FirstRain Archives - The Grassy Road

Why I’m stepping back from being CEO

I’ve loved being a technology CEO. It’s been 20 years, and the CEO journey has taken me from pride to humility, from exhaustion to exhilaration, from courage to fear and often all in the same day. It’s a fantastic job and a huge responsibility and I’m honored to have been trusted with the job not once but twice and in two very different markets. I’ve worked with talented executives, loyal investors, and customers who’ve become friends over the years. And I’ve also always been incredibly conscious of the role I [...]

By Penny Herscher|2017-12-13T06:52:57-08:00November 17, 2015|Leadership, My Personal Journey|0 Comments

5 Ways Trust Impacts Your Productivity In The Office

Published in Inc January 8, 2015 So you want to create something fabulous and new. You want to innovate and create a breakthrough no one has thought of before. Well, you probably have a list of ingredients you need: a few computers, some smart people, project funding... but there is one critical ingredient you need which can't be measured but will have a huge impact on your success. That ingredient is Trust. Trust allows your team to move fast, fail fast and create. It's a simple but true fact so [...]

By Penny Herscher|2017-12-03T02:44:24-08:00January 12, 2015|Career Advice|0 Comments

It’s All About Me! at Defrag 2014

Broomfield, CO - on a cold morning in November... I was invited to be a keynote speaker at Defrag 2014 which is a terrific conference of interesting ideas, and even more interesting people. Personalization is such a key aspect of creating a great experience for our users that I took the tack of total selfishness - It's All About Me! This is what creates the magic for our users. When FirstRain can ask you just a few questions, and then read your mind, it's an enchanting experience. Here's my presentation: [...]

By Penny Herscher|2017-12-06T09:47:47-08:00December 4, 2014|My Personal Journey|0 Comments

The Best Mistake I Ever Made

Asked by a journalist the other day "what is the best mistake you ever made" I had to think for a moment. There are so many - where to begin! But as I pondered the question, there is one decision I look back on and think "What was I thinking?" I became CEO of a raw software startup at 36 when my children were 2 and 4 years old. My husband was working long hours running a small consulting business and I thought I had no limits. I could do [...]

By Penny Herscher|2017-12-03T02:44:24-08:00October 29, 2014|Leadership|2 Comments

Do all CMOs have to be data geeks now?

Written by me in the The Economist Group today Few would argue against data’s importance in marketing today. Data is essential to every marketing decision now, and the techniques used to transform that data into actionable market insight can make or break a company. Given this, some data-intensive companies now require their CMOs to have a background in data science—but will we get to a point where all CMOs and senior marketing leaders have to have a background in data science? Or will tools continue to emerge that will help [...]

By Penny Herscher|2017-12-06T09:49:07-08:00May 20, 2014|Career Advice|0 Comments

Three things you can do to hire women and change your company forever

Posted in the Huffington Post Our world is changing very fast, and the role of women is changing fast with it -- and, mostly, for the positive. We have more women in power, more women in the workforce, more women in control of their lives but there still aren't representative numbers of women at the top of companies. And yet, we now know that diverse teams make better decisions. We know women make 85 percent of consumer buying decisions, and so, if you sell anything to them, you probably want [...]

By Penny Herscher|2017-12-06T09:50:00-08:00February 19, 2014|Equality, Leadership|0 Comments

Triathlon teambuilding

Over the years I've found that real teams form when you have an intense experience together, or repeated intense experiences that force you to be authentic and completely present - and so your true self - because you are reacting to the intensity. This happens on deals, it happens on tough product releases, but it's the most fun when it happens outside the office. In a competition for example... Yesterday 16 Rainmakers competed in the Cupertino Splash and Dash with me. This is a 1 mile lake swim followed by [...]

By Penny Herscher|2017-12-03T02:44:27-08:00August 2, 2013|Leadership|0 Comments

Defining success

Invited to answer a few simple questions about success and leadership I found myself having to think hard. To really think about how to get such a complex concept across simply - and be truly authentic. My answers are here (and if you know me personally some of these will make you nod knowingly): 1. How do you define success? Achieving happiness while making a positive difference to the people around you. 2. What is the key to success? To know what you want to make happen (in work or [...]

By Penny Herscher|2017-12-03T02:44:27-08:00July 18, 2013|Leadership|0 Comments

Why Insight Is Urgent for Today’s Sales Team

Published on the Huffington Post earlier today A year ago I wrote about the economy's gradual turn out of a recession, and the pressure that the recovery put on sales teams to understand not just their customers -- but their customers' customers. Fortunately, the economic recovery has continued and many sales teams within our economy's biggest companies still find themselves in a position of being understaffed, under competitive pressure and struggling to make the kind of methodology transformation in their customer interactions necessary to achieve their urgent sales productivity goals. [...]

By Penny Herscher|2017-12-06T09:53:20-08:00June 14, 2013|Career Advice|0 Comments

Top Five Dos and Don’ts When Employing Interns

Like most Silicon Valley technology companies, we hire interns at FirstRain. Sometimes they are active graduate students looking for work experience and interesting problems to solve while finishing their doctorate, sometimes they are in the final few months of a bachelors and want to try on a job to see if they enjoy it, and sometimes they are full time students working for the Summer. In all cases having them in our company is a huge win for us. So far every one has been an energy source, working hard [...]

By Penny Herscher|2017-12-06T09:53:38-08:00May 29, 2013|Career Advice, Leadership|0 Comments