
Lessons from 3 SaaS Unicorn CEOs
Over the last 20+ years, I have been fortunate to grow my career working across a diverse group of people at multiple business-to-business (B2B) companies.
Working in Software-as-a-Service (SaaS) startups on a sprint to unicorn status has proven to offer the most valuable lessons in my career. The focus and urgency in a high-growth organization is completely different from a Tech Titan — such as Microsoft (where I worked for 4+ years). I’ve been fortunate to work directly with 3 SaaS Unicorn CEOs:
- Chris Heaslip, Pushpay (NZX: PPH)
- Rod Drury, Xero (ASX: XRO)
- Jamie Ellertson, Everbridge (NSDQ: EVBG)
Each of these CEOs brought their own strengths to the game, then hand-picked executives, who are domain experts in their respective areas to fill the gaps, to then optimize for success. My observation is that a CEO tends to demonstrate a core focus in one of five areas: (1) Marketing, (2) Sales, (3) Success, (4) Product, or (5) Operations. A core focus is frequently complemented by a secondary area of attention.
While a competent executive can be proficient in many areas of the business, a CEO’s “world-view” is often shaped by their core focus. I’ve been fortunate to work with 3 SaaS Unicorn CEOs — each with a different primary and secondary area of attention. Here are the lessons that I learned:
Chris Heaslip: Sales (1st) & Success (2nd). At Pushpay, Chris Heaslip built a strong culture maniacally focused on Sales, and increasingly Success. Chris is a self-described “pragmatist” — but the rue of the day is top-line revenue growth which permeates Pushpay culture. This emphasis helped propel Pushpay’s rocket-ship trajectory. Chris also cares deeply about Pushpay customers; he routinely making personal visits to meet face-to-face.
- Lesson #1: Building a great Sales organization can help build a “winning” culture and fuel enthusiasm and energy in the office that is infectious (and attract talent). The risk, of course, is the downside if and when you miss your numbers, and the potential disenfranchisement of failing to recognize the contributions of non-Sales teams.
Rod Drury: Product (1st) & Marketing (2nd). Prior to his retirement, Rod’s leadership as CEO of Xero was characterized by an obsession with Product innovation, and secondarily Marketing (brand). Rod had a gift to see the future of cloud accounting and the financial web (aka “crystal ball”), which enthralled all Xero employees and Xero partners alike. Rod’s careful attention to the perception of Xero’s brand and storytelling helped elevate accountants to look like heros.
- Lesson #2: Product innovation can transform and disrupt even the most mundane professions (e.g. accounting), empowering professionals to transform their lives — and their customers’ lives. The risk here is failing to build your Product to address current needs, while considering future evolution of the industry and/or failing to convey customer stories that accrue to your brand.
Jamie Ellertson: Operations (1st) & Product (2nd). I worked with Jamie when he was CEO of Gomez (prior to Everbridge). As a non-founder CEO, Jamie is probably the most grounded and well-rounded CEO with whom I have worked during my career. He has a gift for Operations and building a strategy and plan to win in a given market. Jamie also recognizes that while Sales and Marketing are always important, Product efficacy is paramount in a SaaS organization to garner the loyalty of your customers. No surprise, Jamie has multiple wins as a repeat-CEO.
- Lesson #3: Assembling the right team is important, but an Operational strategy and plan is fundamental to win. Consider how many “lesser” talented teams and “sub-par” products have won, when they have a great coach and a game plan. In SaaS, customers will only renew their subscription if the Product delivers. The risk, here, is relying too much on hiring top-shelf talent with long resumes (expensive), without articulating a clear strategy and plan to win, or failing to commit resources to Product development.
What’s next for me is employing these lessons at Barn2Door, a B2B ecommerce platform for local Farmers and Chefs. I’ll have the pleasure to work alongside my spouse, Janelle Maiocco, who as a CEO is Success-minded (1st), followed closely by Product (2nd). As her Chief Operations Officer (COO), I’ll aim to complement her strengths with a focus on Marketing, Sales and Operations.
Something attracts me to SaaS Unicorn CEOs — and in the case of Barn2Door, the numbers indicate an even larger market opportunity than the previous companies. I am looking ahead to this next chapter, the lessons and sprint to unicorn status.
