14 leaders share questions to ask before joining an early-stage startup as the VP marketing

Tips from startup marketing leaders
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If you’ve filled a sole marketing role in an early-stage startup, you know it can get risky. It’s also fun and exciting, and you get a chance to manage multiple marketing areas, learn a lot and make an impact. However, you usually hit the road when there’s no infrastructure, no marketing DNA, minimal understanding of marketing, a limited budget, and far too high expectations.

Most B2B startup founders are technical creatures. They understand R&D, sprints, bugs, technical debt, production, CI/CD, and the time it takes to deliver a product version. Unfortunately, they don’t know much about building a brand, what it takes to close a deal, how many touchpoints you need to generate an opportunity, what trust-building elements you must add to your communication materials to ensure you don’t fail the ‘first impression’ challenge, what budgets and timelines are needed, or generally, what’s the journey from initiation of the marketing operation to marketing maturity. They have no clue why you need to invest in a blog, SEO, or anything else for that matter. 

Yet, they are often very opinionated when it comes to marketing 🙂 

Joining an early-stage startup as the first marketer on the team is risky because you don’t really know if the startup will succeed and how long it will last, how valuable the product is, what’s the competitive landscape, how you will be treated (there’s no established HR approach), how the founders behave, what the hidden beliefs about marketing are, and so forth. 

Over the years, I’ve acted as a standalone marketer in many early-stage startups (through G2Mteam). Other times, I’ve worked closely with startup CMOs, executing multiple activities as well as taking part in the strategy and planning.

CMO colleagues who work with me often confessed that they wish they had asked some sharp questions before accepting the position. Many admitted that they didn’t ask all the important questions they should have or did all the needed research ahead of time. 

I realized that all of us marketing professionals, even the most experienced ones, don’t always run optimal due diligence before we decide to join a company. We could use some tips.

I, therefore, decided to ask some of the top marketing leaders in early-stage startups who happen to be my colleagues, as well as some marketing leaders in VCs that are funding early-stage startups, for their two cents on the most important questions that must be asked before joining an early-stage startup in order to make a more informed decision, especially in today’s ecosystem.

(I also included my personal two cents at the end.)


Roni Saban, VP marketing at Helios:


Get a well-rounded understanding of the company, not just from the team itself. Ask (don’t be shy) to meet with one of the investors, or maybe there’s a friendly customer that you can chat with. You’d want the external perspective on opportunities and challenges. Additionally: 

  • Don’t compromise on getting a very clear understanding of the ideal customer profile (ICP). If possible, hunt for such people in your network so you will get unbiased feedback about the product, industry, and perceived value.
  • Make sure you know what your budget is going to be and what are the expected results. Find out how much leeway you will have in approving payments and working with the budget. If there’s no budget defined, tell them what you will need and make sure that they are willing to commit to it.
  • Lastly, understand how the CEO views the marketing role, and whether she has clear expectations on outcomes and timelines.


Omer Primor, Brand and growth leader at bit.dev (formerly VP of marketing at ImVision (acquired by Intuit)


Here are two questions that I really like:

  • What kind of employees flourish in this company? This is a question that the CEO may not expect, and it can help you gain valuable insights into what is really appreciated in the company and what kind of person should fill the role. If you are that person, great! But if not, it’s better to know upfront.
  • An even more interesting question, in my opinion, is how strategic decisions are made. Ask the CEO to describe a process that they are happy with and proud of. I believe that processes are the most significant way to move things forward and make an impact. When things are not organized and decisions are not made with careful thought, it limits the marketer. Healthy processes that include clear stages and letting different team members share their thoughts are critical. This will let you know that you can lead a process, get other team members onboarded, and it won’t eventually vanish due to the way things are managed.” 


Dori Harpaz, CMO at LayerX Security 


From what I’ve been seeing, the reason for not lasting in a marketing role in an early-stage startup is related to mismatched expectations between the head of marketing and the founder/CEO. Founders, especially ‘first-timers’, lack marketing knowledge. This means that their expectations (in terms of the required resources and the expected results), are in many cases unrealistic. My recommendation is to be fully aligned ahead of time in regard to: 

  • The Marketing budget in the first 12 months
  • Marketing areas of responsibility 
  • Marketing authority to sign contracts, approve invoices, work with contractors, etc.
  • Marketing KPIs”


Amit Lavi, Marketing advisor to startups, former Co-Founder at Envy


Short and sweet: I would ask about the expectations for marketing, and how it is perceived. I would also ask about the expectations for brand building and where it should be in 1-2 years. If the answer is “leads, leads, and just leads,” I would advise you to run away.


Yam Regev, CMO, marketing advisor, and former VP of marketing at Elementor


My two cents: 

First, research before you make the decision. Yes, even hunt for former employees and talk to them to better understand how it is like to work in the company. 

Here are a couple of important questions that you may want to ask on top of all the fundamental ones: 

  • Are the founders first-timers or serial? This will define the amount of education you will need to invest in, as well as your perceived position in the company. 
  • Did the founders ever work closely with marketing leaders before? Here’s a good chance to inquire about the experience, what predispositions they have, etc.
  • Who is on the management team? Are they all believers in marketing? Do they all feel it’s critical at this stage? Will they all be easily committed to supporting marketing requirements allocated to their units? You should know ahead if you will have inside objectors and prepare your strategy to win over that challenge.
  • What is the company’s burn rate? Runway? Make sure there’s enough time to run.


Maya Dror Melamed, VP of marketing at Craft.io (Formerly at G2Mteam) 


When you’re thinking about joining an early-stage startup, remember that success depends on the people you work with and the product you’re promoting. Do your research: conduct rigorous due diligence on the management team, ask tough questions, get references, and scrutinize their reputation and online presence. Just as important, make sure the product being developed has real value and addresses a sizable market.” 


Emilia Dariel, VP of marketing at Moodify, formerly at Travelperk, Incredibuild, and G2Mteam


These are the main questions that come to mind: 

  • Goals/objectives for the next 6–12 months: Ask what the goals are and what will be considered a success. In early-stage startups, the management sometimes rushes through various things out of a desire to do many things quickly. If there is no focus on clear objectives or any requirement for them to be kept fluid. Many times there are also no clear measures of success, which can be a place for failure. 
  • Who determines the marketing strategy: Is it the CEO or the marketing person, or both of them as a team? It is important to understand who you will be working with. Usually, a CEO with a business background will have a better understanding of marketing and sales processes than a CEO from a dev background. The challenges of working with them are different, and in the case of a technical CEO, you will need to do quite a bit of education. 
  • Product/business stage: It is important to understand your challenges in terms of market readiness, business stage, and the stage of the product. In early-stage startups, the promise is far from reality, and you should know that ahead and come prepared.”


Yael Eckstein, VP of marketing at StageOne Ventures


“When applying for a marketing role in a startup, I believe it’s essential to ask the following questions: 

  • What are the company’s goals for the next 6–12 months, and how can marketing contribute to achieving them?
  • Is there a predetermined budget for marketing initiatives? If not, what is the estimated budget?
  • Has the company implemented any marketing strategies in the past?


These seemingly straightforward questions hold significant importance, especially within a startup environment. Marketers may often be perceived as magicians, with founders hoping they can work wonders and turn their product into an overnight success. However, successful marketing requires careful planning, patience, and extensive testing to identify effective strategies. The term “marketing” encompasses a vast array of channels, and experienced marketers understand the need to focus on specific channels to reach a well-defined target audience.

Ultimately, the key to a successful collaboration between founders and marketers lies in managing expectations. It’s crucial for both parties to align their understanding of the time, effort, and testing required to achieve marketing goals. By fostering clear communication and a shared understanding of realistic expectations, startups can harness the power of marketing to drive their growth and success.”


Sharon Beilis, marketing advisor (formerly at Pagaya) 


  • Enquire about the startup’s values, business goals, and growth plan to understand its strategic direction and mindset. A well-defined growth plan and clear values indicate effective decision-making. The tendency is for startups with a clear plan to be more organized, proactive, and adaptable to changing conditions over time. They are often better equipped to navigate challenges and make informed decisions based on their guiding principles.
  • Explore the leadership team’s experience and personality. Identify any knowledge gaps related to launching and growing a business and learn how they treat the team. This helps anticipate challenges and assess available support and guidance.
  • Understand how the startup manages its budget and makes resource allocation decisions. It indicates their approach to spending money, whether they have a strategic plan or make ad-hoc decisions. It also determines the limitations or opportunities for executing marketing strategies.” 


Noa Eshed, Co-Founder at Bold Digital (formerly external CMO at Trinity Audio)


Make sure the CEO understands marketing and will let you make strategic decisions. In some startups the marketing team is an executing extension of the sales department, crafting sales collateral – which is super important but can’t be the essence. 

Join an environment where you can turn the startup into a category leader. That takes patience, a deep understanding of long-term goals, and KPIs that are lift based. The rest is a distraction.


Peera Feldman, CMO at Joonko, formerly at Loom and G2Mteam 


My two cents:

  • Setting expectations with leadership and CEO and laying out goals and KPIs. If the expectation from marketing is to bring four paying customers on board in the first quarter (not design partners, actual paying customers), that might be a red flag. If the expectations are to be on WSJ and Inc for the product launch or the single-figure Round A raise—that’s a red flag. Marketing activities take time to take off and accelerate, to create a strong brand, and stick. If the expectations are to organically grow exponentially in the first year—that’s a major flag as well.
  • While we all love to call ourselves full-stack marketers, there is a limit to where our single-handed efforts can get us. Find out what the growth plan is and what resources you can bring on board. Can you utilize a PR agency or a specialized agency that will help you with your first branding and positioning, messaging, first website version, or paid advertising?” 


Nirit Icekson, VP of marketing at Entro Security 


The first and most important thing to do is to understand if the CEO is really looking for a senior VP marketing/CMO,. Someone who will be both strategic and hands on, someone who will be part of the strategic decision making in the company and not just someone who is expected to write LinkedIn posts, for example.

It’s important to set expectations and understand from the CEO what he thinks marketing’s goal is in the first 6–12 months. Is his answer on the tactical side? The strategic side? Both? (For a startup it should be from both angles).

In many cases the answer will involve getting leads that will become deals. So it’s important to set expectations on what this means in terms of marketing.

We are no magicians. Climbing up the SEO ladder takes time. Establishing credibility takes time. Creating content takes time.

Another point: it’s important to understand what the budget is. If the goal is ABC but there is little or no budget, that’s a problem. Will there be a team (small) or leverage agencies?

As we all know, the main challenge with marketing is that everyone thinks they know everything… It’s OK for a startup CEO not to know things and to have unrealistic expectations, but if during the discussion he/she “gets it,” that’s a great sign.


Sharon Seemann, Partner, and CMO at YL ventures


“As part of the considerations for entering your first managerial marketing role in a growing startup, it is important to understand if there has been any marketing activity in the company so far, what the existing marketing strategy is, and who has managed and implemented it. 

For example, does the company have active investors who support its marketing activities and can assist the incoming marketing manager in promoting and executing various goals? This support can be a game-changer in terms of entering the role, and investors who believe in marketing can use their influence to ensure that the founders also recognize the importance of marketing, prioritize it and actively support it as needed. 

In this context, it is important to ascertain how the CEO perceives the role of marketing: is it seen as a force multiplier that the CEO will allocate resources for and promote accordingly?

Beyond the CEO, it is important to examine the relationship between the founders and ensure that they are aligned on the company’s marketing approach and messaging. 

Finally, a marketing manager should be able to rely on all of the founders, not only on the CEO, and on other employees for marketing activities and for promoting the company’s brand, services, or products. The entire company’s active participation and engagement are particularly critical in the early stages.”


Einav Laviv (that’s me), CMO on demand and Co-Founder at G2Mteam

On top of the spot-on tips above, and based on my experience with early-stage startups, I can share a few of the questions that I have learned to ask (written in blood):  

  • Why are you searching for a marketing leader at this time? This question brings up interesting insights and may shed light on past experiences or personal beliefs as well as real expectations. Some answers I received as examples: “I am losing business as the company’s marketing material and website looks unprofessional,” or “I am onboarding SDR and sales team, they will be needing leads and materials,” or “I want to make sure that investors are impressed” and so forth. This will help you understand the real expectations and goals, rather than what you will hear if you ask it straight forward. 
  • How would you describe a successful versus unsuccessful marketing persona? Professionally, personally, leadership style, etc… (I direct them to different angles). This is another question that helps to gain insights into the mind of the CEO. You will understand what makes her tick or what he appreciates. Some told me that for them, a successful marketer knows how to provide value given the limited resources and budget; others said that someone that’s not only a big boss but knows how to implement marketing activities as well. 
  • What is the percentage of firefighting versus following a predefined plan I should expect? There is always firefighting, but in some companies, the noise is just too much, and you can’t follow a planned path. You need to know ahead of time what the attitude is before you start working.
  • What are the main characters of the persona that you are after, the most important ones? This is a straightforward question that can help you better understand if you are a perfect fit for the role. 

Additionally, and very specific to the early stage, you must ensure that you will have enough to play with. I mean, if there are KPIs but almost no means to achieve them (this is related to the budget issue) they may not just yet be ready to set up an internal marketing unit, or you may find yourself needing to execute tasks you don’t know how to operate yourself (just as paid campaigns, SEO, content writing and so forth). In that case, unless you are a truly full-stack marketer, you better give this opportunity up. 


Final words 


Joining an early-stage startup is a bet. Building a marketing DNA and establishing a brand is a HUGE challenge, especially when you have very little budget, and resources and you are usually a sole player at the time of entry. 


You need to know how much time each task should take, what’s too much and what’s too little, what activities should take place right away, and what activities should be executed later on, you should know how much budget to dedicate to specific activities (budget, tools, and vendors in early stage startup are usually different from the ones in later stages). 


All of these challenges are hard enough, you must ensure that you won’t regret the decision of joining that startup later on. For that, you will need to run a thorough due diligence and ensure you ask the tough questions, many of them written here above. 


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Einav Laviv is a tech and startup marketing exec. with 20 years of experience, and a Co-Founder at G2Mteam, which supports Israeli startups with full-stack global marketing services since 2014. She lives, breathes, and loves deep tech & data driven marketing