My 9-Month Sprint Growing a Startup by 1000%

Everyone understands that growth is important. It’s the force that transforms a simple idea into a business and a fledgling startup into a powerhouse. But knowing how to actually create that growth—and do it fast—is a different story. I want to share how I helped one promising more than double its revenue in just the first three months of a wild nine-month ride.

Diving into the Deep End

I joined Spiff, a company that automates sales commission software, in the late summer of 2019. After meeting with the CEO and founder, Jeron Paul, I was originally slated to be an advisor. But the more I learned about the business, the more I wanted in. This had serious potential, and I saw a chance to add some fuel to their fire.

Helping a company scale is an unforgettable ride. It’s a chaotic mix of highs and lows that builds bonds you’ll carry with you for life. Eventually, the entrepreneurial bug bit me again, and I moved on to start my next venture. I’ve since transitioned back to a strategic advisor role at Spiff and helped recruit a fantastic VP of Sales and Marketing to take my place.

During my nine months as Chief Revenue Officer, I had an incredible time working with the team. We grew the company by over 1,000 percent and closed a $10 million Series A round of led by Norwest Venture Partners, EpicVC, and Salesforce Ventures.

While I can’t give away the entire playbook (Spiff’s competitors would love that), I can walk you through the core principles. And a huge thank you to Jeron for his leadership and for letting me share this journey.

So, what does it take to grow a business 1,000 percent in under a year?

Put Your Customers' Success Above All Else

Spiff already had a fantastic product, a base of loyal customers, and a huge market opportunity. They just needed someone to pour gasoline on the fire. My job was to grow revenue, so I rolled up my sleeves, got on the phone, and in my first 30 days, I closed the second-largest deal in the company’s history.

There was no magic trick. We just focused relentlessly on making that customer a massive success. We built a genuine partnership with their 100-person sales team. For any , your survival depends on your customers' success. By making that our top priority, we were able to land top-tier clients. The strategy is simple: stop talking about features and start discussing how you can make your customers win. Listen more than you talk, get to the root of their pain points, and be authentic about wanting to help them. Once you agree on what success looks like, you can use every resource you have to get them there. Your success will naturally follow theirs.

Close the Credibility Gap

Before Spiff, Jeron had already built and sold three businesses, and I’d sold two of my own. But Jeron's knack for seeing market gaps and building solutions was on another level. I knew Spiff had a great story and the experience to back it up. My job was to make sure the world heard it.

I successfully pitched our story to TechCrunch and Forbes and brought on Aaron Ross, the author of and former Director of Sales at Salesforce, as an advisor. This boost in credibility from industry influencers was a key part of our efforts and allowed us to move upmarket. We started working with larger companies, proving that Spiff could handle their complex commission calculations with ease.

Build a Predictable and Repeatable Revenue Model

To accelerate growth, you first have to understand what’s causing it. This means you have to meticulously track your sales and marketing metrics. Your team needs to know how to improve these numbers, how they connect to the company’s growth, and what that growth means for them personally.

When everyone is aligned on growth targets, something amazing happens. People start collaborating. They share tips, tools, and strategies. Instead of a group of individuals working in silos, the team unifies, and growth takes off. It’s also critical to document your sales process. Outlining expected behaviors and best practices from your top reps makes it easier to train new hires and ensures every single prospect gets a consistently great experience.

Get Smart About Your Financial Model

Once you know your growth levers, you have to figure out how much it costs to pull them. You need to understand your Customer Acquisition Costs (CAC), Lifetime Value (LTV), and conversion rates across the funnel—from visitor to lead, lead to qualified lead, and demo to close. These numbers will differ depending on your sales channels.

A smart is about finding where your best leads come from so you know where to invest your time and money. It could be social media, outbound sales, content, or paid ads. Find your most cost-effective channel and focus your resources there instead of trying to do fifty things at once. It’s far better to dominate one channel than to be mediocre in all of them. It's about getting the most out of every minute and every dollar. In the early days, your time is just as scarce as your cash.

Always Be Talking to Your Customers

All growth begins with understanding the people buying your product. The first thing I did at Spiff was talk to customers. I read their reviews and worked to understand the company's strengths and weaknesses. Who loved the product and why? Where did we need to improve? How did we stack up against competitors?

You can learn so much from just a handful of customer conversations. Look for common threads—where they hang out, what they do, and why they picked you. This will reveal quick, easy wins. Most importantly, keep checking in to make sure they’re happy. Your existing customers are your most valuable asset.

Know Your Competition and Market Position

I made it clear that we had to take the high road and never bash our competitors. In fact, I told the team to do the opposite: encourage prospects to research other options. It builds trust and shows you’re confident in what you offer. You might lose a few deals this way, but you’ll learn exactly why and can use that feedback to get better.

Whatever you do, don't play dirty. Don’t send prospects a list of trick questions to ask your competition or a biased spreadsheet comparing features. That actually happened to me when I was researching the market, and it was a huge turnoff. Just focus on your customer’s success, and you'll come out ahead.

Business is a team sport. I say it all the time because it’s true. Growth like this is never a solo effort. The better your team, the faster you’ll grow. The best investment any can make is in its people. If you get that right, you’ll go far.