Job hunting seems to either feel like a drought or a flood. This week I have had so many interviews I cannot count them both hands (though to be fair a number of them were with many people at two different companies, but still.) While I don’t have any official offers – yet – I feel pretty confident that both of these are going to come through (though I really don’t know how the offers will compare or if they’ll come in at the same time… the smaller company is dragging out the hiring process despite, I think, making it clear they want me for the role, and the big company is just moving slow like a big company does.

That said, I’m incredibly torn between these two opportunities. They are just SO different that it’s hard to compare one to the other. The offer and package will definitely influence that (esp if they are drastically different) but ultimately I want to go somewhere that will be my next mid- to long-term thing.

Part of me feels like now before I have kids is maybe the last time when doing a smaller company makes sense, and it’s more a turnaround than startup so it’s a new type of challenge and one I actually think I’m quite suited for. The culture is definitely quirky in all its glory and oddities, but I’m quirky so that probably is mostly a good thing. It would mean working very long hours for the foreseeable future but also potentially really making a huge difference in the business. I keep coming back to the reasons for my last gig not working out and that largely had to do with my inability to get excited about the product — it just wasn’t applicable to enough people in the world, nor did it really improve the world at all. It was a product designed to make money – which all products are – but it had little else going for it in the “help the world” scenario which makes my professional heart sing.

I need some story and interesting space to sink my chompers into. And this smaller company definitely has that. It’s risky in that if I don’t do my job well the company could not grow according to plan and I’d both be out of a job and be responsible for its failure. Meanwhile, the larger company is not an easy role either. It would be very challenging as well, though for different reasons. I surprised myself in how much I enjoyed meeting with the team at this public company, and while I don’t know the results yet I feel like I performed really well in the interview. While often when I interview at smaller companies — who want someone who can do just about everything — I have to stretch the truth a little bit to fit their ideal superwoman, in a bigger company I can just be myself. There are plenty times when that self doesn’t fit a role, but when it does it just seems to click and I feel confident that I’d be going into a position – and surrounded by a team of coaches and peers – who can help me get even better at what I do.

That said – there really is plenty of time in my life to go to a larger company where I don’t necessarily have to stay at the office until 7 or 8pm every night. And in the smaller company there’s still upside, not that I ever expect private company stock to perform well, but the real upside is having a second solid success story – and while I want that to mean that the company does extremely well and everyone is rewarded – it can also mean a lot of other things, as long as I do my job well. I have to just accept that there are a lot of factors I cannot control which effect the outcome – but I can play my part and play it very well. I can bring on top talent to help me (hopefully, knock on wood) and really make a huge difference. Perhaps I like the turnaround better than the startup. There’s a little safety in everyone being more realistic than folks are early on when a company is just launched and product-market fit hasn’t really been defined yet – although the absolute worst thing you could do is even think this when your job is to make everyone want to buy this product.

Even in the case of a new company with really smart executives odds are they’re going to start with a product that won’t look much or anything like what the product is a year or two later. Pivots, even subtle ones, are normal and acceptable. But if you’re in marketing you have to be full speed ahead even if you have a hunch that change is coming soon. Now, this happens in large companies as well, and it can be so jarring because transparency or cross-functional communication isn’t as commonplace as in very small companies. It’s just that in large companies there seems to be a buffer of time and a team to get you motivated on telling one story that might shift a quarter later, vs being on your own in a team moving a thousand miles a minute. Neither world is perfect, they’re just different.

However in certain turnaround situations you have a company that has been through a lot of the back and forth and has found market fit. This is an ideal opportunity to come in, especially for me personally, because what I do best is helping generate consensus around product story and then taking that story and strategically blasting it to the world. Of course this is not going to be an easy path either — a turnaround is simply on its way up, and often in business, as in gravity, what goes up must come down. But unlike gravity, in business, it can go up again. And down again. And up again. That’s business. Even if no one IN business wants that to be the case.

I like the turnaround role to because you have the opportunity to come in and remind everyone — whoever has hung on through the rollercoaster to get the company where it is — that they really do have something great. It’s not a “savior” role per se, but it is a role that is often greatly appreciated because people like cheerleaders… with brains… who can help them take all of their hard work and get everyone, internally and externally, excited about it. So it can be a really fun point of a company to come in. You get to skip the early rollercoaster but you also don’t get stuck in large enterprise politics and layers of management.

But have I convinced myself this is really what I want? It will admittedly be hard to turn down the larger company which – in many ways is a turnaround story in itself – for a smaller company that is much lesser known. At the moment EVERY SINGLE COMPANY on my resume no longer exists, or probably won’t exist soon. That really is not a good thing. Even large company I worked for was acquired with its brand dissolved. Who wants to hire someone with that sort of track record? Having a few years at a company that will probably be around for many years — and doing well at that company with good references there — may be worth a heck of a lot at this point in my career. Plus the vibe is just so different. I have quirk central as one option and level-headed sanity in the other. The two potential opps are seriously night and day — and I could see really enjoying and doing well in both, for different reasons.

I guess at this point I just have to wait and see if I actually get either offer… I tend to have a good sense about whether or not I knocked the interviews out of the park… I could be way off. In each company there was one very challenging interview. In the smaller company I could tell one of the VPs just didn’t like me. He didn’t say quite as much but he just kept criticizing everything I said, which I understand to a point, but it didn’t leave me with a great taste in my mouth for how we’d work together if I were hired for the role. Meanwhile in the larger company one of the senior team members threw a bunch of hard questions at me and I really nailed it. I could tell he was impressed and I think shocked by how I could basically speak the messaging of their product passionately without being a member of the team. Luckily the topic was a space I’m somewhat familiar with but I do seem to have a talent for spin — at least when I actually believe in the product or the vision of the product.

In both of these cases I do care about the product areas… maybe one a little more than the other given its actual ability to benefit society in addition to make companies more money… but really both have elements of societal benefit and are more about the end user experience the user benefits than optimizing process. Hmm. That’s an interesting thought as even though products can both optimize process and provide end user benefit I prefer to work for companies that are focused on the end user benefit versus just increasing efficiencies  alone. There needs to be some sort of “person” that’s part of the story… not just the person who is getting better results because they’re using a product… but the person(s) who are being improved and having their lives improved by using the product. Anyway, both companies cover this requirement, so I guess I have to just wait and see which if either I get offers for. I have a few other potentials in the works as well… when it rains it pours… but many are for companies where they’re focusing on process optimization vs people, so I can’t see myself excelling there over the long term. I want to be smart whatever I choose this time – it’s not just about the paycheck… it’s about where I can really blossom and help and organization blossom as well.

Related Posts:

• Life update and what’s ahead for 2025
• Do something meaningful or just make money or FIRE
• Trying to learn to be a normal, functioning human being
• CoastFI: How do I make $150k a year doing what I love?
• Should I change my career at 40? I need a do over.