My last 3 FTE Marketing roles have lasted < 1 year and in hindsight I wish I did more research before. I don’t blame myself, because we’ve all been there: You’re so excited to find that next job and in this market, you’re just happy to have one. But, then months in something doesn’t feel right and you question if you made the right choice.

What happened?!

You thought you asked enough questions, googled the right things, and talked to the right people. Below, I’ll share the 13 questions I wish I asked before joining and the answers that throw up a red flag.

Before I dive in, here are some caveats:

I expect to be at a company for at least 2 years. Of course, the financial upside is hugely important to me, so I do assess that, but that's not the main reason I'm joining a company. I also won’t be discussing questions about compensation, benefits, or work-life flexibility. Each of us has our own considerations based on our situation.

Having said all that, when I'm interviewing, I look for three things:

Potential → How big is the opportunity and vision of what I’m joining?

People → Do we have the current butts-in-seats or a plan to get us there?

Processes → Is there the right structure to bring potential + people together?

I like to start with potential because at the end of the day, if you're joining a startup or scale-up, this is by far the most important. I learned this at Uber, where even though there were a few brilliant jerks, a tough culture, and many challenges, much of that gets swept under the rug when there's insane growth. The work also tends to be more fun when it's a high-potential opportunity.

🚩 Not having one

🚩 Not understanding what a strategy is. To me, a strategy needs to clearly communicate what the team is going to do, but just as importantly, what the team is not going to do. What channels, or bets, or geos are you not going to pursue?

Good Answer: “Our strategy is to grow X% YoY by doubling down on our North American Markets and continuing with our current product offering. We might test pricing but we’re keeping our ICP the same and still working on geographic expansion across the US instead of more product offerings”

Bad Answer: “Our strategy is to grow X% YoY and dominate the market” 🤮

🚩 Unclear assumptions and grandiose expectations are killers of strategy. There has to be some thought given to the physics of growth and how the scale-up is going to work with those physics. It's okay to have a not-great strategy, but if you don't know why that strategy is bad, then you won't have the self-awareness to be able to correct it.

Let’s follow up using the strategy above

Good Answer: “We don’t have the resources to offer more products right now and still feel that we’ve barely penetrated our TAM in the current offering. We’re seeing great signs in our coastal cities like New York and Washington so we feel that expansion to other major cities like Chicago and San Francisco will be a strong opportunity”

Bad Answer: “We just want to keep growing and growing and feel like we can expand to hit our targets. San Francisco is a big market and so we want to go there next”

🚩 Growing slower than you should be at your expected stage of company. For example, if you're an early-stage company only growing 10-20% year over year, that's a big red flag. Uber Eats is currently growing at 10% year over year, and they've been in the business for 10 years with a lot of competition.

🚩 Huge drop-off between last year and this year. The key word is "huge." YoY growth rates always go down because it's the physics of working with big numbers and baselines, but if you're going from 500% to 50%, that's something to run away from. If YoY growth rates go from 500% to 300%, that is likely okay.

🚩 Year-over-year growth rate that is bigger than this year's. I was recently at a company where we were growing x% and then the projected growth rate for next year was going to be 2x%. I wish I had asked this because it would have greatly changed my decision.

🚩 Unjustified growth rates. Expanding on the strategy question above if they say we’re going to grow the same amount as this year or even slightly less, they should be able to answer why. What tailwinds do they expect to be able to continue on this trajectory?

LTV / CAC is one of the best signals for the potential of a business.

🚩 Don’t know LTV or CAC. Btw, when I say LTV , I mean like 6 month, 1 year, or 2 year depending on the stage of company

🚩 LTV more than 2 years. You don’t have the data and it’s full of BS assumptions. Unless the company has been around for at least 5 years, you have no business building a 2+ year LTV model.

🚩 How they define LTV. If they're using revenue, it’s a huge red flag. It means they've been grossly overestimating their LTV. Also if they’re using like a 4 year LTV when the start up is early, that’s a flag too. Generally 1 year LTV is as much confidence as I have in most consumer tech companies (How to calculate LTV)

🚩 How they calculate CAC and which metrics are included in marketing cost. Here's an article that you can use to help assess at what stage which marketing cost should be included in CAC (How to properly define CAC).

🚩 Low LTV / CAC and low growth. A low LTV to CAC ratio is not a bad thing. What's most important is assessing how this LTV/CAC fits into their growth strategy. For example, if they have high growth and high LTV/CAC, that's incredible. If they have low LTV to CAC and high growth, that is acceptable. But having low LTV to CAC and low growth is a business killer. They’re going to struggle to get out of that sandpit. The ratio alone doesn’t matter as much as how it impacts the strategy and trajectory.

An example of this might be 1 yr LTV / CAC of < 1 and ~ 20% growth rate. That’s a really hard equation to solve out of. This happens in low frequency and AOV products so they need to focus on driving up LTV or cracking a cost efficient acquisition channel.