Rick Kenney, Founder, Leading Lights
Rick Kenney is the Founder and Managing Director of Leading Lights, the benchmark insights firm. Rick has spent the last 20 years in SaaS, helping enterprise brands and retailers grow their digital and direct-to-consumer brands.
He developed the Benchmarking Practice while at Demandware and launched the Salesforce Shopping Index. He's a retired garage rock drummer, wanna-be guitarist, and suburban soccer coach.
What is your favourite social media platform, and why?
The evolution of Twitter, specifically its audience. In the past few years has been transformed into a hi-frequency, must-check. While still titled by how you curate your follows, the promise is often realized, keep current on the topics and community that you seek to know.
Tell us about you and your current role or area of interest.
SaaS has eaten legacy software. As a result, the SaaS ecosystem has been flooded with content pollution, as many have claimed to be thought leaders. I founded Leading Lights to help SaaS companies cut through the noise by transforming their platform data into useful and compelling benchmarks for their market. The market doesn't care what we think, but they will listen to what we know, the data-driven stories that benchmarks decipher.
What do you like about your career or area of focus?
Like many, I swoon for a great story. That story, though, is hardened by tangibility and credibility. As a result, I've fallen hard for benchmarks and the opportunity to tell a true story using proof in the form of data. This pursuit has pushed me to constantly learn how to be a better storyteller, how to read an audience, how to strengthen my analysis skills, how to ask better questions, and how to listen.
What is the best advice you have ever received?
When I was in the 8th grade, my dream was to be a sports broadcaster. I was a sports nut who watched every game, read every newspaper's sports section and had a few sports magazines delivered. It was the pre-internet days, so finding information was an active pursuit.
I remember interviewing a sports radio host, asking him how I could get where he was. His advice seemed rather utilitarian: "learn as much as you can about as many things as you can."
It wasn't about focusing on knowing everything about a given topic (sports) but growing your learning across a multitude of topics. It's a super work (and life) hack, cross-discipline learning and application.
What inspires you, motivates you, or helps you to move forward?
I love creating. The act of developing something from scratch is a massive draw. I played in rock bands for a number of years. The feeling earned by working on and performing a song is still unmatched. And, while creating slides and blog posts may seemingly pale to collaborating with friends to create a few minutes of music, I still get a rise from the process of creating, editing, collaborating, and performing.
What are you proud of in your life so far?
This past spring was the pinnacle of my soccer (football) coaching career. The group of 14 eight and nine-year-olds had been together for the past eight seasons. It was the final season before the age groups became competitive. Over those four years, I saw so many of the boys enjoy the game and have an incredible time together.
I saw the parent group embrace each other. We had a terrific final match, complete with a big save on a penalty kick, a goal from something we practised immediately prior to the match, and best yet, a post-match party that was just right. I have such pride in being a part of that team as a coach and a dad.
What is your preferred way to meet new people/network?
Nothing beats a friend of curated, colleague-contributed 1:1 conversation with alike (or non-so-like) minded contact. I've met so many great people through introductions and have forged lasting relationships.
What skills or qualities do you feel have helped you?
I rely - heavily - on optimism. Whether it be at work, at home, or playing, when I take a lump (and I've taken a number of them) or find my way onto a rocky path, I feel a compulsion to make the best of it. To hold on. To forge ahead. I've come to realize that this is "not" always the best course, and sometimes, you need to fail, or lose, or move on. But, for me, I'll get back up first.
What do you wish you had known when you started out?
Working together and working alone. Earlier in life, I wish I knew how important and how absolutely critical the skill of collaboration is. Think of those people you've enjoyed working with, or spending time with.
Likely, they are great collaborators. They ask you questions. They look to you for answers. They make you feel special, important, and present. We spend so much time learning how to think and celebrate those who achieve, and we don't think enough about those that collaborate and assist folks along the way. Those are the stars.
Who do you most admire in business, academic or creative circles and why?
I've been fortunate to be around a terrific set of leaders. I've worked under great CEOs like John Rizzi, Tom Ebling. John and Tom were very different leaders, but each was successful because of their ability to find answers and make decisions by seeking the right counsel and asking great questions.
Scott Galloway deserves so much credit for building L2 and his latest venture, Section4, by taking something that had been stale and turning it into a must-see. L2 made analyst firms hot. Section4 is scaling high quality and focused executive ed.
Outside of your professional/work area, what hobbies or interests do you have or what other areas of your life are of real importance to you?
Family life is paramount. Spending unstructured time and just being there at the moment is tops for me. But, self-care (sometimes selfishness) helps me appreciate everything around me.
I play soccer, and I go on long walks with audiobooks. And, I get grouchy if I don't get my yoga time in every week. After hearing a song that catches me, I'll even pick up a guitar and hit a few chords. Those moments provide a momentary or, sometimes, lasting boost.
Has the pandemic had a positive or a negative effect on you and/or your business, and how have you managed it?
The COVID pandemic provided the figurative and literal space to launch Leading Lights. What began as a side-hustle during isolation evolved into a full-speed opportunity to create something that provided real value to my clients. At most, Leading Lights wouldn't be alive without the pandemic. But, at least, the pandemic afforded me a balance which de-risked the initial period of a business launch.
Do you have a mentor, or have you ever mentored anyone?
I have a number of folks that I turn to for guidance. I like the concept of micro-mentoring. Connecting and communicating is so frictionless these days. Having a chorus of folks where you can turn for advice is possible. And, likewise, dropping in to share advice or experiences with others gives me great energy.
What advice would you have for someone looking to get into the same area of work or interests?
I often hear, 'I want to do something more strategic.' Of course, it means something different to all, but for most, it is about growing beyond the execution of tasks and being consulted on the assignment of tasks. Moving from doing to thinking. The catch, of course, is that those that are doing it typically have a fantastic perspective.
And, by continuing to do, you find ways to do better, faster, more efficient. That perspective is what leads to being more strategic. It means doing the work to help others appreciate that perspective - the research, the proof, and the presentation that compels others to act.
What do you feel is the most common reason for people failing or giving up?
I'll accept two answers here:
There is no incentive to go further.
Failing or giving up is the right decision.
Is there a phrase, quote or a saying that you really like?
"First, do what is necessary. Then do what is possible. And before you know it, you are doing the impossible." - Saint Francis Assisi.
What companies, brands, or institutions do you like or do you think are getting it right?
Salesforce has done so many brilliant things to make software interesting, largely due to developing a culture that is about supporting the entire employee base - the Ohana.
How do you define success, and what lessons have you learned so far that you could share with our audience/readership?
We own the right to define success. One of the savviest leaders I worked for was Arthur Sweetser. When he joined our team at eDialog in the early 2000s, he took over a team that was performing but had little in the way of confidence. He emboldened us by doing something simple but brilliant - defining success.
He did this for long-term planning, setting our sights on annual growth targets and qualitative measures, and helping to guide short term success with carrots that dangled just a few steps away.
So, often we think of success as winning an account, getting funded or acquiring. Often, though, we can define our own measures that help provide some control over our success.