Foundational business lessons learned while scaling Alteryx from $160M to ~$1B in ARR

From mid-2018 to early 2024, I had the opportunity to report to and work closely with two CEOs at Alteryx. As VP and Chief of Staff to the CEO, I partnered directly with them and the executive leadership team as the Corporate Strategy & Ops leader to define and execute our highest priorities as we scaled the company from $160M to ~$1 Billion in ARR.

Throughout this journey, we experienced many successes. As expected in any fast-growing enterprise that values speed, we also experienced our share of missteps. One of my core values is being a constant, lifelong learner. I’ve found there is no better way to learn than by reflecting deeply on one’s experiences —both successes and misses— and distilling them into generalizable lessons. That is my objective here.

The lessons below link to different posts structured as topic-specific deep dives with insights, generalizable lessons, and frameworks in case study format. I hope these insights can help current and aspiring leaders become better operators and decision-makers. They certainly helped me become one.

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Key lessons

• High-stakes business decision-making is a bedrock leadership skill. The best leaders approach it systematically to improve their odds of being right. Here is a generalizable mental model inferred from observing some of the best at their craft

• The CEO role is highly context-dependent and variable, however, there are at least five universally high-leverage activities that CEOs must lead

• Every technology organization will eventually be faced with a critical product re-platforming decision. There are three fundamental ways to approach this exercise and here are the lessons we learned from our re-platforming journey

• Pricing & packaging is one of the most powerful enterprise growth levers when leveraged correctly. Here’s how it helped fuel Alteryx’s growth from $150M to $1B in ARR

• KPIs are the mechanism for translating amorphous strategic intent into a desired set of concrete actions. Getting these right is critical to success, yet even seasoned managers often fall prey to errors here due to a handful of common reasons. Here are three instances where we were guilty of this and risked success  

• Hiring errors are expensive and exorbitantly so for senior leaders. One way to minimize them is by decomposing the dimensions of an individual’s experience into its core components and looking at common patterns of success and failures across them to assess which elements are the most important for different types of situations

• There are tremendous benefits to aligning a company’s Strategic, Financial and OKR planning processes with a common set of activity and leading-indicator-based targets underpinning each. This makes real-time operational diagnosis and course correction infinitely easier compared to when these three activities are not tightly aligned

• When the macro backdrop rapidly changes, it can be tough to disentangle the impact of exogenous variables from internal execution when diagnosing performance. Here are two ways to approach this exercise objectively to figure out what is really going on

• Averages can be deceiving. It’s dangerous to gauge performance and make critical decisions using averages alone without understanding what is happening underneath. A case study

• How should one go about determining the optimal growth rate for a business? Here’s a generalizable framework for thinking about complex multi-product and multi-channel Go-To-Market strategy and resource investment decisions that optimizes for growth AND efficiency at scale

• When it comes to M&A, be clear on which of the 3 bets you are making, the base rate winning odds of each, and the variables that matter most in driving those outcomes

• When introducing net-new products, an organization needs to “nail it” before they “scale it”. Here, startup and venture rules should apply

• Accountability should always be tied to decision rights, even for complex cross-functional initiatives. Here are some examples of what may happen if those two things diverge