On Deck Chief of Staff

Learn, connect and level up with ambitious Chiefs of Staff

On Deck Chief of Staff (ODCoS) is a community for accomplished Chiefs of Staff who want to empower their principals and teams through professional development and access to a trusted peer network.

Apply by August 1st to join the next onboarding kicking off in early September.
JOIN FELLOWS FROM COMPANIES LIKE

Join a trusted community of Chiefs of Staff

Our fellows are Chiefs of Staff working at high-impact companies who are excited to support each other. They come from diverse backgrounds and all share a strong spirit of service.

Adam Duxbury
Adam Duxbury
CoS to the CEO
Chloe Pi
Chloe Pi
CoS to the CTO
Conor Sweeney
Conor Sweeney
Principal and Chief of Staff
Dennis Yu
Dennis Yu
CoS and VP, PgM
Eva-Marie Costello
Eva-Marie Costello
CoS to the CEO
Kevin Dious
Kevin Dious
CoS to the CEO
Krisanna Spotswood
Krisanna Spotswood
CoS to the CEO
Matt Lanter
Matt Lanter
CoS to Keith Rabois
Maya Kuppermann
Maya Kuppermann
CoS to the CEO
Megan Bianco
Megan Bianco
Chief of Staff
Samuel Massari
Samuel Massari
CoS of Engineering
Shaina Anderson
Shaina Anderson
Chief of Staff, Yelp Restaurants
Viki Wolfe
Viki Wolfe
Chief of Staff

A supportive community who's there for you every step of the way

Enjoy ongoing access to a community of world-class Chiefs of Staff to help brainstorm solutions to the unique everyday challenges you face as a CoS

Meaningful connections with peers, mentors and future collaborators

Build long-lasting relationships with peers for support and accountability through curated connections

Socialize and mingle with the On Deck community

Meet not only fellows in your cohort, but across fellowships, in fun social events and community mixers

Here’s what other Fellows have been saying about their ODCoS experience

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.

Accelerate your career through continuous learning & development led by the best in the industry

Level up your knowledge, skills, and confidence as a Chief of Staff through education modules focused on specific learning outcomes taught by seasoned industry executives.

Establish Credibility

Be an integral part of moving your organization towards common goals
  • Build consensus in your organization
  • Influence without authority
  • Develop fluency in core company responsibilities
  • Present your role to others inside and outside of your org in order to best leverage your position

Navigate Ambiguity

Know when your position allows you to take action and when it’s best to delegate to others
  • Define north stars for your organization
  • Empower your team to follow through on execution
  • Develop a decision-making framework with your principal
  • Improve on OKR processes to make them even more effective

Empower Your Organization

No matter your company’s stage, find the right organizational frameworks for you and your team
  • Build operating models that translate into results
  • Establish an operating rhythm for your strategic needs
  • Develop a common language around processes & frameworks
  • Gain context to get to solutions

Optimize Your Career Trajectory

Know when your position allows you to take action and when it’s best to delegate to others
  • Learn how to make the most out of your role as Chief of Staff
  • Understand and communicate the foundations of your role
  • Bring intentionality into your career development
  • Navigate hard conversations with your principal

What you get with On Deck Chief of Staff Fellowship

One-time fee of $5,000. Pay only when your application is accepted. Installment plans and scholarships available.
Apply Now
12-month membership
Access to the On Deck Directory (10K+ fellows)
1:1s with peers, leaders, and mentors
Speaker sessions with Chiefs of Staff
Customized learning modules
Template Power Hours and Workshops
Remote and IRL networking events
Library of 100+ previously recorded sessions
BOOST YOUR CAREER

Continuously level up and gain confidence by learning from Industry Leaders

Learn to implement tried and true frameworks, mental models, and skills to become a more confident Chief of Staff through live sessions with renowned individuals and an ever-growing library of content.

Practical learning opportunities

Regularly expand and refresh your knowledge on a variety of in-demand and relevant topics that you can apply immediately to your job

Intimate sessions with industry’s best

Ask your questions and get tactical answers from our deep bench of successful speakers

Ever-growing library of content

Enjoy ongoing access to a database of recorded sessions so you can learn on your own schedule
Apply Today
Leading from behind & managing up
Leah Cohen Shohet
,
Symphony
Influencing Organizational Culture
Chris Lyons
,
a16z
Best practices for planning strategic initiatives
Naytri Shroff
,
Github
Lessons from working with Reid Hoffman
Ben Casnocha
,
ex-LinkedIn
Key Lessons from Being a CoS
Brian Rumao
,
LinkedIn
On Personal Career Trajectory
Shrina Kurani
,
Republic

Everything you need to accelerate your career for years to come

Our fellows are Chiefs of Staff working at high-impact companies who can support you throughout your journey. They come from diverse backgrounds and all share a strong spirit of service.

Application Process
Fill out the application form to be considered for the ODCoS Membership
We review each application, putting special emphasis on our core values
Successful candidates will be invited to an interview with the Program Director
4-Week Onboarding
Welcome aboard! The next 4 weeks are an opportunity to get immersed in the community and learn how to navigate On Deck to achieve your goals for the years ahead!
Attend kick-off and orientation sessions
Meet up with your curated connections
Focus on specific learning outcomes with deep-dive educational modules
Join community mixers and build meaningful connections with your Chief of Staff tribe

Lifelong Community

The onboarding is just the beginning! After orientation, you'll continue to benefit from ongoing access to everything your ODR membership has to offer:
Educational Tracks designed and led by leaders you know and respect
Signature sessions with world-class speakers
Mastermind sessions with trusted peers
Social and networking events
Community-led workshops
Curated connections with other members
Access to the On Deck Directory
Opportunity to explore other options within the On Deck ecosystem

Apply to On Deck Chief of Staff

ODCoS Membership is $5,000/year. If accepted, we’ll work with you to help expense through L&D.
Payment plans available.
JOIN FELLOWS WORKING AT
Yelp logo
Reddit
Uber logo
LinkedIn
Google logo
Chime logo

What does a typical month at ODCoS look like?

We schedule 2 - 4 hours of programming for ODCoS each week. While fellows are encouraged to attend sessions live, almost all are recorded. Dive in when you can and scale back when work gets busy.

ODCoS Calendar

mon
4
8AM PT
Navigate Ambiguity #1
Signature Session
tue
5
5PM PT
1:1 with another Fellow
An icon showing two persons
Curated Connection
wed
6
Grayed out area
thur
7
8AM PT
High Performance Coaching
An icon showing two persons
Coaching
fri
8
10AM PT
Bi-weekly Digest & Social
An icon showing connection
Peer to Peer
mon
11
8AM PT
Building Systems as a CoS
Star icon
Signature Session
Tue
12
Grayed out area
Wed
13
10AM PT
Bi-weekly Mastermind
An icon showing connection
Peer to Peer
Thu
14
Grayed out area
fri
15
Grayed out area
mon
18
Grayed out area
tue
19
5PM PT
1:1 with another Fellow
An icon showing two persons
Curated Connection
wed
20
Grayed out area
thu
21
8AM PT
Navigate Ambiguity #2
Signature Session
fri
22
10AM PT
Bi-weekly Digest & Social
An icon showing connection
Peer to Peer
mon
25
10AM PT
OKR Panel Discussion
An icon showing connection
Peer to Peer
Tue
26
Grayed out area
wed
27
10AM PT
Bi-weekly Mastermind
An icon showing connection
Peer to Peer
thu
28
8AM PT
Strategic Initiatives
Star icon
Signature Session
fri
29
Grayed out area
On Deck jOURNAL

Read stories from our team

How to Get OKRs Right

Harry Siggins
12
 min read

Healthy cross-functional relationships are key for customer success teams to do their job. In this indispensable guide for customer success leaders, Rod Cherkas draws from his 15+ years of experience as a post-sales exec to provide a masterclass in building relationships with cross-functional partners.

Read The Full Guide

Build Your Team’s Operating Model on These 4 Principles

Josefin Graebe
23
 min read

Healthy cross-functional relationships are key for customer success teams to do their job. In this indispensable guide for customer success leaders, Rod Cherkas draws from his 15+ years of experience as a post-sales exec to provide a masterclass in building relationships with cross-functional partners.

Read The Full Guide

Designed and led by top operators

The team behind ODCoS has a diverse mix of experience and education, having worked at a range of organizations from AngelList and Uber to Twitter and PAX.
Clara
Ma
Program Director
D'azhane
Cook
Program Associate
Tyler
Parris
Program Partner
Mary
Ostafi
Certified High Performance Coach
Josefin
Graebe
Program Partner
Michael
Sheets
Program Partner
Anne
Warren
Program Partner
Rachel
Lau
Program Partner

Ready to apply?

On Deck Chief of Staff is a year-long membership to help you build lasting relationships from Day 1.

FAQ

What is ODCoS?

On Deck Chief of Staff (ODCoS) is a year-long membership for accomplished Chiefs of Staff who want to empower their principals and teams. We combine comprehensive curriculum, world-class speakers and unmatched community to help you navigate this unique role. Learn from those who have come before you and connect with those who are overcoming similar obstacles in their roles.

✔️ 4-week Intimate onboarding

✔️ World-class speakers and curriculum

✔️ Unparalleled peer network

✔️ Long lasting resources to upskill and uplevel

Our members are Chiefs of Staff working at ambitious and prestigious companies who can support you throughout your Chief of Staff journey. They come from diverse backgrounds but they all share a strong spirit of service.

ODCoS is primarily directed towards current Chiefs of Staff who want to grow and learn in the role and understand how their skillset plays into their career growth, especially at their current company. It's also an opportunity to learn directly from experts in the space and alongside respected and accomplished peers in a supportive community.

Who should apply?

To be a good fit for ODCoS, you are probably:

* A Chief of Staff looking to better understand the role and how to execute to provide your principal / team maximum leverage

* A founder, CEO, or executive looking to level up your current CoS -- have them apply today!

* A Chief of Staff seeking to identify how to weave the role into your broader career trajectory and aspirations

* A Chief of Staff who desires a community of other CoS's to help refine your craft, build a peer group of accountability, and share common experiences with

* An experienced operator who has recently taken a CoS role and is looking to build the network and skillset to crush their new role

* One of a select few superstar operators who aren't currently a Chief of Staff but are seeking to enter the role and have highly relevant experience that would enable them to contribute and get value from this community.

What is the cost associated with ODCoS?

ODCoS costs $5,000/year. The program fee covers:

  1. A year-long membership program and continued access to the community
  2. Access to an extensive curriculum which includes world class speakers, educational modules, workshops, peer to peer learning and more
  3. Access to the online community and access to the On Deck Directory
  4. Access to the ODCoS content library and archive
  5. Thousands of dollars in software and services perks

We encourage prospective fellows to work with their executive teams to expense some or all of the cost of the program as an L&D expense, as this is the most popular option.

We are able to accommodate various divisions of the program fee between employee and employer (i.e. 50/50, 75/25, 10/90 etc.), and understand that each organization has a unique L&D policy. We can also provide invoices or accept corporate cards.

Are there scholarships or financing options available?

Our goal is to make the Fellowship accessible to the absolute best talent, no matter their financial situation.

All Fellows have the option to pay in six monthly installments (with no interest or additional charges). We also have a limited number of scholarships available thanks to our Access Fund. Information about scholarship applications will be provided to accepted Fellows closer to the kickoff date.

What is the time commitment?

You can expect to spend ~1-3 hours per week engaging with the program. We recognize that everyone in the program is working full time with busy schedules and a lot of personal commitments so engagement may vary week to week and that's ok.

We have purposefully structured the program with your busy schedules in mind, allowing for structured content, a speaker series, and more curated small group sessions pairing those with challenges to those who have solved them before. We will also record and share sessions and engage asynchronously on Slack. This structure will continue throughout the annual membership.

Is this a fully remote program?

ODCoS curriculum and networking takes place online right now, but as the world begins to open back up, there will be more opportunities to meet up in person. Most of the key interactions will still take place online since our fellowship is international, but we do have in person On Deck events that are cross fellowship so that fellows can meet others outside of just the ODCoS fellowship as well.

Can I participate from anywhere in the world?

ODCoS is one of our most international-friendly programs given its abundance of peer-to-peer mentoring and coaching.

Group sessions will mostly be in EMEA friendly time zones. Recordings will be available for almost all sessions. There will be additional content specifically designed for Fellows based in Europe.

Fellows in APAC time zones are also encouraged to apply. In fact, our New Zealand and Australia fellow contingencies have been some of our fastest growing! We are working on creating more sessions in APAC-friendly time zones and will continue to do so as we gain more fellows in these geographies.

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