Tank Commanders vs. Foot Soldiers: What Role is Required?

Every good leader knows the importance of making the right hiring decisions. We have previously highlighted that Jim Collins stressed the importance of “getting the right people on the bus” in Good to Great.

Finding the right person for an open role is clearly paramount, but what is sometimes overlooked is determining what is the right role at the right time. This is particularly true when filling out the executive team of a growing technology company. The right hire can accelerate growth, and the wrong hire can set you back, potentially by years.

Here are some of our key lessons learned on hiring executive roles:

Hire for the Current Stage, Not for Future Plans

Early in our SaaS growth journey, we were looking to invest more in sales to drive growth. We thought we needed a functional expert who could build out our Sales capability. So, we hired a Chief Revenue Officer. He had decades of experience leading sales organizations and designing sales processes, and he was an excellent cultural fit. We were confident we had hired the perfect person for the role. But we did not understand that we had hired for the wrong role.

At that time, we only had two dedicated sellers, and we were still innovating and iterating our GTM strategy. One of our board members, himself a former operator, said it best: “You hired a tank commander, but we need foot soldiers.” He was right. We had not positioned our new CRO for success because we did not need a CRO. We didn’t need organizational and process design, we needed quota-carrying sales reps and a sales management leader.

New Functions Need Builders, Not Managers

Around the same time, we were also building out a Marketing capability. In our days of building custom software in our tech-enabled services model, there were not really products to market. So, the notion of product marketing was new. We considered hiring a CMO, but thought that people in that role would be too far removed from the real work of building a product marketing capability: writing content, standing up a MarTech stack, and designing tactical campaigns.

We determined that the right role was a VP of Marketing. We wanted someone eager to be hands-on: willing to partner with us on writing content, possessing the technical know-how to implement a MarTech stack, and comfortable designing, deploying, tracking, and measuring campaigns. For this hire, it quickly became clear that we had hired for the correct role. We found someone excited to partner with the founders to define our strategy for marketing, but who had the skills and desire to take on some of the important work of building tactical capabilities.

Another benefit of hiring a hands-on leader for a new (or to-be transformed) function is that they understand what you are doing at a detailed level. Any new or transformed function is likely to go through a period of rapid iteration as you seek to get it right. When you are innovating and iterating, the right leader needs to be in touch with exactly how things are working and what needs to change to improve performance.

Match the CFO to the Moment

Early-stage tech companies always face the question of when the right time is to bring in a CFO. But equally important is the question of what kind of CFO do you need? CFOs can range from highly tactical, like a next-level Controller, to Finance-focused CFOs, to “jack-of-all-trades” CFOs with experience running more operational functions like HR and IT.

The right kind of CFO depends on the needs of the business. For a bootstrapped business focused on organic growth, the “next-level Controller” CFO is often a good fit. Or one could pair a strong Controller with a fractional CFO. But if a capital raise or a potential exit is on the horizon, the company will need a more strategic CFO. The larger the business and more complex the finance issues, the more a Finance-focused CFO will be required. However, that level of specialization requires a larger team and more functional leaders.

As our ARR surpassed $10m and we began considering raising additional capital, we found the “jack-of-all-trades” CFO to be extremely valuable. It enabled us to keep our leadership team lean, since he could handle leading operations as well as Finance. He could also handle lighter legal work, which saved us both time and money. And most importantly, when it came time for potential investors to do due diligence, the breadth of his role made it easy for him to handle the bulk of the due diligence requests. That helped keep the potential transaction confidential, the team focused on the day-to-day, and the diligence responses rapid and accurate.

The overarching lesson is that the right role at the right time depends on the specific circumstances of the business. For that reason, determining the right role is not a question that can be answered by playbooks alone. The decision must be made within the context of the business. For example, a $15m SaaS company with 1,000 customers (and thus a $15,000 ASP) needs a dramatically different sales organization than a $15m SaaS company with 20 customers ($300,000 ASP). The first needs a large sales team and multi-tiered organization that includes a robust management layer and a strong rev ops function. The second likely relies on a handful of enterprise sellers with 7-figure quotas. They would not need a large management layer, and the deal volume would not support a full-time rev ops function.

Playbooks can tell you what roles to hire. They can't tell you when the time is right for the role. That requires operators who understand the stage of the business. It's one of the most important decisions a board and leadership team can make. Get it right, and you've got the leader your business needs today. Get it wrong, and you might have a tank commander without a tank.