From his start as a Marine Corps officer to leading an impactful EdTech, Jim Brigadier has navigated a career defined by adaptability and purpose. Now the CEO of Ready Education, Jim has spent over 20 years shaping how technology supports student success. In this thought-provoking conversation, Jim reveals how his military experience taught him the power of relationship-building, why curiosity is key to leadership, and how education can break down barriers across the globe.
Hosted by Laureano Díaz, CSO of 27zero, this EdTech Mentor conversation unpacks Jim’s insights on scaling businesses, mentoring talent, and creating solutions that truly make a difference.
Jim’s career is a testament to adaptability and growth. Before venturing into education technology, Jim served eight and a half years as a Marine Corps officer. In his final years, recruiting officers on college campuses, he unknowingly honed the persuasive skills that would later define his sales career. Convincing top students at schools like Duke and UNC Chapel Hill to trade lucrative career paths for the Marine Corps taught him the importance of authentic connection and persuasion.
The leap to EdTech came when a former Marine and associate CIO at Virginia Tech recognized Jim’s recruiting talent and suggested he could sell software—a proposition Jim met with initial skepticism, admitting he barely understood what software sales involved.
Jim’s transition to EdTech in December 2000 was a sharp shift from military life. Still sporting his Marine haircut and shoes, he followed his manager’s advice: "Meet every CIO and CFO in North Carolina, build relationships, and they’ll buy from you." He spent his early days crisscrossing the state, meeting clients, and initiating conversations.
Approaching the role with curiosity, Jim openly admitted his lack of expertise and asked CIOs and CFOs to explain how the software benefited their institutions. This transparency not only accelerated his learning but also built trust and rapport with clients.
These early relationships became lasting professional connections and references. For Jim, the experience highlighted the power of relationship-building and a willingness to learn—principles that have shaped his leadership and strategy throughout his career.
Jim’s sales approach, developed during his early days selling ERP systems, centers on preparation, authenticity, and follow-through. For Jim, success begins with doing your homework.
In 2001, before tools like LinkedIn were common, Jim relied on thorough research to understand his prospects, from published papers to personal interests. This groundwork allowed him to forge genuine connections during conversations, whether about hobbies, challenges, or institutional needs.
After each interaction, Jim meticulously documented what he learned about prospects, using this knowledge to build relationships. He’d send articles or materials tied to their interests, demonstrating attentiveness and care. This effort wasn’t just about remembering details—it was about building trust.
Delivering on promises was another cornerstone of his success. Jim ensured that any commitments he made were fulfilled promptly, often exceeding expectations. This reliability positioned him as a trusted partner to his clients.
Authenticity and curiosity also played key roles. Jim often asked CIOs and CFOs to explain how his company’s software helped their institutions. Their insights not only expanded his understanding but also deepened mutual respect. Many of these conversations turned prospects into advocates, with some even introducing him to peers at other institutions.
For Jim, sales isn’t about the hard sell—it’s about preparation, respect, and authenticity. When done right, he believes, prospects become not just clients but also advocates. As he puts it, “When you promise a little and deliver even more, that really resonates because people view that as integrity and follow-through.”
For Jim, leadership has been a constant, shaped by his upbringing as the son of a Marine Corps colonel and his own service as a Marine officer. While leadership was ingrained early, transitioning from an individual contributor to a sales leader in EdTech brought unique challenges and lessons.
After six years excelling as a sales account executive in North Carolina and Texas, Jim was promoted to regional vice president in 2007. Reflecting on the promotion, he admits it was likely due to his stellar sales numbers rather than proven leadership—a common mistake in organizations. "Just because you're rolling high numbers or doing well in your field doesn't make you a competent leader," he observes.
Jim embraced his new role with determination and curiosity, devouring leadership books, seeking mentorship, and continuously learning. Vulnerability, he believes, is key: “You have to ask questions, admit what you don’t know, and learn from others’ experiences.”
His leadership skills were tested when he suddenly managed a team of 12 account executives—a number that grew to 35. Navigating the transition from peer to manager, Jim adopted a servant leadership approach. “While my team reports to me, I work for them,” he explains, focusing on removing obstacles and empowering his team—a principle central to his leadership style.
At Ellucian, where Jim honed much of his leadership expertise, market fundamentals and buyer personas remained consistent despite organizational transitions. This stability allowed him to refine his approach and lead effectively through change.
Through curiosity, humility, and a commitment to empowering others, Jim demonstrates how embracing growth opportunities can transform a high-performing contributor into a trusted and effective leader.
When it comes to mentorship, Jim values one quality above all: undivided attention. A mentor who makes you feel like the most important person in the room, even briefly, is invaluable. For Jim, mentorship goes beyond advice—it’s about active listening, thoughtful questioning, and genuine engagement.
“I’ve been fortunate to mentor many and be mentored by many,” Jim shares. “The best mentors listen to understand, not just to respond. They solve problems by focusing on your unique challenges, not offering generic solutions.”
Two mentors stand out in Jim’s career. Ron Klausner, CEO at Graduation Alliance, consistently gave Jim his full attention, whether during breakfast meetings or phone calls. “Ron’s depth of experience and focus made him a mentor I aspired to emulate,” Jim recalls. Liz Murphy, CEO at CampusWorks, earned Jim’s admiration even as a competitor. Known for her strategic brilliance and personal touch, Liz remembers the little things—your family’s names, your last vacation—making you feel part of her inner circle.
For anyone seeking a mentor, Jim suggests looking for these qualities:
To Jim, mentorship isn’t about hierarchy—it’s about creating a space for mutual learning and growth. These lessons from his mentors have shaped his leadership and the mentorship he offers, ensuring those he works with always feel like a priority.
Expanding into international markets brings both challenges and opportunities, and for Jim, the journey has been transformative. Starting in 2015 with Campus Management, his focus initially centered on Brazil. Over time, acquisitions and a merger with Blackboard expanded the company’s reach. By 2022, Jim had visited 16 countries, including Brazil, Chile, Peru, Argentina, Mexico, and Colombia.
For Jim, one truth stood out: education is the great equalizer. “Whether in developed or third-world countries, everyone wants students to succeed and for education to uplift their economies,” he noted, reinforcing his belief in education’s transformative power.
Jim’s travels brought vivid examples of education’s impact. In Brazil, a CRM solution enabled an institution to reach a remote Amazonian village where only one person owned a mobile phone. Through outreach, two young women enrolled, walking 90 minutes each way to attend classes. “They would have been the first to earn degrees in their village,” Jim shared, highlighting the ripple effects of opportunity.
In Saudi Arabia, the COVID-19 pandemic dissolved cultural barriers to women’s education. With classrooms closed and online learning surging, Saudi women embraced the chance to study. Using Blackboard’s LMS, female enrollment skyrocketed by 2,300% between 2020 and 2021, a shift aligned with Saudi Arabia’s vision to build a tech-savvy workforce.
Leading across borders has taught Jim that while challenges differ, the goal of empowering students unites institutions worldwide. His advice for international leadership? Respect cultural nuances while focusing on shared values. "At the end of the day, you're part of a team that’s making the world a better place," he said.
By aligning technology with accessibility, Jim has seen education transcend borders, breaking geographic, economic, and cultural barriers. His experiences reinforce a core belief: education doesn’t just change lives—it transforms societies.
The role of a Chief Revenue Officer (CRO) is vital and multifaceted. For Jim, a CRO isn’t just about closing sales—it’s about ensuring a company’s financial growth by overseeing revenue-generating activities across sales, client success, and sometimes marketing. As he puts it, the job is clear-cut but demanding: “Find ways to grow the business. Period.”
Beyond sales, a CRO focuses on client retention, renewals, and identifying new growth opportunities. Marketing often falls under the CRO’s purview, though Jim stresses this depends on expertise. For example, his current Chief Marketing Officer operates independently due to her extensive EdTech experience.
Jim’s transition to CEO has been marked by ongoing learning and strategic hiring. While he has deep expertise in sales, he admits areas like engineering and development require extra effort. “It’s very different from sales—they have their own language,” he says. To address gaps, Jim focuses on assembling a team that complements his strengths. Hiring a CRO, he notes, wasn’t just delegation—it was an opportunity to learn. “I can learn as much from him as he can from me. That makes it deadly.”
As CRO at Anthology, Jim managed 400 people and directly led a dozen senior leaders. His key to success was hiring for both skill and cultural fit. “They need to adapt to the business’s nuances and thrive in its unique environment,” he explains.
Jim’s shift from CRO to CEO came down to timing. After helping Anthology scale from 4 million to 155 million global users and expanding from 12 to 88 countries, he sensed his ability to drive further impact was waning. His gut told him it was time for a new challenge.
Jim’s journey highlights the importance of continuous learning, strategic team-building, and knowing when to pivot—key traits for anyone aiming to succeed in leadership.
At its core, Ready Education aims to transform student success by delivering a student engagement platform that meets learners on their terms, tailored to their unique needs. In a higher education landscape riddled with challenges, the company’s mission is clear: enhancing student engagement to improve retention and outcomes.
Jim describes the platform as more than academic support—it fosters participation, engagement, and community building for both on-campus and remote learners. “The more students are engaged, the better opportunity they have to succeed,” he explains, noting how mental health significantly impacts retention. With 64% of US dropouts citing mental health issues, Ready Education bridges the gap through data-driven insights and tools designed to reach at-risk students. The platform excels at helping institutions build effective services and outreach mechanisms. Whether guiding introverted students in new environments or enabling targeted nudges, Ready Education adapts to diverse needs.
Looking ahead, Jim envisions ambitious growth. With 700 clients in 28 countries, 80% of the market is still in the US, but Latin America is a key focus for rapid expansion within six months. Beyond geography, Ready Education prioritizes brand growth and innovation. “We are our own worst enemy,” Jim reflects, emphasizing the need for continuous improvement to move from “good to great.” This approach drives market relevance and fosters a workplace where employees are energized by the mission.
For Ready Education, growth isn’t just about scaling—it’s about staying true to its mission. “It really comes down to how we can make life better for that institution. What problems do they need us to help them solve as partners?” Jim comments. By addressing these challenges, Ready Education solidifies its position as a trusted ally for institutions, poised to redefine student engagement on a global scale.
Jim’s journey as a board member reflects his sales expertise and commitment to meaningful contributions. As a member of his own board at Ready Education, in partnership with private equity firm Level Equity, and a recent appointee to the board of Lockstep Technology Group, Brigadier approaches his role with mentorship and purpose.
At Lockstep Technology Group, Jim sees board membership as more than governance—it’s about strategic guidance and mentorship. “Being a board member is really about being a board mentor to a degree,” he explains. With a focus on go-to-market expertise, Jim leverages his deep sales knowledge to align insights with company goals, ensuring his contributions are both actionable and impactful.
For Jim, board participation is anything but passive. “As a board member, you can contribute as often or as little as you'd like. I'd like to contribute a lot,” he says, emphasizing his hands-on approach. Whether engaging with the CEO or addressing challenges, he applies the same curiosity and energy that define his leadership.
Jim balances governance with mentorship, viewing board service as a platform to foster growth and innovation. His sales acumen brings perspectives grounded in market realities, enabling him to bridge strategic vision with operational needs.
Jim’s approach offers insights for aspiring board members: contribute with purpose, mentor with intent, and stay curious. By blending operational expertise with strategic oversight, he ensures his time on the board drives meaningful growth for both the organizations he supports and his own professional journey.
For him, being a board member isn’t just a title—it’s an opportunity to mentor, guide, and help organizations achieve their full potential, one decision at a time.
