VP, Operations & Chief of Staff

About Our ClientOur client is the leader in school search. Their mission is to make researching and enrolling in schools easy, transparent, and free. With in-depth profiles on every school and college in America, millions of reviews and ratings, and powerful search tools, they help millions of people find the right school for them. They also help thousands of schools recruit more best-fit students, by highlighting what makes them great and making it easier to visit and apply. The company is all about finding where you belong, and that mission inspires how they operate every day.

They want the company to be a place where people truly enjoy working and can thrive professionally. About The RoleAs the VP, Operations & Chief of Staff, you will be a critical partner to the CEO and executive leadership team, driving strategic initiatives, enabling cross-functional alignment, and ensuring execution across the company. You will operate at both strategic and tactical levels to propel the company forward during a pivotal phase of growth and innovation. What You Will DoStrategic Planning & Execution: Collaborate with the CEO and senior leaders to establish and execute a comprehensive strategic roadmap aligned with company goals.

Manage the strategic planning calendar and ensure accountability through OKRs and key business processes. Operational Leadership: Drive operational excellence through leadership meetings, quarterly planning, and business reviews. Lead the Internal Operations team in monitoring performance and recommending changes to stay on track. Cross-Functional Coordination: Serve as the connective tissue across departments - removing roadblocks and ensuring alignment and progress on top priorities. Special Projects & Corporate Development: Ensure effective execution of high-impact, CEO-driven & cross functional initiatives such as go-to-market strategies, investor updates, strategic partnerships, and M&A activity. Lead the post-transaction integration process when needed. Data-Driven Insights:

Define KPIs and deliver actionable insights to support decision-making and drive measurable results. Business Case Development: Establish a standardized methodology to evaluate new initiatives, including scorecards, prioritization frameworks, and risk assessments, in close collaboration with Finance. Customer & Investor Engagement: Represent the CEO in key meetings with customers, investors, and partners. Develop compelling materials for board meetings, investor communications, and public presentations. Organizational Effectiveness: Ensure on-sites/off-sites are in sync with operational rhythms, lead business reviews, and partner closely with the Chief People Officer to ensure an aligned and high performing leadership team.

What They Are Looking For10+ years of experience in Chief of Staff, strategy, operations, or leadership roles, ideally within high-growth companies or top-tier consulting firmsDemonstrated ability to lead complex, cross-functional initiatives and deliver impactful outcomesProven success managing strategic planning for organizations, with the ability to translate high-level objectives into actionable plansExperience in corporate transactions such as acquisitions, fundraising, or integrations, with a solid understanding of financial drivers and P&L managementStrong analytical skills with experience in business case development, investment analysis, and performance benchmarkingExceptional communication and interpersonal skills, with the ability to influence senior stakeholders and drive alignment across diverse teamsOrganizational prowess with the ability to prioritize competing demands and thrive in a fast-paced, dynamic environmentTrusted advisor mindset—discreet, reliable, and able to build credibility with executive leadershipBachelor’s degree required; MBA or relevant advanced degree preferred CompensationThe national target base salary range is $200,000 - $250,000, plus participation in the Annual Bonus and Stock Option Program.

Base compensation will be commensurate with experience and skills. The Total Rewards Philosophy is centered around creating a workplace environment that attracts, motivates, and retains top talent by providing a comprehensive and competitive rewards package. This philosophy is built on the principles of performance-based compensation, benefits and work-life balance, and employee well-being.

Why This Company?They are a fully flexible workforce empowering their employees to choose to work remotely, in their Pittsburgh office or whatever combination suits youFull time, salaried position with competitive compensation in a fast-growing companyBest-in-class health plan, including vision and dental and supplemental coverageFlexible Paid Time Off PolicyStipend that allows you to build your work from home office in a style and function that suits your personal preferencesParental leave for all employees (fully paid) in addition to short term disability for birthing parentsMeaningful 401(k) with employer matchYour ideas and work will make an immediate impact on the company and millions of usersYou will join a team that cares about you, the mission, the work - and celebrates wins together!Note:

“We are not the EOR (Employer of Record) for this position. Our role in this specific opportunity is to connect outstanding candidates with a top-tier employer. Swooped helps candidates around the world to discover and stay focused on the jobs they want until they can complete a full application in the hiring company career page/ATS. ”