Do you get energized by the challenge of making a great organization run even better?

Do you want to do real strategic and analytical work at a company where the mission actually means something?

Are you a natural bridge-builder, i.e. someone who can sit down with a counselor, a marketer, and a finance lead, and get everyone moving in the same direction?

Who We Are

Collegewise is a college counseling company that helps high school students confidently navigate their journey to college. We believe the college admissions process has spun out of control, with too much confusion, too much anxiety, and too many students losing agency for what should be their path to higher education. We’re out to change all that.

Since 1999, we’ve helped more than 30,000 students apply and get accepted to schools—sometimes famous, often not—that they’re excited to attend. We do it all with just the right mix of advice, encouragement, and occasional cheerleading—all backed by data and experience—to ensure that each student’s college admissions process goes smoothly and thoughtfully. And our work doesn’t stop with students who enroll in our program. We speak in public, write, and constantly look for ways to spread relevant college planning information to anyone who needs it, whether or not they work with us. To learn more about our inspiring work, check out this short video.

What's the Job?

At Collegewise, we believe the college admissions process should feel like an exciting journey. Making that real for students and families requires that our internal systems and services run just as thoughtfully as our counseling does.

As Head of Strategic Initiatives, you'll work closely with our CEO and C-Suite to shape the operational backbone of the company. You will serve as the connective tissue across teams — ensuring that Sales, Services, Marketing, People, and Finance all work in sync to help students succeed. This is a hands-on, high-impact role where no two weeks will look quite the same.

Most importantly, we are looking for a high EQ individual who could grow into a leader at this company; for the right person, this role has a clear path to grow into the Chief of Staff to the CEO.

Cross-Functional Project Leadership & Execution (~30%)

• Lead high-impact projects that improve business efficiency, client experience, or internal workflows.
• Scope, plan, and execute process improvements from ideation through measurement.
• Bring departments together to understand current processes (e.g., sales-to-service handoffs) and design better ways of working.
• Manage deadlines, draft procedural documentation, and identify the right team members to involve in each launch.

Strategic Process Design & Implementation (~30%)

• Design and implement operational processes within service teams to support evolving business needs.
• Ensure our systems surface the right info at the right time and that workflows adapt as our offerings grow.
• Refine internal handoffs and align incentives with the behaviors we want to see across the organization.

Programmatic Documentation & Sales Enablement (~20%)

• Act as the logistical "source of truth" for how our services work across all teams.
• Maintain counseling playbooks, product descriptions in HubSpot, and sales cheat sheets.
• Reduce errors and enable teams to deliver a clear, consistent experience for every family we serve.

Operational Analysis & Optimization (~20%)

• Analyze financial and operational data to identify opportunities for improvement and ensure accuracy.
• Pull performance metrics and provide recommendations for business functions including capacity planning and product margin adjustments.
• Build financial models and perform data reconciliation to support strategic decision-making.

Ambition with Heart. Strategy with Soul.

We have an excellent reputation with both high school counselors and admissions officers. We have an excellent reputation with both high school counselors and admissions officers. We present at NACAC, local ACACs, and at high schools and community events. We partner with community-based organizations to directly support their students and increase college access. We tell the truth, we treat people right, we recycle, and we have at least five confirmed vegetarians on the team. We're biased, but really, this is a pretty great place to work.

Who We're Looking For (You)

You believe in Collegewise's mission. You've seen or experienced the anxiety the college admissions process can wreak on families, and you want to help build the internal infrastructure that lets us keep showing up for them well.

You make work a way of life without making it your actual life. You'd rather be challenged by something important than phone it in for something mundane.

You're energized by ambiguity, not paralyzed by it. You make progress before the perfect definition exists. You zoom in and zoom out: you know when to get into the details of a project and when to step back and see the bigger picture.

You win people over easily and earn trust quickly. You're a natural connector who communicates clearly and earns the confidence of different team types and personalities — whether you're working with Sales, Finance, or Counseling.

On the professional side, here's what we're looking for:

• 3–6+ years of professional experience, ideally with a foundation in management consulting, high-growth tech operations, or a fast-paced mission-driven environment.
• Comfortable with complex data sets; you can build financial or operational models that turn noisy information into a clear strategic path.
• Proven experience managing projects that required buy-in from multiple departments — you can speak the language of sales, finance, marketing, and operations.
• Proficiency with HubSpot, Asana, Notion, and/or advanced Google Sheets.
• High EQ. People enjoy working with you, and they benefit from it.

Work Life at Collegewise

We've worked hard to create the company we'd actually want to work for. That means real investment in the Wisers here — how they grow, how decisions get made, and how we treat each other when things are hard. Senior leaders have real autonomy and real accountability. For more information about our benefits and our approach to work, check out our Careers page.

Compensation & Benefits

• Salary: Competitive base + performance-based incentives.
• Benefits: Medical, dental, and vision coverage; paid parental leave; 401(k) with matching; and generous vacation and sick day policies.
• Start Date: We'd like to fill this role as soon as possible, but we can be flexible for the right person.
• Location: Remote. Candidates are welcome from anywhere in the US or Canada.
• Growth: For the right person, this role has a clear path to Chief of Staff to the CEO.

We Want to Hear from You

If you're excited about this opportunity but unsure if you're the right fit, we hope you'll take a shot. There is no such thing as a perfect applicant (or a perfect job, for that matter). And we promise to give a fair and thorough read to every applicant who takes the time to submit a thoughtful application to us.

Collegewise is stronger because of the different perspectives, backgrounds, and experiences our team brings. We're committed to building a place where everyone can do their best work — and we actively work toward that through our IEA Committee, our resources for students from all backgrounds, and our everyday practices. If that matters to you too, we'd love to meet you.

How to Apply

Instead of a traditional cover letter, please choose 3 of the following questions to answer (150–250 words each is a helpful guideline, but use as much or as little space as you need):

1. Tell us about a complex, cross-functional project you led. How did you get alignment across teams, and what did you learn?
2. Describe a time you used data to drive a meaningful operational or strategic decision. What did the analysis look like, and what happened as a result?
3. What does "operational excellence" mean to you in practice? Give us a concrete example of how you've built or improved a process.
4. What draws you to Collegewise specifically? What do you understand about how families experience the college admissions process, and why does that matter to you?
5. This role sits at the intersection of strategy and execution. How do you personally navigate the tension between thinking big and getting things done?

Please submit your resume and responses through our Careers page. Every single applicant will receive a response from us, and we do our very best to reply within 10 days.

Questions?

Feel free to email us at jobs@collegewise.com (please no phone calls). We promise to respond to you quickly.

Thanks for reading! We'd love to hear from you, but if we don't, we hope you find the perfect professional fit someplace else.