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.

You may have heard this already, but distribution is the new advantage. With the barrier to creating technology lower, the best startups have cracked distribution.

🚩 Single-channel marketing is a huge red flag. If you're past the exploration stage and you've found product-market fit, you should have at least two marketing channels going on. That doesn't mean two paid channels, but you need to have some combination of channels going. You can have the maturity of one channel that you've cracked and another one that you're just building. But if you've been stuck with just one marketing channel for a while, that's a red flag to me.

🚩 No organic presence is also a red flag. As I shared in this article, I believe the new world will have most startups not spend a dollar on paid ads until they have to, which means that brands need to be present on organic channels from the get-go.

🚩 A founder not selling LinkedIn. Sorry this is just a personal one but if you’re not selling on LinkedIn, I immediately question whether you understand Marketing. It’s just one of these biases I have. You don’t need to be posting every day, but I do expect to see ~ 1 a week at least. Founder led marketing is the future to me.

🚩 Over reliance on Google Search → Google Search is a great channel, but it is a pull channel. It can only capture the demand that is available and searching. The problem with Google is you have no control on your ability to scale it up and down. You're heavily reliant on their algorithms. I specifically call out Google over other channels, because, as I mentioned, it's a pull channel. You can scale with all the other channels, but Google is the only one that you can't.

The people questions are some of the hardest to gauge, and often the place where you might not get the most straightforward answers.

The org structure of a company determines the flow of information, and especially in the data world, where you sit has a huge impact. I've also experienced this as a marketer where sitting under a CFO vs. the CEO or even the CPO has a huge difference on the quality of marketing.

🚩 Simply don't work for someone who hasn't done your job. For all the people managers that are seeing this and are triggered, great. You are the exception, but I bet that 95% of managers who have never done the job before are terrible at it. This gets a bit harder the more senior that you get, but an important qualification for a manager is how much they've worked with people in your function before.

🚩 This is a show of character. If the answer is because people couldn't handle the pace, then that's total bullsh*t. Clearly you hired them, and they joined with the expectation that they would be able to handle it. So, either you weren't transparent, or your culture is worse than you think, or they were not as good as they thought. What I look for here is whether the answers they share match other references I've asked or Glassdoor.

🚩 I don’t care about the actual company. I care about the success of those companies while they were there. The sad truth is that only people that have seen high-velocity and high-pressure environments are able to handle that. The startup world is an absolutely different beast.

That doesn't mean that they all have to have been big FAANG companies or unicorn startups, but from my experience, people that understand what's required to fulfill a potential at the largest scale are the ones that can then help fulfill that.

🚩 This is another internal reflection question and best asked to the hiring manager or leadership as the HR person is not likely to know the full answer. A red flag answer to me is “resourcing”. That’s not an excuse because a good company sets the strategy based on resources and is able to deliver based on accounting for that. If they say resourcing then to me it’s a symptom of a broader problem where they have too lofty goals and just put pressure on the team.

You'd be surprised how much an efficient and effective process can make up for gaps everywhere else. What I really care about is strategy and communication, and less about documentation.

When you're working on something that feels meaningful and impactful you are often willing to go the extra distance. Strategic chaos is the opposite of that. It sucks the energy out because it's unclear whether your work is impactful to the business and whether your co-workers are working on things that will help you.

🚩 I look for some semblance of structure where leadership takes a step back from the business, analyzes the needs that they have with the resources that they have, and pivots to adjust. This can be weekly, monthly, or quarterly. A lack of structure is a red flag for me.

🚩 Democracy. A startup is not a democracy. A flat structure sounds great in theory but at the end of the day there needs to be a decision maker. The strategy should have input from many voices but the strategy itself must be singular.

🚩 “We send out an update on Slack.” The next time I hear this, I will pull out of the interview process. Slack is by far the worst channel for communicating strategy. It's virtually the TikTok of corporate conversation.I obviously have nothing against Slack and love Slack itself, but my broader point here is that strategy needs to be communicated in a way that represents its importance.

Companies that don't pull the entire team through the strategy are often the ones that gate keep knowledge and have poor communication. The entire company at any point should be able to understand:

Rituals are the checkpoints that companies must use to understand if they're moving in the right direction. Without rituals, it's hard to know and then requires scrambling at the last minute. What I'm looking for is how do companies keep a pulse on the company, especially in consumer tech. I expect at least weekly reviews and then likely a monthly one as well.

🚩 If anyone ever told me that they don't believe in these rituals and that they do everything async as it goes, I will also stop the interview process because I know you just haven't figured out your shit. Weekly and monthly business reviews will exist forever because they're an effective medium when done right to spot problems and close gaps.

🚩 Ineffective Weekly Business Reviews. This is not a huge red flag but it’s a red flag. An effective WBR is a proxy for how are decisions made and things communicated. I’ve been 3 for 3 on companies that have had shitty WBRs were not great at keeping everyone in the loop. On the flip side, Uber had the best weekly all hands I’ve ever seen. Even with 30K people it was still a must watch. (Read here on how to run an effective WBR)

That’s it for this week, but I want to hear from you!

What questions do you ask before joining that I need to add to this list?

Sincerely,

Sundar