Lara Caimi
Samsara’s President of Worldwide Field Operations, Lara Caimi, talks about scaling your business from a start-up to a multi-billion dollar enterprise. Learn how to navigate growth phases, build a customer-centric culture, and adapt to market changes to achieve sustainable success.
Scaling a business is a lot like predicting the weather.
Just like forecasters use past weather patterns to predict future conditions, in business, you analyze sales trends, customer feedback, and market conditions to plan your next steps. It's about looking beyond the day-to-day numbers to see the bigger picture—connecting different data points to make informed decisions for your business through its different phases of growth.
During my time at Bain, ServiceNow, and now at Samsara, I've seen companies progress through various growth phases up close—and, so has Yvonne Wassenaar, Board Director & former CEO of Puppet. This is why I was so excited to sit down with her in November at this year’s Endgame Summit to talk about how capitalizing on growth patterns can help you scale to $1B in ARR and beyond.
Every company, regardless of industry, goes through similar stages as it grows. Frank Slootman, CEO at Snowflake, helped me frame these patterns into a helpful journey framework:
When you’re scaling, it’s easy to get things really, really right, or really, really wrong. So, it's important to have a multi-year vision of where you're going and ask yourself critical questions as you consider your future:
What does the next phase look like?
What seeds do you have to plant now?
For example, you might start with a product-led growth (PLG) motion, but end up pivoting to a top-down selling motion as you move up market. Or, in Samsara's case, you might start mid-market and move up market, to a classic enterprise sales motion.
These aren’t just slight changes in strategy. Each motion is so different that you may need a complete overhaul of skill sets, processes, compensation models, leadership, and roles and responsibilities— from pre-sales to post-sales.
If you know where you are on your growth journey as a company and as a leader, and you're looking toward the future, then you can build out a proactive game plan, rather than tactically responding to your Board, customer needs, or the market.
That starts with outlining the vision of your company.
Start by identifying your origin and your destination. Where are you right now, and where do you want the company to go? Make sure everyone at your company understands the following:
At this point, don’t worry about going too big. In fact, be bold. Setting a super optimistic and ambitious goal is incredibly important—I learned this lesson from my former boss and mentor, Bill McDermott, Chairman and CEO at ServiceNow.
As a once-upon-a-time consultant, my approach has always tended to be conservative. I built detailed, bottoms-up models, focusing on reasonable growth rates with a clear, practical path. But Bill, in his eternal optimism, taught me that when presented with ambitious targets, people often rise to the challenge – a big dream helps everyone take higher aim. Everyone elevates their performance, pushing beyond the 'reasonable' to achieve remarkable results.
Not only is the glass half full, it’s also so much bigger than you ever imagined it would be!
When you encourage your sales team to push beyond the usual incremental changes and consider larger, more ambitious outcomes—you initiate a complete mindset shift—especially when those goals are anchored in a powerful purpose. Instead of focusing solely on your next steps based on where you are now, think about larger goals that can inspire your team to achieve more.
Within each growth phase, the talent you need to attract, retain, and grow will shift. It's tough, but sometimes you have to let go of old strategies and team structures to make room for new ones that better fit your current goals.
Your job is to make all these changes smoothly and to keep your team informed with each shift. To make these changes as smooth as possible, I recommend a three-pronged approach:
If you don't have the right team in place for where your business is heading, start building it now. Do it before you actually need it so you're always prepared for the next stage.
This reminds me of a story Yvonne shared that perfectly sums up this approach. A former colleague of hers always kept an organizational chart, but not for the present—it was for three years into the future. He did this with a dual purpose: to identify which members of his current team could advance into new roles down the line, and to understand what new positions he would need to fill in the future.
My best advice? ABH: Always Be Hiring. Proactively network and keep an eye out for great talent and perspectives, so that when you hit your targets—whether that's a certain pipeline size or a growth goal—you have the talent you need already in your network.
You’ve got your guiding vision and a plan for your team… But what about the final (and arguably, most important) element—the customer experience? How do you make sure this last mile is just as strong as the rest of your strategy?
We can all take a page from the B2C playbook here, as they’ve written the playbook on excellence in this dimension. A story I like to share is about the pet products company, Chewy. Whenever Chewy’s customer representatives learn that a customer’s pet dies, they send flowers. My mom lost her dog, Dudley, during the pandemic and, though she was devastated, this thoughtful gesture made her (and frankly the rest of the family) a customer for life.
Creating a customer-centric culture is about more than catchy phrases. It requires a deep-rooted cultural transformation that begins at the leadership level and is owned by every part of the organization.
In a B2B context, this means you have to craft a frictionless experience for your customer. Their interactions with your company should be easy and valuable. You need to deliver tangible business value without the fluff.
So, adopt an 'outside-in' perspective to uncover how customers interact with your business. Reflect on your processes and establish a framework that resonates with the experiences we all encounter in our everyday lives. And, above all, make every engagement with your customers delightful.
The best part? When you interweave customer experience throughout all of your organizational functions, you’ll also gain an unexpected benefit: employee engagement skyrockets. Your employees become more invested and passionate because they have a newfound sense of purpose.
At Endgame, we empower sales teams to do their best work. That’s why we host the Endgame Summit each year—to have seasoned sales and revenue leaders share exactly what's worked, and what hasn't. Sign up for our newsletter for more market insights.