CMO Interview Series: Roger Greene

Eliza Jaskolski
Talent Manager at HireCMO

During my journey of building HireCMO, Roger was one of the smartest and kindest Chief Marketing Officers I came across. His sound of knowledge in marketing, combined with his patience for explaining complex topics, makes him a perfect mentor and colleague.

I had the privilege of asking him some questions that a lot of newbie CMOs often struggle with. These are uncomfortable topics that, when asked, might make your boss almost question your integrity/skillset as a marketer - but not with Roger.

Roger understands that we all start from somewhere. He is an entrepreneur at heart and built two companies himself, in addition to having multiple exits - one a company he founded and another being one he joined. It’s crazy (and pretty unique) when you think about it!

Given his scrappy mindset and ability to scale things from scratch, Roger has driven defensible growth across a variety of Direct-to-Consumer (DTC) and Software-as-a-Service (SaaS) businesses. And today, I’m hyped to have him on as a guest! Let’s get started.


Roger, absolute pleasure having you on today. The first time I talked to you, your demeanour and attitude of welcoming my questions about your CMO interview process really caught my attention. And so given that we’re going into a turbulent economy where many senior marketers are exploring the fractional CMO role, I thought this might be the perfect topic to talk about. Ready to dive in?




Q1 - When you went through the CMO hiring process, you mentioned you had to go through several rounds of interviews from your current company.

Is there anything that stood out as particularly unique about the overall process/filtering steps they took?


The hiring process for my current role (at was pretty unique in general because the situation, while not unique, wasn't typical. I joined this company after it was purchased by a Private Equity firm to scale up and flip (as PE firms do).

There was no marketing department before hand so no one was being replaced, a function was being added. Additionally the founders of the company were stepping back so an entirely new executive leadership team was being added. Therefore I wasn't interviewed by an existing CEO, COO, etc. I was interviewed by the PE owners and only had a quick 30 minute interview with the incoming CEO after he was hired, but hadn't started yet.

Since the marketing function was completely new to the org, the interviews centered around what people, processes, and tools would be needed to build the department and rapidly scale the organization. It was very focused on what the means were to accomplish the PE firm's objective of having a big exit in 3-5 years.


Q2 - What type of questions were you asked that you believe are extremely, extremely crucial to ask CMOs who want to join a high stakes business?


As a CMO you're responsible for the overall marketing department so I think it is critical to arm yourself with as much information about the situation you're entering as possible. Less so about being asked questions and more so about asking a lot questions to establish what is needed to be successful.

Most of the questions you get will be centered around outcomes, so you have to marry the what the outcomes need to be with what you need in order to achieve them. Coherently explaining why you need X & Y in order to accomplish Z is the most critical thing you can do in the interview process.


Q3 - Being a c-suite executive/marketing leader means handling much more than just the growth/marketing objectives of the company. There's company dynamics, politics, carefully handling employees' expectations, bonus surprises, etc.

Since you've led such roles at 5 companies so far, could you talk to us about some crucial challenges that a newbie CMO / Head of Marketing is likely to face in their role? Would love a good story here haha.


For a newbie CMO/Head of Marketing specifically, you need to think about how you set yourself up for success. If you're coming into a new organization or being promoted, you need to consider the environment you're entering and the expectations: is the team underperforming and in need of a turnaround? Is the company entering a phase of rapid expansion and you need to create a growth plan?

Regardless of the situation, you need to have a clear view of what you're stepping into so that you can assess how to bank early wins. This is absolutely critical for someone new to the lead role. You don't have a track record of C-level experience to fall back on, so you need to make sure you identify a handful of wins so that the rest of the team (and board) feel confident that you're going to be successful.


Q4 - A lot of marketing operators who've been in the field for 10+ years often face a dilemma/imposter syndrome when applying for the "grand" Chief Marketing Officer role. And it makes sense, you know? It's a new thing for them. More responsibility. More skin in the game. More to lose.

What're 2 unintuitive, yet highly important tips to keep in mind as an aspiring CMO steps into his/her role? This can be around any topic that you personally think is crucial.


I don't know about everyone but I definitely felt the imposter syndrome when I stepped into leadership. I don't know if I have two tips for helping with it, I just have one that helped me a lot and unfortunately took me way too long to figure out: It's okay to not know everything.

Part of imposter syndrome is that you feel like everyone else is a million miles ahead of you, that they already know everything and you don't and therefore you don't belong. Relax.

There are gaps in everyone's knowledge, everyone is building the plane as they fly it, it's okay to not know everything. Ask questions, ask for advice, consult with your mentors. Ultimately remember that you have a team of smart people working for you and around you, all of whom want to share their expertise and be successful.

Let them help you.

What I loved about Roger’s responses is that he’s very grounded and does not make excess effort of masking his true experiences. After having interviewed and spoken with 100+ founders and marketers as part of building HireCMO, I’ve realized that the most confident individuals are those who are open to being wrong and actively learning from others.

And that holds true especially in the realm of marketing and leadership, where you’re challenged every month by your competition to find creative ways to grow your bottom line and continue cutting costs in this turbulent economy.

I sincerely hope that if you’re a marketer aiming to step into the Fractional Chief Marketing Officer role, that this article boosts your confidence and gives you actionable items to work with!

And if you would like to work with Roger as your senior marketing leader within your startup or organization, feel free to have a chat with me and I’ll personally take care of you. You can always use the search function on our site if you're looking for something specific.

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