The "passion over pedigree" principle: How Simon O'Kane scaled 4 unicorns without hiring "perfect" candidates

From Salesforce pioneer to revenue architect

What was the pivotal experience that shaped your approach to building revenue teams?

Joining Salesforce in 2005, when it was a really tiny company, was transformative. Before that, everything was traditional on-premise solutions. We were there for the birth of software as a service—they hadn't even invented "SaaS" as a phrase yet. It was a privilege to see that whole industry being born over seven years.

What struck me was how small companies could disrupt massive incumbents. The history of tech is littered with examples because smaller companies can move faster, they're more joined up, and there's less politics. That became my template: find high-quality SaaS products that are disruptive and help them scale through the right people and execution.

Since then, whether taking Ideagen Huddle™ into the US market, scaling Qualtrics from a handful of people in Europe to 700+ across 11 offices, or growing Asana's enterprise business, it's always been about joining companies that are disrupting legacy players with modern technology.

The contrarian hiring philosophy

You've mentioned rejecting candidates with impressive backgrounds in favor of "passion over pedigree." Why do you take this approach?

Recruiters always want me to say I need candidates with X years of experience from these specific companies. I actually care very little about that. For a new business that's scrappy and early-stage, it all starts with passion, drive, and enthusiasm.

I know that sounds fluffy, but here's the reality: anybody can do the first three months. After six months, ten months, or two years, when you're beaten down and facing obstacles and failures, it's that inner drive that keeps you going. We used to call it looking for "that chip on the shoulder"—what's really eating away at that person to drive them to greater success?

The temptation to lower the hiring bar when you're driving for growth is enormous. But if you can resist that and go through all the steps—reference checking, committee decisions where anyone can veto—then everything gets easier. We build in rigorous processes, but the foundation is still that spark, that drive.

Building scalable revenue operations

How do you balance empowerment with the need for consistent execution across global teams?

My style is to treat people as grown-ups. There are two management styles—parent and child, where you keep telling people what to do, versus empowering people. I provide vision and direction, keep people inspired and motivated, and then make sure they have the resources and space to execute.

We're over 200 people now at Yokoy. If you can get everyone of those 200 thinking like an owner and believing they have autonomy to act, it's exciting. That's what I saw work at Salesforce, Qualtrics, and Asana.

But empowerment without structure fails. People tell me every country is special and unique. I honestly don't buy it. Maybe 5% is different, but 95% should be the same. We need a cookie-cutter approach because we're building a machine that's repeatable. If we start having different approaches in each country, the whole thing unravels.

The "cracked the code" moment

When should a growing company stop experimenting and standardize its approach?

As soon as you've really cracked the code, figured out your ideal customer profile, and the right way to sell. That can take a year or two, but once you've identified what works, baking that into a playbook approach is powerful.

I always get into debates with salespeople who say they don't believe in prospecting or sending emails. I'm like, "I've got the data. Bring me your data that proves you can do it better, and we'll do it all day long. But until then, do it our way."

Once we've proven the model works, you want consistency. Salespeople are creative, and young people want to reinvent selling, but we don't have time for that. What we ask them to do isn't fun—it's repetitive prospecting—but it works.

AI as enhancement, not replacement

What's your perspective on AI replacing sales development representatives?

I believe AI can replace certain SDR functions, and I've seen it proven. A friend tested AI against his SDRs—first month SDRs won, second month SDRs won, third month AI won.

AI can do a better job at baseline prospecting, finding names, and initial outreach. But I think the SDR role evolves: AI gets you to a qualified prospect, then an SDR takes the conversation forward. This enhances the role and gets them ready for sales faster, which is what most SDRs want.

All the AI tools are fantastic, but they enhance sales to focus on what successful salespeople do—manage relationships and build consultative, trusted connections. That's what AI won't do in the short term. When I advise young salespeople, I tell them to become strong consultative sellers, not just transactional order-takers.

The pipeline obsession

What metrics drive sustainable revenue growth?

Beyond hitting targets, it's activity levels and pipeline. People want nuanced approaches, but over time, high activity levels correlate with success. We obsess about pipeline daily, by individual, country, team, and lead sources.

We break down silos through what I call a "pipeline council" - marketing, customer success, sales, SDRs working as a team instead of blaming each other. The first meetings are tough because everyone's pointing fingers, but once you realize "we all own this," it becomes powerful.

Win rates fascinate me. Two salespeople sitting next to each other with the same opportunity shouldn't have dramatically different win rates, yet they do. That tells you something about process, training, or fit.

The Salesforce customer success revelation

How did your early Salesforce experience influence your approach to enterprise customers?

Before Salesforce, customer success didn't exist - you had support, but not success. In traditional on-premise companies, customers weren't having success, and frankly, as salespeople, we just moved to the next deal.

Salesforce changed that. With monthly subscriptions, you have to ensure customers succeed. That philosophy became core to every SaaS company I've joined: get maniacally focused on customer success. It's not just a role or job title - it's a philosophy where every employee cares passionately about customers getting more value each year.

Back in pre-Salesforce days, we'd fight to find one customer to speak at an event. At Salesforce, they were queuing up because they were passionate and excited. When customers talk to each other about you positively, the network effect is magic—you notice it in your leads, and people start coming to you.

Post-merger integration mastery

Yokoy was recently acquired by TravelPerk. What makes M&A integration successful?

We were very lucky—TravelPerk and Yokoy have worked together almost since Yokoy's formation. We know each other extremely well, and there are complementary elements with no real overlap.

The key is to communicate, communicate, communicate. I've seen companies remain silos three or four years post-merger - then two plus two equals less than four. Heavy communication, being open with people, and providing opportunities are crucial. In a bigger organization, you should create more career opportunities rather than hiring externally.

We're four or five months in since the announcement, and it already feels like one company. We've been lucky with cultural alignment, complementary products, and meeting a real market need - people want a combined travel and expense solution.

Lessons for revenue leaders

What advice would you give to other revenue leaders scaling in uncertain times?

Everything starts with product and people. If you've got a good product and can bring in high-quality people, everything else gets easier. Focus on execution, be scrappy, and win deals.

Don't get caught up in the complexity. Sales is simple: do the right activities, drive the right pipeline, know your win rate, and hit your targets. Strip away the myths and fancy talk—if you're driving the right pipeline consistently, you'll be successful this quarter and the next.

Most importantly, hire for that inner drive. Skills can be taught, processes can be learned, but that chip on the shoulder—that's what separates good from great.

Book recommendation

When asked about essential reading for revenue leaders, Simon recommends "The Hard Thing About Hard Things" by Ben Horowitz: "It's the most honest book about what it's really like to build and scale companies. Horowitz doesn't sugarcoat the difficult decisions you have to make, especially around people and culture. Every revenue leader should read this—it prepares you for the reality that building something great is hard, but that's exactly what makes it worth doing."

Final thoughts

What resonates most about Simon's approach is his commitment to simplicity in an industry obsessed with complexity. While others chase perfect resumes and elaborate strategies, he's built four unicorns by focusing on fundamental human qualities: passion, drive, and the willingness to do the work that others find boring.

In an era where AI threatens to automate everything, Simon reminds us that the future belongs to those who can combine technology with human insight, data with intuition, and global scale with personal connection. For revenue leaders navigating hypergrowth, his philosophy offers both practical frameworks and timeless wisdom: hire for character, standardize what works, and never stop focusing on the fundamentals that drive results.

Simon O'Kane is Chief Revenue Officer at Yokoy , where he oversees Sales, Marketing, Customer Success, and Professional Services. Under his leadership, Yokoy has disrupted traditional spend management with AI-powered solutions and was recently acquired by TravelPerk. Connect with Simon on LinkedIn to follow his insights on scaling revenue operations.