Which Game Are You Playing?

The Paths

In every early-stage startup’s life cycle, there comes a time when you have to decide what game your employees should be playing: the Grow the Pie (GtP) game, or the Grow the Resume (GtR) game.

In the world of GtP we forget about the CV and impressive titles for a few years and agree to do everything in our power to make the value of our respective shares go up. We’re all, to a greater or lesser extent, sizable shareholders in the company, and we want it to grow and be as valuable and desirable as it can be. We hope one day we’re able to sell all or part of our ownership, and be handsomely rewarded for it thanks to all that effort we put into making the company a real meteor.

GtR, on the other hand, is the path most people are used to. Your ability to influence the company is minimal. There’s only so much you can do to make your shares’ worth go in either direction. And your percentage of the company is tiny at best. Best bet is to focus on the resume and plan the next move. Accumulate important titles. Crush impressive projects. Tell a killer story to a future hiring manager. Get a big pay bump at the next gig. Rinse and repeat.

The Early-Stage Siren Call

The magic of an early-to-mid-stage startup is that if your company is going up and to the right—a prerequisite for success as far as VC-backed startups go—then everybody onboard is incentivized to make the company be worth even more. Yes, there’s always the risk that things will not pan out, the hours are long, the pressure is high, and compensation is nothing to write home about. But landing a role at a rocketship is a rare feat, and, if you don’t need the cash right away, you might as well take advantage of it.

Nobody accidentally ends up at a high-growth early-stage startup; it’s usually a career bet on an unlikely horse, mixed with the desire to grow professionally as far as any situation will ever allow. The first few hundred employees at many of today’s rising star companies (along the lines of OpenAI, Claude Code, Cursor, ElevenLabs, Perplexity, etc.) did not get a founder’s amount of shares, but the value of even that smaller slice is absolutely eye-watering.

Of course, most firms do not reach their aspired valuations, but many do. And if you live in the Bay Area for a while, you end up meeting plenty who were just early enough at just the right company at least once in their career. They are recipients of a major windfall, either through an exit or a secondary sale, and they inspire others to try their luck at the early-stage lottery themselves. The cycle repeats with every next batch of hopefuls descending upon the peninsula as they have done since the 1840s.

Selling the Pie

It should go without saying that you yourself as a founder or a leader on the team should genuinely believe that your equity will be worth something one day, otherwise you’re in the business of selling lemons. Some industries will have more desirable equity than others. AI-anything in the peak frothiness of 2025 is a valuable ticket. Other industries like game development will have candidates scratching their heads, wondering what options even are. Many were never issued any in the past, and only ever experienced being paid in cash and bonuses.

Know your field and be honest about the prospects. Are you actually a small business masquerading as a startup? Selling staff on high-growth startup equity returns when your business is not in that race is sketchy, and you’re only delaying a reckoning once the reality catches up to the lofty promises you made to the team. Unfortunately there’s always a new wave of young space cadets entering the field, uninformed about equity and startup outcomes math, and unscrupulous founders can get pretty far without anybody realizing their slice never had a chance of going anywhere. Buyer beware.

Career Progression Complexity Awaits Us All

The reality is that it’s inevitable that a company will eventually have its employees play the GtR game. Given enough scale and an unimpressive option grant, it doesn’t make much sense for you to bet the farm on a big company exit. Even if it happens, the effect it will have on most employees is negligible, short of a trillion-dollar-scale outcome.

There is not much you can do to prevent resume prioritization once you hit scale; it’s just economics at work. The best you can do is delay it, or at least soften its onset. Growth fixes everything, and as long as you’re raising back-to-back rounds, riding the hockey stick and the company’s buzz is strong, everybody feels like their pot of gold is only getting bigger. Throw a couple of secondaries into the mix and people get validation that the magical Monopoly money can be worth something.

But once that fountain of growth dries up, the shift to GtR occurs. So what do you do before that occurs?

GtP In Practice

Some development teams decide that everybody is an Engineer (or AI Engineer, Data Scientist, Product Manager, UX Designer, etc.) until informed otherwise, regardless of experience. Or perhaps you’re a Member of the Technical Staff, or a Software Developer or whatever else sounds good. There’s one tier, that’s it. You tell your staff: “At least for now, stop worrying about your internal title, merit increases and getting to the next level. Focus on building the company and when we all succeed, you won’t have to care about your title ever again.” Some other teams choose to convey seniority with more granularity, and end up with Engineer and Senior Engineer as the only two options. Others provide many levels, but still don’t spend any time on frameworks. They eyeball you to one of the tiers and move on, and if you spend too much time arguing over what title you should have gotten, you weren’t a fit for this company stage anyway. All of these strategies have worked in the past.

Even without internal titles, don’t let seniority be what determines who’s right. Make sure that people’s arguments are what wins, and not their years of experience. If someone presents a better design, better data, or is able to more elegantly argue their side, they should win on those merits. Avoid being eaten by the HiPPO (Highest Paid Person Opinion) or its implicit title equivalent. An Engineer with 20 years of experience should lose to one with two if their arguments are worse. One of my fondest memories of working with engineers at Freckle was how free they felt to tell me, the CTO, when I was wrong, leading to my own thinking being improved at a much higher rate than it would be otherwise. It was a little short-term sting to the ego in exchange for actually getting better at my job longer term.

There are also plenty of titles that do not make sense at early-stage startups. If you’re anywhere prior to Series B and you already have Principal, Staff or Distinguished engineers, something went off the rails. Many super-senior titles are a reflection of the scope of responsibilities and the need to interface with many teams and nurture complex systems which simply do not exist at those earlier stages of a company.

“But wait,” I hear you say, “Don’t titles make sense for coordination? Won’t people get confused about who does what if everybody is just X?” Great question, but it’s mixing up the desire to signal one’s career progression with the need to make one’s responsibilities visible to the team. You can be explicit about who leads what, who owns what part of the company’s processes, or who’s the go-to person for critical module ABC. People can be given those roles regardless of their career progression label.

The same one or two bands of seniority can be applied to other roles as well; this compression of titles isn’t only applicable to product teams. The main difference is that product teams tend to be internally focused and don’t need to impress the outside world with important-sounding titles. The same can’t be said for the wine-and-dine disciplines charming customers into an eventual ACH transfer. There the title someone displays should be part of a broader strategy, not left up to them to decide.

Speaking of external titles, how do you handle that side of the equation?

External Titles

Of course, as far as the outer world is concerned, titles very much do matter, and yet you’re not in the business of controlling what your employees choose to put on their LinkedIn profile.

A popular approach is to allow employees to use whatever title they want to signal externally, and to have their managers confirm those titles in case anybody from the outside ever asks, for example, years later when they need a referral. If that’s something that helps them get hired or present well to future employers, great, no reason not to play ball. Most people will be reasonable and not inflate their title beyond what’s plausibly defensible, so you might as well validate it.

At the same time, you internally bucket people into whatever few categories you create, and those buckets are known and visible to everybody internally. Regardless of what they choose to put on their LinkedIn, their peers know what seniority they have internally to the company.

“Okay, but, what does this mean for people’s compensation?” you might sensibly ask. “Won’t it be super opaque as to whether people are being paid fairly?” I’ll cover this in a future article, but the short version is that I’ve tried both approaches and they each have their tradeoffs.

At Double Dusk, we went all the way to the extreme by making everybody’s compensation and equity visible to the company. Everybody could see that people were compensated fairly and there was a system behind it. Nobody was treated any differently from anybody else just because they happened to negotiate better. No chance of being stuck working for years in the same exact role as someone else, making less than them. This approach requires more titles though, and it will lose you the extreme talent that does not fit into those boxes. If we use the $100M AI researcher as an extreme example, some individual contributors can make 1000x more than others, and people understand that’s just the state of the market. Of course if someone ends up with a dramatically higher pay and performs at the same level as someone else who’s paid less, you have a ticking timebomb on your hands once a Google Sheet of people’s salaries starts circulating the office.

The fewer career tiers you have for a discipline, the more compensation will be a judgment call rather than the result of a strict and perfectly equitable formula. Early stage, that’s arguably for the best. You’re a temporary dictatorship formed to survive inevitable company death within x months, and there is little time for making the perfect fair process with a single- or double-digit sample size of staff. Once you’ve guaranteed foreseeable survival, you can go back to fixing all of the shortcuts you took to get there.

So when do you do that?

Timing GtR

A simple rule of thumb is to not worry about titles and career progression until Series B or later, assuming the company isn’t stuck getting there for a decade. You’re not out of the woods until that point. It might turn out that product-market fit was a mirage, and you were stabilizing and adding process to a company that didn’t have legs. Premature scaling is the root of all evil in early-stage companies, whether that’s with regards to staff, process, or technology.

Once you’ve confirmed a repeatable, sustainable, and scalable cycle for generating revenue, you’re Default Alive (to borrow Paul Graham’s term) and Probably Going To Do Well (to borrow mine). It’s time to add more structure to people’s career progression. Until then, you may be months away from shutting down, in which case their career progression will have to progress at a different company, not a bankrupt one.

Once you start shifting away from the land of pie-growing, it will be time to pay for all the debt you accumulated up until that point.

Paying the Debt

Of course, if you choose to go without titles or with an extremely quantized version of them, you’re going to have to have a day of reckoning when the time to level up comes.

Once the astronomical growth slows down—and it always does, even in the biggest success cases—the former carrot needs to be tossed out. Time to roll out the traditional career progression management tools. Career frameworks, competency matrices, arguing with your staff over why they got 3 out of 5 on one particular box of a complex model. That’s now your reality. True, it’s not as high-adrenaline an activity as adding digits to your company’s market cap each year. That’s not to say that some won’t still do well equity-wise, but for most the math will stop making as much sense.

You must clean up the debt that you deferred addressing. You have to make sure people are placed in the right buckets. You want to make the compensation fair based on those groupings, with all of the predictable messiness of that process. Some might get a better title than they would otherwise because you’ve been paying them more than you should have. Others may be performing at a higher level than their pay, in which case you end up bumping them up in comp to reflect that. Either way, you can never reduce someone’s comp without a serious, and understandable, morale hit. You may have to grandfather them in and hope you don’t have too many of these exceptions.

And watch out for the cultural whiplash of this change. People who signed up to play the Grow the Pie game—“we’re scrappy, titles don’t matter, let’s just build something valuable”—suddenly find themselves in a world where career progression is tracked via a spreadsheet, you’re doing 360 reviews and your impact is translated into a box in column D. Some will adapt and say, “Alright, I get it, we grew up.” Some will breathe a sigh of relief, glad they are given more structure. Others will feel like the original social contract quietly expired. They joined a pirate crew, and now you’re asking them to wear naval uniforms and salute.

Some stick around and adjust to the new reality. A few bounce, looking for more green fields where they can be pioneers again. Most have only so many attempts in them at chasing the thrill of early stage chaos and following an 18-year-old founder with tens of millions in funding into the breach. They remember what you were like when you had just started as a founder and they don’t want to see that movie a second time. Most will seek a more stable, more predictable workplace, especially now that they’re older and have more real-world obligations than when the current company was in its infancy.

As the technical founder/CTO, you need to be prepared for wading through the Resume-Driven Development swamps, fighting against adopting complex tech that brings little value to the business, but looks good to future employers. Growing the Resume understandably pushes engineers towards this, but it’s in the company’s interest to focus their growth on other dimensions of their competency, rather than slapping yet another hot tool onto the CV. Seen much Hadoop on resumes lately? I would rather see senior-plus individual contributors demonstrate the ability to manage serious complexity with elegance rather than playing tool bingo or reinventing the wheel.

Some late stage companies do a 180 and do the exact opposite of what I suggest. Mature scale-ups like Affirm allegedly have their engineers rewrite the core of their product on a yearly basis in order to always have something big and impressive for them to do. It’s a serious investment only to spin one’s wheels, all just to retain competent and hungry staff that are constantly craving for a challenge and an opportunity. With sufficiently successful products and sufficiently hot markets you often see companies fall into the pattern of doing whatever it takes to retain their staff, even if they’re not given much to do, so this is far from the worst option on the table. Still, not one that makes much sense for early stage teams that have plenty of lower hanging fruit to pursue.

Conclusion

To recap, an early-stage company’s best bet is to focus on Growing the Pie rather than Growing the Resume. Delay the distraction of resume-building until much later, lest the team spend time on all the wrong pursuits which will only accelerate its demise. There’s always time for ladder climbing once the firm has reached escape velocity. That’s a fortunate state that the company has to first earn.