28 Questions to Ask Before You Become the First Marketer in a Startup

Joining a startup as the first marketing hire can be really exciting but it can also be a unique and challenging role to fill. Before you sign the offer letter and jump right in, make sure you have properly vetted the company and their expectations of you.

In January of 2011, I joined Sprout Social as the first marketer and 18th employee. I had originally connected with the CEO (Justyn) in October 2010 and over the course of ~8 weeks, we had several phone calls and exchanged even more emails.

I asked so many questions about every part of the business and the product that I’m honestly surprised it didn’t annoy him (maybe it did). It was important for me to make sure I thought I was a good fit for the expectations of the role and the company itself.

Doing this helped me come into the company and role with a good understanding of what was expected of me and even then there were still things that were different that I had to adjust.

No matter how new or established a startup may be, when you are the first marketer hired it is always going to be uncharted territory for everyone. If you are considering this type of role, I’ve documented as many questions as I can remember asking as well as things that I would ask today if I were considering that role again.

Honestly, most of these are good questions to ask before joining a startup in any role but far more critical when you alone will make up the entire marketing function.

*Note: I shouldn’t have to say this but you really should try to answer some of these on your own by researching ahead of time. You should get the answers to most or all of these, just don’t make the team answer all of them for you.

Business Fundamentals

The goal of asking these questions is to get a feel for the financial health of the company so that you know that you’ll still have a job in 6 months but ALSO so that you get a sense of what kind pressure you are walking into. If there’s spotty revenue, high cash burn and the answer to all of these problems is “that’s why we’re hiring you!” then you know you are coming into a much more intense situation than a company with a good revenue trend (even if small), low cash burn and a good path to more funding.

How much money has the company raised (if any)?
What is the current cash runway and plans for additional fundraising?
Is there currently any revenue? If so, how has that changed over the last few months?
How do current investors feel about the progress of the company so far?
Are you trying to build up a viable business to sell off quickly or are you building a company for the long haul?

Product

A good product makes your job a lot easier. However, it is pretty easy these days to spin up a nice UI but that doesn’t mean that it is a good product. You should really understand how the product is built, how it will scale, how engaged the users are, if it is solving real problems for the users and so on.

What code languages have been used to build the current application?
What is the team focused on building right now?
What is the bigger vision for the product roadmap?
What are the daily/monthly active users of the product?
How much time do active users spend in the application in a day/week?
What is the NPS? (if they have it yet)
What roles or demographics make up the existing user base?

Team/Culture

With the team & culture questions, this is more than just the typical culture questions and more focused on what the team is like today, how they anticipate it will grow, whether or not there will be challenges in hiring for certain skill sets and so on. If you are told they plan to hire 30 outbounds sales reps in the next 18 months, that’s a different landscape vs 30 engineers or perhaps only 2-3 other key hires for the next year or so. Even though things change rapidly in startups, you want to understand where things are headed to better understand what your role and Marketing’s role will be in all of it.

What is the team made up of today and what other roles are you actively hiring/planning to hire?
Where do you see the most hiring and team growth happening over the next 12-18 months?
Who do you think my role will be working with most over the next several months?
What skillsets do you think we’ll need that are highly competitive or rare in our market (if not a remote team)?
What is the culture like? Does the team hang out together? What hours does everyone typically work?

Performance

Moving deeper than the business fundamentals, it is important to get a sense of what any sort of pipeline, lead generation, traffic, acquisition marketing performance looks like or if there is literally none. This will help give you a sense of what is working, what isn’t, where there may be low hanging fruit and most importantly, a better idea of how your skill set does or does not fit the needs of the business. If you can get read-only access to some of this data ahead of time, even better.

What is current volume of traffic, leads/trials/signups, new customers, etc. each month?
What are the current conversion rates? (ideally known at a few stages of the funnel)
What is the average deal size of recently closed new customers?
What channels or tactics do you think would perform well but haven’t been tested yet?
What has been tried that didn’t work? Why do you think it didn’t work?

Your Role

Last but not least, you need to dig deep to understand what the company will be expecting of you as the first marketer. Marketing is an extremely broad discipline and everyone has had different experiences with marketers and has their own viewpoints on how marketing should be done. Because of this, it is imperative that you understand how they think about marketing, what they believe success looks like, where they expect you to focus and what resources you will have to accomplish it all.

You can’t be charged with “building an amazing brand” and then given a budget of $2k/month or asked 3 months into the job why you haven’t tripled leads already. On the flip side, you can’t be charged with growing leads and revenue and then expected to stop spending time in the weeds and figure out how to make the brand bigger and make the company a thought leader in your space. They are different motions and different skill sets so it is crucial to make sure that you dig in to understand what the company needs and what they expect when they hire you to “do marketing” for them.

What is the ONE thing that if I succeeded at it in the first 6 months, you would be really happy?
What are some of the areas you would expect me to focus on the most?
What is the marketing budget allocated for the next 6-12 months and is any of it already committed to something?
If we find some areas that are growing and make sense, is the plan for me to start hiring and build a team or will you be building the team around me?
What level of importance do you place on brand-building activities in the first year or two?
How do you view the role of marketing for this company? Is it to lead Growth, Sales and Product direction? To assist Sales? To make swag and other nice-looking things?

While you certainly could take this list and ask the questions exactly as I laid them out but that’s not really the point. The goal is really to help you shape your mindset around what pieces of information you need to make an informed decision and then figuring out a plan to get that data.

Most likely, you’ll ask one or two questions in a certain area and then the rest of the information you can pick up from the conversation that unfolds.

Take the time to make sure the company and the role are a good fit for you and that you know the expectations they have for you when you join. You’ll be glad you did.