100+ Questions to Ask
When Exploring or Starting a
New Marketing Job

David Berkowitz

Founder Serial Marketer

About this guide

What questions should you ask when exploring or assuming a marketing leadership role?

Having been on all sides of this (interviewing for full-time or consulting jobs, onboarding clients for marketing programs, hiring full-time marketers and consultants), I’ve asked a lot of questions.

I’ve also forgotten so many of the best questions to ask. 

Have you ever started a job or gig and thought, “I should have asked this before I started”?

Have you ever interviewed for a job and wished you could have asked a few more questions that reveal insightful answers?

Bookmark this guide, or save a copy, and you won’t have to worry about that anymore.

Have other questions that should be here? Let me know. I’ll add others over time, and I’m always looking to learn. If you care to share this, feel free to use the shorter link http://bit.ly/serialqs.

David Berkowitz
Serial Marketer

If you only ask these 5 questions...

All of the questions in this guide matter. You won’t get to ask all of these questions before you start a job or gig, and some matter more than others. If you need to be selective, such as for a brief meeting with the CEO or CMO, here are a few favorites:

  1. What kinds of marketing are working best for you right now? What’s not working?
  2. Are you looking to focus more on top-of-funnel or down-funnel activity? 
  3. How will you know what success looks like for the new hire coming in? After the first 90 days, how will you know they’ve been successful? What about after the first year?
  4. What does the current marketing team look like? Are there any additional hires you have planned? Are there key external resources (freelancers, agencies)?
  5. How does the Marketing team currently interface with Sales?

Getting to know you

  1. What values define your company and brand?
  2. What’s your mission? Do you have a tagline? Strapline?
  3. What’s your company’s unique selling proposition (USP) or key differentiators?
  4. How many people work there?
  5. What are the biggest challenges your business faces right now?
  6. What are your biggest marketing challenges and needs?
  7. Why was the company founded? 
    1. If dealing with founders: Why did you found the company?
  8. What is the story behind the company’s name?
  9. Is this a new role or are you hiring a replacement? 
    1. Either way, what’s the reason for hiring right now?

Measuring success

  1. What does success look like for you in 30 vs 90 vs 180 days for this marketing hire? How much of it is tangible vs. intangible? 
  2. What does success look like after a year? 
    1. Compare that answer to the shorter-term plan. It’s also helpful to the company you’re working with to show them you’re thinking about long-term success. 
  3. How will you know if you’ve made the right hire here and if marketing is working?
  4. How often do you currently get reports of marketing activity? How often do you want to receive them?
  5. How transparent is the information coming from Marketing? Does this degree of transparency align with what you want? Are you looking for more — or potentially less?


  1. Who are your top customers right now?
  2. What percentage of your business is your largest customer? What about the share of your top five?
  3. What are the titles of the decision-makers at your customers?
  4. What are the titles of your day-to-day contacts at these customers — the ones interfacing with you and/or your product/service?
  5. Is there a difference between your best customer (in terms of company and/or title of buyer) today and your ideal customer you are targeting?
  6. Do you have personas of your target customers? Have you ever created these?
  7. Have you created a customer journey map?
  8. What geographic markets are most important for you? 
  9. Do you plan to change or expand geographic targets? Will you need someone with experience in certain regions soon or later on?

Current marketing effectiveness

  1. How have your current customers found out about you?
  2. What are the sources for most of the leads in your pipeline?
  3. Is there a difference between the sources for your marketing qualified leads (MQLs) and your sales qualified leads (SQLs)?
  4. What kinds of marketing are working best for you right now?
  5. What kinds of marketing aren’t working for you?
  6. Are there any kinds of marketing you used to do that you know worked or thought might work but that you’re not currently doing?
    1. This could be due to budget issues, but some past programs may have been discontinued due to internal resources (e.g. staffing), so by adding you to the team, that could allow you to revisit past programs.
  7. Are there any kinds of marketing you’re doing that you’re not sure if they’re working or not?
  8. Are there any kinds of marketing you wanted to do but haven’t yet?


  1. Do you want marketing to focus more on top-of-funnel or down-funnel?
  2. Of the marketing goals below, are any of these more important for you than others? 
    1. Raise brand awareness
    2. Generate inbound leads / MQLs
    3. Shorten sales cycles
    4. Expand accounts with current customers
    5. Turn customers into advocates

Integration with sales

  1. Do you currently define marketing qualified leads (MQLs)? If so, how?
  2. Do you currently define sales qualified leads (SQLs)? If so, how?
  3. How do you currently track MQLs and SQLs?
  4. When referring MQLs to the sales team, how ‘qualified’ do you want them? Does the sales team want as many leads as they can vet, or would they prefer to only focus on the most likely leads to convert?
  5. What are your sales goals?
  6. Do you have a certain expectation for Marketing’s contribution to sales goals?
  7. What’s your current sales cycle? How long does it typically take to close a deal?

Revenue and Pricing

  1. What’s your annual revenue?
  2. What are the different price points for your offering?
  3. What is your average order value (AOV)?
  4. How does the current AOV compare to where it was one year ago?
  5. What is your target AOV one year from now?
    1. One can expect most business seek to increase AOV, but many look to go down-market to expand their customer base and thus decrease AOV. This can be a revealing question.
  6. What’s your customer lifetime value (LTV)?


  1. What is your current marketing budget?
  2. Do you have a current budget you can share?
  3. What are the largest line items on your marketing budget?
  4. Are there any major budget commitments that you have (e.g., for sponsorship, media buying, event participation, channel partner promotion, etc)? 


  1. What does your marketing team look like?
  2. Are there other hires you currently plan on making for marketing?
  3. What freelancers, agencies, and outside resources do you use?
  4. What resources could we use more effectively?
  5. What are other key hires for your organization that you are making now or planning on?

Inventory: Team / Resources

These could be internal hires, external people / firms, or tech-driven offerings.

DisciplineInternal ResourceExternal ResourceTech / Product Solution
Advertising / paid media   
Content production   
Social media management   
Community management   
Influencer marketing   
Design / creative   
Video production   
Analytics / measurement / reporting   
Freelancer management   
Web development   
Public relations (PR)   
Analyst relations (AR)   

Calendar / Timeline / Events

  1. Is there any seasonality to your business? Do certain months, quarters, holidays, or other events matter more than others for you?
  2. Are there certain cultural events, holidays, sporting events, political events, or other noteworthy such milestones that you focus on or that are important for your business?
  3. Are there certain industry events, conferences, or award shows that matter to you?
  4. Do you host any recurring events?
  5. Do you currently do anything to support diversity & inclusion events like Pride Month, Black History Month, Women’s History Month / International Women’s Day, or others? If not, do you want to, and are any particularly pertinent to your business?
    1. Note that all such events matter to the various groups represented and to the broader population, but a company with Black founders or that has a disproportionate base of female or LGBTQ customers may have a deeper connection to certain events.
  6. Do you currently have a content calendar or editorial calendar?

Public relations (PR)

  1. Who is handling your PR? 
  2. Is there an analyst relations (AR) discipline? If so, who is handling that? 
  3. Which outlets (defined broadly) are most important for your customers?
  4. Which outlets are you most interested in appearing in?
  5. Which events do you participate in as speakers, attendees, or sponsors?
  6. Which of these events are more or less valuable for you?
  7. Which events are most important for your customers?
  8. Have you won any industry awards? 
  9. Are there any awards you want to win?

Social and influencer marketing

  1. What are your goals for social media marketing?
  2. What social channels are most important for you? Why?
  3. Who manages those? 
  4. Who creates content (text, images, video, audio)? 
  5. Are there any social channels you want to use but haven’t yet?
  6. Do you have your own community?
  7. Are there other communities you participate in? Which ones?
  8. Have you worked with influencers? Who? How have you measured success?

Content marketing

  1. Do you have any content series or themes that you focus on?
  2. Do you have a blog? Podcast? YouTube or other video series? Clubhouse room?
  3. Do you have any data you release? Scorecards, benchmarks, etc?
  4. Do you ever release white papers? 
  5. Do you publish customer case studies? Do you have testimonials? Do you have a process for getting these?

Email marketing

  1. Do you have an email list?
  2. How do people opt in?
  3. Is the list fully opt-in?
  4. How often do you communicate with them?
  5. What kinds of emails do you send?
  6. Who puts it together?
  7. Which email service provider or tools do you use?


  1. Who are your current competitors?
  2. Who do you most want to compete against? Are there aspirational competitors you’re not competing with now?
  3. Are there perceived competitors — businesses that your prospects or customers think compete directly with you, even if they don’t?
  4. Have you conducted any competitive review in the past 6-12 months? Do you have any such information you can share?

Funding (for startups)

  1. How much money have you raised?
  2. What is the size and stage of your latest round?
  3. What is your current company valuation?
  4. Are you currently raising or planning to raise a round? If so, what is the size and stage of that round?
  5. When you get future funding, what will you spend it on?
  6. How many months of cash flow do you have at your current burn rate?
    1. This is like asking how long you have to live if your spending and revenue continue at the current pace.

Your package (startups)

  1. How many shares outstanding are there?
  2. What is the price per share?
  3. What is the vesting period for shares?
  4. Who are your lead investors?
  5. Are your current investors likely to participate in your next round?


  1. What trademarks and service marks do you own?
    1. You can also scan the US Patent and Trademark Office database at uspto.gov
  2. Are there any legal disputes that are public or could become public?
    1. This matters far more for PR and communications roles. 
  3. Do your contracts with customers or clients state whether you can mention them and publicly use their logos on websites, collateral, presentations, and other materials?
  4. Do your contracts with customers or clients state whether you can cite work you do with them in public channels (e.g., social media, press releases, awards submissions, etc)? 
  5. Do you have a database where you track which clients or customers you can mention?

Who you can talk to

You might not be able to talk to everyone you want, especially depending on how confidential the search is, but you may ask to talk to:

  • Any founders you didn’t yet
  • The CEO, if they’re not part of your process and if you are likely to interface with them in your role
  • The head of sales
  • Any potential direct reports you’ll have
  • Investors in the company

For your own diligence, you should be sure to check LinkedIn to see if you know anyone at the company or people who used to work there. 

Be mindful of the degree of confidentiality of the search. If you are taking the role of a current staff member who may not be aware of the search, be especially careful and respectful, and realize that many people will take a look at who views their profiles.


Thanks to these contributors who informed this document. 

  • Jovana Kovac is my lead strategist on marketing programs, and her intake forms contributed many questions to this series.
  • Skip Graham sent a document around several years ago to the Oldtimers List that inspired some of my thinking about this.
  • Joe Koufman and the team at Setup created a brilliant list of questions to ask candidates for marketing roles, and it includes some questions candidates can ask too.
  • Alona Fromberg-Elkayam gave me some terrific ideas.
  • Devin Brown contributed the question about if this is a replacement hire.

I asked for some ideas on LinkedIn and appreciate others who contributed as well. You can read their responses and contribute more there too.

Learn even more

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Thank you,