Senior Leadership Gathering

This event is now sold out.

One of the great joys of my career has been the Leadership Academy on Ending Homelessness and Master Class. Ann Oliva and I are shifting things up a bit this year, focusing on having a gathering exclusively for senior leaders…Managers, Directors, Executive Directors, Presidents, Vice-Presidents, CFOs, COOs, CEOs, CPOs and Board Chairs – or comparable positions within your respective organization.

The gathering is set for Pittsburgh November 13, 14 and 15, 2019. It is three full days. Attendees will be placed in a cohort with 9 other people of comparable experience and work through six modules: Leadership Capacity and Momentum; Funding; Awkward Conversations and Conflict; Navigating Politics and Community Interests; Performance; and Relationships. Each module is a half day. Each module has its own senior leader as a facilitator. There are also plenary sessions on Equity, the Psychology of Change, and Why is This So Hard?

Registration is limited to 60 people. First come, first served. Registration up to July 31, 2019 is $779 and you can sign up through our friends at the West Virginia Coalition to End Homelessness OR If three or more people from your organization are planning on attending, please contact for a reduced rate.

A block of rooms is available at a discounted rate at the Sheraton Pittsburgh Hotel at Station Square. Call 1-800-325-3535 to make your reservation.

Attendees do not have to have completed the Leadership Academy or Master Class. However, attendees must be in a senior leadership position within their organization, and believe that ending homelessness, while daunting, is possible. You will be a good fit for this event if, even in your position and given your experience, there are still leadership challenges that you are confronted with where skill development and creation of a peer network would be helpful to you.

We are creating a safe space for senior leaders to build a network with other senior leaders that will last beyond the event. It is our intention to delve into each of the topics from a senior leadership perspective, and to equip senior leaders with tools, strategies and critical questions that help propel their work forward. We know that this work is difficult and that those in senior leadership positions are often without a peer group to explore challenges and opportunities.

Prior to the event, each registrant will be required to complete an online survey to help match them to the most appropriate cohort of other attendees. It is not a particularly long survey. You will receive it when we are a couple months out from the event.

If you have questions about content of the event, please contact me (Iain) at OR if you have questions about registration or coming as a group, reach out to

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