive advantage.

When launching your next company, product, or feature, it’s important to keep in mind how you’re going to market it. This shouldn’t be something you leave as a last step; instead, it should be deeply integrated into your development life-cycle and considered with every decision you make. As you continue to build, always ask yourself - how will we market this?

Healthy Paranoia


I recently gave a talk at Lyndbrook High School for a family friend of mine. I spoke about my career thus far, what it’s like working for a fun start up, and also some lessons learned in my 8+ years in the workforce. During my discussion, one of the lessons I spoke about was having healthy paranoia.

Healthy paranoia can be a good thing. A recent example of this was during the keynote I had during our recent BoxDev conference. I was on stage presenting a metadata demo via an iPhone app I wrote. This app was a construction app that searched for Box files based on metadata, in addition to taking pictures and submitting them back to Box with associated attributes. All of it was live and projected on screen in front of a crowd of around 1000 attendees.

Do you know how many back up plans I had in case this demo went wrong? 4!

You might think I’m crazy, but I was paranoid about anything malfunctioning, so I wanted to do everything in my power to control the environment. First, I had a MiFi in my back pocket in case the wifi connection was spotty. Second, I had another iPhone on me in case the demo phone was malfunctioning. Third, I had an iOS simulator ready to go on the demo computer in case both the MiFi and Wifi didn’t work with the phone. Fourth, I had a video recorded as a last ditch effort in case all three of the other solutions failed. As an added measure, I even rehearsed what I would say if things went haywire.

Luckily, the demo went smoothly and I didn’t have to resort to any of my backups; however, my nerves were much more calm during the presentation knowing I was covered. It’s a good reminder that healthy paranoia is a good thing every now and then—especially when it comes to game time.



When you look at successful companies and entrepreneurs, what do you see in common? Is it that they were in the right place and the right time? Was it that they were harder working than their competition or peers? Or was it purely luck that played a role in their success? Depending on who it was, it could be one or the combination of all of these—but there’s one thing that is common across all successful companies and entrepreneurs - acceleration.

I first became more aware of acceleration when playing competitive tennis growing up. When playing, you realize there’s a point in a match when you started feeling like you could overtake your opponent. There may be a couple missed shots by him, a couple winners by you, and then you would start to feel the tide turn. When it does, you don’t let off the gas petal—you accelerate. You accelerate by hitting more winners, forcing more unforced errors by your opponent, and you string together enough momentum so that you separate yourself enough that even at steady state, your opponent can’t comeback. Opportunities for acceleration are almost difficult to describe, but it’s something more derived from the gut. But when you feel it, it’s crucial that you capitalize on it.

Another great example of acceleration was when I first started selling at Box. About 6 months into my sales role, I started feeling this inner confidence that I never had before. I felt like I knew how to qualify well, understood the messaging and benefits of our product, and felt comfortable developing rapport with customers. When all of this was clicking, I started to accelerate. In our early days, we used to have a phone system for leads that rang to everyone’s desk, and the first person who picked it up would be able to sell to that customer. Feeling momentum on my side, I came in earlier and left later. I sat at my desk during lunch breaks. I literally placed my phone next to my keyboard so that I could pick it up faster with my left hand. I took every opportunity I had to get on the phone with customers. I accelerated as fast as I could, and it left me as a top ranked sales rep for the year.

If you look at three of our recent entrepreneurial success stories—Evan Williams, Andrew Mason, and Kevin Systrom—they each accelerated to build billion dollar businesses. What’s common across all three of these founders is that they all had unsuccessful ventures first, then created new opportunities to accelerate into hyper growth . Evan Williams branched from the fledgling Odeo to found Twitter, then leveraged South by Southwest in 2007 to accelerate into the main stream. Andrew Mason transformed his first site, the Point, to Groupon, and accelerated to a $1B valuation in just 16 months through a hustling sales force and non-stop media attention. Kevin Systrom pivoted from an unsuccessful check-in service called Burbn to Instagram, garnering 50 million mobile users in under 2 years through social acceleration, network effects, and top-notch usability. None of these founders sat idle when they started to see their numbers tick upwards. They each threw a ton of time, effort, and venture capital into accelerating their growth.

To grow as a successful product manager, it’s important to always be on the lookout for acceleration opportunities. If you feel like your team is really hitting its stride, don’t let them settle for the status quo—push them to get even more done. If you start seeing trends in user acquisition, invest even more into those channels. If customers start loving a specific new feature, don’t hesitate to dig deeper and draw even more attention to it. Acceleration opportunities don’t usually wait around, so when you see them, make sure you seize them.

BoxWorks 2013 keynote. I come in around 58:15 to present metadata to the world for the first time. More coverage here: http://techcrunch.com/2013/09/16/box-metadata/

Dusting off the cobwebs and getting back into Rails this weekend.  My goal was to build an app, but focus on test-driven development.  I still find myself learning new things every time I read through http://ruby.railstutorial.org/—it’s probably one of the best rails tutorials on the market.  

The app is an automator for Box.  By adding in a valid access token, you can fill up an enterprise account for purposes of testing.  I’m about 75% complete and hope to finish this up on my spare time over the next couple of weeks.  Here’s the github repo: https://github.com/tblos/box_automator

Had the opportunity to speak at an SVForum meetup the other night at the MSFT campus in Mt View.  To my surprise, I thought this was going to be a 5-10 person roundtable with only a 15-20 minute presentation, when it turned out to be a 30-40 person meeting for a 60 minute time slot!
However, I improvised, told a few stories, and filled the rest of the time with good old-fashioned white boarding and Q&A.  I was impressed with how engaged the members were and it reminded me that Silicon Valley is not just filled with 20 something whiz kids; there’s also a large breed of engineers and developers that have been around tech for 20-30 years.  
  • Camera: Canon PowerShot G11
  • Aperture: f/2.8
  • Exposure: 1/30th
  • Focal Length: 34mm

Had the opportunity to speak at an SVForum meetup the other night at the MSFT campus in Mt View.  To my surprise, I thought this was going to be a 5-10 person roundtable with only a 15-20 minute presentation, when it turned out to be a 30-40 person meeting for a 60 minute time slot!

However, I improvised, told a few stories, and filled the rest of the time with good old-fashioned white boarding and Q&A.  I was impressed with how engaged the members were and it reminded me that Silicon Valley is not just filled with 20 something whiz kids; there’s also a large breed of engineers and developers that have been around tech for 20-30 years.