Exec Assistant & Chief of Staff at Rupa
Ever since hiring a kick ass Chief of Staff (9 months ago) & Executive Assistant (2 months ago), I’ve gotten a ton of questions from friends on how we three operate efficiently as the “office of the CEO”.
Context: Rupa is now ~60 people & on a multi-million annualized run rate. We also raised a $20M series A a few months ago.
Over the last few months, we’ve iterated a bunch on how we work together — and we are now hitting our groove! 💃 Here’s some quick thoughts on how it works.
Philosophy: A Single Team.
Me, my Executive Assistant (EA) & my Chief of Staff (CoS) operate as a unit. We have one singular to-do list —> essentially it’s all the things on my plate. To triage — my EA goes first. She takes over whatever tasks she can do well and own fully. Then, my chief of staff takes over whatever she can do well and own fully. Finally, whatever is left over is my scope of work (usually higher level and/or highly contextual work). My Chief of Staff should not be doing any work my EA is capable of doing. The goal is to find where each of their limits are and give them ownership up until that point.
Basically, I think of it as — whatever my EA and CoS are capable of doing — they should take that over, even if it’s not in the “traditional” job description. For example — my EA will handle my LinkedIn messages, but not my scheduling (I am particular about my scheduling). They are here to be force multipliers for me. I created their job descriptions based off what I & the company need + what they are capable of, rather than a “traditional” JD.
In practice it looks like this:
Executive Assistant: Example of What She Owns
Builds out slides for weekly all hands (Done by Sunday evening for Monday morning all hands)
Drafts team messages on behalf of me -- progress towards our goals, etc.
Combs through and responds to LinkedIn messages
Sends daily updates
morning: what’s on her plate for the day, team & investor birthdays, anniversaries etc.
evening: what she accomplished and what is still in progress
Sends morning messages about special occasions
Birthdays, anniversaries, teammates out sick etc.
Will draft messages for me to send each person
Owns gifts for all of my direct reports, investors etc.
Handles all bills, physical mail (will physically go pick it up from our company address), & filing away company documents.
Organizes leadership planning offsites / logistics (airbnb, flights, food etc.)
Will own from start to finish — little to no involvement from me or CoS after the 1st one
Owns Expensify & reimbursements
Plans company offsite (with support from CoS)
Onboards new team members (sends laptops etc)
Owns Lever for me — I can forward her candidates and she’ll input them into lever / keep that organized for me
Also — when we were short staffed on customer operations, she learned how to do this and jumped in to help the team 💥
Chief of Staff: Example of What She Owns
My Chief of Staff and I plan our weeks together at the beginning of the week (Sunday evenings). We prioritize work based on the important / urgent matrix & then split it up based on our strengths.
Her work changes frequently — weekly, monthly & quarterly based on what holes we have at the company. The role is extremely dynamic. This is a subset of what she does currently:
Owns HR & people ops completely (until we hire for this)
Owns Rippling & all company systems
Sends offers, does offboarding, point of contact for hiring managers
Owns taxes & company admin
Sourced & interviewed tax firms, managed the entire process
Handles state registration etc.
Owns vendor management
Point of contact for G&A vendors
Owns our weekly all hands
Builds out schedule & manages guest speakers etc.
Owns quarterly transitions
Builds out end of quarter presentations for me
These are epic 100+ slide presentations that go over everything we’ve built in the quarter, etc. they are hilarious and super fun.
Manages end of quarter retros, builds out surveys, makes sure managers get feedback from their teams, etc.
Builds resources for the team — Q2 goals document etc.
Overall makes sure this transition is super smooth.
Building out executive onboarding in preparation for hiring new execs
Will take intro calls with candidates / partners when I am slammed
How We Communicate
My EA & Chief of Staff and I primarily use signal to communicate
I’ve found I need a separation from slack, text, and email (which are all noisy)
The only people I communicate with signal on are my cofounder, our board member, my Chief of Staff, and my EA —> so this medium has high signal to noise ratio 😉. I have notifications ON for signal, but off for everything else (email, slack, text., etc.)
We have a group thread with all 3 of us, and then 1:1 threads as well.
I don’t expect replies right away on Signal. They know that if it’s urgent, I will call them. Signal message if not time sensitive. I expect all messages I send to be acknowledged by EOD at latest (but usually within a couple hours) I expect them to pick up if I call.
Most of our communication is ad hoc. We signal message throughout the day. Here’s what’s NOT ad hoc.
We all three join all of our team wide all hands calls.
My CoS joins our Monday morning leadership meeting (my EA does not yet, but she is only a couple months into the role).
I get a weekly prep message from my CoS outlining her week & priorities.
I get a daily prep message from my EA every morning from 8:30-9AM and an evening recap around 6PM. She is working / online beyond those hours, but those are the times I get the messages.
Generally, I have 1:1 face time with both of them each week — but it’s not scheduled in the calendar. The expectation is their schedules are fluid, just like mine.
Lastly, we are all colocated in San Francisco. This was important for me based on the work I wanted to get done. (i.e. my EA picking up mail and physically combing through it, etc.)
I also have written out clear “success criteria” documents for each of them so they know expectations.
This is just a start and as the company evolves, all three of our roles will evolve too. So take it all with a grain of salt — it’s highly contextual! 💙
P.S. Here’s the job description that I used to hire my chief of staff in 10 days. 🦄