Do you believe that great marketing and great sales aren't about pressure—they're about trust?

Do you want to own the full revenue engine at a company where the mission actually means something?

Are you ready to lead a talented team, shape strategy from the ground up, and make a real impact on families during one of the most consequential seasons of their lives?

Collegewise is looking for our next Head of Sales & Marketing. If you believe that great marketing and great sales are really about trust—and you want to lead the team that helps families find us, choose us, and feel good about it—you might be exactly who we're looking for.

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?

Collegewise has spent 26 years building genuine trust with families during one of the most stressful seasons of their lives. The way families find and connect with companies like ours has changed—but what makes us special hasn't. As our Head of Sales & Marketing, your job is to translate that into a more modern, visible, and compelling experience, and to lead the exceptional teams already doing this work.

This role owns the full revenue engine—from the moment a family first discovers us to the moment they enroll. You'll coach a team of Program Advisors while staying close enough to the work to know what families are actually experiencing in the sales process. You'll care deeply about performance and just as deeply about the people behind it.

Revenue & Pipeline Strategy

• Own monthly, quarterly, and annual revenue targets and marketing's contribution to the pipeline.
• Partner across teams to prioritize pipeline quality—not just volume—ensuring we're attracting well-matched, high-intent families.
• Drive full-funnel improvements from lead generation through conversion, identifying and acting on bottlenecks with urgency.
• Collaborate with leadership on forecasting, pricing, packaging, and new market expansion opportunities.

Sales & Marketing Operations

• Evolve our sales and marketing frameworks to improve efficiency, consistency, and brand authenticity.
• Leverage data—conversion rates, pacing, cohort analysis—to inform decisions across all channels and campaigns.
• Shape how Collegewise shows up in the world, ensuring our story resonates with families and reflects our core values.

Team Leadership & Development

• Lead and develop a growing team of Program Advisors and marketing professionals.
• Set a high-performance bar while maintaining a strong culture of accountability, trust, and genuine care for the team.
• Identify skill gaps and implement targeted coaching so every Wiser has the opportunity to do their best work.

Ambition with Heart. Strategy with Soul.

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 be part of fixing that—not by lowering the bar, but by raising trust at every touchpoint.

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 win people over easily and earn trust quickly. Whether you're coaching a Program Advisor through a tough call, reviewing campaign metrics, or thinking through messaging strategy, people enjoy working with you—and benefit from it.

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

• 8–12+ years in sales and/or marketing with a track record of driving measurable, meaningful growth.
• Experience managing and developing high-performing teams of 15+ people—and genuinely caring about their development.
• Deep expertise in high-consideration services (education, consulting, or similar); experience in the education space is a significant plus.
• Analytical instincts—you think in funnels, and you know how to break down performance to find what's actually working.
• Proficiency with HubSpot and Google Analytics (or close equivalents).
• Comfort with autonomy and accountability in equal measure. You take ownership of problems and outcomes without needing to be told where to start.

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. For the right candidate, we're open to considering this role at the CRO level—bring your experience and let's have a real conversation.
• Benefits: Full 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 welcome from anywhere in the US or Canada.

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 respond to the following questions (150–250 words each is a helpful guideline, but use as much or as little space as you need):

1. Tell us about a time you led a team through a significant sales or marketing challenge. What was your approach, and what did you learn?
2. How do you think about the relationship between brand and sales? Give us a concrete example of how you've navigated that tension.
3. Describe your philosophy for coaching a sales team. How do you balance accountability with genuine support for your people?

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.