Chief of Staff

Chief of Staff

New York, USA

About LearnLux

LearnLux is the leading provider of workplace financial wellbeing, blending fiduciary digital planning with access to one-on-one guidance from Certified Financial Planner™ professionals. Our award-winning program helps employees navigate critical financial decisions from budgeting and benefits elections to equity compensation, home buying, and retirement so they can feel confident about their money and focused at work. Advanced reporting helps our partners understand impact, driving outcomes like reduced financial stress, increased productivity, and improved retention.

We're building LearnLux with intention. We move quickly, operate with a high bar for quality, and value people who take ownership of their work. If you're energized by solving new problems, taking accountability, and pushing yourself to do your best work every day, you'll find this a rewarding environment.

We're a venture-backed company that has raised over $35M to date and is supported by experienced investors and long-term partners. We're a growth-focused business building for scale, and we're excited by the opportunities and challenges that come with that journey.

The Role

As Chief of Staff to the CEO, your primary responsibility will be maximizing the effectiveness of the CEO. You will ensure the CEO enters every meeting exceptionally prepared, leaves every meeting with clear actions and decisions, and maintains focus on the highest-priority opportunities and challenges facing LearnLux.

This role is ideal for someone who thrives on turning information into insight, complexity into clarity, and conversations into action. You will serve as the CEO's thought partner, strategic advisor, and operational extension, helping the CEO process complex information, identify patterns, anticipate risks, and drive execution across the organization.

The strongest candidates will possess exceptional critical thinking skills, intellectual curiosity, sound judgment, and the ability to synthesize large amounts of information into clear recommendations and next steps.

This is a hybrid role in New York City and will report to the CEO.

What You'll Do

• Own all meeting preparation for the CEO, ensuring she enters every internal and external meeting fully prepared with relevant context, key decisions, stakeholder backgrounds, discussion objectives, and recommended talking points.
• Develop concise executive briefs that synthesize complex information into actionable insights, recommendations, and decision frameworks.
• Attend key meetings with the CEO, capture critical discussions, identify decisions made, and ensure clear follow-through on commitments and action items.
• Drive post-meeting execution by documenting outcomes, assigning ownership, tracking progress, and escalating risks or blockers as needed.
• Identify themes, patterns, opportunities, and risks across meetings and communications, surfacing insights that help the CEO make better and faster decisions.
• Own and improve operating cadences (e.g., leadership meetings, planning cycles, goal tracking, and follow-ups).
• Bring structure to ambiguous problems, translating high-level direction into clear plans, owners, and next steps.
• Act as an extension of the CEO in certain contexts, ensuring follow-through and clear communication across teams.
• Lead and execute high-impact, cross-functional projects that do not have a clear owner.
• Build trusted relationships across the leadership team to gather information, drive alignment, and ensure accountability on key priorities and commitments.
• Step into both strategic and tactical work as needed; no task is too big or too small when it comes to driving outcomes.
• Identify gaps, inefficiencies, or risks across the organization and proactively address them.

Success in This Role

• The LearnLux CEO is consistently the best-prepared person in every room she enters, with the information, context, and recommendations needed to make high-quality decisions. The Chief of Staff operates as a trusted extension of the CEO and is equally prepared for all critical discussions and decisions.
• Leadership team priorities, decisions, and commitments are documented, tracked, and executed with greater consistency.
• Important issues are anticipated before they become problems.
• Executive communications and decision-making become faster, clearer, and more effective.
• The CEO gains meaningful capacity to focus on strategic priorities because the Chief of Staff is effectively managing information flow, preparation, and execution.

You Should Bring

• Exceptional critical thinking and analytical capabilities. You can quickly absorb large amounts of information, identify patterns, challenge assumptions, separate signal from noise, and develop thoughtful recommendations.
• Proven ability to synthesize complex information into concise executive-level briefs, recommendations, and decision frameworks.
• Strong business judgment and intellectual curiosity, with a demonstrated ability to anticipate issues, identify risks, and think several steps ahead.
• 5–8+ years of experience in consulting, investment banking, private equity, high-growth startup operations, or a similarly rigorous environment.
• Confidence and maturity to challenge assumptions, provide candid feedback, and influence decisions when appropriate.
• Proven ability to operate in high-performance, fast-paced environments with senior stakeholders.
• Strong executive presence and communication skills.
• Highly organized with exceptional attention to detail and follow-through.

LearnLux Is a Fit for You If You

• Thrive in fast-moving environments and enjoy building in moments of change. We operate with urgency, and roles, priorities, and approaches evolve quickly as we grow.
• Like wearing multiple hats and helping define the path forward. At LearnLux, roles evolve as we grow, and employees often help create clarity, structure, and direction where it didn't previously exist, often in close partnership with leadership.
• Take initiative and don't wait to be asked. You see problems as opportunities and are comfortable stepping in to move work forward, especially in high-priority or high-stakes situations.
• Are energized by ambiguity and willing to make decisions with imperfect information. We learn quickly by doing, and pace is a competitive advantage for us.
• Enjoy being hands-on and owning work end to end. While strategic thinking matters, execution, follow-through, and accountability are what drive impact here. No task is too big or too small.
• Are motivated by high standards and continuous improvement. As we hit new milestones, we intentionally raise the bar on quality, ownership, and outcomes.
• Value clear, frequent communication and collaboration. As a remote team, staying aligned through proactive communication and responsiveness is core to how we operate.

Interview Process

To ensure a strong match for this role, candidates should expect a rigorous interview process that assesses critical thinking, executive communication, judgment, and problem-solving capabilities. Finalists will complete a practical case exercise that simulates core responsibilities of the Chief of Staff role, including information synthesis, executive briefing preparation, and recommendation development.

Benefits

• Remote-first company structure
• Medical, dental, and vision
• 401(k)
• Mental wellbeing (Talkspace)
• Financial wellbeing (LearnLux)
• Paid vacation and sick leave
• Paid sabbatical after 5 years of service
• A supportive, inclusive team culture
• Opportunities for continuous learning and growth at a fast-growing startup at the cutting edge intersection of financial wellness and technology

Closing

LearnLux strives to be an inclusive workplace and values learning from and engaging across different perspectives. Women, people of color, LGBTQIA+ individuals, and members of other minority or marginalized groups are strongly encouraged to apply.

LearnLux is proud to be an equal opportunity employer and does not discriminate against candidates on the basis of race, ethnicity, color, national origin, age, religion, sex, gender, sexual orientation, gender identity, marital status, disability, or veteran status.

We are committed to fostering an environment that embraces diversity and inclusion and are seeking candidates from a variety of backgrounds, experiences, abilities, and perspectives to join our team. If you are interested in this opportunity but not sure if you fit this role, please apply and include a note to let us know of your interest. We're excited to speak with you about joining our team!