Director of School Success - East Region

About GradGuard

As the leader in college tuition and renters insurance, GradGuard serves more than 1.7 million students across 1,900+ institutions. 

Our national technology platform embeds innovative insurance protections into the enrollment processes of over 700 institutional partners, empowering schools to increase college completion rates and reduce the financial impact of preventable losses.

GradGuard supports College Life Protected, a social purpose entity that promotes research, professional development, and best practices that strengthen campus communities, families, society and the economic competitiveness of our nation. 

GradGuard was recognized as one of the Top 50 Financial Technology Companies of 2025 by The Financial Technology Report, a RISE Internship Award winner, and a Phoenix Business Journal Best Places to Work finalist, GradGuard remains committed to innovation, excellence, and supporting students and families.

Hear from our students, families, and partners:https://www.youtube.com/@GradGuard

About the role

You've spent time in higher education, maybe in housing, student affairs, or campus operations, and somewhere along the way you realized you're wired a little differently than most. You care deeply about students and the institutions that serve them, but you're also energized by goals, growth, and getting things done. You like building relationships that actually mean something. You get restless when there's no challenge in front of you.

If that sounds familiar, keep reading.

At GradGuard, we provide a critical safety net for college students and their families, protecting them from the unexpected so they can stay focused on what matters. We are looking for a Director of School Success for our East team. This is an individual contributor role, no direct reports, no management ladder. We use the "Director" title because of the level of ownership you will carry and the senior campus leaders you will work alongside. You will be the strategic account owner and primary relationship manager for a dedicated portfolio of university partners, and the results in that portfolio will be yours.

The ideal person for this role brings two things together. First, you have real, firsthand experience in higher education, you know how campuses work, how decisions get made, and what it actually takes to support students and families. Second, you know how to partner with institutions, consult on what will move the needle, identify opportunities to grow, and drive results. You do not need to be a perfect 50/50 split, but you need to genuinely bring both.

You will operate with a high degree of autonomy. That means setting your own strategy, owning your outcomes, and making decisions without waiting to be told what to do. At the same time, you will have a team behind you, marketing, product, and sales, who are invested in your success. Your campus credibility will open doors. Your drive will determine what happens next.

This is a chance to stop choosing between the work you care about and the career you want to build, and do both. We are looking for sincere professionals who embrace GradGuard’s mission which is to help schools educate and protect students from the risks of college life.

This is position is remote and open to candidates in most U.S. states, with the exception of: California, Colorado, Hawaii, Illinois, Maine, Maryland, Massachusetts, New Jersey, New York, Vermont, Washington, and Washington, D.C.

What you'll do

• Partner deeply with your institutions. You will build genuine, trust-based relationships with the people who matter most at your partner campuses, housing directors, student affairs leaders, financial services teams, and risk management offices. You will show up as a peer and a resource, not just a vendor. Campuses will come to rely on you.
• Consult on what actually matters. You will use your campus experience to help institutions see what is working, what is not, and where GradGuard can make a real difference for their students. You will ask good questions, listen carefully, and bring solutions that fit, not just products.
• Identify and pursue opportunities. You will proactively look for ways to expand GradGuard's impact across your portfolio, across departments, across products, across relationships. You will not wait for opportunities to come to you.
• Drive results. You will own the financial performance of your book of business. Retention, expansion, and revenue growth are yours to lead. You will set strategies, execute with discipline, and hold yourself accountable to outcomes that matter.
• Advocate for your partners internally. You will bring your partners' voices into GradGuard, working closely with internal teams to surface insights, flag needs, and help shape how we serve the higher education market.

Qualifications

• Experience: 2–5+ years in a role that meaningfully combines higher education (student housing, residence life, student affairs, campus operations) with account management, customer success, or strategic partnerships. If you have made the transition from a campus role into a commercial environment and thrived, we want to hear from you.
• Industry Knowledge: Firsthand experience in higher education administration or student housing operations is highly preferred. Familiarity with embedded insurance, EdTech, or financial services is a plus.
• Drive: A demonstrated track record of owning outcomes, retaining and growing a portfolio, hitting goals, and finding ways to win even when it is not easy.
• Strategic Mindset: The ability to work independently, navigate complex organizations, find the right people, and build a plan without needing someone to hand you one.
• Communication Skills: You can build real relationships and hold a room — whether you are presenting to a VP of Student Affairs or working through a problem with a housing coordinator.
• Tech Savvy: Comfortable using modern sales and CRM tools (Salesforce experience is strongly preferred). Familiarity with the Apple ecosystem (including Keynote) is a plus.
• Education: Bachelor's degree preferred.
• Flexibility: Willingness and ability to travel up to 30% of the time for campus visits, conferences, and partner events.