Break into a Chief of Staff role.
In 6 weeks.

The Chief of Staff Academy is a 6-week remote program for aspiring and new Chiefs of Staff who want to accelerate their career growth alongside a global community of peers.

apply Today

Apply by July 1st to join the next onboarding kicking off on June 13th.

LEARN BEST PRACTICES FROM CHIEFS OF STAFF AT
Wise Systems logo

Tried and true frameworks to help you hit the ground running.

If you are an aspiring Chief of Staff or have just stepped into the role, the CoS Academy gives you the skills and the confidence
to be successful right from the start.

Aspiring Chief of Staff

Looking to pursue a new role as Chief of Staff?

Learn practical skills, build an outstanding resume, and do it together with a network of similarly-ambitious professionals.
Peer-to-peer learning
Job search resources & prep
apply Today

Growing Chief of Staff

Want to set yourself up for success as Chief of Staff?

Hone on your knowledge with advice from seasoned practitioners and fast-track your career trajectory.
Learn alongside leaders
Actionable frameworks
apply Today

How the Chief of Staff Academy is different from the Fellowship

No matter where you are in your career,
On Deck’s got your back.

Join the Chief of Staff Academy if you:
Have 3-5 years of general work experience
Aspire to become CoS or have just become one
Can commit to 6-weeks, up to 7h per week
Enjoy learning alongside peers and instructors
Love learning through a structured curriculum
Want help landing your first job as Chief of Staff
APPLY FOR THE CHIEF OF STAFF ACADEMY
Join the Chief of Staff Fellowship if you:
Have 7-10+ years of career experience
Are 6+ months into your role as a Chief of Staff
Want to better empower your principal & team
Enjoy learning alongside industry leaders
Are looking for expert advice and mentorship
Are keen to build a network of top Chiefs of Staff
APPLY FOR THE CHIEF OF STAFF FELLOWSHIP

Join a global community of entrepreneurial learners

Carolyn Kopprasch
Carolyn Kopprasch
Chief of Staff, Buffer
ODF4

On Deck is like a cheat code - the access to a high quality community alone beats almost any other type of learning!

Eva-Marie Costello
Eva-Marie Costello
Chief of Staff to the CEO, Springboard
ODF4

The community gave me the opportunity to confidentially share my honest thoughts without risk, and receive advice from people who had walked the walk.

Matthew Donne
Matthew Donne
Chief of Staff to the CEO, Spring Discovery
ODF4

So much of being a successful Chief of Staff is your network and ability to execute. The On Deck program has vastly expanded my network and resources, giving me confidence to do my job better - to the point where my CEO actually called out this change in me during my most recent mid-year review.

Krisanna Spotswood
Krisanna Spotswood
Chief of Staff to the CEO, Thumbtack
ODF4

The best part of the program for me is connecting with others to learn, problem solve and inspire one another. One of the reasons I was drawn to the program are the mastermind groups where I can bring whatever challenge I have that week and get real time input + lessons from other Chiefs of Staff. It's real time coaching and motivation!

Megan Leetch
Megan Leetch
Chief of Staff to the CEO, Rev
ODF4

ODCoS gives you a sense of belonging in a lonely position at times. It provides you with resources and allows you to give experience where experience is needed.

Ellise McDonald
Ellise McDonald
Chief of Staff, Wise Systems
ODF4

ODCoS is a network of talented individuals who can learn, coach, and grow from one another’s experiences. The program offers relevant guest speakers who have experience in the role who can not only help with strategy to do the CoS role more effectively, but also discuss paths for growth after the CoS tour.

Rachel Kastner
Rachel Kastner
Chief of Staff, OneStep
ODF4

An opportunity to finally meet people in similar roles/positions. CoS is a lonely role but ODCoS makes it much easier!

Layla Lyne-Winkler
Layla Lyne-Winkler
Chief of Staff to the CEO, Catch&Release
ODF4

ODCoS has enabled me to bring validation (and acceptance!) to the ambiguity that is running OKRs, and understand there can be different ways of organizing them depending on what the org needs at the time. I can now say with confidence to my vision-focused CEO that "we're doing fine," grounding us all and recognizing the exec teams hard work in the strategic planning/tracking process.

Piero Marlia
Piero Marlia
Strategy & Operations Manager, Google
ODF4

The peer and speaker-led sessions improved my confidence in dealing with challenging situations with my principal, manager and stakeholders.

Much more than a global, remote program.

The Chief of Staff Academy is the go-to place for aspiring Chiefs of Staff looking to break into their next career altering role.

Decode the organization

Deeply understand the core components of a company: how teams work together, what makes them tick, and what constitutes success.

Learn from seasoned leaders

Master proven frameworks in topics like leadership communications, effective relationship building, and ruthless prioritization.

Navigate complex challenges

Learn how to make decisions, build consensus, and become a confident, relevant thinker that is valued across the organization.

Launch & manage strategic projects

Familiarize yourself with goal setting, balancing high-level strategy with meticulous operational execution, and spearheading new projects.

Fast-track your job search

Get first-hand support preparing for your Chief of Staff job interview with career workshops, resume building strategies and job search resources.

Build a network of peers

Share your journey and feedback with a global group of professionals and make lifelong friends that will outlast your 6 weeks.

What does ODCoS Academy look like?

We have 4-5 hours of programming weekly and expect fellows to spend an additional 2 hours per week outside of live sessions working on assignments, attending office hours, and connecting with other members of the cohort. You can dive into everything, or take a step back when you’re too busy - live sessions will be recorded.
Calendar below is meant to give you an idea of our programming cadence and timing. Exact session dates and times are subject to change.

June

mon
13
10:30AM PT
Kick-off
tue
14
11:00am - 12:00pm PT
Orientation
wed
15
10:30am - 12:00pm PT
Know thyself
A purple book icon
Workshop
thur
16
8:30am - 9:00am PT
Office hours
1:30pm - 2:00pm PT
Office hours
fri
17
2:00pm - 3:00pm PT
Social
20
Juneteenth (observed)
Holiday
21
2:00pm - 3:00pm PT
Speaker session
22
10:30am - 12:00pm PT
Do a lot knowing little
A purple book icon
Workshop
23
9:00am - 9:30am PT
Office hours
10:00am - 12:00pm PT
Deep work
1:30pm - 2:00pm PT
Office hours
24
10:30am - 12:00pm PT
A purple book icon
Discussion
27
10:30am - 12:00pm PT
Ruthless prioritization & decision making
A purple book icon
Workshop
28
2:00pm - 3:00pm PT
Speaker session
29
8:30am - 9:00am PT
Office hours
10:00am - 12:00pm PT
Deep work
1:30pm - 2:00pm PT
Office hours
30
10:30am - 12:00pm PT
A purple book icon
Discussion
July 1
July 4
July 4th break
Holiday
July 5
July 4th break
Holiday
July 6
July 4th break
Holiday
July 7
July 4th break
Holiday
July 8
July 4th break
Holiday

July

mon
11
10:30am - 12:00pm PT
Future planning & strategic frameworks
A purple book icon
Workshop
tue
12
11:00am - 12:00pm PT
Speaker session
wed
13
8:30am - 9:00am PT
Office hours
10:00am - 12:00pm PT
Deep work
1:30pm - 2:00pm PT
Office hours
thur
14
10:30am - 12:00pm PT
A purple book icon
Discussion
fri
15
2:00pm - 3:00pm PT
Social
18
10:30am - 12:00pm PT
Crack the CoS interview
A purple book icon
Workshop
19
2:00pm - 3:00pm PT
Speaker session
20
9:00am - 9:30am PT
Office hours
10:00am - 12:00pm PT
Deep work
1:30pm - 2:00pm PT
Office hours
21
10:30am - 12:00pm PT
A purple book icon
Discussion
22
25
10:30am - 12:00pm PT
Your first 30, 60, 90 days as Chief of Staff
A purple book icon
Workshop
26
2:00pm - 3:00pm PT
Speaker session
27
8:30am - 9:00am PT
Office hours
10:00am - 12:00pm PT
Deep work
1:30pm - 2:00pm PT
Office hours
28
10:30am - 12:00pm PT
A purple book icon
Discussion
29
2:00pm - 3:00pm PT
Social

Step onboard with the Chief of Staff Academy

Becoming a Chief of Staff was confusing and ambiguous — until now.
1. Apply today
Complete a brief application outlining why you want to join the Chief of Staff Academy.
2. Complete onboarding week
Enjoy a first week of orientation with your peers and a personalized onboarding with your instructors to set you up for success.
3. Track your progress with weekly checkpoints
Dive into engaging live sessions, carefully-prepared materials, and weekly assignments — learn and master practical skills that you’ll apply every day in your role.
4. Get support to land your next role
Upon completion of the program, On Deck will support you for your Chief of Staff job interview with career workshops, resume building strategies and job search resources.

Join us today for our inaugural cohort of the Chief of Staff Academy

Sign up before April 30th to get early-bird pricing.
LEARN BEST PRACTICES FROM CHIEFS OF STAFF AT
Wise Systems logo

What you get with the Chief of Staff Academy

One-time fee of $1,250. Pay only when your application is accepted. Payment plans available.
Apply Now
Applicable frameworks & case studies
Weekly assignments to apply your skills
Engaging live sessions with leaders
Office hours with seasoned Chiefs of Staff
Job interview prep & useful resources
Educational curriculum created by current and former Chiefs of Staff
BOOST YOUR CAREER

FAQ

Who should apply to Academies?

You should apply to the Chief of Staff Academy if you have 3-5 years of general work experience, and you aspire to become a Chief of Staff, or you’ve just landed your first role as one. Also, you should align with On Deck’s community guiding values.

How is On Deck Academies different from On Deck Fellowships?

The Chief of Staff Fellowship is for current Chiefs of Staff that want to further level up their skills alongside expanding their professional network. On the other hand, the Academy is for aspiring Chiefs of Staff who want to hit the ground running and learn the frameworks needed to fast-track their career growth.

Think of it this way — If the Fellowship is an accelerant for your Chief of Staff career, the Academy is the foundation. The Academy aims at setting you up for success and making sure you lay the groundwork for yourself before propelling your career forward.

I work full time. What’s the time commitment every week?

This program is a mix of live sessions, assignments to complete on your own, and social networking events with your peers. Overall, expect to spend 5-7 hours per week on the program materials and events.

Is the program fully remote? What’s the time zone?

Yes, the program is fully remote and usually runs on Eastern Time (ET) time zone. There may be optional in-person events, but the core program is designed to be fully remote, so you can access it from anywhere. Session times are generally more US and European friendly.

How much does the Chief of Staff Academy cost?

Early bird pricing for this Academy is $1,250 — it includes 6 weeks of educational content and networking opportunities, as well as an optional 7th week dedicated to supporting you with resume building, job interview and job search prep.

Do I have to attend all of the live sessions?

Live sessions are highly interactive and are an opportunity to practice what you are learning while building relationships with your peers and instructors. 

Attendance is strongly encouraged, but if you miss a session, feel free to reach out to your instructor to set a time to catch up.

Office hours and social events are optional.

Did we miss your question? Drop us a line and we will get back to you asap.
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