Too Big, Too Small, Just Right: What Actually Travels When You Move Between Big Companies and Startups

Written by: Geoff Sanders, Director of Digital Marketing, Reality Labs @ Meta

I’ve spent my career working at companies across the size spectrum. I’m currently Director of Digital Marketing at Meta’s Reality Labs, the division behind Meta glasses, Ray-Ban Meta, Oakley Meta, Meta Ray-Ban Display, and the Quest headsets. Before Meta, I’ve led Marketing teams at Fortune 50 companies like Citi, mid-size firms like Gilt Groupe and Betterment, and DTC startups like Casper and Firstleaf, where I was CMO prior to joining Meta. My sweet spot has stayed the same regardless of size: combining marketing, data, and technology to drive business performance.

What changes job to job and company to company isn’t the work you love. It’s everything around it: how decisions get made, how much process exists, and how many people you lean on to get anything done. Most people preparing to switch worry about whether they’ll fit the culture. But culture is the easy part, because you can read it and adapt to it within a few months. The harder thing is adapting the set of reflexes you built in your old environment, the automatic ways you learned to operate, because those feel like judgment rather than habit. You don’t notice them until they misfire. And they break in opposite directions. Big companies teach you to work the system; startups teach you to be the system. The reflexes that make you great at one are exactly the ones that misfire in the other.

1. The “Switch” Mindset: What are the defining psychological traits of someone who successfully navigates the jump from a structured, resource-rich big company to the “build it as you fly it” environment of a startup – or vice versa?

Going small: what you need

• Comfort with ambiguity. At an early stage company there’s often no established way to do something and no history to plan against. You have to be comfortable when there’s no clear right answer and the call is yours. People who need a playbook handed to them struggle. People who can write the first version thrive.
• Genuine curiosity. Roles are broader but shallower than the specialized ones at big companies. You’ll touch finance, product, ops, and support in ways you never did before, and the people who succeed actually want to. If the sprawl exhausts you rather than energizes you, it’ll wear on you fast.
• Persuasion over authority. With no process to lean on, you influence directly, and that matters most at founder-led companies where the founder’s biases shape everything. I’ve worked with founders who didn’t believe in brand advertising, and only real skill at connecting brand work to what they already believed made the team successful.

What can go wrong: you wait for a green light that’s never coming, and read its absence as “not yet” instead of “go.” That doesn’t look diligent at a startup. It looks like someone who can’t be trusted with ambiguity, which is the whole job.

Going big: what has to switch

• Coalition over conviction. Ambiguity gets replaced by alignment, and the founder’s gut by a room of stakeholders who all have a legitimate say. Persuasion still travels, but now you’re building consensus, not convincing one person.

The trap: you treat every review as an obstacle to route around, ship first and socialize never, and burn political capital in month one that you needed in month twelve. I learned this at Casper, which was in the midst of evolving from a DTC ecommerce company into an omnichannel retailer. I extended a promotion on our website, a call that was right for the ecommerce business I ran but put our owned retail and wholesale groups in a tough spot, because their businesses moved at a different pace than mine. At a startup, moving fast rarely cost you, because there were few other teams to knock over. The bigger the company, the more that same speed creates collateral damage you didn’t see coming.

2. The Skillset Gap: Is there a specific “superpower” or skill set that high-performers from large corporations are forced to acquire quickly when entering the startup world?  What about moving in the other direction?

Going small: the skill is trailblazing

The easy answer is “scrappiness,” but that’s too general to be useful. I’d call what’s needed “trailblazing.”

• From “why” to “why not.” When I moved from Citi to Gilt, things that took three months at Citi took my new team an afternoon. That flipped my default question from “why should we do this?” to “why not?” The bottleneck stopped being approval and became conviction.
• Own the call. At a startup nobody makes the decision for you, because there’s no one else to make it. You get comfortable being the person who decides and then owns the outcome.

The trap: the big-company star keeps convening the meetings and building the decks to gain alignment, recreating the ceremony of a process that no longer exists because the ceremony was where they felt safe. Meanwhile the window of opportunity closes.

Going big: the skill is navigating the system

• Orchestrating beats doing. At a big company your leverage isn’t in the work itself, it’s in directing specialists who each go deeper than you ever could alone. You have to find where a decision actually gets made, then work through the right people to get there. The doing is no longer the job.

Where it stalls: you keep doing the work yourself, the way you did when you were the whole department. You out-execute your own team on one slice of the problem while the other nine sit unmanaged.

3. The “Goldilocks” Factor: How should a candidate assess whether their experience level is “too big” or “too small” for a specific company stage (e.g., Seed vs. Series B vs. Series C vs larger)?

The most common answer here is with years of experience: am I senior enough, or too senior, for this stage? That’s the wrong axis in both directions. The real question is what kind of work gives you energy, because size and stage shape how you’ll spend your days far more than they decide whether you’re qualified.

Going small: match the seat to your energy, not your resume

• Follow the energy. The smaller the company, the more in-the-weeds execution any one person does. If you love being in the data yourself and getting into the AdWords account, an early stage startup can be a joy. If that work drains you, it’ll grind you down no matter how good at it you are.
• Plan for the loneliness of being the expert. As CMO at Firstleaf, I was the most experienced marketer in the building, a seat plenty of senior people want. Nobody warns you it’s lonely. There was no marketer above me to learn from and no peer to pressure-test a call at 11pm. The job didn’t get easier with seniority; it got quieter. I had to manufacture what a bigger company gives you for free, leaning on my personal network for the sounding board the org couldn’t provide. 
• Match the stage to the seat. Seed, Series B, and Series C are different jobs, not bigger versions of each other. Seed is building the thing. Series B is scaling what works. Series C is professionalizing it without killing what made it work. Pick the one that matches the work you want, not your title on paper.

The trap: you take an early stage role for the title and find there’s no one to delegate to. You wanted to be a CMO. You didn’t want to build the dashboard, write the copy, and run the account, which at that stage is the job.

Going big: the scope you gain can feel like the scope you lost

• Depth over breadth. The pull is real: bigger budgets, real teams, and finally not being the only expert in the room. At Firstleaf I owned all of marketing and customer service, about 30 people at peak. At Meta, that same surface area is spread across at least 300, and probably more I don’t even know about. Some find that a relief and go deep for the first time. Others find it a cage, and don’t notice until they’re already miserable.

Where it chafes: you reach for scope that isn’t yours anymore, wading into the analytics team’s model or rewriting the brand team’s brief. The breadth that was your superpower now reads as someone who won’t stay in their lane.

The Thread That Ties It Together

The hard part of switching isn’t learning new things. It’s unlearning the reflexes your last environment rewarded. Every trap above is the same mistake in different clothing: running yesterday’s instinct in today’s environment and refusing to notice. The people who move well know which instinct they’re running on, and switch it off when the ground shifts underneath them.