Taking the Elevator for an Early Rise to the C-Suite

There is a famous quote that reads ‘when you’ve reached the top, send the elevator back down for the others.’ When I consider this in the context of my own journey to becoming a Chief Revenue Officer (CRO), I know I have been fortunate to have mentors who subscribed to this same view.

For a C-level executive, I am at the younger end of the age spectrum. If you asked me for career advice, I will say that a key to my early success has been getting comfortable with being uncomfortable, and surrounding myself with mentors who offer their wisdom and guidance based on their own hard-won experiences.

The clear metaphor of the famous elevator quote is to be prepared to help those behind you on the ladder. By sharing what you have previously learned, you practice the critical management skill of coaching others; while also helping to build the next generation of leaders.

The path to the C-suite is paved with…

leaders who failed to make the fundamental shifts needed to lead at an enterprise level. Too often, companies fall back on a traditional path to senior leadership that relies on incremental increases in responsibility. I arrived at my position in the C-suite faster than many executives, and with barely more than three decades of life experiences to draw upon.

Getting comfortable being uncomfortable isn’t an easy thing to do. We try to put on a costume of what we believe a leader should be. The end result is a palpable sense of inauthenticity. Realizing that I didn’t get here alone is a double-edged sword – an authentic sense of humility is a valuable leadership skill…self-doubt is not. I subscribe to self-confidence, not ego. I aim to be transparent even in failure, with a scrappier mentality that comes from being raised in a blue-collar household and resulted in a desire for more.

As the first in my family to attend college and go on to graduate school, I learned that a fire in your gut is what propels you when 95 percent of your job is not fun. The majority of the CRO job is navigating uncertainty. There must be a sense of ‘something greater’ that motivates you. It feeds the fire.

Inspiring and leading a workforce

Right now, my org is nearly 250 people. This group spans Marketing and Sales delivering all service to our clients. For a team this broad, it’s critical to realize that different motivators work for different people and situations. For example, when it comes to sales, my team is already hyper-focused on results. So, it matters less to me what methodology they use than it does that they are process-focused and understand how to hit a number. I frequently tell reps that if they fail to get buy in from customers on what we are selling, or if they fail to establish a reliability and predictability for everything they do – we will quickly lose the trust of our CEO and the Board of Directors. You cannot close a sale through sheer force of will. If you try, what comes next is called ‘job hunting!’

Providing the best service to our clients is my key concern. Here, it is more about balancing headcount with value creation to deliver what sales is selling. While the vast majority of this team is more technically astute than I am, the value I provide is an understanding of business operations and removing obstacles. Often, the goal to provide the most value while increasing productivity can seem diametrically opposed, making the balance difficult to achieve.

I aim to inspire the team through accountability, both to me, and from me. I want my teams to face problems head on and talk with me about what impedes their progress. I want them to have trust in me, but to know my expectations very clearly. By working to eliminate uncertainty, I remove ambiguity, and I always help to develop a plan for getting them where they want or need to be. Everyone’s KPIs are based on the organizational goals we share. This approach gives everyone clarity, and through the same philosophy for getting the work done, we experience success.

Being vulnerable is not a weakness

As a leader, there is great power in showing vulnerability and admitting failures. To show value in your organization, the buck must stop with the executive in charge. If I see that members of my team have hit a wall, I’m the first to encourage them to shut the computer and take a break. We are human, and there will be times we need to refocus energies around personal priorities. In fact, this is never more true than in recent months, as the global COVID-19 pandemic sidelined most people’s planned vacations and other outlets that normally take them away from work for a period of time. Burnout is real and it’s incumbent to lead from the front in allowing your team to see you power down.

To build a cohesive and functioning team, I try to cultivate real relationships with my employees. I do this by showing vulnerability and being authentic to who I am – both the good and bad.

Learning to take a compliment

A team member once said that it worries them that I am always calm. While humorous, I took this as a compliment. It reminds me of watching a duck calmly floating on the surface of the water, while its feet are frantically paddling beneath. If I allow my composure to fluctuate, I risk creating an environment where staff is fearful, or too timid to ask for help when something happens.

I want my team to feel empowered as part of the solution and turn difficulties that we encounter into a collaborative effort to win.

Paving the road while you are on it

Organizations change over time and have to maintain a toughness amid fluctuating market conditions. Despite the pandemic, working from home has had a positive impact on team productivity. There is no doubt that this has been the most stressful time in my career. Managing the unknown is never easy – and what’s worse is the lack of roadmap for operating a business in a fully remote arrangement. Anything we previously relied upon is out. Anyone who says they have done this before or managed through this amount of change is lying.

This is especially true when navigating business forecasting. Missing a number or mismanaging the business can have a significant impact on someone’s job and life. On any day, I am balancing numbers, ensuring we are delivering value to clients, adjusting processes, asking VPs to be aggressively realistic, examining markets, working cross-functionally with our executive team, and more. None of us know what is going to happen in the long term. So, I am trying to also apply empathy to my team’s efforts and remember that holding their feet to the fire unrealistically will only erode the trust and confidence I have been working to build.

My team and I have learned that we must make every effort to understand our customers and how our portfolio of products impact their businesses. In examining what drives their decision to buy, we can inform how we choose to communicate and ultimately what their perception is of the value we deliver to them. Unless a customer believes in the value you’ve delivered, you haven’t delivered any value.

Finally, be prepared for times that you might need to pave a road while you are on it. You might need to rewrite the rules of your job as you go. And that is okay, as long as you remember to send the elevator back down.

About Dave Gerry 1 Article
Dave Gerry is a global revenue and operations executive leader specializing in turning-around, leading, and growing revenue and service delivery engines to drive profitable, double and triple digit bookings growth. Focused on the cybersecurity industry, Dave has held executive roles at dynamic organizations like WhiteHat Security, Sumo Logic, Veracode and The Herjavec Group. He holds an MBA from Suffolk University and a BA from Merrimack College.