My Journey into the Wonderful World of Product

By Kyle Leavitt February 17, 2015

Pragmatic Marketer Volume 12 Issue 1

Notwithstanding a few delusional years in high school when I believed I was destined to become a grunge rock star, I was one of those kids who didn’t really know what I wanted to be when I grew up. After graduating high school and spending a couple of years in Russia as a missionary, I entered college and opted for a general business degree at Arizona State University.

Four years later, I found myself interviewing for jobs in a variety of industries and still not really knowing what I wanted to do. Thus began my journey of finding a career passion via a process of elimination. I took the highest paying job offer I could find out of college: an assistant store manager in the retail industry. It didn’t take long to figure out that wasn’t the right place for me. I left after a year and took a job in sales, although I didn’t expect that to be my final destination either. My lack of experience was pretty obvious. One of the other salespeople commented on my futile efforts, announcing to me and all of my surrounding cube mates that I “couldn’t sell ice cream in the desert if my life depended on it.” Looking back, I can’t really disagree with his statement, although I did eventually become a top salesperson, and even worked my way into the company’s management training program.

Just when I thought I was ready to put down roots, my techy brother introduced me to Infusionsoft, a small software startup. I became its first full-time salesperson in what seemed like a risky move at the time (and seems even more risky when I look back on it now). That was the beginning of what has turned into a 10-year, life-changing love affair with Infusionsoft. Today, I head up the company’s product management, product marketing and product design teams. I’m still learning and growing as a vice president, but I can honestly say that I love my chosen career path and the company I work for. I feel like I was destined to do this. So how exactly did I get here and how does one go about pursuing a career in product?

Cutting my product teeth


Looking back on my career, it’s clear I was learning how to be a product strategist long before I got into the product profession. It actually started back with my first phone sales job. I figured out that to have any degree of success I had to stop talking and start listening. My golden ticket was to listen intently to my sales prospects, identify and articulate their problems and provide a solution to eliminate their pain points. I also learned to focus my time and energy on prospects that fit the profile of how my other customers looked and acted. I began saying no to anyone who seemed likely to waste my time.

I continued to refine my selling skills at Infusionsoft and eventually became director of sales. My career shifted course again when my brother and I left Infusionsoft in early 2008 to pursue another dream: building a small business together. That was when I accidentally learned my next important product lesson.

My brother and I wanted to build an Infusionsoft add-on software product to solve problems I’d become intimately acquainted with while speaking to prospects and customers at Infusionsoft. However, before we could focus 100 percent on building software, we had to figure out how to make enough money to keep the lights on. We started offering implementation and consulting services to help Infusionsoft customers and I became even more in tune with the market. The most important product lesson I learned as a business owner was how to run a profitable business. By necessity, I had to figure out how to position and price our offerings, fulfill orders, support and retain customers, all in a way that would drive revenue up faster than expenses. In retrospect, I don’t know if there is any more relevant experience than being a business owner to teach someone how to be a product manager or product marketer.

After building the business for a couple of years, we reached our goal: the software business was profitable. This allowed us to phase out our service offerings and focus fully on growing our software subscription base. We eventually garnered enough attention from Infusionsoft to become their first ever acquisition in late 2011.

The gangly teenage years


When I returned to Infusionsoft, I had learned enough to know that the product department was the right place for me. I spent the next couple of years learning the more formal side of product management. I picked up industry terminology and refined my ability to think in a market-driven way by rubbing shoulders with other product people.

However, much of the unique product methodology Infusionsoft created wasn’t documented or systematized. The lack of a strong product foundation, coupled with the company’s fast growth and mounting list of demands, made it difficult to cut through the noise and maintain focus on the real needs of the market. I clearly remember the day I reviewed a detailed product roadmap. I counted more than 80 features that had been committed to, most of which could not be tied directly back to market research data and had not been sufficiently tested. I realized that our product teams were
acting in a reactive mode. We were on the brink of wasting a lot of time and money by adding a bunch of low-impact product features.

Soon after, I attended my first Pragmatic Institute training. The timing couldn’t have been more perfect. All of my questions were answered and all of my past experiences converged with my new awareness. For the first time, I felt clear about what I needed to do to become a better product leader and what changes we needed to make to help level up our product teams. I even called my fiancée to tell her how excited I was about what I was learning, and that I felt like I had gained the clarity and tools to confidently run a product organization at a VP level (although I had no intention of becoming one at the time). In an ironic twist of fate, my boss called the next evening to say he’d made a change in leadership and wanted me to be the next VP of product. True story.

Leveling up


Armed with new knowledge and inspiration, my first order of business as the new product leader was to implement a more scalable and reliable product methodology. This came in the form of the newly learned Pragmatic Institute Framework. It proved to be a stable foundation for the team to build on. In addition to providing a common language and shared set of templates and tools, the Pragmatic curriculum helped clarify individual and team roles and responsibilities, strengthened our process for making data-driven decisions and helped us prioritize our work and focus our time.

We threw our feature-bloated roadmap into the garbage and returned to our market research data to find the answers. We organized our roadmap into a set of problems and prioritized the list based on what the data told us. Most importantly, we started saying “no.” I have developed a deep appreciation and understanding for what Steve Jobs meant when he said:

“People think focus means saying yes to the thing you’ve got to focus on. But that’s not what it means at all. It means saying no to the hundred other good ideas that there are. You have to pick carefully. I’m actually as proud of the things we haven’t done as the things we have done. Innovation is saying no to 1,000 things.”

In summary, we’ve made the necessary changes to focus our efforts and work more efficiently than ever before, and the results have been remarkable. The product development team has produced solutions that are making a real impact. Today, Infusionsoft’s market-leading sales and marketing software helps thousands of small businesses across the globe. Customer acquisition costs and churn are down while revenue, NPS and lifetime customer value are up. Partners have also expressed renewed confidence in our team. At our recent annual partner event, a prominent partner exclaimed that “Infusionsoft has its mojo back!” Even our CEO and other executive leaders have noted the difference and made a point to communicate internally that product has raised the bar and is leading the way.

There were other changes that contributed to our success over the last year, particularly having the right leaders in place and the right support at the executive level. But to say that implementing the Pragmatic Institute Framework and curriculum was a key to leveling our product team up—and helping me to be more successful as a product leader—would be a massive understatement.

Final thoughts


Recently, I participated in a review of one of my favorite Pragmatic Institute courses. Every time I attend a course it helps me get regrounded and refocused on what is important. I’m so passionate about the principles of Pragmatic Institute that the first order of business for every new employee in my product department is to get Pragmatic Institute Certified. I know this will not only give them the right foundation to make a real impact in product, but also get them into the trenches and contributing more quickly.

When I think about how I found my love for product creation and got into the product profession, it’s pretty clear that it was not a pre-planned or deliberate path. In many ways it seems to have happened by accident. Having talked to quite a few people in the product profession, I’ve learned that my story is really not that unique. The fact is that most people who end up in this industry didn’t grow up dreaming about becoming a product manager or product marketer.

That said, I’m grateful to have found the wonderful world of product. I feel fortunate to have an opportunity to make a real impact on the people around me, and serve the small business community with products and services that can have a massive impact in their lives. It’s great to smile every morning on the drive to the office knowing that I work with great people and am doing something that I love ... even if I arrived here through a series of chance events, absent any deliberate long-term planning.

Categories: Working with Development Leadership Roles & Activities
Kyle Leavitt

Kyle Leavitt

Kyle Leavitt is a SaaS product leader who brings a market-driven approach to building products and services that solve real problems for small businesses. As VP of Product at Infusionsoft, Kyle has clarified the product vision and concentrated department focus around building to the unique strengths of the product, leveraging partnerships and integrations, and accelerating platform and technology investments for the future. Previously, Kyle was director of sales, helping to lead Infusionsoft to 900 percent revenue growth from 2005 to 2008. As president and co-founder of Infused Systems he created CustomerHub, rejoining Infusionsoft in 2011 when it acquired his company. Kyle can be reached at kyle.leavitt@infusionsoft.com.

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