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Executive Assistant to the CEO
$80-$120k base + equity
1
Broomfield, CO
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:
3+ 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 American 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.
Apply now
Your application will be reviewed by us. We'll get back to you quickly. We can't wait to meet you!
About the job
Job type
Adminstrative
Salary
$80-$120k base + equity
Benefit you’ll get
Flexible Work Environment – We offer hybrid and remote options so you can work where you’re most productive, whether that’s at home, in-office, or a mix of both.
Equity Ownership – As an early team member, you’ll receive equity in the form of options or RSUs—your contributions grow the company, and you share in the upside.
Unlimited PTO – Take the time you need to rest, recharge, or handle life outside of work. We trust our team to balance time off with results.
Health & Wellness Coverage – Comprehensive medical, dental, and vision plans help keep you and your family healthy, with 100% employee premium coverage on select plans.
Paid Parental Leave – We support growing families with fully paid time off for new parents, including adoption and foster care.
Professional Development – We invest in your growth with paid courses, certifications, and conference opportunities tailored to your role and interests.
Home Office & Equipment Stipend – Receive a stipend to set up your home workspace and get the tools you need to work comfortably and effectively.
Team Retreats – We host regular offsites to align on strategy, collaborate face-to-face, and have fun as a team.
Autonomy & Ownership – We give you space to lead initiatives, own outcomes, and shape the direction of your work without micromanagement.
Mission-Driven Work – Help build infrastructure that moves money more efficiently, securely, and transparently for modern businesses.
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