Leadership on the High Seas – Dawn Riley at the America True

Leadership is a critically important factor affecting any team or group venture. In this paper, I analyze the leadership and management style of Dawn Riley, CEO and Captain of the America True Sailing Team, as she guides her team to race for the 1999 America’s Cup.

Dawn Riley Case Abstract

From: http://iacc120cup.altervista.org/immagini/immaginiACC/51-USA.jpg
From: http://iacc120cup.altervista.org/immagini/immaginiACC/51-USA.jpg

Dawn Riley is the CEO/Captain of America True, the first coed syndicate to race for the America’s Cup. Over three years, based on her vision for America True, she built the syndicate from scratch, bringing on investors and sponsors, designing and building a boat, and hiring a sailing crew to race it. In June 1999, Riley must decide how to handle the San Francisco office now that America True’s base of operations is moving to Auckland, New Zealand, where racing will begin in four months. She is facing pressure to phase out the office to cut down on costs, but Riley believes that the people in San Francisco and the work they are doing are key to her vision for America True. She must weigh the tension between immediate pressures to win and the longer-term sustainability of her vision.

The full case is available for purchase directly from Harvard Business School.

Leadership Analysis – Dawn Riley at the America True

By Jeffrey Donenfeld, Spring 2016

Executive Summary

The Dawn Riley case (Hill, 2000) describes the circumstances, goals, and challenges that CEO Dawn Riley faces in managing and preparing the America True sailing team for the Louis Vuitton Cup sailing regatta, as well as the challenges of adapting her role to the highest benefit of the team. Dawn Riley is a veteran sailor, and now in this most critical point in her team’s history, she must make decisions as to her leadership style, responsibility undertaking, and focus. Additionally, a veteran upper management team, leading designers, expert office staff, and a solid boat crew all stand to benefit from her leadership. There are various factors at play, including her team and company’s organizational structure, prismatic personalities among the team members, and rapidly changing goal requirements, all on a rapid timescale leading up to the defining event in this team’s history.

Key Issues and Recommendations

  • Dawn Riley fills a variety of roles within the team, must strive to specifically define her optimized position and fulfillment of these roles.
  • The America True team is diverse and multi-talented, but also hotheaded and driven. They  must bond together and work towards a common goal.
  • Key leaders within the team must support Dawn in her role as CEO, as well as step up to lead the team within their areas of expertise.


Dawn Riley, while an experienced sailor and longtime CEO of the America True sailing team faces personal and team leadership challenges within her team. In this most trying moment, Riley must revolutionize and define her role within the team in order to ascend as the best leader for her team.


Dawn Riley is the CEO and Captain of the America True Sailing Team. In preparation for the Louis Vuitton Challenger sailing regatta, Riley faces management, organizational, and team challenges which she must address both with herself, as well as the rest of her team. Implications of this case study include analysis of broad team and corporate leadership methodologies, an understanding of basic sailing and regatta mechanics based on the author’s personal sailing and regatta experience, and an in-depth look at Riley’s personal leadership and management style. The key issue of the case is determining the optimal course of action for Riley in defining and refining her role within the team. Recommendations contained within this study are critical because the success of the America True sailing team depends heavily on Riley’s own success as a leader, manager, and sailor.

The Dawn Riley case is difficult to analyse. On one hand, Dawn Riley is an admirable, multitalented, and successful leader who has brought her team to the upper echelons of the competitive sailing community. On the other hand, Riley can be seen as an overstressed, thinly spread micromanager who presents conflicting directions to her team and has driven them almost to the brink of organizational paralysis, unable to effectively compete in the Louis Vuitton Challenger series.  

These two sides of the issue make proper evaluation, refined recommendations, and exacting follow through important. At stake here are Dawn Riley’s pride, career, and professional sailing record. More importantly, her entire team’s success is on the line her. Riley getting her act together as CEO and Captain is the most important task at the present moment for Team America True.



The questions that need to be answered in evaluating this case are:

  • What roles is Riley currently undertaking within the team?
  • What does the team most need out of Riley in these final six weeks before the regatta?
  • How can the rest of the team members step in to help Riley define and refine her job roles?
  • How specifically should Riley define her roles to best benefit the team?
  • What else needs to happen on the team to give them the best chance of success in the Louis Vuitton Challenger?

These questions must be answered collectively by Dawn and the team immediately, and deliberation and decision should include all levels of team members.


Analysis and Recommendations

One pervasive issue facing the team is their focus on meetings. The team consistently spends time, energy, and resources assembling themselves in various factions to discuss issues that could have been handled one on one, or by other means of communication. Some amount of meetings are good – they build team synergy, allow for groupthink, announcements, and collaboration. However, the amount of time the America True team spends on meetings takes away from their time and resources they could be spending on other more important items. In the case material  it’s noted that Riley seeks to encourage the boat crew to connect and collaborate with the design crew. (O’Toole 1996) This is admirable. However, in the current form, the meetings don’t actually encourage a free  and open exchange of ideas. They do just the opposite by setting a rigid and terse environment in which ideas are stifled and time is wasted. In order to step away from the rigid meeting structure and encourage more productive and free-flowing communication, novel new methods should be employed. This could include asynchronous communications such as email and instant messaging, as well as synchronous communications such as one-on-one chats and calls. (Lifehacker 2012) As discussed in class, leaders don’t necessarily always need to be rulers or dictators to effect change and communication among those being led. By relaxing her command over the team with rigid meetings and allowing communication to organically flow, Riley will become a more effective leader. (O’Toole 1996)

Riley works on both a management level as CEO, as well as on a crew level as a member of the boat crew. This creates an increased workload for Riley, and hampers lines between her professional and crew personas.  Ultimately, Riley needs to be removed from the crew. In limited instances, Riley should join the boat crews only an outside observer in order for her to maintain basic connection to on-water development. She could sail with the crew on a semi-regular basis in order to integrate between business leadership and on-water intelligence. However, she should not be working as a consistent member of the race day A or B crews.

Unfortunately, sexism is rampant in our world today, and especially with high-level leadership. (Beswick 2015)  Riley’s diversified position puts her in the hotseat, and open from attacks from all sides. In order to combat sexism from the outside, as well as within the team combat sexism, Riley should ascend to her core CEO role, and put in the time to make the team shine. By focusing more time on CEO duties, she can make the team better competitively, as well as tackle other “press worthy” tasks that could help gain future sponsorship and funding. These could include gender equality, under dogness, and altruistic funding partnerships/sponsorships. It’s her undeniable success in this one role that may help insulate her from a myriad of criticisms, including the scourge of sexism.

Riley faces a team bonding issue that’s arising from the “A” and “B” crews being selected just prior to race day   limits the amount of bonding and “synergy” that can be built.(Beauchamp 2013)  Optimally, “A” crew selection needs to happen well prior to race day in order or develop sub-team synergy. Waiting until race day or just prior to race day eliminates the possibility of building crucial sub-crew synergy. It’s that potential synergy that could make or break the team during the critically stressful regatta day.

Currently, the America True team, at the request of Riley, begins their post-practice debriefing on the boat, as they’re being dragged back to port. This is a measure that was implemented by Riley as a way of saving time and getting the debriefs done as soon as possible. However, setting up debriefings so soon after racing fails to give crew members adequate time to decompress and develop their own thoughts and feelings about how the day’s practice unfolded. In order to give the crew appropriate down time after practice, and to enact a structure that allows Riley to stay off the boat during practice, formal debriefs should happen on the dock. Sure, it may take a bit longer, but those minutes of rest and reflection for the crew as they’re being towed into port may prove to be valuable.



In order for Riley to become a more effective leader of her team, she must step fully into the role of CEO, giving up her conflicting duties as a member of the boat crew. As CEO, a number of changes must be made. These include:

  • Streamline team communications by reducing meetings, introducing novel new communication tactics.
  • Give the team rest after practice, before debriefs.
  • Focus on team fundraising and sponsorships as full-time CEO.
  • Delegate other design and staffing decisions to other experienced members of her team’s senior management.



The core question of the Dawn Riley case was how can Riley change her management techniques and roles within her team in order to give them the best chance of winning the Louis Vuitton Challenger regatta. It was found that there were a number of structural, functional, social, and hierarchical changes that should be made. Class material on ethics and leadership styles, as well as other outside sources was drawn from. Further analysis of the issue could reveal additional efficiencies, techniques, and ideas for bringing the America True team to victory.





  • Jeffrey, H. L., Beswick, E., & Meade, J. (2015). Learning and unlearning sexism in the workplace. Human Resource Management International Digest, 23(5), 18-20. doi:10.1108/HRMID-05-2015-0086



  • Bruner, M. W., Eys, M. A., Beauchamp, M. R., & Côté, J. (2013). Examining the origins of team building in sport: A citation network and genealogical approach. Group Dynamics: Theory, Research, and Practice, 17(1), 30-42. doi:10.1037/a0030114



  • O’Toole, J. (1996). Leading change: The argument for values-based leadership. New York: Ballentine Books.



Written by Jeffrey Donenfeld, originally for the University of Denver Daniels College of Business Executive MBA Program Executive Leadership Class, Spring 2016. I received a 94/100 on this assignment. (Original paper PDF)

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One response to “Leadership on the High Seas – Dawn Riley at the America True”

  1. “The key issue of the case is determining the optimal course of action for Riley in defining and refining her role within the team”
    I disagree that