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Laying the Groundwork: How to evaluate a Marketing Leader as Founder or CEO

Let me get one thing out of the way real fast. Don't waste time with having marketing leaders do a full-scale strategic plan or project to make it through rounds of interviews. When you hired your Sales leader did you have them go build out their entire forecast for the month, year, and book pipe before they are hired? I highly doubt it. Don't do that to Marketing Leaders or it will start off on a bad foot. A good leader will see this as a red flag. Truth bomb: I have had orgs steal my plans and have a different leader implement them because I didn't meet diversity requirements. Don't be those people.

This is not the way. A good leader will have a plan, be able to communicate it at a high-level, and tease their strengths, secret sauce, and ideas without revealing the whole thing.

Define the role and responsibilities

  • Clearly outline the responsibilities and expectations for the marketing leadership position.

  • Set clear expectations on what the role will not turn into. If you are hiring for a Head of Marketing or VP of Marketing as your first Marketing leadership role, make sure you set the expectation clear. if you have no plans to make the initial role into a C-Suite in the future, like a Chief Marketing Officer, then don't say you will. This is often times a big reason Marketing Leaders leave

  • Identify the key performance indicators (KPIs) that will be used to measure their success

  • Make sure you give them a seat at the table. Make sure they ask for one.

Assess their experience and qualifications

  • Review the candidate's body of work. Do they have examples of how they have helped previous companies grow? Does some of their previous experience focus on relevant experience in your industry or with similar companies

  • Remember that not all experience warrants a successful outcome. Just because the start-up they worked for last didn't make it that doesn't mean it was a reflection on that leader. Be careful not to immediately disqualify people like this.

  • Do they have experience hiring teams, building a strong team, and finding the right talent

  • Remember not every start-up is successful that doesn't mean that leader was solely responsible so don't just look at successes look at how they come out of failures as well

  • Hot take on Degrees: I really don't think they mean anything TBH. But, if you are a believer in that. Check for any advanced degrees or certifications in marketing or related fields

Budget Management

  • Have they owned a P&L before or at minimum a budget?

    • If they haven't that's not terrible you can help them and there is tech out there that can make it super easy and efficient check out plannuh.

  • If they owned a budget:

    • Ask them what the biggest budget they have owned is

    • Ask them what their CAC was in previous roles

  • Ask them if they had a budget at your company what they think it should be and work through, collaboratively, to define it on the call. They should be prepared to ask questions like: What's your ACV? How long is the sales cycle? What channels have worked in the past?

Evaluate their strategic thinking and problem-solving skills

  • Ask the candidate to provide examples of how they have developed and executed successful marketing strategies in the past

  • Ask them to talk about how they would work with the leadership team currently and how they would collaborate with them for insight and execution

  • Discuss potential challenges your organization is facing and ask for their approach to addressing these issues

  • Make sure they come into the conversation with their homework done on the company

Do they see the bigger picture of their responsibilities outside of just the function of marketing? This is a slide I have used in my 30-60-90 day strategic plans to illustrate the areas of focus

Assess their leadership and management abilities

  • Determine their experience in leading and managing marketing teams, including hiring, training, and performance management

  • Ask for examples of how they have built and maintained a positive team culture

  • Consider talking to people that they have managed before and peers that they have worked alongside

  • Here are some examples of Vision, Mission, and Motos i've created amongst the teams I serve. These have helped keep a pulse and a general culture amongst the team of empowerment, work life balance, and an enjoyable job

The Vision & Mission that we rolled out at Flip during our rebrand

Marketing Principles or Mottos we keep individuals accountable to as we work together

Gauge their adaptability and flexibility

  • Assess their ability to adapt to new technologies, trends, and market conditions

  • Request examples of how they have successfully pivoted marketing strategies in response to changing circumstances

  • Give them a scenario and ask them to work through the adjustment with you collaboratively

Examine their communication and presentation skills

  • Observe how well they communicate their ideas and strategies, both in writing and verbally

  • Challenge one of their philosophies even if you believe in it and see how they approach a rebuttal

  • Request a presentation or case study to evaluate their ability to effectively convey complex information

Review their data-driven approach to decision-making

  • Make sure they are asking you questions about your funnel structure, close rates, current conversion rates if any, sales process, sales cycles, average contract value, etc.

  • Assess their familiarity with marketing analytics tools and methodologies

  • Ask for examples of how they have used data to drive marketing decisions and improve results

Love this framework from an amazing person and CMO Peter Mahoney and the team at at Planful. Go check them out when you get a second.

Assess their ability to collaborate cross-functionally

  • Ask for examples of how they have worked with other departments (e.g., sales, product development) to achieve shared goals

  • Determine their experience in aligning marketing efforts with overall company objectives

Evaluate their industry knowledge and network

  • Assess their understanding of your industry's trends, challenges, and opportunities

  • Determine their connections and relationships within the industry that can benefit your organization

  • Do they understand their GTM motions and where they are needed

  • Ask how they plan to learn the product and industry


  • A very underutilized qualification criteria.

  • Observe if they have soft skills. Do they say thank you for taking time with them? Do they follow-up with a thank you note or email? Do they say "I" or "Me" a lot or are they saying "we" "our team" "the team I serve" etc.

  • Do they talk about how they "know" something or rather saying,

    • "I've been doing this a long time and here is what I know will work for you" VS "There is still so much to learn in this area, but here are some things I've learned that work."

  • Consider challenging them or walking through an experience together that requires a deeper level of mindfulness

Trends and Unconventional Thinking

  • To stand out in marketing you need to understand trends and sometimes take unconventional approaches. If all you hear them talk about is product marketing, SEO, and paid you need to move-on

  • Ask them about some unconventional campaigns they have ran

Conduct thorough reference checks

  • Reach out to former colleagues, supervisors, or direct reports to gather insights into the candidate's work style, strengths, and areas for improvement

  • Consider using a third-party background check service to verify their credentials and employment history

15/30/45 & 30/60/90 Day Plans

  • Ask them what their high-level plan is. DO NOT ask for the full thing, this is not okay.

Bonus: Network

  • Hiring a senior leader that is well connected across your ICP or across other executives will only make them that much better

  • Consider if they have a following on Social media. This can be a competitive advantage to you and your organization. Be considerate about how they present themselves on social but also be considerate enough to ask what their personal brand goals are so you can better understand why they may be presenting themselves that way. Never assume you know this.

Use this Checklist for Evaluating High-Level Marketing Leadership:

If you have 80% of these checked than that is a great hire! If you have 100% that is a top 5% talent. If you have 50%-80%, decide which areas are non-negotiable and be transparent in the hire. Tell them that you'd like to work with them on those areas. Trust me they will love you for that type of feedback and willingness to help them.

  • Defined role and responsibilities

  • Relevant experience and qualifications

  • Budget management

  • Strategic thinking and problem-solving skills

  • Leadership and management abilities

  • Adaptability and flexibility

  • Communication and presentation skills

  • Data-driven decision-making approach

  • Cross-functional collaboration

  • Industry knowledge and network

  • Mindfulness

  • Trends and Unconventional Approaches

  • Thorough reference checks

  • 30/60/90 day plan

  • Bonus: Network

Diving Deeper: So what do the best of the best look like?

Innovation and Creativity

  • Top CMOs understand that creativity and innovation drive marketing success. Ask candidates for examples of innovative marketing campaigns they've developed or their approach to fostering a creative environment within their team.

Thought Leadership and Ability to Influence others

  • Leading CMOs are not only marketing experts but also thought leaders in their industries. Assess candidates' knowledge and ability to inspire and influence others through speaking engagements, published articles, or social media presence.

Integrated Marketing Approach

  • Top CMOs recognize the importance of creating a seamless customer experience by integrating various marketing channels. Ask candidates how they have aligned traditional, digital, and social media marketing efforts to deliver a consistent brand message and drive results.

Anticipate and Capitalize on Trends

  • Successful CMOs are adept at spotting emerging trends and leveraging them for their organization's advantage. Ask candidates how they stay informed about industry developments and their approach to incorporating new trends into their marketing strategies.

Global mindset

  • Many top CMOs have experience navigating the complexities of international marketing. Assess candidates' experience and understanding of marketing in different regions, cultures, and languages, as well as their ability to adapt strategies for diverse audiences.

Customer-centric approach

  • Top CMOs place a strong emphasis on understanding and addressing customer needs. Ask candidates how they have used customer insights to inform marketing strategies and create personalized, engaging experiences.

Commitment to continuous learning and professional development

  • Leading CMOs are lifelong learners who constantly seek to improve their skills and knowledge. Assess candidates' dedication to ongoing professional development by asking about their involvement in industry conferences, workshops, or certification programs.

Navigating organizational politics

  • Top CMOs understand the importance of building strong relationships with key stakeholders and navigating internal politics to drive marketing success. Ask candidates how they have managed conflicts or challenges within their organization and their approach to fostering collaboration and buy-in.

Driving digital transformation

  • Successful CMOs are at the forefront of digital transformation, embracing new technologies and platforms to enhance marketing efforts. Ask candidates about their experience implementing marketing technology solutions and their approach to staying current with evolving digital trends.

By following this comprehensive guide and checklist, CEOs can effectively evaluate high-level marketing leadership candidates and make an informed decision on the best fit for their organization.

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