What advice do you have for someone stepping into the CEO role?
When stepping into the CEO role, there are two crucial aspects to focus on: sales and people selection.
As it relates to sales, it’s important that you understand your company's dynamics, including the sales cycle, average selling price, and the marketplace landscape. Take your time to assess these factors before rushing to select a sales leader. Document your understanding, recognizing that you won't have all the answers right away, but you'll gradually move in the right direction over time. This process will equip you to make a more informed choice when picking who you’d like to lead your sales team.
As it relates to people selection more generally, this is arguably the most important responsibility a CEO has, particularly in larger companies. Even experienced executives can struggle with this, so establishing a systematic approach is key.
A valuable hack that I recommend to searchers is to hire a coach early on following the acquisition of your company. Utilizing a structured system for hiring relies on cycles of pattern recognition. When you spot a potential red flag, your pattern recognition skills will help you identify it. Coaches can provide valuable data points that will often be more accurate than your own judgments. Listening to expert advice and understanding their data collection methods can remove emotions from the equation. However, you’ll want to ensure that your coach provides clear explanations for their conclusions so that you can also learn and improve your own decision-making skills over time.
What accomplishments as an operator are you most proud of?
I’ve been proud of our team’s ability to craft and rally behind a compelling vision for the Company’s future. At Omatic, our vision is to make a significant positive impact in the world by empowering non-profits through technology as they drive to create meaningful change.
I firmly believe that having a clear and inspiring vision is crucial to every organization. As this vision has become institutionalized throughout Omatic, it’s allowed us to attract exceptional talent, which is our life blood.
What unexpected challenges have you faced?
One unexpected challenge was balancing our desire to hire top-notch talent while initially operating within the financial constraints of a small organization. We had to carefully assess who would be the best fit for our organization at a given time, which necessitated a more analytical approach to hiring.
I've come across numerous podcasts featuring former searcher-CEOs discussing this very issue. Dave Dodson, for instance, emphasizes the concept of hiring individuals today who align with your organization’s vision five years down the road. In my view, there are key areas within your organization where investing more heavily may be justified; while in other areas hiring less experienced individuals who can grow into their roles can be more strategic. However, it's crucial that these junior hires possess the capabilities to evolve into their roles. This process is akin to building a sports team: you need both established stars and future stars to succeed.
Do you have any advice for prospective searchers and/or those just starting their search?
I think that searchers should reflect on why they want to pursue entrepreneurship. Understanding your “why” will be essential when you inevitably face challenges both during the search and while operating your company. It will give you the strength required to persevere through setbacks, as well as the discipline to understand when to pass on certain opportunities.