Member Spotlight: Max Bray, Chief of Staff at Generation Home

In this Chief of Staff Network member spotlight, you will learn about how Max Bray got his first Chief of Staff role at Founders Forum, and how he transitioned to his next and current Chief of Staff role at Generation Home. During his 4 year-stint at Founders Forum and more, he shares insightful and actionable career and operating advice for you and your Chief of Staff role.

How did you get into your CoS role at Founders Forum and now Generation Home?

  • I realized during my time in consulting that I wanted to move into an operational role where the output of my work would be immediately evident. At the point I knew I was leaving Founders Intelligence, I was quietly looking for CoS-style positions.
  • Fortunately I was lucky enough to have a great relationship with Founders Forum’s group COO, who suggested my an open role when I told him I wanted a new role.
  • As with many CoS hires, the role was never a formally advertised position. We basically established the scope through the interview process and then in my first months in the role.
  • 2.5 years later, having then reached the end of my natural tenure at Founders Forum, I knew I wanted a similar position with a more straightforward trajectory (i.e. a single product company vs. a group of organizations).
  • By speaking to a bunch of VCs and operators I respected (and laying out my parameters clearly), I had the chance to meet Generation Home CEO Will. We immediately clicked: the company size (70+ people), funding state (post big Series A), growth potential (massive market with major unsolved problems) and focus (mission driven business) all made sense.
  • I’ve been very lucky to work with two principals I get along with really well. While many other factors have been important in assessing roles, focusing on my relationship with these individuals has served me well to date.

What are you working on right now?

  • Right now, I’ve got a textbook Chief of Staff chaotic combination of tasks on my plate. I am working closely with our Design & Marketing teams at Generation Home to develop a major TV campaign to go live mid 2022, re-working our ESOP and employee incentivization set-ups with our Capital Markets team, ensuring we’re fully insured across various areas of the business, running & supporting hiring processes across a number of functions, and trying to optimize our CEO to scale with the organization in the coming months.
  • The variety is fantastic, but the context switching and prioritization can be exhausting. Finding pauses to actually get written work done can be a nightmare, but its part and parcel of the role, and something you have to get comfortable with to enjoy the position.

What were some of the key learnings or breakthroughs you had while working as a CoS?

  • The main piece of advice I give to aspirant CoS’s is: pick the principal, not the organization. The role can be lonely as you don't have a team or function, so your relationship with your principal is pivotal to your happiness and success.
  • Similarly, many of the sexiest companies on the outside aren’t actually that interesting internally. Look for smart, low-ego people solving big problems and you’re likely to have a far better time than hunting for the “coolest” brands.
  • Beyond that, the structure of the organization is also key. If an org doesn’t have a fleshed-out C-Suite, or there are issues between the CEO and C-Suite, I’d consider these major red flags. I thought about this in a (semi tongue-in-cheek) article a while back.
  • Lastly, to be effective you have to tread a careful line between carrot and stick work. As a CoS you spend a lot of time persuading people to do things they either haven't done before or don't have full context on. This often involves suspicion or resistance at first.
  • Spend more time upfront taking a team on a journey around why something is important or exciting. That way you will have less work down-the-line when it comes to getting things done. Normally this is done by asking nicely, but every now and then you have to crack the whip too :)

What have been the most challenging and rewarding parts of your CoS experience?

  • The most rewarding is certainly the variety of deliverables you get to work across: not having a specific function or department, and being able to dive into whatever’s most pressing can be gloriously diverse, etc.
  • At Founders Forum, I was lucky enough to be seconded (e.g. the temporary transfer of a worker to another position) for six months as COO into 01 Founders, a new type of coding school born out of the FF network. If I had not been in the CoS position at that point, I would’ve never had the ability to dive straight into an embryonic business for ~six months, close the fundraise, hire the founding team, build the brand and then pass it on as they got going.
  • I also love the ability to work across teams and get to know the whole organization. The great privilege of the role is having a birds eye view of the company as a whole, and being able to work with individuals in every department. This contrasts to potentially being pigeon-holed in one area. 
  • The exposure is also fantastic - you get to punch far above your weight and see things you wouldn’t normally at this level of seniority.
  • The most challenging thing is certainly the constant imposter syndrome. You’re rarely working on something you’ve fully done before (i.e. fundraising, marketing, internal ops, people/HR or strategy, etc), and you have to get comfortable with the uncertainty very quickly or you’ll have a terrible time.
  • You’re also often the youngest person in the room. While you’ve have been delegated authority via the CEO, it can be daunting leading meetings when you are outside of your knowledge depth.

What’s your professional goal in the next ~10 years?  

  • I’m keeping my options as open as possible, but I’m pretty certain I’d like to launch something full time in the not too distant future. Being a Founder feels like a natural next step from a CoS position, so I’m definitely trying to take in as much as I can in the role now.
  • In my spare time, I run a high-end belts brand, Stray, with a friend. I love the idea of being the founder of a product-led business that has a strong vein of creativity in it in the future.

If you could wave a magic wand, with 3 wishes for your role, what would they be?

  • Fewer meetings, fewer meetings & fewer meetings.

What’s something that you want to learn? (professional or not!)

  • I’ve been fumbling my way through learning Spanish for the past three years, including spending a fantastic six months in Central America. While I’m pretty confident conversationally, I know I’m a fair way off work-proficient. 
  • After I’m done at Generation Home, I’d love to spend a proper chunk of time in a Hispanophone country to get it more confident, but that’s a fair way off now.

What’s something that you’re sneaky good at or that people wouldn’t expect about you?

  • I’m exceptionally proud of my Spotify playlists (and spend far too much time curating them).

What’s the best professional advice that you’ve ever been given?

  • It’s a marathon not a sprint. You don’t have to feel like you’re achieving everything now, or even do the thing you want to right away. As long as you enjoy each role, and move the next towards something closer to where you think your dream role lies, you’re doing ok.


What’s something that you’d like help with?

  • My to-do list.

And.... that's a wrap! Thank you so much, Max! You can Learn more actionable tips for your Chief of Staff role and career on our blog.

PS: who or what else would you like to learn from? Let David know at david@chiefofstaff.network!

Download the complete report today!

In-depth analysis of the compensation data based on CoS Level, experience, gender, and more.

Great! We just sent the report to your inbox.
Chief of Staff Compensation Report 2021
Oops! Something went wrong while submitting the form.

Download the complete report today!

In-depth research of the career paths and opportunities the top Chiefs of Staff pursue.

Great! We just sent the report to your inbox.
Chief of Staff Compensation Report 2021
Oops! Something went wrong while submitting the form.
Read Time:
5
Min

Want to join the cos network?

We are an invite only community welcoming new members who meet the following criteria.

You are currently a Chief of Staff*
You work in the private sector (non-government)
You’re ready to actively participate in the community
*Your job title should include Chief of Staff in your public profile.
Not a Chief of Staff yet? Contact Us