“How did they do that? How did they get there?” Companies succeed because of the people who build them - operating leaders who grow businesses to new heights and make decisions every day that can impact entire industries. Each month, our Operator Spotlight gives you the inside track from one of our incredible Operator LPs (Limited Partners) who are changing the game – building and scaling some of the world’s most successful companies. Read on for lessons learned and mistakes made, perspectives from the top, practical advice, and ideas on what’s next. 

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This month, we chatted with Helen Wang, Chief Financial Officer at OpCo PortCo Ironclad, the global leader in digital contracting. Prior to Ironclad, she was the Chief Financial Officer for eBay’s Global Payments business, where she helped scale eBay’s Managed Payments platform to over $2 billion in run rate revenue. Helen began her career in M&A, leading teams at both eBay and Rothschild Inc. She graduated from Harvard Business School as a George F. Baker Scholar. In her free time, Helen can be found chasing after her children and/or playing doubles pickleball with her husband.

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What was it about Ironclad that inspired you to make the jump from eBay?

When I thought about my next role, there were three things that I was looking for - I wanted to step into a job that would challenge me, and where I felt I could contribute. I wanted to be in a space that would be new to me, and where there was a substantial addressable market that we could go after. And finally and probably most important, I wanted to work with amazing people that I enjoyed and could learn from. Ironclad offered all three.

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After spending seven years at a large public company, what were some of the biggest challenges and key learnings you experienced joining a startup?

At a big company, the infrastructure is usually already in place. One of the things that drew me to Ironclad was the opportunity to build something from scratch. The job is just so different when you are creating something new! It’s harder in many ways, but you have the chance to build it the way you want from the bottom up.

One surprising lesson, to me, is the extent to which previous experience can apply to a very new environment. What we do at Ironclad (B2B SaaS) is so different from eBay (consumer internet) and my past work, but there are still opportunities to apply what I’ve learned. I think of it as pattern recognition. I can look at some metric or trend, and think, Where have I seen this before? And you realize, oh I know what’s going on here, because it’s something that connects to something that I saw years ago. The principles of finance apply everywhere if you are looking for them!

Another huge area of learning, and source of joy, for me is the experience of building a team. That has been such a special opportunity and a huge part of the reason why I love my work so much.

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What practices have you adapted in response to the current macro environment, and any predictions on what’s to come? 

Cash flow always matters, in good times or bad, but when things get tight it is absolutely vital. The game really does become about free cash forecasting. During the 2008 financial crisis, I saw some really good companies shut down – not because they didn’t have product market fit or great customers who loved their product, but simply because they couldn’t make payroll! These were promising businesses with strong teams and innovative products, but they just ran out of runway.

That’s how important cash flow is. It’s not just another metric on your dashboard. It is freedom, the ability to control your own destiny, and it should be everyone’s first priority right now.

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There’s a lot of chatter about the impact of AI in the legal field, how are you thinking about its application and the evolution of legal tech? What are you most excited about? 

For so long, Legal was the last place you would go to see cutting-edge technology. The industry has always been seen as slow to evolve, resistant to new practices and ideas. That started changing a few years back with the rise of a vibrant Legal Tech sector, and now this new wave of AI is accelerating everything tremendously. Legal is a perfect playground for generative AI, so it makes sense that our industry is now seen as an innovation leader.

The opportunities for impact are quite vast. At Ironclad, we’re seeing our customers, in-house legal teams, use AI to review contracts 20 times faster, eliminating the drudgery that has always defined so much of their work. That isn’t evolution - it’s revolution. The technology is freeing them up to focus on the higher-level strategic thinking that they went to law school to do. It is not just improving their job; it is shifting their role in a fundamental way.

That’s what I’m most excited about - how AI can be used to help lawyers and legal professionals do the jobs they entered the field to do, rather than the manual paperwork that occupies a lot of their day. 

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What are some things that people often get wrong about the finance organization in a company? 

There are so many! I always tell people: “We are not CF-Nos”. We are not here to deny you and to restrict the business. We are here to enable our operating partners. Our job is to help those partners make bigger, better decisions faster. So yes, we have to look at dimensions like risk and cost, but we also have to look at strategic context and opportunity.

We are not specialists who occasionally step out of our “finance lane.” We consistently engage with all of the parts of the business and all of the people who make the decisions and do the work. The relationship side of things is vital. I think that gets missed sometimes.

Finally, I think the role that CFOs play as “connectors-in-chief” isn’t widely understood. Because of where we are in the organization, we have a view that spans everything - every operating decision, incremental headcount, and dollar spent shows up in the P&L. So who else is better positioned to ensure that all the pieces and plans fit together? So if you see the product team is pushing to develop a new higher-end product, for example, you should be looking at the service organization and making sure they are building the skills and capacity to support it. A good finance team helps ensure that the teams are all aligned to a common strategy and to each other.

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How have you made a mark in your industry? What’s something you’ve done that’s perhaps counterintuitive in your field - broken any rules with interesting results?  

I would say one thing that I do that may be a bit different than the norm lies in the curiosity I bring. I hate the idea of just staying in one lane, just being the finance person who asks the classic questions and focuses on the usual numbers. I’ve always been really interested in how and why things work the way they do, and I think that curiosity helps me be a better partner and CFO.

When you ask questions, when you pull on threads, you can sometimes spot opportunities that might be hidden. Sometimes, something that seems totally disconnected can lead to a really interesting discovery or uncover a fresh opportunity. And that’s something you miss if you don’t have the interest and the openness to go deep with the people and the business.

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What’s one piece of advice you would give to yourself ten years ago, if you had the opportunity? 

Do the scary things! It is really easy to stay in your comfort zone, to keep doing the things that you think you know you do well. In hindsight, I probably waited too long to move out of doing deals as an investment banker and corporate development professional into operating finance, and when I did it felt scary and very new. But once I made the change, I loved it and have never looked back! 

Just because you are good at something doesn’t mean you should do it forever. Once you know a path is not for you, move on! Close that door and open a new one, because that’s how you find what’s right for you. Seemingly shutting down and closing off paths can be hard to do for all of us, particularly when we are younger and earlier in our career, but it’s such an important lesson.