About the role

As Executive Assistant to the CEO, you'll be the founder's force multiplier—protecting time, sharpening focus, and operationalizing priorities across product, go-to-market, investors, and talent. For the right candidate who demonstrates strategic thinking, operational excellence, and the ability to drive cross-functional initiatives, this role offers a path to Chief of Staff based on performance and business needs.

The best EAs operate as extensions of their executives: anticipating needs, making decisions with founder-level judgment, and keeping the company moving at startup velocity. This is a high-trust, high-visibility role for someone who thrives on creating order from chaos and wants to learn the inner workings of building a category-defining company.

Your impact

Starting Foundation (EA Focus)

• Create leverage: Transform CEO priorities into actionable systems—calendar, communications, and workflows that multiply output

• Raise the operating bar: Build repeatable processes that make execution predictable and delegation safe

• Be the information hub: Synthesize inputs, track decisions, and ensure nothing falls through the cracks

Growth Trajectory (Chief of Staff Evolution) As you master the core EA responsibilities and demonstrate strategic capability:

• Strategic initiatives: Lead special projects spanning product launches, fundraising, and organizational design

• Cross-functional orchestration: Drive alignment between engineering, sales, and operations on company-wide OKRs

• Executive team enablement: Extend your operating system to the broader leadership team

Key responsibilities

Time & Focus Management

• Design and defend the "ideal week" aligned to company priorities

• Run daily calendar reviews and weekly planning sessions

• Manage inbox to zero with <24hr response SLA on critical items

Meeting & Decision Architecture

• Own end-to-end meeting lifecycle: agendas → facilitation → decisions → follow-ups

• Prepare briefing documents for board meetings, customer calls, and investor updates

• Track action items with clear DRIs and deadlines across all touchpoints

Systems & Knowledge Management

• Build the "Executive Atlas"—a living knowledge base of SOPs, templates, and playbooks

• Document decision frameworks and institutional knowledge

• Create scalable processes that outlive any single person

Strategic Support

• Research and synthesize market intelligence for strategic decisions

• Coordinate CEO-sponsored initiatives with measurable outcomes

• Handle confidential matters with unwavering discretion

Structured Onboarding & Development

We'll invest in your success through a 12-week Executive Management System (EMS) program alongside the CEO, installing one high-leverage system each week. This structured approach ensures you build a world-class EA/CEO relationship while creating immediate value.

30-60-90 Day Milestones:

• Day 30: Operating rhythm established—daily standups, weekly reviews, role scorecard defined

• Day 60: Core systems live—Inbox zero, calendar system, meeting workflows standardized

• Day 90: Force multiplication achieved—meaningful increase in CEO focus time, Straddle OS documented

What We're Looking For

Must-Haves:

• 5+ years supporting a founder/CEO or C-level executive in high-growth tech

• Systems thinker who turns ambiguity into structured plans

• Exceptional written and verbal communication—you write like an executive

• Mastery of modern productivity tools (Google Workspace/Office, Notion, Slack, Linear/Jira)

• Uncompromising discretion with sensitive information

Bonus Points:

• Fintech/payments industry experience

• Board meeting and investor relations exposure

• Project management certification or demonstrated experience

• Interest in growing into strategic leadership roles

Why This Role, Why Now

This isn't just an EA role—it's an apprenticeship in company building. You'll have:

• Unparalleled visibility: Front-row seat to every strategic decision, from product roadmap to fundraising

• Clear growth path: Performance-based progression to Chief of Staff with expanding scope and compensation

• Learning investment: Sponsored training, mentorship, and exposure to world-class operators

• Meaningful equity: Own a piece of the company you're helping build

• Impact at scale: Help modernize how $80T moves through the U.S. economy

You'll Thrive If...

• You're intellectually curious and love learning how businesses work

• You find joy in creating order and enabling others to do their best work

• You're comfortable with ambiguity but allergic to dropping balls

• You want to grow from operational excellence to strategic leadership

Not a Fit If...

• You prefer predictable 9-5 schedules in established companies

• You're looking for a traditional EA role without growth ambitions

• You're uncomfortable with the pace and pivots of early-stage startups

Ready to be part of rebuilding payments infrastructure?

Join us in creating the payment rails that the next generation of companies will build on. This role offers a unique combination of immediate impact, structured development, and a clear path to executive leadership.

Straddle is an equal opportunity employer committed to building a diverse and inclusive team.