From Freelancer to CMO at comet — An Early Stage Startup Employee Playbook to Thrive in the Fastest Growing Companies

TODO when you read this article
✅ You can download this article as a google doc at the end of the page. Just open it, go to file, then copy it
✅ Copy whatever you want. You can focus on the grey boxes if you don't have time
✅ Modify whatever you want
✅ Adapt it to your situation
✅ Jump to the TL;DR at the end if you wish

A bit more than 1 and a half years ago I quit my job at Withings (now Nokia Health) to learn the basis of web development at Le Wagon bootcamp.

Right after, I would follow courses given by entrepreneurs at the first season of Lion by The Family, now counting hundreds and hundreds of Alumni.

6 months later, after having met Charles during Lion, I would join him as a freelance growth hacker to propel skillee (now comet).

Almost a year later I found myself teaching a class in front of the last Lion winter session as the CMO of comet.

My course was titled: the early stage startup employee playbook.

When Marion from Lion contacted me, my idea was to give a class that could be useful to new startup employees. Indeed working for a tiny/fast growing startup is not the same as working for an big/established company. As the 4th employee of comet, I knew what kind of attitude or mindset could be helpful to succeed (we are now more than 30).

First, I’ll talk about what you’re supposed to do before joining a startup: I/Due diligence.

In a second part, I’ll show you how your knowledge and the company’s will be your best friends: II/knowledge as your main foundations.

Finally, in the last section of this article, I’ll show you how you can thrive in your new company: III/Be the most effective and efficient person in your company.

Don’t take this article as gospel, it is based on my own experience. It’s not a perfect guide, don’t take it as GPS coordinates but more like a compass that will show you the right direction, not the exact location.

Moreover, I won’t teach you how to become a Chief Marketing Officer but how to navigate when you join an early stage startup. Either as a marketer, as a sales person, as a developer, etc.

Here’s how it’ll work:

I’ll tell you what I did at comet, then I’ll give you clear actionnable actions you can find in the grey boxes.

You can therefore skip some parts and go directly to each Key learnings sections if you wish.

I/ Due Diligence 🔎

Working for a startup is like dating someone.

You’ll spend a shit ton of time with this company. Even more than with your partner!

You won’t only see it from 9 to 5 like a “regular” company. No. You’ll think about it from sunrise to sunset. After that, your unconscious will takeover and you’ll start to dream about it.

Really, be careful when you choose the startup you want to work for. Just like any relationship, it’s better to know the person you’ve got in front of you before jumping in the relationship. This doesn’t mean it can’t be love at first sight. But even though. Dig a little bit.

Worst-case scenario you’ll leave after a few months but it’s better to save this time (and money) for you and for the company which is running a sprint while burning cash.

The plan is to: A, gather infos about the startup (vision and team) B, meet the team.

Let’s dive in.

A/ Gather as much information as possible about the startup/vision/team

As I met Charles 6 months before joining, I was able to discuss with him about his project. Hence, I knew plenty about the future of work, and about freelancing.

Plus, I even had an entrepreneurial project about the same topic:

This is my evernote folder with 145 notes about the Future of Work

Even if you don’t have to go that deep, it’s a great idea to search for as much information as you can to see if the company, the vision , and the team are good fits for you.

Key learnings / TODO to gather information about the startup
✅ Gather everything you can about the team in an Evernote, spreadsheet or whatever you want 
✅ Gather everything you can about the business 
✅ Start to analyze and write down everything that goes through your head about what you found 
✅ Write down all the questions you’d like to ask to employees, co-founders, or investors 

B/ Meet employees and founders

My story is a bit different than regular employees as I started as a freelancer.

I had plenty of time to talk with the team, to socialize, to see how they were seriously working during the day or goofing around during parties. This is when I truly fell in love with them.

I knew the vision was right, I knew the people working there were fun to work with, I knew they all wanted to walk toward the same future.

But this took me a few days to realize. As a freelancer, my risks were close to 0 and theirs as well. Starting as a freelancer is actually better than a regular trial period. That’s another story.

Right now at comet, we have a 2-days observation period. Candidates join us to meet the different teams. Each team will expose its purpose and how they work + we will all chit chat about basically anything.

After this tiny trial period, we have a pretty accurate gut feeling about this person, and they do have their own gut feelings about us.

It’s important not to be focused on the executive team only when you discover a person. For instance, I like to alternate with my marketing team members to present our team to potential future employees. You’ll work with a team, not only one person.

Key learnings / TODO about meeting employees and founders
✅ Meet 3/4 employees during work time if possible
✅ Meet 3/4 employees during a party or around a beer
✅ If you can, spend 2/3 entire days in the startup and make sure not to only meet the executives. Be natural. Don't take it as an interview
✅ Take a lot of notes during those meetings
✅ Ask as many questions as you can. Don’t be afraid to ask. I love when candidates ask me questions. It’s nice to answer questions and it’s nice to see that someone is interested about what you’re doing. Really

Now that you’re working for your dream company, you should continue to gather knowledge about the business, the business model, its market, etc. Knowledge will be the foundations of your success.

II/ Knowledge as your main foundations

If you let your learning lead to knowledge, you become a fool. If you let your learning lead to action, you become wealthy.
- Jim Rohn

I love that quote because it tells us that knowledge and learning without actions is worth nothing. Now that you’re working in your new startup, you should take this really seriously. In my opinion, the process should be something like:

Learning → Knowledge → Action

This is exactly what you should do when you start working for a startup. You learn as much as you can about the business you’re working in and your current position.

Your mission will also be to share that knowledge with the entire company in order to coordinate and to be able to take actions at the team/company level.

The above process updated now looks like that: A, gather the existing knowledge, B, create your own knowledge, C, centralize in order to take actions

Gather the existing knowledge → create knowledge by learning → centralize knowledge, and take actions

A/ Gather the existing knowledge

First, gather all the existing knowledge you can find at the startup level. Ask questions, meet people, read internal documents, write notes about them.

Then, gather all the existing knowledge you can find in articles, white papers, books, etc. about the vertical you’re working in. For instance, if you work for a Fintech startup, focalize on this specific topic.

Finally, gather all the existing knowledge you can find about your job. If you’re working as a marketing manager, read everything you can about marketing and take notes about those articles.

Pro tip: use First Search to find a lot of content → https://search.firstround.com/
Key learnings / TODO for gathering existing knowledge
✅ Find articles / books / white papers about the startup you're interested in and its business (note that you should already know a lot from your due diligence. Still, you will be able to fine tune what you're looking for here)
✅ Use Instapaper / Kindle to read and to highlight content / take notes easily
✅ Extract those notes in your smartphone notes app and organize (for instance I have a comet folder with a note called managers' notes where I add all the notes about management)

B/ Create your own knowledge

Sometimes you won’t find what you’re looking for, or maybe you won’t be satisfied about the existing knowledge. Therefore you’ll have to create it from scratch or by talking to experts.

For instance, at comet, when I was Head of B2B and taking care of some of the sales processes, I wasn’t satisfied with what I found so we built our own Sales Machine:

A part of the comet Sales Machine processes
Key learnings / TODO for creating new knowledge
✅ Create new knowledge by talking to experts
✅ Combine different sources of knowledge to create your own
✅ Work with your team to create this new knowledge
✅ Ask for unbiased feedbacks outside the company

C/ Centralize the knowledge

Now you should have tens of notes hanging around everywhere. Google docs, notes, written notes, spreadsheets, words, lucid charts, etc.

Your job is to centralize everything.

This is probably the most important part. Centralization. It’s what will help you and your team to take proper actions.

Most early stage startups don’t focus on what we call knowledge management. Big error.

If you work with 5 or 10 people, you want everybody to be aligned, to have the same level of information in order to steer the ship together towards the same direction.

Without some kind of knowledge centralization, you’re startup is doomed to fail in the long run.

The challenge is to create a momentum in order to build adoption. It’s usually the job of the CEO, but anybody can initiate these kind of actions, and you can help the CEO to create this momentum.

A concrete example of how to create momentum and build a company-wide knowledge management tool

From the very beginning at comet, we used a great tool called stiki which is the best, and most simple tool to gather everything you need to onboard employees.

This was great, but not enough to collaborate and to easily visualize all the accumulated knowledge.

A few months ago, what I did was to centralize and gather everything marketing-related for myself in Confluence.

Confluence parenthesis
Confluence is the perfect tool to build a knowledge base for a team or a company. You can gather everything in what they call spaces and easily collaborate with your coworkers. For instance, you can embed and work on a Trello board right from confluence, you can embed spreadsheets, link to Google doc, etc.
The marketing team Confluence homepage

I built my own marketing space and started to work alone in Confluence. After having set up this first foundation, I took my team onboard. Which was easy as I already added a lot of things in this tool.

This created a momentum as I was able to show our CEO and other team members that Confluence wasn’t an empty shell and just a tool, but something that added a lot of value to the marketing team.

After that, it was only a matter of days before the tool was adopted by the entire company.

Now we are able to see all the knowledge accumulated and built by the other teams. This is great when you want to break communication barriers between teams. Especially when you’re growing super fast and communication is not the #1 priority.

Key learnings / TODO for centralizing knowledge
✅ Find a tool to organize all your knowledge. I like Confluence but pick the tool of your choice
✅ Fill it with all the knowledge you’ve accumulated and document everything in this tool
✅ Embark 2/3 team members and make sure they’re adopting the tool
✅ Spread this momentum to the entire team

This is not a one-time process but an ongoing one. You should do this from day one and keep updating your knowledge foundations.

Gathering knowledge is great, but how do you use it to shine in your organization? How do you become the most effective and efficient employee?

III/ Be the most effective and efficient person in your company

If you want to thrive in the startup world, you have to be the most effective person in your company, or at least, aim for that position.

Effective and efficient doesn’t mean you have to work 70 hours per week. On the contrary. Effective means you’ll work on the right thing, and efficient means that you’ll work on those things by saving as much energy and time as possible.

A startup can be quite dreadful as you’ll be bombarded by informations and everything will move super fast. If you don’t want to get lost or overwhelmed, you’ll have to build processes, routines, automation, and means to prioritize everything.

You want to become the person in your company that transforms an idea into successful actions.

You’ll have to learn, A how to prioritize, B how to be disciplined, and C how to be an innovation catalyst.

Let’s start by prioritization.

A/ Prioritize like a machine: ITINDY

What is ITINDY? it stands for Important Things I’m Not Doing Yet. It’s a method invented by T.A. McCann that can be super effective and can work in parallel with other prioritization methods such as OKRs (Objective Key Results). But let’s focus on ITINDY.

As the business changes and evolves, a founder (you) will also get lots of ideas (some good, some bad) from your team, customers, investors, other companies…but how do you know when or if to act on these? T.A. McCann

You don’t have to be a founder to apply this methods. Anybody can.

When you work for a startup, you’ll certainly have a lot of freedom. Freedom could be your best friend or your worst enemy.

If you can pick the right ideas and implement them, then you’ll be successful. If you don’t and try a little bit of everything, then you’ll fail.

Enters the ITINDY method. Here is what T.A. McCann said about it in his blog post:

As the ideas with merit roll in, I add them to this list, acknowledging both their value (Important) and the fact that I am not losing my current focus to act on them (Randomizing) but I might in the future. Then, I set 2 types of milestones to review the list or specific items; one is “date based” like at the beginning of the quarter or June 1. The second type of milestone and the one we use most often is a “success metric” which could be achieved in the near future or never depending on how the business grows and how right our assumptions were. Examples would include revenue (X MRR), Y number of customers, a funding round > Z, the 10th new hire…all very specific and quantified. If you chose incorrectly on a market, pricing, a sales strategy…you might never achieve these metrics which is where the date-based milestone comes in, giving you an out to make major changes in strategy.
Key learnings / TODO for prioritizing
✅ Create an ITINDY (Important Things I'm not Doing Yet) list. It can be on Trello, in Confluence, or just in a Google Spreadsheet
✅ As soon as you have an idea, or somebody in your team has one, add it to the ITINDY list and see where it fits
✅ In front of each idea add two things. A success metric and a deadline. Indeed maybe you're thinking that you'll reach for instance 10,000 followers on Instagram but maybe you will never because it's not the right channel. The deadline helps you to kill ideas that are meant to never succeed
✅ Be strict with yourself and follow the list
✅ Read the original article by T.A McCann here

B/ Discipline, discipline, discipline

Now that you have a way to be efficient by working on the right ideas thanks to the ITINDY methods, you’ll need a way to be efficient and to tackle these ideas as efficiently as possible.

In order to do so, you’ll have to build discipline.

There’s no one-size-fits-all method but most people rely on building routines that work for them.

I’ll give you the simplified version of mine and you can do whatever you want with it. The best thing you can do is to try, test, and iterate.

  • 5:30am-7am: Breakfast, reading articles, doing some personal administrative stuff, writing articles
  • 7am-7:40am: sports (usually running alternatively with Freeletics program)
  • 8am-8:40am: transportation (I use this time to read on my Kindle or Instapaper app, I highlight things, take notes, and then extract everything during the week)
  • 8:40am-9am: coffee at the office, facebook, and other activities which are not brain-intensive
  • 9am-10am: meetings
  • 10am-3pm: hardcore deep/soft work (focus on the task demanding the most brain power)
  • 3pm-5pm: admin work (answering emails, management-related things, etc.)
  • 5pm-6:30pm: meetings
  • 7pm: home or hanging out with friends
Key learnings / TODO to increase your discipline
✅ Try to find when you’re the most efficient to do deep work (usually during the morning)
✅ Build your day around this time. Try to do early and late meetings, not during the day
✅ Use google Calendar to set up your routines

Now that you’re disciplined and you know how to prioritize, how can you use these new super powers to propel your company?

C/ Become the best Innovator in your organization

The idea is that you’ll start with baby steps, with micro innovations in order to achieve bigger ones.

You’re a maker, a leader, not a follower. Be aware that I’m talking about innovation here but it doesn’t mean creating something totally new. I’m talking about implementing new things improving your companies output. At an individual or team level.

Innovation roadmap
🕑 Months 1-2: you're starting to work and innovate on the smallest unit of the company, yourself
🕘 Months 3-9: you're innovating in your own department
🕛 Month 10-12: you unleash your innovation power at the company level

a/ Months 1 and 2

You’ll work essentially on the two previous point at a personal level: prioritization and discipline.

Here’s a non exhaustive list of things you’ll like to work on:

  • organize your desk
  • build your first professional routine
  • define your successes. Is it helping out a colleague, sharing your knowledge, achieving a business goal, sharing some good time with your team mate, all of them? It’s important to define this in order to feel every single little wins
  • if you don’t have any, work on your personal routine because it’ll affect your professional one. If you’re a mess outside the office for instance, it’s very likely that you’ll be a mess at work. You don’t have to be a tyran, but some organisation has never killed anyone and doesn’t turn your life into something horribly boring. On the contrary, it buys you more time to do more fun stuff
  • work on your personal knowledge management and find a way to make what you learn actionable. Read articles and books, Take notes, classify them, read them on a regular basis, check if they’re aligned with your personal and professional goals, if not, put them away, if yes, apply what you learn to your own life
  • Start to automate things that takes a lot of time but doesn’t add any value to your job. For instance, uploading an article on wordpress can easily takes 40 minutes of your time. Asking someone on Upwork to do it for you costs as little as 3 dollars per article. Totally worth your 40 minutes
Tips for innovating during the first two months
1️⃣ Organize your desk and computer
2️⃣ Work on your personal and professional routine
3️⃣ Work on your personal knowledge management
4️⃣ Work on making what your learn actionable
5️⃣ Start to automate tasks that are time consuming with a low added value

b/ Months 3 to 9

It’s time to expand your innovation scope. Innovate at the department level. How can you make the life of your team mate easier? How can you automate things so that you can all focus on more important stuff? How can you achieve this?

Think of your department as a micro startup inside your startup. And start to think about different things. The following bullet points are some things you can focus on to start innovating (but you could think of tens of others):

  • Define what is the external output of your department (outside the startup). is it happiness for your customers? that might be the case if you work for the customer care. Is it visibility for your brand? How can you improve some processes, what can you automate?
  • How do you communicate with your internal clients (your colleagues from other teams). There are certainly better way to communicate with others. Start a team newsletter for instance. Or set up lunches focused on your current actions
  • How does your department manage new employees’ onboardings. Is there a way to make a new hire more efficient in a shorter amount of time?
  • How do you centralize your department knowledge? Do you write a playbook?
  • etc.
Tips for innovating in your department between month 3 and 9
Focus on the simplest innovations in the beginning to create a momentum. A simple innovation is:
1️⃣ An innovation you can do alone
2️⃣ In a very short amount of time
3️⃣ That will affect all your team mates
4️⃣ Easy or necessary to adopt
5️⃣ Free or super cheap to implement

c/ Months 10 to 12

You’re now known as someone who’s tackling problems and bring innovation to your department. It is now one of your mission to bring this innovative power to the entire organization.

This won’t be an easy task as you’ll face some reticence and unresponsiveness from your colleagues. Change is always hard to implement since we are wired to embrace the status quo.

But here’s a masterplan you can follow

Tips for innovating in your company between month 10 and 12
1️⃣ Focus on only one thing
2️⃣ Choose your target by looking for a company-wide problem
3️⃣ Analyze thoroughly the problem and find a solution
4️⃣ Start to implement it within your team
5️⃣ Slowly embarks the other team by showing them how it improved your team's life

This is exactly what I kinda did with Confluence.

First I started to use it only for myself, then I asked Ludivine and Benjamin, my teammates to join me, then I showed the entire company during a all-hand meeting how we’re using it. Charles (our CEO) was sold on this tool and helped me to implement it at the company level.

This doesn’t work if you don’t find the perfect solution. That’s why you have to try it first at a small scale, see if it works, then diffuse it to the entire company. Be careful not to turn this into politics though. If people don’t want to adopt your solution right away, don’t throw yourself into a political rally trying to convince and convert people by arguing or using rhetoric. Leading by example is the way to go. Show that you’re applying what you’re proposing to yourself and your team and show that it works.

I want to highlight the fact that you don’t have to be a Chief of something or Head of something to implement new things at a team or company level. Especially if you’re working in a Startup which has a culture of pushing and encouraging innovation. If it’s not the case, maybe you should look somewhere else.


Conclusion

Working in a young and fast growing startup is not easy. You’ll have to adapt and grow faster than the business itself in order to add enough value to it.

I gave you a framework of what, I think, are good steps to follow before and after joining the startup of your dream but feel free to adapt it to yourself, even to improve it thanks to your own experience.

After reading this article you might think that everything orbits around knowledge. That’s the case. You need a decent amount of knowledge in order to take the most efficient and effective actions. Sometimes you have to tell yourself that even though you can still gather and analyze more info, it’s better to take action now, analyze results and iterate.

Here’s the Google doc link to download this article. Feel free to comment on my version if you think I should modify some parts. To copy your own version just open the Gdoc, click on “file” then “create a copy”.

TL;DR

I/ Before joining a startup, do your due diligence by gathering everything you can about the company. The plan is to: A, gather infos about the startup, vision and team, B, meet the team. To do so you’ll make your own research by googling, meeting team members, spending a few days in immersion in order to have a good sense of what it’s like to work there.

II/ When you’re in, gather all the information you can as it’ll be the foundations of your growth and the growth of the company. The idea is to: A, gather the existing knowledge, B, create your own knowledge, C, centralize in order to take actions. First see if there’s a centralization of knowledge at your company, if not, gather everything you can wherever you want. From there, build your own knowledge by learning, meeting experts, etc. In the meantime build a knowledge centralization for yourself and for the entire company.

III/ As you grow in the company, you have to reach for the stars by becoming the most efficient and effective person of the company. You’ll have to learn, A, how to prioritize, B, how to be disciplined, C, how to be an innovation catalyst. Learning prioritization and discipline are the cornerstone of becoming a serial innovator. By innovation, I’m not talking about breakthrough innovation, but ways to make the life of you and your team mates easier, more effective, and more efficient through the implementation of automation, new tools, or new processes.