Chapter 7

Justifying your Digital Enablement Investment

When working at a large company, sometimes your voice can be lost in the noise. “Big Swing” ideas are pushed aside for the safer alternative. When an opportunity arose to join Hippo in 2019—an Insurtech company bent on transforming the home insurance sector into the digital era with an inherent focus on what’s best for the customer—I knew I had to take it.

I cut my teeth at a large legacy insurance company, starting in claims before sidestepping into marketing, sales, and training. My work was rewarding and interesting—I was there for almost 12 years. But all the while, something was nagging at the back of my mind.

When working at a large company, sometimes your voice can be lost in the noise. “Big Swing” ideas are pushed aside for the safer alternative. When an opportunity arose to join Hippo in 2019—an Insurtech company bent on transforming the home insurance sector into the digital era with an inherent focus on what’s best for the customer—I knew I had to take it.

Building the learning and development org

When it comes to building a learning team, the challenges are the same for all of us. We want to build a world-class organization with engaging content, innovative learning tech, and flawless facilitation. The reality is that there are new hires to train, processes to document, and endless hours of prep to get everything where it needs to be.

In the tech sector or a startup environment, a relentless pace like this is all too common. So how can we as learning leaders deal with companies that are changing quickly, but growing to a state where formal learning is vital? The first place to start is with a plan—a learning and development transformation roadmap. The way I explain this master plan is with concentric circles. The nice-to-haves live on the outer ring. Our serious, but not time-sensitive, challenges live in the middle circle. And the core contains our most pressing concern.

But, wait. How do you know what the most pressing concern is?

Here’s how. Spend your first few weeks touring the company—not with just leaders, but EVERYONE. Listen to calls, shadow an engineer, attend staff meetings. Embed yourself in the business and soon you will see where there are learning challenges. Maybe the issue is change management and the focus should be on existing employees; maybe it’s an influx of new employees and on-the-job training is suffering from the volume. If you listen and observe enough, you will see the issues and add them to the plan.

Now that you have discovered the “what,” you need to determine the “how.”  Ask yourself: “What would I do if my dishwasher broke, or your car started making a funky sound?” My first stop would be YouTube, where I’d search for DIY fixes. Failing that, I might check the manufacturer’s knowledge base. In most cases, we need a solution that mirrors our learners’ personal lives. Something that replicates that self-service education in the workplace.

Solutions like Spekit can help solve this problem by giving you a searchable knowledge database—a Wikipedia for your company.

When an employee hits a problem, they jump on Spekit and ask their question. The tool automatically searches through all your content and returns the answer. You can take all the tribal training and knowledge and formalize it into an effective program. After a few months, you can have a bona fide learning and development organization—but that’s not all.

Winning over the C-suite

Tracking the return on investment for training has always been a challenge, but it’s now easier than it ever was before. By tracking ramp time, for example, it’s easy to measure something like decreasing ramp time from five months to three. With this metric you can demonstrate the impact of your onboarding program.

The same is true for quota fulfillment for customer support. Generally, we have all the data we need to draw a line between our initiatives and improved business performance. The issue is being in the meeting, getting the reports, and having a seat at the table to get that data. Even when we do have all the data we need, building a business case for learning needs more than just stats. 

The average executive is highly intelligent and experienced. They pick up things quickly, and have unrivaled knowledge about your business and industry. To win over their hearts and minds, we have to be really good storytellers. We have to understand our learners and tell their stories at the highest level. Here’s an example:

Recently, we made a change to some of our industry knowledge training. At a meeting with a sales leader, I said, “Let me tell you about one of our new hires, Rishi. He wasn’t from the insurance industry, but he had all these great transferable skills and a desire to learn. We built up his industry knowledge through this new learning program and now he’s crushing it.”

This story demonstrates the need for a particular training program and will resonate with all leaders, regardless of their experience, background or feelings on learning and development.

Once we’ve earned that buy-in at the top, we can parlay it into a powerful strategic voice.

Striving for a strategic voice

Over the years, many departments have slipped into purely functional roles. Think about customer service, logistics or accounting. In many companies, learning and development is one of these “functional” business units—and I believe that’s a huge missed opportunity.

Ultimately, my goal isn’t to encourage executives to buy into the value of a new onboarding program, it’s to have them get behind a long-term learning culture. I don’t want training to be the first two weeks of someone’s time at a company. I want training to be part of everything we do. Because that’s the way it should be.

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