The Operators Who Make the Machine Run

Why your work as an operator really matters, and how to get everyone to recognize it

Preface

Hi everyone,

Welcome to the first edition of Force Multipliers!

I have been overwhelmed by the enthusiasm and excitement surrounding the concept of this newsletter. Over the past 72 hours, hundreds of you have reached out through email, text, DMs, and more, expressing eagerness to see this come to life:

I’m thrilled to get the chance to make Force Multipliers a place where real operational leaders - those who tirelessly contribute to the growth and sustainability of unicorn companies and profitable businesses - can swap stories, strategies, and learn from one another.

I’m also excited to tell the real lessons learned of what actually happens behind closed doors of billion-dollar companies: the shit no one wants to talk about.

I feel a huge personal responsibility to make these newsletters as good as possible, so I’ve chosen the following as topics of discussion for the first three editions:

  • Operational leaders are the unsung heroes that make the machine run

  • Why most of us experience imposter syndrome and what to do about it (yes, seriously - even the unicorn leaders worth billions)

  • The Playbook on managing difficult personalities and clashing egos on your exec team

I want to note, these are real questions posed by real operators at real companies.

It’s my hope you’ll love these discussions and stories as much as I do. I’ll always try to make it as actionable as possible, but sometimes, simply holding space is enough to let you know that you’re not alone, and your work really matters.

Onward,

Regina

Issue No. 001: Is my work really worth it?

Dear Regina,

I think many operators share my sentiment that sometimes, I wonder whether my work really matters or not.

On one hand, there are some days where it feels like if I wasn’t here, nothing would get done and the company would be a chaotic mess. On other days, it feels like the company wouldn’t need me at all, because rather than owning one clear domain, I own many smaller things that make up “running operations.”

A big part of that comes from the lack of definition on what an operator really is:

Are we finance people? Business people? Do we do people-related stuff? Do we take out the garbage? Is it all of the above?

I sometimes find myself feeling envious of other people on the team whose roles are better defined, especially technical people. There is zero ambiguity on whether their work matters or not, and from my POV, areas of responsibility look more properly defined.

How can I process feeling like my work simultaneously is super important, while also feeling like it isn’t mission-critical sometimes?

Sincerely,

VP of Operations, Series B company, ~75 people, ~$90M raised

Dear Operator,

You are certainly not alone in feeling this way. Every operator I’ve encountered has grappled with the sense that they bear a heavy load of responsibilities. A big part of it includes tackling functions that nobody else in the organization is equipped to manage.

I once spoke with a really talented operator at a similar stage as you. They gave me an analogy I love using in my coaching sessions:

In a house, “operations” are the equivalent of plumbing and electrical.

It doesn’t matter how aesthetically pleasing a house is: if the plumbing and electrical don’t work, no one wants to live in it.

Similarly, because operations work is in large part utilitarian, people only really think of it when something goes wrong.

Much like no one cares about plumbing or electricity until a pipe bursts or the lights won’t turn on, no one really thinks about operations until something goes wrong. It can feel utterly shitty to only be thought of when things are on fire.

I’ve written the playbook on how to make your work matter - to you, and to everyone else at the company.

The Playbook on Making Your Work Matter

Here are a few tactics several operators have found actionable and helpful to combat feeling like the unsung heroes of their companies:

Communicate proactively.

Perhaps more than anyone else, operators have to do work around the work.

What I mean is, it’s your responsibility to tell everyone what the hell is going on and what you’re doing. Most operators are the train conductors of their companies. They are responsible for making sure the trains run on time, all personnel know what to do, and whatever other hurdles fall on their plate.

When someone says they’re not being recognized for their work, or they don’t feel like their work is really meaningful, you’d be surprised at how far a memo can go. Take the 5-10 minutes to write something, or highlight the contributions other operators on your team have made. People love having a reason to celebrate and share their appreciation, and the more opportunities you can create for this to happen, the better.

💡 TACTICAL TIP: To structure your memo or update, write out:

- A reminder of what your objectives were with the predicted deadlines

- What has happened since then (when things were done by, and give credit to the people who helped you - this wins you trust! Share the credit; it’s multiplicative, not zero sum.)

- What actions will come next with what deadlines, and who you need to help you (BOLD their names so they understand you are making an explicit ask)

Do this on a regular cadence - e.g.: fortnightly for leadership meetings, during project syncs, or 1-1s with your manager. These memos are also easily distributable on Slack and should be stored somewhere with visibility.

Ideally, if it’s project-based, create a central hub for all documents related to that project.

Document and organize your notes as cleanly as possible.

There was an operator I met last year who sat at the helm of helping the CEO make the acquisition of a 150-person team go as smoothly as possible. She was fundamental in the startup’s success in acquiring this company and integrating the cultures as quickly and seamlessly as possible.

One of the biggest reasons it went so well is because she had a killer Wiki hub that outlined exactly what was happening, on what timeline, and who was responsible for doing what and by when.

I remain firmly convinced that the acquisition wouldn’t have gone through as it did if she wasn’t a part of the team.

The best part is, she wasn’t a COO or even a VP of Ops. She was the EA.

She did not give a rat’s ass that she was an EA - she never stopped for a second to consider whether it was her job to manage the acquisition or not.

She just did it.

She’s still one of the most excellent operators I’ve ever met. I think she honestly puts a lot of other operators I’ve met with much more senior titles to shame - because of how organized and proactive she was.

She came from a background of fashion before jumping into startups (she worked for a certain billionaire influencer who is very known and popular for a certain line of women’s clothing…so she probably got her prowess on being ridiculously organized from being on-call 24/7 to this person.)

Operators by default have to be organized. If you’re not organized, you’re in the wrong line of work.

Organized, clean docs can act as a central hub for information, whether it’s a really sleek-looking Coda doc, or a Notion page with all crucial pieces of information readily available to other teammates.

It feels almost silly to write here, but you would be surprised at the number of operators I’ve met who brush off documentation as unnecessary bureaucratic work.

Attention to detail goes a really long way. Document well, and you’ll find yourself soon enough defacto running every operational part of the company. This will help you feel like your work really, tangibly matters.

Be ready to elevate yourself by hiring and writing yourself out of a job.

Many operators end up stuck taking on responsibilities that shouldn’t be theirs in the first place.

The most common example of this is in early-stage startups, when operators function as generalists that plug in all the stopgaps. You’ll see Ops Generalists, BizOps people, and especially Chiefs of Staff that have incredible scope creep.

Again, where is your responsibility in doing something about this? It’s your job to speak up and make sure that it’s clear when it’s time to hire someone to take on a job function.

For example, at some point, your company will need a proper recruiter; you probably can’t do it on your own forever, and it would actually be irresponsible for you to own it beyond your current capabilities.

This is the point where you would:

- make sure you’ve documented all of your processes as Standard Operating Procedures (I recommend storing them in a database like this one)

- declare your intention of hiring for the role to your exec

- write a compelling job description, and

- train and pass off your responsibility to the new hire

By implementing all three of the strategies above, you can elevate your work in a way that showcases your value and minimizes the feeling of being an unsung hero. Recognizing your own contributions proactively will encourage others to acknowledge how integral your role is to the company’s functioning.

Thank you for joining me in this inaugural edition! 🎉

Next week, I’ll be sharing stories around Imposters Syndrome: why it’s a very real thing, and how many billionaire operators still feel it to this day. (Bonus: I’ll also write about why some VCs incorrectly think it doesn’t exist…)

What did you think - did you like the topic discussed today? Did you like the stories I shared? How can these be even better? Please let me know in the comments or by DMing me. I promise I read everything.

Until next time,

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Want more operational content?

Check out Coaching Founder for over a dozen free, downloadable Notion templates to use at your company, and tons of write-ups on how to level up your execs, your teams, and yourself.

About Regina Gerbeaux

Regina Gerbeaux was the first Chief of Staff to an executive coach who worked with Silicon Valley’s most successful entrepreneurs, including Brian Armstrong (Coinbase), Naval Ravikant (AngelList), Sam Altman (OpenAI / Y Combinator), and Alexandr Wang (Scale).

Shortly after her role as Chief of Staff, then COO, she opened her own coaching practice, Coaching Founder, and has worked with outrageously talented operators on teams like Delphi AI, dYdX, Astronomer, Fanatics Live, and many more companies backed by funds like Sequoia and Andreessen Horowitz.

Her open-sourced write-ups on Operational Excellence and how to run a scaling company can be found here and her templates can be found here.

She lives in the Pacific Northwest with her partner Lucas and dog Leia, and can be found frequenting 6:00AM Orangetheory classes or hiking trails nearby.

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