Hilina Ajakaiye draws on her experience as an immigrant — and conference organizer — to invite everyone to the table in the Boston hospitality and events industry.
When Hilina Ajakaiye joined the Greater Boston Convention & Visitors Bureau (GBCVB) in 2020 as executive vice president, she was new to working in the hospitality and events industry — but not to organizing conferences. Ajakaiye is the founder and executive director of the R.I.S.E. Women’s Leadership Conference (Realizing Inspiration & Sustaining Excellence), held for the fifth time on Sept. 8 at the Rhode Island Convention Center in Providence. Ajakaiye, who previously worked as a marketing and brand strategy executive for a global food retailer, had known next to nothing about the logistics of organizing meetings when she conceived of the women’s leadership conference in 2017, she told Convene, but she knew about the powerful influence of mentors from her own experience.
When she was 12, her mother sent Ajakaiye and her two sisters to Boston from Ethiopia, where they were born, to live with their father, who had previously left the country for reasons including political ones. Although he had practiced law in Ethiopia, he had to repeat his education in the U.S., which he did, “while driving cabs and working overnight in hotels,” Ajakaiye said. “My sisters and I were latchkey kids running up and down Mass Avenue. What saved me … is that I have always run into women who have embraced me. I’ve had all this incredible support.”
She also was influenced by her father’s dedication to education — he eventually rejoined the legal profession as a professor and lawyer. At 20, Ajakaiye graduated with a degree in communications and English from the University of Massachusetts and continued to earn credentials from New York University and Cornell University, as she rose through the executive ranks in the retail grocery industry.
During those years, Ajakaiye also was a passionate and committed volunteer, honored by organizations including Big Brothers Big Sisters in Rhode Island for her work with immigrant communities. In 2015, she took a break from her job to earn an MBA in international marketing from Northeastern University in Boston. “Then,” she said, “when I finished that in 2017, I started asking myself: ‘What does giving back look like?’”
One response was to create a platform that would help women connect with the kinds of support that nurtured her and her career, she said. She was conscious of the advantages of the connections and insights that had come from the business conferences she attended as a perk of corporate life, she said. “When I was in those rooms, I left always feeling inspired, but I always thought: ‘Wow, I don’t see enough women have access to this.’”
Ajakaiye convened 17 female friends, all leaders in their fields, and successfully pitched them on the idea of collectively bringing 200 more women together to offer them support. “I didn’t know that day that it would be a women’s conference — I called it a conversation,” she said. “I marched into the Rhode Island Convention Center and said, ‘I want to rent some space.’ I had no idea about things like food and beverage, and all of the overhead that it takes to do a conference, but we figured it out.”
Eight months later, more than 500 women attended the inaugural R.I.S.E. conference in Providence in 2018. By the fifth conference, held both in-person and digitally in September, attendance had almost tripled, with 1,400 women attending the day-long conference, where session topics included financial literacy, entrepreneurship, leadership, wellness, and inclusion. (The conference was held online in 2019, and has offered a digital option along with in-person attendance for the last two years.) R.I.S.E. is a nonprofit enterprise, supported by grants and corporate sponsors, and its organizers, including Ajakaiye, are all volunteers.
“We raise money to give money,” Ajakaiye said, “and to support young women and girls who need us.”
‘A Leap of Faith’
Ironically, the conference Ajakaiye founded to pave the way for others proved to be the vehicle that connected her with the next phase of her own career. Ajakaiye met Martha Sheridan, who at the time was president and CEO of Providence Warwick CVB, when both were guests on a radio program in Providence, where Ajakaiye spoke about R.I.S.E. Months later, after Sheridan became GBCVB’s president and CEO, she called Ajakaiye to talk to her about a job helping to lead the organization.
It was a leap of faith to enter a new industry, Ajakaiye said, but she was drawn by Sheridan’s vision of the role that tourism and events can play in mobilizing economic empowerment for individuals and businesses, she said. The hospitality industry is diverse in Boston, a majority-minority city where more than 148 languages are spoken, but not necessarily within its leadership ranks, she said. As the first Black executive at GBCVB, “I’ve used my presence and my face as a Black woman and as a leader within the CVB to be accessible to women and small business owners in Boston’s 23 neighborhoods,” she said. “I am speaking to Black- and brown-owned businesses, and speaking to women-owned businesses,” asking questions about how accessible the CVB and the hospitality industry are to them, she said. “I have 15 to 20 leaders within the city of Boston who are looking to move up, who are managers and above, who want to be the next CEO or GM at a hotel. How do you teach them how to do that? I’ve been really thinking about what does development look like?” she said. “It’s been a passion of mine, just teaching people that the CVB is here to help them out.”
Ajakaiye said that her leadership style is “100-percent focused on inclusion, because I think when you give people opportunities, great things happen. Whether it’s the team at the CVB that we’re building or the volunteer organizers of the R.I.S.E. conference, good change happens when you bring all the stakeholders.to the table. We’re trying to change the narrative of how we lead as people.”
‘Boots out on the Ground’
When Hilina Ajakaiye joined the Greater Boston Convention & Visitors Bureau (GBCVB) in March 2020, she was not only joining an industry that was new to her, but she joined exactly one week before the pandemic shut down the GBCVB offices.
Convene asked Ajakaiye to share her strategy for starting a new job in a new industry in a pandemic:
“I want to tell you that I had this fancy formula, but what I did have was a really committed way of approaching meeting people and developing a network that builds on your network — and really understanding the difference between giving and taking.
“I think you can hear this from anyone who onboarded during the pandemic: I’ve reached out to folks and introduced myself over and over again. And I’ve gotten to know that — whether it’s the mayor, the chief of economic development, or anyone else in the city of Boston who touches our business — everyone is just a phone call or an email away to say, ‘Hey, I see what you’re doing.’
“It’s also putting together some meetings. In 2021, I hosted a luncheon with … those who lead each neighborhood in the city of Boston. I invited 23 of them, including the director of small businesses with the city of Boston. I hosted that to say, ‘I need your buy-in. I want you to support this work.’ We’re hosting a focus group call once a month, then I also do an in-person meeting once a month. I just hired a community liaison manager, but it’s really boots out on the ground. It’s getting out there talking about the initiatives that we have coming up, and also saying: ‘We’re accessible. We want to hear from you.’”
Barbara Palmer is deputy editor of Convene. Ascent is supported by the PCMA Foundation.