Women Of The C-Suite: Christina Ross Of Cube On The Five Things You Need To Succeed As A Senior Executive

An Interview With Sara Connell

… I think anyone can be an executive, but being a great leader is about fit and readiness. I was not always ready to be the leader that I am today and it took a lot of learning from leaders I’ve worked with, both great ones and not-so-great ones. They taught me what works, what doesn’t work, and to have empathy for what the other person in that situation may feel like. I’ve been the most junior person and most senior person at various stages in my career, so I bring that perspective in my experience as a leader.

As a part of our interview series called “Women Of The C-Suite”, we had the pleasure of interviewing Christina Ross.

Christina Ross is CEO and co-founder of Cube. She’s a 3x CFO and former finance transformation leader with experience in start-ups, pre-IPO, and enterprise companies such as Deloitte, Rent The Runway, GE, and Criteo. She is passionately mission-driven to help finance leaders become the heroes of every org.

Thank you so much for joining us in this interview series! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

Many founders follow the serial entrepreneur path; I am a recovering “serial CFO”. I started my career in finance at large companies like GE and Deloitte. I later found my way into the startup world at companies like Rent the Runway and Criteo — both which went public.

Similar to the transformation of HR into people operations, the role of the CFO is changing from a back office cost center to a value-driving strategic business partner. The challenge with this evolution is that finance teams now have greater responsibility, but are stuck with the same old tools. More than 80% of companies still manage all of their financial planning and analysis (FP&A) in standalone spreadsheets. Enterprise solutions in this space are clunky and challenging to maintain, sending most companies back to their trusty spreadsheets.

I faced this challenge head-on when I decided to implement a leading solution in my last role as CFO. After the implementation dragged on for months, the team couldn’t fully adopt the solution and we ended up going back to spreadsheets. In speaking with my peers, I learned that many others had the same experience and preferred to work within the tools they had been using for years, such as Excel and Google Sheets.

The problem was so clear and so large, that I couldn’t NOT do something about it. I quit my steady job as a CFO and took the plunge into the world of being a founder with no team, no product, and no funding. My idea was simple but profoundly different: spreadsheets are not the enemy, but they are no longer enough. Instead of replacing them, you must embrace them as part of a broader solution that meets the user where they are. Cube pairs the power and performance of enterprise software with the flexibility and familiarity of the stalwart spreadsheet.

Can you share the most interesting story that happened to you since you began leading your company?

Everyone has their pandemic story and ours was raising our seed round (after a successful pre-seed), during what seemed like the right time, March 2020. The first week of fundraising was from our offices, the second was from home, and by the third or so week, the Dow dropped 9,000 points in one day. Not the best time to raise capital! We were very lucky, though, and ended up with a few great options and signed with an amazing lead. We thought we were free and clear before we realized we needed to fill the rest of the round (very) remotely, as I left NYC for Vermont to camp out with my family waiting for this Covid thing to pass (little did I know)…

I spent the next few weeks raising the rest of the capital from a rental house, hunched over a spare nightstand as my desk, eating Newman’s Own pizzas — which we had stocked in a spare freezer — and drinking lots and lots of coffee. We were thankful for our health and ended up closing the round while still up north, which is where we spent the next three months figuring out what the world (and Cube) would look like.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

I accidentally kicked off a fundraise (and unsuccessfully)! A leading venture capitalist reached out when Cube was just an idea. A friend who was new to the investment community gave me some well-intentioned — but not the best — advice to take the meeting: if asked how much I was raising, to throw out a number. I didn’t realize that once you tell one VC that you’re raising a certain amount, the rest of the investment community will find out. Suddenly, I got tons of intros to other investors who thought I was raising. Before I knew it, I had fallen into an accidental fundraise before I was ready. Moving forward, I learned to control my own timeline and to manage fundraising on my own terms.

I’m an author and I believe that books have the power to change lives. Do you have a book in your life that impacted you and inspired you to be an effective leader? Can you share a story?

The Art of Learning by Josh Waitzkin. Its message is to work and train with people who are more advanced than you in your craft, appreciate the challenge they’ve provided you with, and have them make you better. At Cube, we value being nimble, so we need to always be learning and growing.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

There are too many to name; it took a village! A critical skill is learning who to turn to for specific knowledge or help. In the early days, it was friends and family who helped me get our initial investment and provided the early feedback to get Cube off of the ground. Now that we are at a later stage, our investors and my network of fellow founders and CEOs have become invaluable.

My biggest advice: spend time building your village, and it will pay off. I have my CEO network, investor network, friends, family, the people who take my calls late at night, people who are there to answer my little dumb questions (LDQs), and then the true-believers (the people who support me through it all).

As you know, the United States is facing a very important self-reckoning about race, diversity, equality and inclusion. This may be obvious to you, but it will be helpful to spell this out. Can you articulate to our readers a few reasons why it is so important for a business or organization to have a diverse executive team?

The world is full of complexity and nuance. To address it and understand your customers, market, and team, your top decision makers must have diverse backgrounds — so you can balance different perspectives. A diverse executive team will lead and serve as role models across your organization, and help you attract more diverse talent. If the team is homogeneous, it will be more and more difficult to become diverse.

As a business leader, can you please share a few steps we must take to truly create an inclusive, representative, and equitable society? Kindly share a story or example for each.

First off, think of DEIB as part of a company’s DNA, not an initiative to fill a gap or check box. We need to create an inclusive environment for our team and customers, which starts with values, and continues with culture. It is not solely about hiring.

We made a Director of People one of our early hires and quickly brought in several DEI consultants from the very early days. Through this early focus, we learned that fostering an inclusive culture that can support a diverse team is one of the foundational building blocks. For example, we use the term “culture add” vs. “culture fit”.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. Most of our readers — in fact, most people — think they have a pretty good idea of what a CEO or executive does. But in just a few words can you explain what an executive does that is different from the responsibilities of the other leaders?

The leader is the “Chief Clarity Officer”, communicating a vision, and bringing it to life by hiring the best people, giving clear direction, then working to support and unblock them for the good of the whole.

Clarity also means focus, and focus means having to say ‘no’… a lot. One of my favorite sayings is that “most startups die of indigestion, not starvation”, meaning that focus around time, resources, and capital will help you achieve your goals long term.

What are the “myths” that you would like to dispel about being a CEO or executive. Can you explain what you mean?

A common misconception is that CEOs don’t report to anyone or have a ‘boss’. In reality, as CEO, you serve your customers, team, and shareholders, meaning you ultimately report to everyone! I subscribe to the philosophy of “servant leadership”, which states that the goal of the leader is to serve their team, not the other way around. I focus much of my time on providing direction, decisions, and unblocking the team, while encouraging them to grow for the good of the whole.

In your opinion, what are the biggest challenges faced by women executives that aren’t typically faced by their male counterparts?

Being a female executive means dealing with the fact that attention is naturally drawn to your gender and away from the work that you’re doing. Being a “female CEO” shouldn’t be novel, it’s normal.

What is the most striking difference between your actual job and how you thought the job would be?

Staying laser-focused on your mission and goals means you have to cut out any and all distractions. I didn’t know I’d constantly be challenging myself to do less and lean in more on the things that truly matter. I think it’s important for all leaders to get used to saying ‘no’ with their teams. It’ll result in saying ‘yes’ to the things that really move the needle.

Is everyone cut out to be an executive? In your opinion, which specific traits increase the likelihood that a person will be a successful executive and what type of person should avoid aspiring to be an executive? Can you explain what you mean?

I think anyone can be an executive, but being a great leader is about fit and readiness. I was not always ready to be the leader that I am today and it took a lot of learning from leaders I’ve worked with, both great ones and not-so-great ones. They taught me what works, what doesn’t work, and to have empathy for what the other person in that situation may feel like. I’ve been the most junior person and most senior person at various stages in my career, so I bring that perspective in my experience as a leader.

What advice would you give to other leaders to help their team to thrive?

Practice calm persistence. Knowing that challenges are part of the journey will help you stay calm and focus on the solutions not the problems. This mindset will help your team practice calm persistence and that makes its way across the organization.

What are your “5 Things I Wish Someone Told Me Before I Started” and why?

1. You will get lots of advice, often conflicting with other advice you’ve gotten. Your job as a leader is to assess which advice to take.
2. It’s OK to apologize. Admitting you’ve made a mistake allows others to do the same and creates a more open environment where you can quickly move on and focus on solutions and learning instead of blame.
3. Guard your schedule with your life. It defines your energy, your priorities, and ultimately the direction of the company.
4. Trust your instincts. If something feels right or wrong, it probably is.
5. If this were supposed to be easy, everyone would do it.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.

Let’s normalize the idea that women and mothers make great CEOs. My hope is to encourage others to take the leap because having more positive female role models at the table is critical to inspiring others to do the same.

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them.

I’d love to meet the Prime Minister of New Zealand, Jacinda Ardern. Not only do I want to see a world where we normalize the idea that women and mothers make great CEOs, how about one where they make great world leaders too? She’s proven that acting with compassion, confidence, and humility is the future of leadership. It’s something I’m trying to instill in myself each and every day.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.