Head of Strategic Initiatives

Collegewise

1d•Remote

About The Position

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. 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.

Requirements

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.
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.

Responsibilities

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.
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.
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.
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.