Learn, connect and level up with ambitious Chiefs of Staff
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Join a trusted community of Chiefs of Staff
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A community to fall back upon whenever you need
Meaningful connections with peers, mentors and future collaborators
Socialize and mingle with the On Deck community
Navigate your career supported by intimate masterminds with trusted peers
Regular check-ins
First-hand advice
Meaningful connections
Accelerate your career through continuous learning & development led by the best in the industry
Establish Credibility
- 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
- 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
- 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
- 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
Continuously level up and gain confidence with learning sessions
Practical learning opportunities
High-signal sessions with industry’s best
Ever-growing library of content
Everything you need to accelerate your career for years to come
Application Process
4-Week Onboarding
Life-long Community
Apply to On Deck Chief of Staff
Payment plans available.
TESTIMONIALS
Here’s what other Fellows have been saying about their ODCoS experience
On Deck is like a cheat code - the access to a high quality community alone beats almost any other type of learning!
The community gave me the opportunity to confidentially share my honest thoughts without risk, and receive advice from people who had walked the walked.
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.
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!
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.
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.
An opportunity to finally meet people in similar roles/positions. CoS is a lonely role but ODCoS makes it much easier!
The peer and speaker-led sessions improved my confidence in dealing with challenging situations with my principal, manager and stakeholders.
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.
What does a typical month at ODCoS look like?
October
On Deck jOURNAL
Read stories from our team
How to Get OKRs Right
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.
How to Bring an Operating Model to Life (and Keep It Alive)
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.
MEET THE TEAM
Designed and led by top operators
Ready to apply?
FAQ
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.
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.
ODCoS costs $5,000/year. The program fee covers:
- A year-long membership program and continued access to the community
- Access to an extensive curriculum which includes world class speakers, educational modules, workshops, peer to peer learning and more
- Access to the online community and access to the On Deck Directory
- Access to the ODCoS content library and archive
- 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.
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 four 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.
Between attending sessions, meeting other fellows 1:1, and curated expert groups 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.
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.
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.