Maria Pergolino
This article, written by Maria Pergolino, provides off-the-shelf questions and activities to use when interviewing candidates for brand, demand, or product marketing leadership positions. The questions are meant to evaluate everything from technical marketing chops to leadership and interpersonal skills, and are tailored to the size of your marketing organization. If you want to view the questions for Series C+ sized companies, please look here.
Section 1: Technical marketing skills
Messaging / brand
Example questions
- Share an example of when you started from ground zero. How did you learn the product and translate that into a unique message and brand?
- Share some examples of how you have supported a founder’s thought leadership and social media presence in the past. What were the outcomes?
- Which of the assets you’ve created over your career has resonated most with prospects and customers? How did you know it worked, and how did you measure its success?
Example rubric
Element | Excellent response |
Branding | Provided an example of creating a concise brand message |
ICP | Demonstrated identification of the ideal customer profile (ICP) |
Segmentation | Shared how they tailored messages for different customer profiles |
Differentiation | Highlighted messaging that set the brand apart from competitors |
Value creation | Provided messaging that clearly communicated brand value |
Social media | Shared examples of supporting founder branding and leveraging social media |
Thought leadership | Shared examples of thought leadership that resonated with media, prospects, and customers |
Demand generation
Example questions
- We typically sell to [insert audience], and our deal sizes are $[X]. We currently have [X] customers. What type of demand generation strategy would you recommend, and how would you begin?
- Follow-up: Can you share an example of doing this in the past?
- How have you reported on marketing success and demonstrated ROI in the past?
- What does a marketing tech stack look like for a company of our size? Which tools do you consider critical?
Example rubric
Element | Excellent response |
Pipeline motion | Identified the right model (PLG for high-volume B2B, ecommerce for high-volume B2C, ABM for high-value B2B, etc.) |
Digital marketing | Shared successful examples from digital channels (SEO/SEM, PPC, performance marketing, etc.) |
Event marketing | Provided success stories involving event-driven strategies |
Earned media | Gave examples of success with PR, analysts, and social channels |
Sales & marketing alignment | Articulated what strong alignment looks like, including examples and proof points |
Reporting | Explained how to build a marketing funnel and report on ROI |
Operations | Outlined a modern, AI-forward tech stack suited for Series A/B-stage infrastructure |
Product marketing
Example questions
- Tell me about a successful product launch. What was required, and what outcomes did you achieve?
- Describe a competitive market you’ve worked in. How did you use messaging to stand out?
- How have you used customer stories and community to amplify a brand?
- The messaging needed to attract a customer is often different from what’s needed to close them. What materials have been most helpful in each case in your past work?
Element | Excellent response |
Competition | Explained how they created differentiation and demonstrated competitor knowledge |
Community | Shared how community-building supported marketing efforts |
Customer stories | Gave examples of using customer success stories in programs |
Sales enablement | Articulated specific enablement tools that influenced business outcomes |
Section 2: Leadership and job organization
Start-up resources
Example questions
- You’ll be a team of one to start. What would you do if you lacked the technical skills to complete a task critical to your strategy?
- Our marketing budget is $[Y] until we reach $[X] in revenue or [X] customers. What should we expect to achieve with this budget? How would you maximize its impact?
Innovation
Example questions
- Tell me about a campaign or approach you took that differed from standard best practices and led to outsized results.
- With AI driving gains in marketing productivity and efficiency, how have you integrated AI into your work?
Element | Excellent response |
Network | Shared examples of consultants or freelance talent they’ve worked with |
Resources | Demonstrated ability to deliver results with limited budget and headcount |
Innovation | Provided innovative approaches that delivered above-average outcomes |
AI | Showed how they use AI to enhance marketing execution or results |
Section 3: Example activity
Example description
Prepare a 15-minute presentation covering your first-year approach to building marketing at <company>. Please create a slide (or two) for each:
- Your marketing strategy
- How would you split your time across core functions (e.g., brand/comms, demand generation, product marketing)?
- We assume everyone we are meeting can do great marketing, but how will you differentiate us from other brands so that our marketing stands out?
- What outcomes do you want each to achieve in the first year and how will you measure success? (This can be presented as key goals or metrics.)
- Budget utilization for maximum impact
- How would you allocate a $<amount> budget across marketing areas to achieve stated goals, including paid media / advertising, events, content PR/comms, tools/tech, freelancers/contractors, headcount, and other areas?
- Tool stack
- What tools or platforms would you consider essential to run an efficient, modern marketing org at this stage?
- AI
- How will your marketing strategy leverage AI?
- Brand inspiration
- What are 1-2 brands <company> should look to emulate with our marketing, and why?
- What are 1-2 brands you think are doing a poor job with their marketing, and what are they doing that we should avoid?
Optional additions
You can ask for one or more of the following in the activity description, if useful to your hiring process:
- Light messaging or positioning refresh recommendations.
- Campaign ideas or early GTM tactics.
- Any red flags or areas for improvement the candidate already sees.
Example rubric
Element | Guidance for the interviewer |
Marketing strategy |
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Budget allocation |
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Tools |
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AI |
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Brand Inspiration |
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