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On Being a Pragmatic Marketing Instructor

This week, I was fortunate enough to receive a new opportunity within Pragmatic Marketing, and accepted a new role as Vice President of Products.  It’s a rare occasion that the stars align and you’re able to do work you love for a company you love with a team you love – but that’s exactly how I describe working at Pragmatic.  If you haven’t experienced that feeling, I sincerely hope that you will, and I’d like to share some thoughts on the best job in the world with you in the hopes that it piques your interest, and points you down a path of achieving success, however you define the term.

In 2010, I worked for Dell, and managed a small team who was responsible for portfolio management of several acquisitions that Dell had made over the years.  Prior to Dell, I worked for Cisco, a company Cisco had acquired called NetSolve, and a startup called NetStreams, amongst others.  All of these were good experiences in their own ways, but at a certain point I realized that I had the itch for something smaller, where I could see an immediate impact.  I had an idea for a startup of my own that I was trying to pursue but had come to a point that I needed to either quit and do it full time, or abandon the idea.

Key Learning: Why kind of person are you?  Do you prefer the stability and structure of big companies, or do you prefer the chaos of smaller?  Know your preference and use it to narrow your choices.

Around the Spring of 2010, Pragmatic Marketing opened a role for a new Instructor position.  While I had never considered it an option before, I found myself stepping back and asking “Why are you thinking about making a change?” “What do you really like?”  My self-realization was that I did love managing products, driving strategy, and beating the competition.  But what I liked even more was seeing the successes of my team.  I got energy from seeing people from my teams grow, seeing them nail a presentation to the executive team, and even seeing them quit and move on to bigger opportunities (although that’s always painful).  Their success was my success, and I loved it.

In a “normal” career, you might manage a few dozen products, you might touch a few hundred people directly.  But as an Instructor, I’d get to affect thousands of people.  It’s intimidating to move from a “doing” track to a “teaching” track, especially if you’ve climbed the ladder your whole career.  It wasn’t until I got into the role that I realized how good the fit could be.

Key Learning: What is your passion?  Do you love what you’ve done so far, or do you need to go in a different direction?

After going through an intensive hiring process, eventually I joined Pragmatic as an Instructor in August of 2010.  Immediately, I was paired with a mentor Instructor to learn the what and how of what we teach.

Most people come to three or four training days with Pragmatic, but it’s difficult to convey how much depth in our teaching is developed behind the scenes.  In any given class, we just scratch the surface – and the Instructors on the team all come from executive backgrounds and have loads of experience across industries and business models to fit any situation.  It feels like a Marketing MBA every time you step into the room with the Instructor team, because they are some of the smartest people in the world with regard to the application of market-driven techniques and strategies.

Key Learning: Where can you work with the smartest people?  When you work with A-players, and people smarter than yourself, it forces you to raise your game.

After completing the mentor/protege process and becoming certified to teach, I started to travel the world to deliver our training.  It’s no lie to say that teaching a marketing class can be intimidating:

  • You have to master topics ranging from pricing to competitive analysis to organizational alignment to roadmaps to business planning
  • You have to command the room and have the answers to everyone’s questions
  • You have to supply energy and keep some traditionally dry topics interesting and fun
  • You have to do all of this in front a room of smart, Type A people who are or will become executives

It’s a challenge, in a good way.  In the past six years I’ve delivered our trainings in 20+ states in the U.S., the UK, Paris, Sydney, Hong Kong, Singapore, and many others.  Training is a marathon; a few years ago I was on the road 47 weeks in a year teaching.  You can’t do that for something you don’t love.

Key Learning: Love and passion aren’t enough.  Do you have or can you develop the skills you need to thrive in your new role?

Today, when I step in front a room, my first step is always to observe the class.  Who are these people, and why are they here?  Some people are eager, excited, and ready to learn.  Others are here because their boss told them to be.  Others are evaluating switching roles from Engineering or Sales into Product Management or Marketing.  None of them quite know what to expect because their past experiences with other training classes have been so poor.  We have a chance to blow them all away with the best professional experience of their lifetime, and make an impact that lasts far beyond the time I’ll spend with them.

Within the first 15 minutes of class, everyone realizes that this class will be unlike any other class they’ve ever been to.  It’s not theoretical, it’s practical and actionable.  It’s enlightening and fun.  It embodies a philosophy of asking “What problem are we trying to solve for our market?” that will stick with them throughout their careers.

It’s not uncommon for students to approach me and other Instructors at the first break to say “Wow, I feel like I’ve already got my money’s worth and we’re not even through the morning session!  This is the best training I’ve ever attended!”  I often get emails from alumni of our classes years later, who tell me that I taught their class long ago, and they still use what they learned, and that they carry their tattered books around as reference manuals and clutch their Pragmatic Framework tight to their chest as a Rosetta Stone for their jobs.  That’s the feeling I got when I first attended a Pragmatic Marketing class as a student.  That’s the feeling I want to give to all of my students.

What we teach impacts students throughout their careers, affecting them, their peers, the products they work on, and the businesses they work in.

I’m an Instructor.  I don’t “train people.”  I change lives, and businesses for the better.  When people ask me: “Why did you stop doing Product Management to teach people like me?”  I tell them: “I never stopped doing Product Management.  I do it every single day – only now, my product is you.”

If you made it this far, and you can envision yourself as an Instructor, I’m looking for the next great member of our team.  Head over to our careers page, read the requirements, and let’s get to work changing the lives of students around the world.

The Big Company Survival Kit for Startup PM’s

There is so much territory to cover on this topic that this is probably the beginning of another series.  This post focuses on differences and expectation setting between small and big companies, and lessons learned making the leap between the two.

I’ve always considered myself a startup kind of guy, and for the past two years I ran Product Management at a small company called NetStreams.  However, two months ago an opportunity came up that I had to consider, and ultimately took, to help Dell build out their SaaS business.  Over these two months I’ve formed some new opinions about how Product Management is different at a small company vs. a large company.  Now that I’ve bounced between small and large (NetSolve to Cisco to NetStreams to Dell), the contrasts are stark and important – especially if you are considering changing jobs.


Scope is very different between small and large companies – but not how you might think.  My assumption was that coming into a large company, that roles would be very well defined and delineated, and that the scope of your role would be set.  The reality is far from that – I’ve found that there are plenty of opportunity to define what Product Management means.  This may differ depending on the part of the business you are in (legacy/sustaining vs. new/conquest).

In the startup world, very few people know what Product Management is or does.  So there is a lot more education that you need to take on.  Explaining to the Development team for the Nth time about what Product Management does can wear you down.  Butting heads with Executives who believe that their experiences trump the data you’re bringing back from the Market can wear you down.  The excitement from seeing the decisions you make and the products you bring to Market gives you a boost.  The energy/excitement level is much more boom/bust in a startup.  Big companies want a steady hand on the wheel.

Business Opportunity

Who do we want to be (when we grow up)?  In a small company you are constantly asking and answering this question.  Often times, the answer changes and evolves over time.  In a good Market you’re faced with the question of “It’s not what do we need to do to succeed, it’s which of these excellent opportunities are the best?”

In the large company, you are already grown up.  Now your job is to sustain, and not screw up the business.  Even minor risks look much bigger.  Do we want to push the envelope on a product?  Maybe not if it means we’ll end up on the front page of the NY Times for something bad.  “The unknown” takes a much bigger place in planning and you devote a lot of effort to reducing the unknown variables.  The good news is that you have a big team and lots of people to help.  The bad news is that decision making can be infuriatingly slow and involve dozens of people with competing priorities.


When you’re at a startup, you’re all in the same “rowboat in the ocean.”  Everyone must contribute for survival, and it is pretty easy to see who is dead weight.  This fosters tight teams and passionate arguments over everything, but there is always a family feel (or at least there was for me), meaning that everyone is doing what they genuinely believe is best to make the company succeed.  There’s just no room for ulterior motives.

Lots of people talk about the politics inside big companies, and some of that is true.  However, at least in my experiences it isn’t as bad as most people portray.  So much of this has to do with how you carry yourself: are you “above the fray,” and not interesting in having political conversations?  If yes, you can avoid much of the mess.  If you enjoy that kind of thing (why?), those conversations and people will seek you out.

Note that not proactively involving yourself in politics does not mean being politically unaware.  You always need to know your manager’s motivation and your manager’s manager’s motivation, and what drives the team around you, so you can pull those levers at the right time.

Context is very important in a larger company.  For example, big company have lots of semi-overlapping products and projects that are competing for scarce resources.  Is the person you’re talking to someone who owns a competing initiative?  That may not be a bad thing, maybe you can find common ground between your projects and collaborate on requirements – but always keep your market justification for your product at the ready so you can pull it up when called upon.

Someone recently described large companies to me as “tribal.”  If you’re in a company of 50,000 people, all searching for justification for their own jobs and their own products, thought patterns can change to “What’s best for me, What’s best for my group, What’s best for the company.”  In that order; it’s survival.


Small companies meet face to face and in the hallways.  Decisions are made informally and sometimes with little deliberation.  If you’re not careful that can cause lots of flapping in the wind downstream, as individual contributors catch up with the “strategy of the week.”  That problem is compounded because many executives in startups are in their first executive position and were great individual contributors or team leads but possibly poor department heads.  Communication filters down through the organization as fast as Word of Mouth can take it.

Another aspect of startups is that most communication is verbal – there aren’t memos, Project Managers doing daily status updates, etc.  If you miss a meeting, you need to seek out someone from that meeting and get a face to face update.

In the large company world, PowerPoint rules.  I recently had to give a presentation to an Executive and I was shocked at the amount of time that my manager and I spent wordsmithing.  The reason is that at a larger company, there are so many people vyying for your time that you get overbooked for meetings, and can’t make all of them.  So you ask people to send you the deck, and PowerPoint becomes a defacto memo.  If you’re used to all of your slides coming with your voiceover, forget it.  Your slides must stand on their own, and deliver your message clearly, concisely, and quickly.  The good news is that it’s good practice to hone your message down to the key points, a skill I obviously need help with as evidenced by the length of my posts.

Another big difference in the big company is that you’re on a campus.  There are multiple buildings and you’re working with people in different areas, cities, timezones and countries.  Meeting face to face just isn’t practical every time.  The result is conference calls.  Lots and lots of conference calls.  It’s a culture shock at first and you need to amp up your active listening skills to make them work.

Execution and Overlap

Small companies don’t have overlap because they can’t afford to.  On the other hand, execution lags because you don’t have the resources to properly develop, QA, document, market, or sell.  That problem is compounded because most startups (not all) don’t wish to set a target market, believing that they really can be all things to all people and are deathly afraid of turning down any business.

Big companies are execution oriented.  They have formal measurement processes and you are judged every six months or every year on your performance.  Measurement is a good thing, but it also fosters a culture of justification – you need to show why you exist and what you’re doing to advance the business.

Normally it is a good thing to have lots of execution minded people running around picking up dropped balls.  The problem is that in a company with 50K employees, sometimes the right hand doesn’t know that the left hand exists, let alone what it is doing.  There have been multiple times at both Cisco and Dell that I’ve been in meetings doing introductions and have given the standard “this is who I am this is what I’m doing” and had people approach me after the meeting saying “wait a minute…I’m working on the exact same thing!  What’s your name again?”  Just finding the right people can be half the battle.


Big companies have lots of resources, but you have to fight to get access to them.  Big companies spend a lot of money on research, customer interviews, focus groups, product testing, etc.  Unlike a small company, there aren’t a lot of long shot bets in a large company.  You need to be able to illustrate ROI and time to payoff, or you’re dead in the water.  If you can, you’ll get access to what you need to make your product successful, and if it’s not…it’s on you.

You also have leverage resources when you’re at a larger company.  You can negotiate better deals, you have multiple companies that want to tap into your sales force and installed base, and you can use these to put together partner solutions that may be superior to other offerings in the Market.


My wife and I recently had a baby girl.  I started at Dell on a Monday, and Addison (at right) came on Wednesday.  One lesson learned is not to start a new job and have a baby in the same week.  However, it enabled us to take advantage of the better benefits that a big company brings to the table.  To cover the family at the startup would be have been just short of $1000/month.  Now I pay less than a fifth of that.  For better coverage.  And 401k matching.

At the startup you get lots and lots of equity.  Will it ever be worth anything?  Part of that has to do with you and the work you put in, there is also luck and timing involved.  I’d advise anyone going to a startup to understand the time frame to a liquidity event very clearly before making the leap.  Are you willing to accept that standard of living for five+ years?  What if your family situation changes?  Something to consider…

Making it Work

Can someone with a small company, entreprenural heart be happy at a big company?  Ask me again in a year.

Changing Jobs in Product Management: Self Evaluation and Farming (Part I of III)

FarmingFirst, I’d like to thank those of you who keep up with Product Beautiful. Many of you I’ve had a chance to meet through networking, ProductCamp, at tradeshows, or we just ran into one another. Something I try to do with Product Beautiful is give Product Managers some helpful strategic thoughts and tactical tips for situations that you face in your job. This series of posts is about the process of changing jobs in Product Management and Product Marketing.

I am currently in the job change process, leaving NetStreams and moving to much larger company in a different industry. Going through the process has made me reflect and think about what people mean when they say “He left the right way.” To be successful in business and in life you need to build more bridges than you burn, so it is important to know the unspoken rules about entering and leaving jobs, because while people may say “it’s just business;” it is personal, relationships matter, and telling your boss that you’re leaving can be a sensitive conversation.

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Webinar – To Startup or Not to Startup

On Friday at 10-11AM Pacific, John Milburn of Pragmatic Marketing and I will host a webinar on Product Management in a startup. John is a true expert, and has been in the Product Management game for 20 years from companies as big as IBM, down to being the founder of a company in a startup. My experiences come from making the move from a Big Company (Cisco) two years ago, to a small startup, and building the Product Management and Marketing functions from the ground up. This should be an interesting and fun hour, so please join us for the discussion!

If you haven’t seen the original article that we wrote for the Pragmatic Marketer, go give it a read, we will expand on these themes and toss out some ideas about how to succeed in a startup.

Cisco Marketing Has Gone Crazy…Like a Fox!

CiscoUsually, when a big company decides to get hip to the newest Marketing trend, it’s like watching your Dad trying to dance to hip-hop: painful. Cisco is as big as they come, so I was really skeptical when I heard that they were putting a full court press on Product Marketing in new media like blogs, SecondLife , and Facebook (companies != people, you’re not my “friend”). Plus, Cisco has already had some bumps in the road with regards to blogging.

On the web, knowing your limits is key, and keeping the message light and self-depreciating is a skill that most big-company Product Marketers don’t have. No one wants to read a blog about heavy specifications; it’s boring. Believe me, as someone who is (gulp) responsible for some of that Cisco datasheet content, I can attest to how dry it is. Collateral might accurately convey information, but how do you capture mindshare and get in front of people in the first place? You need a hook, and Cisco’s trying to use new media for this purpose.

Cisco Edge QuestOne innovative tactic Cisco’s using is an online game called Edge Quest. It’s silly, but fun – you “fly” a “hovering router” around a virtual arena picking up “packets” to upgrade your “ship.” It reminded me of Tron. Cisco is running an contest for $10,000 and new ASR router give-away for the highest score. Here’s what I see as the pros and cons:


  • It’s different; there aren’t a lot of these advergames out there yet, so people will play out of curiosity
  • iMedia Connection says that games like these offer better brand retention and key message absorption than other methods and…
  • Games engage us at an emotional level…the place every Marketer wants to be! As much as we’d like to think that buying, especially B2B purchasing is rational, it’s not. Remember the saying “Nobody ever got fired for buying IBM?”


  • Routers and switches are complex, high tech devices. I’m all for boiling down to key messages, but are they devaluing the product by associating it with a game? Would this be more appropriate for Linksys?
  • Some people turn up their noses at games that are also try to “teach.” I think Cisco struck a good balance here, but some people will take any product info in the game as an affront. Dude – it’s free.

Overall I think this is a really cool idea and I’m curious to see how it goes.

The Cisco Team pinged me about answering some questions on this topic, so I’ll close with these:

How many hours do you game each week (sandbag accordingly if your boss will read this) and whats your favorite one?

I’d say about 4 hours. I’m known as a merciless killer on Team Fortress 2.

What do you consider your biggest accomplishment in your gaming life? (Come on, I know you have one! Mine was mastering the expert slope on the Intellivision ski game If only my actual skiing were a tenth as good)

The original NFL2K on Dreamcast had a bug where you could throw a long bomb to Randy Moss and get a touchdown every time. I exploited that and had over 200 points scored in each of 16 games against the computer, and ended the season with something like 20,000 yards and 450 TDs. Just like in real life!

How key is the speed and quality of your broadband connection when you play games, and how much (if any) would you be willing to pay your provider for a faster, better connection?

That’s a really interesting question, because 6 months ago I would have said “very important” and “yes.” Since then, I paid for the upgrade to RoadRunner Turbo, and I didn’t see much of a difference, so I went back to the standard package. I’ll still say yes, but only if I can get Japan-like speeds to my desktop. C’mon Cisco, make it happen!

I am sure youve seen lots of game contests where you play to win skins or stickers or a virtual t-shirt but have you ever participated in an online gaming tournament where the winner won money, and how much of a draw was this prize to encourage you to participate?

I’ve played in online tournaments before that had money as a prize, but never with the expectation that I’d actually compete for the top spot, it was always about the competition and beating my personal best. That’s my story and I’m sticking to it since I didn’t win.

What will you do with $10,000 if you win the tournament?

To quote one of my favorite lines from my RTFProduction professor, Richard Lewis, “I have multiple projects in various stages of development.” I’m sure they could all benefit!

Also if you win, what would you do with the Cisco ASR 1002?

I dream of the day that I would actually need a router like that.

We have a lively debate going in the office along the lines of fantasy edgequest (you can tell we tend to live this stuff.): One camp says the eventual winner will be a technical networking type (and game enthusiast) who loves Cisco, the other says that pro gamers will come in dominate the leader board. What say you which camp will dominate?

The Pros, absolutely. At this very moment there are teams training around the clock in China to win this contest. Of course they just want to win the ASR to reverse engineer it!

Our intent with this game is to find new ways to engage with our customers and to have fun in the process (not to create a separate gaming line of business for the Company!) Is it effective, do you know more about the Cisco ASR 1000 as a result of playing, and should we continue to engage you with such games in the future?

Granted that I’m not Cisco’s target persona for this product, but I say at least this is different. It’s worth a try to get the feedback and then evaluate. The risk is that IT managers probably don’t want all of their vendors sending games to fill up their employees in-boxes. That will quickly devolve into “I can’t fix her laptop, I’m ‘learning’ about routers!”

The ROI may be tough to measure, but the great thing about Web 2.0 marketing is that the “I” does not have to be large, so you can try lots of different tactics and find what works.

Full Disclosure: I used to work @ Cisco until 2006, and still have many friends there.