VP of Strategic Services

Collegewise is looking for a VP of Strategic Services to join our Executive team. This is a new role, and you'll report directly to our CEO and take full ownership of the services that sit alongside our core counseling business: including tutoring and testing. This is a remote position, and candidates must be located in the United States.

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 35,000 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 of our work is 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.

Ambition with heart. Strategy with soul.

You definitely wouldn't be crossing over to the for-profit "dark side" here. 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.

What's the Job?

Collegewise has spent 27 years building the most trusted name in college counseling, and the services around that core have grown fast. This is a new role, and it's time to bring in our next Wiser to help the work already happening in these teams keep growing. The teams doing this work are strong. You'll help them build on it, with the judgment to lead without close supervision.

Tutoring & Testing. You'll give the division strategic direction and own its P&L. Working with division leadership, you'll drive utilization, manage capacity, find the next growth opportunities, and keep the team staffed and supported enough to scale.

Partnership Counseling. Families come to us through corporate, institutional, and organizational partners, and they should get the same quality as anyone who finds Collegewise on their own. You'll set the division's revenue and quality targets, manage its leadership team, and hold it to a bar that is indistinguishable from our core offering.

New Programs. You'll identify, design, and launch new offerings that extend our reach. For example, launching a writing course for high schoolers, developing an AI readiness program, or building a program to enhance our affiliate experience. You'll own each idea from concept to launch, working with Marketing, Sales, and Operations to bring it to market.

Teams. Each business line needs strong leadership and capable teams. You'll find the gaps, recruit ahead of need, and build organizations that can execute without you checking in on every decision.

Each of these departments partners closely with Counseling, Sales, Marketing, and Operations, so you'll spend real time building relationships with the leaders of those teams. These three lines operate differently, move at different speeds, and share almost no common playbook. The job is knowing how to prioritize across all of them at once.

Who We're Looking For (You)

• You've owned P&L end to end, and you've hit revenue and margin targets. You know how to run a business line, not just manage one.
• You've run businesses, led teams, and built things from scratch. You're comfortable being the person who makes the call.
• You've led multiple teams at the same time, ideally a mix of big and small.
• You've launched programs, hired teams, and created structures where none existed.
• You gather the right information, make an thoughtful decision, and then make sure it happens. When you get it wrong, you own it and adjust.
• You work well across functions. You build alignment, and you know when to stop planning and start executing.
• You operate without close oversight and set your own priorities.
• You’re high EQ. People enjoy working with you, and they come away better for it.

Most importantly, you believe in Collegewise's mission. You want to help students access higher education, and you see this role as a way to do that at scale.

Compensation & Benefits

• Salary: $140,000+ base, plus a performance-based bonus
• Employment Type: Full-time, salaried
• Benefits: Medical, dental, and vision coverage; paid parental leave; 401(k) with matching; flexible PTO; and paid holidays.
• Start Date: January 2027
• Location: Remote, anywhere in the U.S. We are not able to sponsor work authorization for this role. 

How to Apply

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

Application questions (choose 3):

1. Tell us about a time you had to make a call without all the information you wanted. How did you decide what you needed to know, when did you stop gathering information, and what happened next?
2. Tell us about a time you built or scaled a team. How did you find the gaps, who did you hire first, and what did you do when a hire or a plan didn't work out?
3. Describe a program or service you launched that didn't exist before. How did you test the idea before committing to it, and what did you change once it was live?
4. Tell us about a time you had to get functions with different priorities, such as sales, marketing, and operations, moving toward the same goal. What did you do to bring people along when they disagreed with you, and how did the team experience it?
5. Describe a time you held a team to a quality standard that was hard to measure. How did you define that standard, and how did you enforce it without managing every decision?

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.

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 Inclusion, Equity, and Access (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.

Questions? Feel free to email us at [email protected] (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.