Chief of Staff to the COO

Location: Boston, MA (Hybrid — 2 days per week in office)

About Us

Clasp is a venture-backed, mission-driven startup transforming access to education and career pathways. We are revolutionizing the way employers attract and retain critical talent, while simultaneously tackling the student debt crisis. (Yep, we think BIG.) Our innovative platform meaningfully connects employers, educational institutions, and diverse talent to drive mutual benefit—using accessible education financing as the thread. We like to think of ourselves as more than a fintech; we’re a catalyst for economic mobility.

A Forbes Fintech 50 company, portfolio company of SHRM (Society of Human Resource Management — the largest HR organization out there!) and recipient of “43 Start Ups to Bet Your Career On in 2025” by Business Insider, Clasp is driven by our commitment to social impact and innovation. We are reshaping the future of the workforce one opportunity at a time. Join us on our journey to give power to learners and unlock fulfilling careers that drive positive change in their communities and beyond.

What We Need

We are seeking a wildly trustworthy, analytical, and proactive Chief of Staff to serve as a "force multiplier" for our COO. This is not an administrative role; it is a strategic partnership. You will be the "control tower," keeping the COO focused and the team aligned on our most critical business outcomes.

The ideal candidate thrives in ambiguity and is an expert at "measuring what matters". You are someone who can turn raw data into simple, executive-level insights and maintain the operational rigor required to scale a high-growth startup.

What You’ll Do

• KPI & OKR Management: Establish and manage the systems for tracking Key Performance Indicators (KPIs) and Key Results (KRs) with absolute rigor and consistency.

• Operational Cadence: Facilitate executive and team meetings, ensuring agendas are clear, time is optimized, and information flows seamlessly across departments.

• Special Projects & Analysis: Lead high-stakes analytical assignments, ranging from pricing strategy pressure tests to market research and financial analytics.

• Executive Support & Insights: Translate complex data sets into polished presentations and concise bulleted insights for client-facing and all-hands decks.

• Strategic Accountability: Act as a trusted partner to the COO, identifying blind spots and providing tough, honest feedback to ensure leadership remains effective.

• Information Flow: Proactively identify and implement tools and processes to bridge communication gaps between cross-functional teams.

• Own Meeting Coordination and Follow-Ups: Pair with the COO to support meeting scheduling and logistics, and to scale, streamline, and accelerate meeting follow-ups on his behalf.

What You’ll Need

• Experience: 2-4+ years of experience in management consulting, investment banking, private equity, or a high-growth and/or scaled Business Operations role, where extreme detail orientation and organizational skills are key.

• Analytical Mastery: Expert-level proficiency in Excel (the COO’s "love language") with the ability to build trusted, insight-driven models. Power user and veracious consumer of agentic AI tools to scale own and team efficiency.

• Exceptional Written and Verbal Communication: Ability to take complex information and distill it into simple, executive-level narratives for PowerPoint or email. Ability to speak clearly, concisely, and persuasively in all settings.

• Elite Organizational & Prioritization Skills: An ability to keep track of dozens of follow-ups and many workstreams without dropping a ball.

• Quick Learner: Ability to listen attentively, learn quickly, and not make the same mistake twice.

• High Emotional Intelligence: A "trained extrovert" (i.e not necessarily an actual extrovert) who is comfortable navigating complexity and holding senior leaders accountable with professionalism and polish.

• Discretion: Demonstrated ability to handle the company’s most sensitive and confidential information with 100% integrity.

• The "Scrappy" Mindset: A resourceful problem-solver who can move from high-level strategy to "getting in the weeds" of a project without missing a beat.

• Deep Curiosity and Desire to Learn & Grow FAST: This role is not a 9-5, not nearly! You’ll love this role if you view this as an amazing opportunity to build something amazing with a view from the cockpit, and an opportunity to learn, stretch, and grow. If you’re doing it for prestige, compensation, or work-life balance, this won’t be a fit.

What We Give In Return

• Competitive cash and equity compensation

• Health benefits (health, dental, & vision)

• 401k matching

• Commuter benefits

• Flexible PTO policy

• Opportunities to grow and perform in a fast-paced environment alongside a stellar team.

Salary

The salary range for this position is competitive and will be commensurate with the candidate's experience, qualifications, and industry knowledge, ranging between $80,000 to $100,000 annually. In addition to the base salary, we offer an attractive equity component as part of our compensation package, providing an opportunity for eligible employees to share in the success and growth of our company. We are committed to offering competitive compensation and benefits packages to attract and retain top talent.

Closing

If you are a highly driven individual with a passion for technology, and you thrive in a dynamic and fast-paced environment, we want to hear from you! Join us in revolutionizing the workforce solution industry and making a meaningful impact on businesses worldwide. Apply now to be a part of our growing team!

We are committed to creating a diverse and inclusive workplace where all employees feel valued, respected, and empowered to contribute their unique perspectives and talents. Clasp is an equal opportunity employer and prohibits discrimination and harassment of any kind. We embrace diversity and are dedicated to providing equal employment opportunities to all individuals regardless of race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, veteran status, or any other characteristic protected by law.