Winning five out of seven votes of the Boston school committee Wednesday night ended the easy part for Brenda Cassellius. Now the hard part begins for the next superintendent.

Despite broad support from district stakeholders, Cassellius faces a complex district with a maze of political and logistical challenges, plus shattered trust between the system and the families it serves.

“It is not a secret that there are some very broken relationships when it comes to the work of our school committee and the relationship that they have with our ... communities,” said at-large Councilor Annissa Essaibi-George, chair of the city council’s committee on education. “Having that connection and that engagement and that involvement with our kids and our families, and that sort of respectful and responsible relationship, will be key to success.”

Cassellius, 51, is the former education commissioner for the state of Minnesota. She will start as the fifth Boston superintendent in 10 years this September.

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Many stakeholders agree Cassellius confronts an uphill climb after a whirlwind few years in the Boston Public Schools, following the abrupt resignation of Tommy Chang as superintendent, the hiring of Laura Perille as his interim successor despite having no experience as an educator in public schools, the closure of two of the district’s high schools and perennial snafus with student transportation.

“I think she’s got a lot to learn when it comes to our city,” said Essaibi-George. “She’ll have a lot to learn, I think, when it comes to the politics of this city, no doubt. But I think that she’s ready for it.”

Chang struggled to heal a strained relationship with Mayor Marty Walsh. His failed attempt to make high school days start later and the discovery of mismanaged student activity accounts brought Chang's three-year tenure to a screeching halt last summer.

Paul Reville, a former Massachusetts education secretary, said working with the major players in City Hall would be key to a successful superintendency for Cassellius.

“The mayor has been shy of the kind of dissent that typically arises when you make changes in a public school system. Tommy Chang proposed a number of changes, and the mayor pulled back on a number of those,” Reville told WGBH News Thursday. “I think political savviness is critical. That’s something Tommy Chang lacked.”

Cassellius’ work in the state of Minnesota has been brought forth as evidence that she can weave policy with politics. There, she helped overhaul the state’s education funding formula and brought more pre-kindergarten opportunities to children.

“She has experience leading educational reform at a large scale in the state of Minnesota,” said Matt Savage, a co-chair on Boston’s Citywide Parent Council. “We thought she was clearly the best candidate.”

The school committee faced blowback earlier this year after it suddenly announced the closures of West Roxbury Academy and Urban Science Academy, two high schools that serve mostly black and Hispanic students and many with special needs.

Savage also voiced support for Cassellius’ promise to bring students, teachers, parents and community members into the district’s decision-making process.

"She looks to be somebody who’s going to authentically engage with the parent community, but also the Boston community at large, which we think is an awesome thing,” said Savage.

Savage said he was “not thrilled” that the search process itself was emblematic of the lack of transparency in the district. The unnamed 39 prospective candidates were whittled down to a pool of three finalists. Savage said he would have liked to see more of the candidates himself.

“The interviews were announced during school vacation week, and they were announced for the [following] week ... which also coincided with the Easter holiday and the Passover holiday,” he said. “We’re trying not to get the process mixed up with the result. We are certainly very excited about the result.”

The district also went back on a promise to use private foundation donations instead of district funds to pay for the search firm.

For Amanda Fernandez, the co-founder of Latinos for Education, the lack of community engagement in the search process underscored the need for a superintendent able to build trust.

“If we are moving in a direction where we are asking our superintendent to be someone who is working in the community ... as we move forward with searches like this or of any kind, [it’s important that] we do reflect that belief and include that in our processes going forward,” said Fernandez.

Latinos for Education endorsed another candidate, Marie Izquierdo, chief academic officer in Miami-Dade’s public schools. The other finalist was another Latino, Oscar Santos, head of school at Cathedral High School in Boston.

Fernandez said Cassellius will have to work to adequately serve the district’s Hispanic population, which makes up more than 40 percent of the district.

“Minnesota does have a lower population of Latino students and Latino students served in large districts like Minneapolis,” she said. “It is a real opportunity for not only the superintendent, but Boston Public Schools, to really engage with the Latino community.”

Despite hoping for a different result, Fernandez called Cassellius’ selection a “great decision.”

“At this point, what we need is to come together to ensure success,” she said. “Given the issues we’ve had as a city in terms of being segregated, and the racial issues that have existed for so long, we do need a leader that has the capabilities, the competencies to be able to work in all kinds of communities and bring those communities toward a common vision.”

Boston is caught in the push-pull between the mayor and the families in the district, who have stood at odds on issues like Perille’s appointment, school closures, massive budget cuts caused by declining enrollment and a months-overdue teacher’s contract.

Stakeholders hope Cassellius can bridge that gap.

"She did have a lot of strength, particularly in her vision for how to really rebuild trust and transparency in the district and make sure that different stakeholder voices are heard,” said Jessica Tang, president of the Boston Teachers Union. “Finding a candidate that really did have that widespread support, I think, is important to the success of [our] district.”

Our coverage of K through 12 education is made possible with support from the Nellie Mae Education Foundation.