Celebrating 25 years

Not quite the same type of anniversary, but still a type of one
Photo by Joy Memon / Unsplash

It's quite the moment when you realize that, in the next week, you'll have been in the full time workforce for 25 years. Sure, there were a couple down periods in there, where you were sitting on the bench as a consultant, or looking for your next gig after getting downsized, but for the most part, you've been at this a quarter of a century now.

This year is also a different milestone, marking my departure from large corporate life to that of a startup. It's strange, going from two and a half decades of working at places whose revenue is measured in increments of 'billions' to one that is nearly a rounding error to that. Going from managing teams of a size that are bigger than my entire new company. Yet, that is in no way a bad thing, merely different.

To that end, this weekend I spent a little time reflecting upon the time working at a tech startup, and the ways in which it is significantly different from that large corporate lifestyle. Sure, not having a corporate Amex, robust HR systems and processes, lots of support departments, and a pretty reliable, at least in the short term, revenue stream, is a strange change, but those are the surface level things which, when you work in a product role, are largely outside of your daily concern. No, its the things that happen every day which are coming to my mind and I want to consider for this post, so let's start talking about how the small company life has required me to adjust.

Its still meeting customer needs

Yes, customers have changed, from historically end customers and franchisees, to now being other companies, but at the end of the day, all those entities are just groups of people. My job is still to figure out what will make the most difference to them, making their jobs easier, and then delivering on solutions to meet those needs. How I do that might look different, but what I'm doing really isn't.

If you know me, then you know that the last couple decades have seen me spend a great deal of time doing turnarounds in those large companies who were my employer. I typically was brought in, saw a mess of decades old technology, and was part of large efforts to retire the old stuff and replace it with something modern. At the beginning, I was just one person on the team, but by the end, I was the one setting the strategy and leading the charge to get it done. It was something that I became really good at doing.

You'd think that a startup would have next to no legacy; well, you'd be wrong. Lots of them outgrow their code rapidly, but we're a bit of a unicorn, having merged two smaller companies and relaunched into a new organization, so lots of legacy stuff still exists that needs to be retired. That's actually a strange comfort in knowing that the skills I've honed for years are finding a new home.

Skills transfer, methods may not

At the end of the day, the skills I've developed over my career largely still apply; it's when and I how I use them that have changed. Setting a product vision isn't really different, but the subject matter has changed a lot. Building out a prioritization and alignment process are still the same, it's just the players and the passions that look a bit different at a tech company. I'm still me, I still do what I do, with the realization that there will be some variations on the theme I need to dig further into, to find a new routine.

People are still people

The media tends to hype startups as being the place where all the smart people with brilliant ideas congregate. As much as it would benefit me to claim that were true, since it's my new home, I must say, that just isn't true. That's not to say I don't work with a ton of smart, motivated people; I absolutely do! I also worked with a lot of smart, dedicated people in my old roles, too. You have people who do just enough to get by in their situation, everywhere you go. You have above and below average people, everywhere you go. That doesn't change.

a red chili in a sea of green chilis
Photo by David Rotimi / Unsplash

Sure, a lot has stayed the same, or at least very similar, but there are some differences, too. Some of the problems are universal, but as I said for many years, problems of scale are just not the same types of problems. You don't typically do the same things at a company where you have headcount in the double digits, as you do in companies where you have staffing of six digits plus. They are just fundamentally different problems.

One further step away is huge

In my old roles, I was one step away from the customer. I could at any time walk into a restaurant and see what they're doing, how they're doing it, and ask them why. Now, those customers are one step removed, as they are the customers of my clients, not my customers. Yes, my customers are now clients, but that is a significant step away from being able to make a real-time improvement. Now, I can show someone where to improve, give them the tools to find that insight on their own, but at the end of the day, I'm no longer responsible for making that improvement.

Metrics are not the same

My old roles were at companies with decades of history as large organizations. They were titans in their markets, well past the days of explosive growth, so that if you grew sales at 3% you did fine, and 5% people thought you were a genius. Now, those levels of growth are a sign you're not cut out for this. I'm more than happy with this change, as the slow growth in those other companies always frustrated me, as I felt we were caught in a doom loop from which no one knew how to escape. I'm not one who believes in growth just to be growing, but growth is a sign of an organization who can do more in the future than they do today.

Profit was often times king in my old world, typically taking up the largest percentage of the team bonus factor every year. Now that is all contingent upon growth. Sure, you can't go cash flow negative trying to get there, at least not for more than a short period, but if its a choice between them, grow first.

Urgency & Ownership

Starting my career in the helpdesk, I got to see first hand, every time the phone rang, what it meant when someone didn't take ownership of a problem. I could fix issues for one customer at a time, but the people whose job it was to take care of those problems for good, were clearly failing to do so. One helpdesk role I had, involved fixing the same 6 problems over and over, all day. That team literally had nothing else to do but those 6 calls. Had engineering fixed those issues, which were so well known and documented that the fixes for them all fit on a single piece of double sided paper, they could have eliminated the calls for an entire team. Yet, those issues went unfixed for as long as I was at that company.

Smaller companies typically don't have that problem. People are faced with the reality of those problems day in and day out, and the only way to survive is to fix those issues. No, they may not always get fixed as timely as we might want, but they get fixed as fast as possible, otherwise clients and internal support teams will not leave you alone, and rightly so.

Rules may not apply

I'm not saying it's the Wild West, but it sure isn't a place with an employee handbook thick as the encyclopedia Brittanica, either. Yes, rules still exist, and in some ways we have a more well defined internal compass, but official rules are things that don't get as much air-time. Doing the right thing is expected to the point that no one feels the need to sit and list out what is a "company sin" and what isn't. Ten Commandments are fine; you don't need a priestly commentary, to know if you're doing something dumb or not.

Fashionable tech

It's marketing. Yeah, that's dumb, but it is what it is. I've always been more of a "does it get the job done in the most reliable way possible" kind of tech decision maker. I don't care how much chrome it has or how large a number of transactions it can process. Does it meet my needs in a way that I don't need to think about it, is my main criteria.

That's not an incorrect viewpoint with a startup, but there is also an element of cool factor that is included in a technology selection. When I worked for a restaurant brand, your operations team had no idea if you were using cool tech, nor did they care. If it didn't put an order out the window faster, why were we bothering them about the brand name tech we wanted?

For a start up, who is looking to attract great people, who want to work on new and interesting tools, suddenly using buzzword tech stack is a more important thing. I'm not really loving that idea, although personally it has given me opportunities to look at new ways of doing things I hadn't ever had the opportunity to do before.

white printer paper
Photo by Kate Trysh / Unsplash

Fluid culture

When you're working for an established company, you tend to keep to the same culture, even if individual leaders put their own specific spin on it. There is a level of continuity and renewal that slowly occurs over time in these businesses. For a small start up, even one that is two companies merging into a new entity, that largely does not exist. Sure, all the people coming in have their expectations and legacy, but as a collective, its suddenly all new.

That leaves a lot of room to be finding your way. Things that seem like they're going to be core values, after you socialize them, you find out that they really don't mean much to the people who need to do the work every day. So, you change, you adjust, and you try again. You're doing this in real time, with everyone seeing it happen, and they're largely not bothered by the shuffling around. Suddenly, the stability you had in your old role becomes more a familiarity with constant change and shuffle, in the new role.

Being different

When you have fewer people and far less cash, you quickly come to the realization that focus matters. That big company you worked for may have seem resourced constrained, but you can do a lot with hundreds of people, even if it feels like little that matters is being done. Having a small team means any waste is a larger percentage loss, so you do everything you can to minimize that friction.

That mindset means, you have to think differently about every situation. How do we get this done given no one available to do it? What is the minimum we can do to reach this goal? Most importantly, you find yourself constantly asking, if I could only do one thing, what is the one thing that will set us apart from everyone else, that clients will really care about us doing. When you find that thing, you know you're on the right track.

I'm not just talking about the big brands you see in every town. Those might seem like behemoths, and they are, but they pale in comparison to the thousands of smaller organizations out there who are growing all the time. I can't even keep the different ones straight; their names keep blurring together in my head. Sure, living in a largely rural suburb in the middle of nowhere, where none of these brands exist, make it a challenge for me to fully experience what makes each of them different, yet I'm doing my best. Maybe my 2024 resolution will be to visit as many of them as I can, to experience their uniquenesses in person. There are worse goals in life.