Lessons Serial CEOs Wish They Knew When They Started


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Dr. James Canton, a futurist, stresses that companies must continually change to survive. “Uber-connectivity, high velocity, real time transactions, IoT and data overwhelm the average company struggling with fragmented technology, data and asynchronous transactions,” Canton recently shared with me.

Most leaders, of any generation, are ill-equipped to deal with the multitude of challenges in front of them. There is a handful of successful CEOs that have figured it out and know how to blend intuition with technology and when to abandon traditional practices.

I asked Sandra Kurtzig, CEO of Kenandy, a SaaS ERP solution; Keith Krach, CEO of DocuSign, a digital transaction management vendor; Andres Reiner, CEO of PROS, big data software; and Sid Banerjee, CEO of Clarabridge, customer experience software, to share the lessons they’ve learned that shape their leadership and companies.

What is striking about all four of these serial success stories is how grounded and personable they are.  Each is driven by a passion to solve customer problems first and foremost followed by building a healthy company. They lead from passion and vision, not from ego. And eagerly shared their top five lessons learned.

Be Customer Obsessed

All four CEOs are obsessive about being “sticky with customers.” Kurtzig shared that “being close to the customer is paramount. Speed and agility are core requirements to responding to customers, on their terms.” Customers, today, have shorter attention spans and products need to support customer behavior just as much as key capabilities.

Focusing on what the customer really needs instead of “trying to build everything into the product” was a lesson for Kurtzig. Her fourth company, named for her two sons Ken and Andy, started by accident like all her companies, to address a glaring need she just couldn’t ignore – the lack of a comprehensive cloud-based ERP software solution.

Building the first release is a balancing trap many companies fall into, they either hold off market release believing robustness will be the defining differentiator or they release less than a minimum viable product. Her advice is to actively involve target customers as partners early in the product planning process.

An engineer, one of Reiner’s hardest lessons was that the product didn’t matter. Enabling customers is crucial, “while products and technology are important, training and change management are the keys to success,” he shares.  “As a company scales, be watchful to not leave your customers behind.”

The language and mindset of these CEOs is well beyond today’s popular customer experience rhetoric.  They expect their teams to not only understand customer behaviors along the entire lifecycle, but to build products that effectively engage those behaviors along the way.

As the global standard for digital transaction management, DocuSign’s Krach shares, “We measure our success by our customers’ success.” In fact, all employees are aligned around a single, non-financial performance metric indicative of customer success: Successful Transactions.  And by aligning the company around this critical metric with everyone laser focused on ensuring the customer’s ability to successfully transact business on The DocuSign Global Trust Network, the company saw more successful transactions in 2014 than the previous, and its first, 10 years in business.

While PROS is in the big data space, Reiner’s focus is no longer on features/functions but on how big data enables customers with recommendations and actions at key moments.  He believes that enablement drives consistent customer experience while increasing agility, for his company as well his customers.

It’s All About People

A common characteristic of these four CEOs is a passion for employees and culture.  Having the right skill mix for each stage of the company’s growth was a key lesson each learned.

Kurtzig believes in mixing the generations.  “Millenniums have high expectations of how software should perform. They bring a consumer mindset to enterprise applications. While seasoned employees bring deep experience and adult supervision,” she shares. “You need both.”

Banerjee’s lesson is that people can make or break you, “invest heavily in finding and retaining the smartest people to work for you.” Along with building a culture rooted in accountability, “it’s important that team members understand why people succeed or fail. There are weak links and you have to move them into a different role or out of the organization,” shares Banerjee. “A culture of complete transparency, where everyone knows who’s accountable for what and how they are progressing is essential for high-growth companies.”

Krach furthers, “The company with the best people wins.” Krach makes a habit of – and encourages his team to – “surround yourself with people who are better than you.”

Kill Silos From The Start

As companies hit the growth curve, knowing how to manage sales, training and employee onboarding in addition to products and customers is crucial.

One of Reiner’s lessons was the dampening effect silos have on growth.  “Silo-prevention has to be part of the culture,” shares Reiner. “And that starts with leadership.”  For him, preventing silos comes down to hiring smart people that leave their egos at the door.

“Diversity creates strong organizations where people naturally help each other,” stresses Reiner. “That, along with growing people from within by moving them across departments and roles, builds deep connections and empathy.”

His advice is to look for people who measure their success by how well peer teams achieve their goals.  The bottom line is that all employees must model the desired behavior.

Keep Life In Balance

Krach emphasizes that humor is core to his leadership model. It keeps teams together and motivated through the inevitable bad times as well as the good times.  “Keep the vision in front of everyone,” shares Krach along with “don’t take yourself too seriously and keep a healthy work/life balance.” He’s quick to show you pictures of his children as well as the mementos from team building and company meetings.

Kurtzig shares the same principle of keeping one foot solidly in family and life.  Family is priority and she actively seeks the input and advice of her sons. She does readily admit that being an engaged CEO and maintaining balance is hard.  Any C-Suite executive who claims to have ‘nailed balance’ is either not doing their job or delusional.

Watch Trends More Than Competitors

Keeping a close eye on the market while forging new paths is a lesson all shared.  Before Kurtzig started development of Kenandy’s first ERP application, she looked at Oracle, SAP, Google and Microsoft technology foundations.  Convinced the platforms were not future-ready, she (with some prodding by Mark Benioff of Salesforce) decided on Force.com.

Her advice is to “keep a close watch on market trends” and don’t get too attached to your technology. “Take risks. In today’s market, proven methods are not always the best methods,” Kurtzig stresses. “If an emerging trend looks strong and is better than what you’re working with, embrace it.”

Competition, viewed the right way, makes your company better because it forces the team to step up.  “At the same time, it’s important to focus a company on its own strengths and its own strategic vision, rather than being overly consumed with what the competition is doing,” stresses Banerjee. “It’s important to closely monitor the competition but not to the extent that it derails your strategy or causes the team to become destructive.”

The Net, Net

These five lessons are not what most readers might have expected.  Raising capital, hiring the first VP of Sales or Marketing, finding those initial customers, managing a board – none of these topics came up. These lessons were, in retrospect, the things these CEOs wish they knew when they started out.

“You’re going to make mistakes,” Kurtzig emphasizes. “Learn from them.”  Banerjee offers six additional pieces of advice:

  1. Conserve cash
  2. Get comfortable with conflict and confrontation
  3. Be highly adaptive and flexible, especially with people
  4. Surround yourself with a support system of seasoned CEOs
  5. Don’t solve problems for your team, let them do it themselves
  6. When you’ve stopped growing personally, it’s time to move on.

Republished with author's permission from original post.

Christine Crandell
An accomplished and passionate leader, Christine Crandell has over 20 years strategy and marketing experience in enterprise technology. An expert in defining, implementing and sustaining transformative strategy, Christine is a serial CMO and has served as CEO, COO, and board of director advisor to dozens of early and growth stage private and public companies.


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