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Software Mentors, Mavericks and Management

By June 17, 2014Article

Growth-stage technology companies are invariably led by visionaries seeking to disrupt or improve the status quo. Investors provide market insights, their network and experienced resources to help CEOs scale their businesses. They also mentor — a less-acknowledged value for helping CEOs succeed. 

Tech executives are maverick, strong willed and driven. These traits are the bedrock of success. They rarely want regular advice from an investor; while they may have accepted investor money, they can’t be forced to accept their guidance, especially since effective mentorship typically requires regular oversight. 

However, good mentors can and do make a difference, helping senior executives avoid the stumbles that often accompany explosive growth. 

To determine what makes a good mentor, I talked with five executives from Insight’s portfolio about Peter Sobiloff, a managing director at Insight with 30 years’ experience in the software industry. All five claim him as a mentor — someone who helped them grow their companies and expand their professional horizons. They say Peter appears to follow six basic guidelines: 

  1. Ask the right questions and listen to the answers
  2. Walk the walk
  3. Play whatever role; leave ego at the door
  4. Find solutions, not someone to blame
  5. Focus on long-term success, not short-term results
  6. Keep your word 

1. Ask the right questions and listen to the answers 

Peter SobiloffThis applies to all aspects of the business, but particularly for recruiting the right people. Knowing what questions to ask derives from experience, but listening and building strong relationships is central to a mentor’s value. “If you take the time to understand people and what they want,” Peter says, “their behaviors can be predicted.”

“I watched Peter interview a candidate for the head of sales position,” says Jason Kassin, co-founder of FilmTrack, a cloud-based SaaS company that serves the media and entertainment industry. “I’d probably done 200 interviews in my life, and I realized in that one conversation how much I was doing wrong. 

“I thought it was a casual conversation. And then I realized that Peter was following a specific roadmap — everything from how he physically set up the interview to essentially a scorecard of the types of answers and the way the answers were delivered. In the end we got a really complete picture of the candidate. 

“I’ve adopted Peter’s style. It’s not as good as the original, but I use it, and not just for sales. The aim is to learn where candidates will be impactful and where they will be detractors or harmful to the organization. You’re almost leading them to tell you whether they’re right for the position. But it takes time, and requires listening.” 

Justin Lafayette co-founded DWL, an enterprise software company that he later sold to IBM. After an investment from Insight, he began bringing Peter to detailed quarterly sales team meetings and pipeline reviews. 

“The salespeople would feel like Peter wasn’t just there to talk with us but was paying attention to what we thought would work, how we could try it and adapt it to make it better. Peter had his ideas and tremendous experience to draw from, but he adapted them to our situation by listening to us. He was involved for five years until DWL was eventually acquired.” 

2. Walk the walk 

Jonathan Flatow joined Greenfield Online in 2000 and helped lead the company to an IPO in 2004 and a sale to Microsoft in 2008. “Peter was a board member who could put himself in a manager’s shoes and talk with you about your problems,” he said. “Peter would see opportunities for us to partner with vendors or other industry players, looking for a joint way to work together. He could see scenarios we hadn’t thought of. He’s been to the goat-roping many times.” 

Having started his career in the trenches of software sales, Peter’s experience helps him recognize patterns in a lot of situations — what entrepreneurs sometimes claim as an ability to “see around corners.” His experience resonates with the founders of software companies. 

But, the tech executives note that there’s no point in a board member telling them what to do. Rather, effective mentors explain what worked for them in similar situations and what hasn’t, so that the executives can make their own decisions. 

While managers know more about their businesses, many acknowledge that they don’t always see the bigger picture because they’re running a company day in and day out. This is the value of a mentor who has run a business and can recognize the patterns. “I’ve been a parent and it’s hard work,” notes Peter. “Now I get to be the grandparent who knows what needs to be done and has perspective.” 

“I use Peter as a mentor to validate things I am thinking of doing but am unsure of the best practice,” says Scott Hester, VP sales at Kinnser Software, which provides a SaaS-based business management solution to the owners of home healthcare businesses. “If Peter says that will work or not and gives me the reasons why, it stops me from second-guessing myself. I now have an answer I believe in and can instead focus on the execution.” 

“My commitment to their success builds trust,” Peter says, “And by sharing my perspective on the big picture with teams, I can help get them excited about possibilities; but I know from experience that it takes grinding in the trenches and hard work to make things happen. I counsel them not to underestimate the long hours and hard work required to be successful.” 

3. Play whatever role, leaving ego at the door

As a mentor, Peter plays whatever role the management team wants him to. “I can be chairman of the board, the big dog, or I can be the sales manager who talks about tactics one-on-one with a rep on a specific deal — whatever’s needed. I can also just shut up and listen.” 

Tailoring the pitch to the situation is important. “A lot of companies would be reluctant to expose everybody on the sales team to an investor,” Justin Lafayette says. “But Peter was a mentor who inspired them. People would leave the meetings feeling like they had all these new sales angles to try, all these new, improved processes, and that we were going to sell more. He didn’t come across as an intimidating board member.” 

4. Find solutions, not someone to blame 

When something goes wrong, a good mentor never says “How could you do that?” or “Who’s to blame?” Rather, the questions are, “Do you know why that happened?” and “How are we going to fix it?” 

Tarek Sherif co-founded Medidata Solutions to provide cloud-based services to the life science industry. The firm now supports clinical trials in over 115 countries. As a first-time CEO, he looked to Peter for advice. 

“Our challenges had to do with managing explosive growth and ensuring we made the most of the market opportunity,” Tarek says. “At one point our implementation services organization wasn’t keeping up with our sales and we were giving away work for free to make up for it. Peter said, ‘Here are some of my experiences with software implementation that you might be able to draw from,’ and also ‘Let’s find some software implementation partners that we can train and make successful.’ 

That response was pretty amazing. He helped us get past the issue; not only did we improve our service delivery but we subsequently developed strong partnerships with CROs (clinical research organizations).” 

Collaboration is important in a mentor. A mentor doesn’t have to know all the answers but needs to be able to “problem solve with the executive,” while drawing on prior experience.

Scott Hester added, “Once we understood that Peter was an ally, we became more candid about what was happening because we realized that he would have ideas about how to avoid land mines and find solutions.” We are in the situation together. 

5. Focus on mentees’ long-term success, not their short-term results 

Short-term tactical decisions to make one quarter or achieve a specific milestone can be limiting. Good mentors encourage company leaders to consider the long term. 

“Our mantra has never been about an exit strategy,” says Tarek Sherif. “Medidata was built with a 10-year time horizon that always rolls forward. Today we’re building a multibillion-dollar revenue company, and not focused only on the next tactical move.” 

FilmTrack’s Jason Kassin agrees. “At the enterprise software level, Peter has worked with all the big players — Oracle, Microsoft, SAP. He knows that it takes time to build great companies and what the building blocks are for long-term success. We are building a lasting company and Peter understands that it’s important to focus on the big picture, as well as the short-term tactics.” 

6. Keep your word 

The financial markets can change overnight. Breaking news can give investors fresh leverage to make a deal that’s more favorable to them. 

At DWL, for example, the deal dynamics changed after 9/11. “A lot of experienced investors told us we would need more money and that the terms would change,” says Justin Lafayette. “But Peter and Insight stuck with the same deal. Their attitude was:  ‘What kind of relationship is that? It’s not good for long-term value creation.’” 

Tarek Sherif had a similar experience. “Peter’s willingness to be genuine and direct and stick to his word is what made us want him as an investor.” 

Mentors want their protégées to succeed for their own sakes. For executives, growing a business requires growing professionally as a manager and a leader. A mentor helps the executive scale so that the business can too. 

“I’m intensely competitive,” Peter says. “I like to win. I’m in this business because I want to win alongside management teams. I’ve run a successful software company, so the fun of this job and being a mentor is helping other people get to life-changing events.” 

He notes further: “When this happens, they can go out and be mentors to other entrepreneurs.” 

Hilary Gosher manages Insight Onsite, Insight Venture Partners’ team of operations and growth experts who help drive scale and growth at Insight’s portfolio companies. Hilary founded this team in 2000 and has worked with more than 90 software and Internet companies, advising on strategy, sales, marketing and M&A. She sits on Insight’s investment committee, manages due diligence and runs Insight’s marketing and PR activities. She currently serves on the boards of OverDrive Inc, Planview and Ikano. 

Peter Sobiloff joined Insight Venture Partners as managing director in 1998. He was president of Think Systems, an Insight portfolio company acquired by i2 Technologies. Before that, he was president of Datalogix and held senior roles at Ross Systems; he led both companies to successful IPOs. As president of Datalogix, he also led its sale to Oracle. Peter was previously a member of the board of directors at DWL, Greenfield Online and Medidata Solutions.  He currently sits on the boards of Achieve3000, Anaqua, DrillingInfo, FilmTrack, Kinnser Software, Kony Solutions, Mediaspectrum, Overdive, Planview, Syncsort and Workforce Solutions.











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