Culture-Focused: Finding your Second in Command

In the next series of posts, I’ll answer some questions I received related to hiring a #2 to help with company development and growth, building a team, bringing service management in-house, and OMG hiring/onboarding best practices. We have learned a lot over the past 10 years of growing our agency and these insights can help you skip several years of trial and error, even if you tweak for what best suits your personality and culture.

Q: I run an ad agency much smaller than OMG, but we’ve grown quite a bit. I’m looking to hire someone who can help my company continue to grow, take things off my plate and do so profitably. Up until now I’ve mostly worked with contractors. Do you have any thoughts on where I could start?

I started my career with OMG eight years ago when it was a team of five, with a master's in accounting and no prior knowledge of digital marketing. At the time I had a 19 month old and a two week old, and was just thankful to have found a job that allowed me to work part-time from home. I spent the first eight months cleaning up the books, sending out invoices and paying bills as needed. After eight months I approached Brett and Chris with a personal circumstance that had the potential to impact me professionally, as I was leaving my (now ex) husband and needed to be able to support myself and my children solo. This was an unexpected watershed moment in all of our lives as their decision to make me full-time allowed me to start working in the office, connecting with the team and getting exposed to the actual day-to-day of the business. I very quickly discovered what you likely already know - entrepreneurs are great at building businesses, but not always so great at developing them. New business was coming in on a weekly if not daily basis, but internally there was a lack of structure around pricing, processes, systems, and communication, not to mention hiring, onboarding, and training. Spontaneous decisions and inconsistency in process isn’t that big of a deal for a team of two, but as the team grew, structure was quickly becoming a crucial need. As the person responsible for our books and with so much on the accounting side revolving around the service side, my own need for consistency and structure quickly translated into process development. Over time, I became business manager and then COO, due to my ability to manage both people and processes.

When developing your initial leadership team, first focus on finding (or utilizing) someone who:

1. Shares your culture values.

We were very fortunate that Chris, Brett, and I all share similar values. When we sat down to define our mission, vision, and culture statements, we were in full agreement about what we did and did not want to be part of OMG. That said - not every value comes instinctively in every situation, for any one of us. Our culture is a standard to constantly be striving for, and we can hold each other accountable to it safely knowing we are aligned in the importance of those values. You may find yourself with a partner or team member in leadership who is not in alignment with your mission, vision, or culture values. It may seem like you have no option but to keep working with them, but while this may seem like it saves your business from crumbling in the short-term, it is guaranteed that you will regret it in the long run. A lack of agreement at the leadership level will break things at every other level, often getting deeper and more widespread than you’ll ever know until you finally A) let them go or B) crumble as a result. At the very least you’ll stifle both your fulfillment and potential success. 

It’s also important that each member of leadership has individual proactive autonomy, a true sense of ownership of their responsibilities, combined with a collaborative mentality. This keeps growth constant, delays minimal, and ensures that while everyone is moving forward of their own motivation, they are also committed to maintaining unity by communicating those decisions with each other as they go.

2. Has a combination of people skills and data skills, and balances your strengths/weaknesses.

What OMG didn’t need was another entrepreneur, all gas, no brake personality. They needed someone:

  • who could get shit done AND create processes and systems to help others GSD, who could see the big picture and the gaps in the details and implement what’s needed to achieve the vision. 
  • who had people skills and emotional intelligence, as they needed someone to take over the day-to-day management of the team.
  • who could understand and utilize data to make decisions. Digital marketing is a data-heavy industry, which excites some people and causes others to zone out. It wasn’t a stretch for me (retail+accounting) to enjoy learning about Google Ads and SEO in order to put efficient and effective processes in place. 

Now, just in case it sounds like I was alone in this effort, we had other team members who are also very process oriented and I collaborated very closely with them to create systems and processes (and who are also now in leadership… more on that later!). The primary value I brought to the table was being able to connect the people and the process, internally motivated to ask the hard questions without shutting people down, to question why and how and what we needed to support our team and our clients, and push to implement whatever we needed to become world-class.

3. Has the hard skills to be able to evaluate and make good business decisions (even if they have no digital marketing experience).

Anyone can learn digital marketing - if you find someone that has a questioning, proactive personality who enjoys working with people, processes, and data, that's a great start to building a partner you can rely on. My education in accounting and general business, as well as several years working in the retail industry deemphasized my lack of knowledge and experience in digital marketing and gave me the tools I needed to support the growth and development of the business. That said, I’m a huge believer in learning as much as possible about the actual work of the business no matter the role, both high-level and granular, because increased knowledge makes decision making, process and resource development, and communication that much more impactful. Additionally, my accounting background and initial accounting responsibilities for OMG means that I can’t help but mesh organizational development with financial planning and justification.

4. Is able to have candid conversations with you about the future of your business. 

Brett and Chris are 50/50 partners, and after a few years of growth, having two captains of the ship was taking its toll on the team and causing tension and a lack of unity in vision. Both of them dislike conflict, so it took objective perspectives to help them see the importance and value of defining their roles and responsibilities, a conversation that risks discomfort and tension by its very nature. I don’t like conflict any more than they do, but because I have the back of the team and the business, I was just as responsible to show them the need for the conversation as they were to have it. Your leadership team needs to be given the freedom and safety to say the hard things to you, or you risk limiting the true potential and success of your business. 

Brett then became CEO, and neither he nor I had ever run an agency or grown a business. It has been a learning experience for both of us at every stage of growth. It has been especially important for us to continually communicate and clarify what each of our roles are in order to avoid overlap and confusion with the team and frustration between us when we end up in the inevitable "mom vs. dad" scenarios. The great thing about our working relationship is that we both want to end up at the right place, and are willing to talk through our differing opinions and perspectives to get there. Our willingness to do this with each other, even in front of our team, sets an example of respect, transparency, vulnerability, and accountability from the top down. My directors know they can push back on my vision and perspective safely. Our team members know they can provide candid feedback about processes, roles, and clients without any fear of backlash.  In fact, it’s known to be a bigger danger to the team if they don’t share their perspectives!

You can always find people with experience growing a business through an Indeed posting, but our experience in clarifying our leadership and developing new team roles has been more organic than an intentional search, so I can only speak to that. Keep in mind that the statements I made in this post are my own opinions and are based on my personality and the needs of our business and may not be the exact recipe for success that works for you. However, if you are leading with character and candidness, once you have the right people in the right seats, I am confident you will have great success.

Related Articles

How to Crush your Q2 Email Marketing

As we step into Q2, all I can think is… WOW, Q1 came out swinging.

January 2023 - Conquer Your Email Marketing This Month

A new year brings new opportunities to grow your brand and make it more resilient.

How to Market in an Economic Downturn

We’ll always need stuff. That hasn’t changed and won’t change in this or any future downturn. How we market may have to change a bit.