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.
A growth framework from $0 to $5B+
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:
- $0-$100M Phase: This is the thick of the startup-y grind, when you’re looking for the elusive product-market fit. Embrace the chaos, experiment, stay flexible, and listen to what your customers tell you.
- $100M-$1B Phase: Once you hit that $100M mark, it's all about scaling. But do it thoughtfully. Focus on building capacity, refining your product, and expanding your team in a way that aligns with your company's values and vision. Growth is great, but chaotic growth in this phase can stifle your ultimate potential.
- $1B-$5B Phase: When you hit this phase of growth, your organization is likely a hundred times the scale as when you started. What got your company to this level might be on the precipice of breaking down if you haven’t actively been managing and optimizing your approach and systems along the way —so, phase 3 is a great time to revamp old processes and ways of working. By now your existing customers make up a pretty significant chunk of your revenue. So, double down on your customer journey—nurture your existing relationships, make sure your customers feel valued and understood. Then, think about how to leverage these strong relationships to support your sales approach. Instead of just selling to the usual buyers, aim higher—talk to the C-suite. Selling to the head of sales is one thing, but when you can actually sell to the CEO, and solve real board-level business issues, you end up with much bigger deals. This also means you need to consider your verticalization strategy more, so your teams can connect with your customers in their language and provide them with industry-specific offers. Partners also become increasingly important to amplify your growth.
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.
As a leader, you have to paint the vision for where you’re going
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:
- Your company’s aspiration and vision- where do you want to go?
- What impact your company will have on the world- what is your purpose, why does it matter to customers, to employees, to the world?
- How do you work backwards from success- what are the bridges between here and there, and how do you prioritize what you need to build?
- And what does that mean the rank and file need to deliver each quarter to help you get there?
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.
Reevaluate and rebuild your talent at each stage
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:
- Ensure everyone understands the ultimate goal and why it's beneficial.
- Highlight the team members who are instrumental in paving the pathway to this goal. This is your ‘special forces’ team. Their job is to carve out the path for future growth—testing new strategies, setting up processes, and handling initial challenges.
- Maintain current operations to finance this journey and set the stage for the next growth phase. This is where your ‘business as usual’ team shines. They’re the people maintaining and growing your current business model.
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.
Take notes from B2C customer culture
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.