CHEYENNE — This story could tell you what Food Group Director Jess Riley wore to the Leap into Leadership dinner and reception Thursday in Cheyenne, but it won’t.

This story could tell you how much salad and chocolate cake Riley ate, but it won’t.

Because when it comes to being a woman in leadership, those things don’t matter, even though it may seem they do sometimes with how women leaders are portrayed in the media.

What this story will tell you is that Riley has learned a lot about leadership in her nearly two years as the director of a nonprofit organization that provides food for children who may go without each weekend when they are not in school.

And it will tell you that Riley is keen to learn more about being an effective leader, and that she has an eye on running for elected office some day to add one more number to the ranks of women leaders who are discovering they have a voice, and that voice matters.


Finding the Food Group


Riley moved to Sheridan about two years ago when her husband, Brett, took a position as director of K-Life, an organization dedicated to improving the lives of youth through solid relationships and the love of Christ.

She began to volunteer with the Food Group within months after settling in Sheridan.

Then, in September 2012, the Food Group decided it had grown to a point where it needed leadership. Riley was asked to become the organization’s only paid staff member and guide the program as it began to grow.

“Running a nonprofit, working in policy and advocacy, has always been a passion,” Riley said.

Riley has a master’s in social work with an emphasis on organizational leadership, so the idea of leadership was not foreign to her.

However, certain things can’t be learned in a classroom.

As the program has grown to a county-wide effort to send food home each weekend with nearly 320 students — an effort that employs more than 100 volunteers — Riley has discovered there are small nuances every day that require constant problem solving and relational management.

Like bags, for instance.

Enough food to feed a child at least seven square meals over the weekend gets heavy. After the program had been running a while, it was discovered that bags were breaking and causing trouble for the students.

The fix was easy — double bag — but Riley said it’s tiny issues like breaking bags, and bigger issues like volunteer management and working with each school to find a process that works best for it, that can make or break a day.

That is why Riley felt it was a good time to increase her own leadership knowledge and begin expanding her network across the state in order to better prevent food insecurity and serve children in need.

“Every one of those 312 kids is worth it,” Riley said.


Leaping into Leadership


Riley discovered Leap into Leadership, which is a collaboration between the Wyoming Women’s Foundation and the Wyoming Women’s Legislative Caucus, on Facebook. She clicked in, and was immediately intrigued.

“I believe strongly we need more women in leadership roles, so it was a perfect fit,” Riley said.

When she arrived, Riley sought out Rep. Rosie Berger, R-Big Horn, who was one of the founders of Leap into Leadership.

“She came up to me, and I didn’t know her, but she came up and said, ‘You are the woman I’m meant to meet,’” Berger said.

Berger was impressed with Riley’s eagerness and forthrightness.

Riley also sought out one of the keynote speakers — Kellyanne Conway, a Republican pollster who co-wrote the book, “What Women Really Want” with Democratic political strategist Celinda Lake — minutes after arriving to discuss an introductory speech Conway gave earlier Thursday.

Riley was also able to connect with several women from around the state who will help her strengthen her work with the Food Group and make it a stronger organization, she said.


Take home points


The keynote addresses given by Conway and Lake during the dinner for the Leap into Leadership conference focused on a wide variety of issues facing women in leadership.

Lake, a Montana native, spoke about the Rising American Electorate, which comprises nearly half of the electorate in America and consists of people under the age of 30, unmarried women and people of color.

This new electorate, Lake said, supports women candidates and values social issues like abortion, gay marriage and environmental protection, making 2016 and beyond an ideal time for women to try to enter political leadership.

Conway focused on how women view politics and leadership. She said they tend to ask two questions: Do I like it? And is it like me? She then talked about how women’s issues are much broader than abortion and contraception. Women considering leadership need to know they could have a voice in issues regarding putting food on the table, fuel in the car and more.

Conway also talked about how the media need to change the way it portrays women in leadership, to stop talking about pant suits and cleavage and start talking about how women are adding their unique voices to important issues that affect men and women alike.

Conway ended with the question, “Why bother?” She told the hundreds of women in the room that they need to figure out why they are Republican or Democrat, why they came to Leap into Leadership, and why they care about what they care about in order to build bridges into leadership.

“I feel that we have a unique voice that isn’t heard equally at this point, so I feel the more women we can get to run and the more women that are involved and engaged, the more our voice will be heard and the more that what we have to offer will be heard in the government,” Riley said in response to the “Why bother?” question.

“Every single woman has a different story, and I think the more you get those voices in there, the more that a well-rounded story will be told as opposed to just those issues that people automatically identify with women.”