Recent Blogs

Lessons learned from an Enterprise CEO: Pam Kostka

Software Eats Travel: Discoveries from a regular coast-hopper

The Second Time Around:
An Interview with Edj CEO Sean O’Leary

Advice from the Trenches

Lessons learned from an Enterprise CEO: Pam Kostka

pamupdatedPam Kostka has been an enterprise software marketing executive covering the full marketing spectrum, including product management and marketing, go-to-market strategies, demand generation, business development and branding, for over 19 years. As the VP of Marketing for Bluebox, Pam worked with KBD for the company’s initial launch and with all marketing materials since. Earlier this year, Pam moved into the CEO position for Bluebox. We spoke to her to get her unique perspective on both marketing and management at an enterprise software company.

Share a little bit about the path you took to become the CEO of a security company.
I’ve always loved the dynamics of being in a startup environment. I’ve been in Silicon Valley and enterprise startups since 1995, primarily up the product marketing and management route into the CEO chair. Product management is essentially a mini general manager function. As a result I got a lot of practice understanding product market fit, go to market strategy, involvement with customers, and also in leading cross-functional teams to success, which is great training ground for a CEO.

I’ve had multiple successes, but not always. There were IPOs and acquisitions along the way, but I also shut down a company.. There’s a lot you learn from the failure; sometimes more than successes, that makes you better prepared for the next at bat. When it comes to picking my next company, I look for big pain points and strong teams. My resume doesn’t read classically. I’ve hopscotched from industry to industry, but the consistent theme is finding dynamic, revolutionary markets, getting in on the ground floor, and driving to a successful exit. I landed at Bluebox because they where poised at the intersection of three big trends shaping Silicon Valley and the industry moving forward—mobility and security meets big data—and a team that was smart and hungry to win.

You mentioned successes and failures along the way. Is there one situation, good or bad, that influences the way you run Bluebox today?

I think there’s a lot of companies today that are not paying enough attention to product market fit. Don’t misguide yourself looking for flash-in-the-pan momentum; rather, look for what has staying power, what has stickiness, what is a true need in the market. Work on pain killers, not vitamins.

When I look at my past, and at the places where things took longer than they should have and we ended up with a suboptimal outcome, it was because we go caught up in the excitement of drinking our own Kool Aid instead of balancing the real feedback that we were getting from the marketplace. Things are constantly moving and changing so fast. Pay attention to the market signals that you are getting and play devil’s advocate. Sticking your head in the sand and not adjusting your strategy accordingly is where companies can fail.

So you wear a lot of hats as a CEO. You came up through product marketing, how do you deal with things that you know you don’t like but you still have to do? What advice would you give to a CEO that is still trying to juggle those different hats.

First, pay attention to your core responsibility, which is the strategy of the company. Strategy is hard and often involves tough and difficult decisions. You can get easily mired down in all your other responsibilities, and take your eye off that ball.

Always take time out of your day to move your company forward. It’s a startup and there’s 24 hours in the day, maybe 20, if you want to sleep 4. And there’s always 40 or 80 hours of work to do that day. So pick what is going to be most meaningful actions towards moving you to your end goal and let the other stuff slip. For example, you can’t ignore your employee culture or HR problems, but if you don’t have product market fit there are some HR issues that just aren’t going to matter anymore. So it’s balancing and prioritizing..

There are certain responsibilities that you can outsource, so find your trusted resources to help you execute better than you could alone. For example, I have someone in HR that I’ve worked with for 10 plus years now, she doesn’t work full-time for me, maybe 8-16 hours a week. But I know she’s got it covered and I trust her, so I don’t have to focus on that area as much and know she will escalate what’s needed to my attention. Some entrepreneurs try to do everything hoping that they are scrimping and saving in the right area, and they are really doing a disservice to the company. If non-core activities take too much of your time, then the real horsepower you need, the cleanness of mind and focus and strategy will fall to the wayside. By the way, 4 hours of sleep also isn’t any good. I learned that in my youth. You need sleep and some time away from the business to be able to have perspective.

What advice do you have for CEOs who are out there looking for funding?

Venture capitalists want big opportunities , but big rewards come with big risks. As CEO it’s your job to capitalize on the opportunity while reducing risk. Depending on the stage of the company, investors will be looking for different proof points that validates the market opportunity and increasingly removes risk.

You need to have equal parts visionary strategist and operational excellence. Silicon Valley is never short on vision, it’s operational execution that is harder. Pivot is a common term in Silicon Valley for a reason; start-ups rarely end up executing EXACTLY what they set out to do. The path to success has failure as a necessary pre-requisite of success. If you are lucky enough to have a very frothy market you can still get traction and perhaps overlook execution, but that’s the exception, not the norm. But even most overnight successes are five years in the making. If you are strong on vision, make sure you hire sharp shooters in each function who can ensure operational execution. If you know your destination requirements for the next round, lay out the goals and how you and your team will execute to get there.

Look for investors who will be your partners, who will ask the tough questions, and who are willing to lend their expertise around the table. Worry less about meteoric valuations and focus on building to the core value proposition and the valuation will come.

What is the best way to best leverage the services your VCs will offer you?

VCs services are facilitators to help you and advise you, not do things for you. That’s an important distinction. A VC may introduce you to customers to help you land business, but they aren’t going to make the call for you or even write the email. An operating partner in HR may introduce you to a trusted recruiting firm but they are not going line up a roster of candidates and recruit for you. They’re not going to run your interview process for you.

You need to know who to ask, what to ask, and be very pointed in your request. “I don’t know how to interview well” is very different than “Can you give me some questions to ask a VP, Sales in an interview and introduce me to someone that has a track record of hiring great sales people so I can learn.”

As you look at VCs and their services, look for those that have brought in operating partners–people who have recently been in the trenches, fighting the same challenges and opportunities that you are facing and will face. CEOs need other CEOs that have been in their chair and have gone through the challenges that they have gone through. As an entrepreneur be open to lessons learned and how they can pave over the potholes that are ahead of you. And find and invest in the relationships with service advisors that yield the most benefit.

What is the most important thing a company needs to work on in the early stage?

You can have the best vision, but if you don’t execute to it you’re dead. A lot of people fail to have operational excellence. Particularly when you are starting up your company, you need to set goals—tangible goals—and revisit them religiously for success and failure.

I’m a big fan of setting strategic goals for the company and then having trickle down operating goals for functions down to each individual. At a startup, there’s so much everyone *can* do, but goals keep everyone sharp and focused on the most important objectives for success. Plus, having strategic goals and aligning MBOs, gives the message from the CEO that “I’m trusting you, you’re my sales head, you’re my marketing head, you’re my finance head, etc., we are in violent agreement about what we want to achieve, now go make it happen.” You hire talented people and allow them to exercise that talent.

We start out every year with strategic objectives for the company, line up the MBOs function by function, then revisit them at the 6-month mark to determine if our assumptions were wrong and we need course correction. As a CEO I have a vision and the performance scorecard that helps us course correct. Without that structure it can take you 2 or 3 or 4 or 5 times as long to figure something out, because you don’t have the structure to get the product feedback or sales feedback or to understand financially what’s happening with your company and the economics about how you are building it.

There’s been a lot of buzz lately about the importance of design in business, but for the most part, it has primarily applied to consumer companies like Apple and Nike. Are you starting to see it trickle down into the enterprise side? How has it affected your business?

I’ve spent my entire career in enterprise, and historically we didn’t need to be cool and sexy. But that is changing, and I think mobility is the primary driver. As a user you are now exposed to great consumer design. When you bring your device to work, even as an IT buyer you are starting to expect the same usability and user experience you are getting on the consumer side. You’ve been educated about what’s possible.

As the lines blur between your personal life and your work life so does design. Enterprise companies can no longer get away with not having the something that is easy to use and aesthetically pleasing. You will crater if you don’t. You have to have an unbelievably cool value concept to overcome design flaws now. The expectation has just ratcheted up because of this blending and blurring of lines, so any enterprise company has to consider design. If you don’t, your competition will get it right and you will not. You may be the technically best solution but if you’re not the easiest to use you won’t win the battle. I give a lot of credit to Bluebox’s co-founders, Adam and Caleb, for instituting it from the ground up. They could have just been security purists but from day one usability was a core value proposition that permeated the culture and product.

The browser you are using is outdated. For the best experience please download or update your browser to one of the following: