Fresh set of eyes on sailing in the USA

Published on June 1st, 2022

When US Sailing named Alan Ostfield as the organization’s new Chief Executive Officer, it was an interesting choice. Unlike previous administrators, Ostfield was not a sailor, or at least not yet. But he knows sports, and is a fresh set of eyes for the job. Scuttlebutt editor Craig Leweck checked in with the US boss after his first year on the job:

What was life like before US Sailing?
I’ve been in the sports business my entire career, from Outside Counsel to the Dallas Cowboys to General Counsel of the San Diego Padres, to Chief Operating Officer, President, and CEO of an organization that owns the Detroit Pistons and the Tampa Bay Lightning.

So I’ve been in the sports and entertainment world for 25 years and have seen firsthand the importance of sports teams in the community. So if you work for a quality sports organization, you’re active in the community, and you’re using sports to make a difference in the world.

When I joined the Board of the US Tennis Association, which is the national governing body, I found it to be the same mission. So whether it’s an NGB or nonprofit or professional sports organization that’s doing its job appropriately, they’re active in the community. So this was a natural transition to leverage sailing and all its great attributes to make a difference.

Given your experience as a team working within leagues, how is it now to be in charge of a league?
Well, it is exciting to help structure the sport, to help enable an organization to do something good for the participants, to do something good for the athletes, to do something good for the world. Our kids programs, for example, are teaching sailing but also teaching things far beyond sailing.

That’s the difference we can make. The Siebel Sailors Program is teaching kids to not just be good sailors, but be quality adults. The Reach Program is teaching kids STEM subjects. So its programs like that which are inspiring and great to be involved in.

You are a fresh set of eyes. What do you see that the rest of us missed?
I’m not sure if people have missed it, but to come in as I did, as a fresh set of eyes, as you say, to see the passion that people have for sailing is really amazing. Maybe if you’ve been involved in it so long, you sort of take that passion for granted, but for someone like me, the passion that people bring to the sport is inspiring.

From a business perspective, how do we capitalize on that? How do we better serve our constituents? How do we use that to drive revenue to allow us to provide more for the sailing community? Those are things that we’re all focused on.

Speaking of constituents, there is a broad range from new sailors to Olympic sailors and every ability and boat type in between.
You’re right, we are here to serve the entire gamut of sailing. So whether it’s the five year old that’s afraid of the water, who has never been on the water, who hasn’t experienced the wonders of it, or the elite athletes with Olympic goals, we’re here to serve them all from soup to nuts.

I think that while there’s maybe a natural question of allocation of resources, time and money, every business in America does that. Every person does that. You always make decisions on a daily basis where do I spend my time and resources today. We’re no different in that regard but our focus is to serve everybody because that’s our fundamental mission.

US Sailing is one of 47 National Governing Bodies that works with the United States Olympic & Paralympic Committee. How’s that going?
There’s an ongoing conversation from a couple of different perspectives, but certainly the focus is supporting the high performance and elite athletes.

Paul Cayard, who is the Executive Director of US Olympic Sailing, is working tirelessly to advance the program so we interact with them on a regular basis to make sure that we’re supporting our athletes in the best manner possible. It is a good relationship as they’re very supportive of us. They’re very supportive of Paul being on Board and of me joining the organization and trying to make a difference. So far so good!

I suspect you’ve got your team in place now…
It’s a bit of a new team, for sure, as the board really took the bull by the horns and decided that changes needed to be made. It is a compliment to them for caring about the sailing community as much as they did to do some heavy lifting. So, obviously, Paul’s new, and that’s a consequential change. Me, of course, Andrew Clouston, and most recently Eric Krasnoo. But I will say that there’s a lot of great history at the same time.

I think good organizations find a way to blend the old with the new. I think anybody can keep the old and anybody can blow things up and get the new. I think both of those are wrong. I think good organizations, good people find a way to blend it.

So while the new hires get the attention, its people like Betsy Alison, John, Pearce, and Stu Gilfillen, and Blair Overman, and Jen Guimaraes, and so many others who are serving our constituents perfectly now and have been for years. I think my trick is to find a way to blend the old with the new. Wish me luck!

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