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Four and a half years ago, I left my role at Google as a product manager to join the team at Redpoint. The transition became the biggest professional challenge of my career up to that point. Suddenly, I was working with a smaller team, managing massive ambiguity in job definition, time allocation and decision-making, and giving up the adrenaline of launch day.

But far and away my biggest challenge was effective communication. I simply couldn’t articulate my points in convincing ways. During the first few weeks, I felt like an ineffective babbling mess. What had worked at Google was failing at Redpoint.

Products aren’t sold in isolation - they exist within ecosystems. Great product market fit and sales pitches hinge on understanding and serving all the members of an ecosystem. Should a product fail to meet the needs of any one member, company success and sales velocity will falter.

One tool I use with portfolio companies is the Value Proposition Diagram (VPD) which shows why a product is compelling to every customer - and most products are sold to more than one customer at the same time.

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If you’re like me, you switch task managers every six months at the point that you have added a bunch of items in your list that you’ll never get around to and can’t bear to be reminded of them again. At which point, you conclude that the app has failed you. It must have because you haven’t completed any of these tasks!

Task management tools fail users because they operate without context. How many times have you been to the grocery store and forgotten the dill pickles you were asked to buy? Or met someone and tens minutes later realized you forgot to ask an important question?

Many of the SaaS companies I work with are buzzing about a new concept: product qualified leads (PQL). It’s typical to see outbound sales teams create new leads by cold-calling - think Glengarry. And marketing also qualifies leads (MQL) using online advertising, branding, content, email and other channels. But the PQL concept is novel.

PQLs are potential customers who have used a product and reached pre-defined triggers that signify a strong likelihood to become a paying customer. A hypothetical example at Expensify might be if a user uploads 10 receipts and invites one friend, this user is a PQL and should be sent to the sales team.

I don’t remember much of junior year chemistry class except the lab experiment in which we made fireworks. My lab partner and I doubled and tripled the amounts of strontium, potassium, calcium and other explosives specified in the instructions. Our firecracker dwarfed our classmates' in size and when we lit them after two unbearable weeks of baking, there was no question we misunderstood chemistry. We expected an inferno and were rewarded with a pathetic fizzle and a C-.

Startups are discovery teams - they venture into the abyss, like Shackleton, aspiring to cross the Antarctic, plant a flag and live to tell the tale. Because every expedition is unique, no one knows what will work: product features, marketing tactics, sales pitches, fundraising stories. Nor can the team fully anticipate the precipices and risks: competitive, legal, hiring, market timing and management risks.

A philosophy was put to me by a close friend this week. “Succeed despite your every effort to fail.” He meant founders must set lofty goals and challenge themselves and their companies to reach them. The product of such a policy is struggle and consistent failure.

Hardware competition is cut-throat. Walking through the halls of CES, every Android phone is identical. LG has copied each Samsung model. Because of the competition, tablet prices are plummeting - I saw a $49 7inch tablet (and some were giving Nexus 7s away for free with subscription. Not constrained to large competitors, startups like FitBit and Jawbone launched competing (and nearly identical) products within weeks of each other: the FitBit Flex and the Jawbone Up Even newer segments like gesture control of TVs or GoPro self-recording cameras are addressed by six competitors, many of them white-label.

There is no prouder boast, but also no better prescription, for executive leadership than the words Andrew Carnegie, the father of the U.S. steel industry, chose for his own tombstone: “Here lies a man who knew how to bring into his service men better than he was himself.”

Amen.

This epitaph captures succinctly so much of leadership: the ability to articulate a vision and convince others of the importance of that mission; the self awareness of knowing one’s strengths and weaknesses; the desire to be the dumbest guy in the room; and the capacity to build and maintain those relationships during a life’s work.

In December, I was lucky enough to be asked to become part of the LinkedIn influencer program. I jumped at the opportunity to bring my writing to a broader audience. And the experience has been eye-opening.

The influencer program asks a few hundred LinkedIn members to write periodic blog posts which are highlighted on the home page and in email marketing campaigns. LinkedIn staffed a fantastic editorial team who assists writers with content creation and editing, but most importantly, content marketing.

In the last 12 years, marketing has been reinvented. No segment has benefitted more from this transformation than startups who have both created the new marketing and leveraged its skills to transform industries. These new marketers creating this wave have been so effective they can delay or even obviate the need for outside sales teams.

Historically marketing has been pseudoscience - an undisciplined hand-wavy concoction of story telling and a “throw stuff on the wall and see what sticks” mentality protected by unmeasurable results and three martini lunches.