Senior Executive Assistant, Executive Operations Partner
Swooped
Job Overview
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Job Description
About Our Client
The U.S. mortgage market, a $14 trillion economic pillar, still heavily relies on outdated methods like fax machines and manual workflows. Our client is revolutionizing this by offering a platform that currently powers 20% of all real estate closings nationwide. They design workflow software and AI-driven automation that seamlessly connects lenders, settlement teams, notaries, and investors. This innovation eliminates friction, reduces risk, and delivers a faster, simpler closing experience for every borrower. Their diverse customer base includes both large mortgage lenders and independent title companies, all of whom trust the organization for its empathetic, rigorous, and reliable solutions to real operational challenges. Backed by prominent investors like Sequoia, Y Combinator, and F-Prime, our client is committed to long-term growth and impact.
About The Role
As a Senior Executive Assistant, Executive Operations Partner, you will play a pivotal role in supporting leaders within the Go-To-Market function. This position is at the nexus of revenue, customers, regulators, partners, and internal teams, operating in an environment where executive calendars are demanding, priorities shift rapidly, and time is a critically constrained resource. Your primary objective will be to protect, optimize, and strategically deploy executive time, acting as a force multiplier across logistics, workflows, and decision-making. This role demands high autonomy, a proactive approach to anticipating needs, and the ability to design systems that reduce friction for executives and the broader Senior Leadership Team (SLT). While challenging, you will be closely partnered with experienced leaders and the Executive Support Manager, operating with significant trust and independence. Success in this role hinges on your ability to anticipate problems, exercise sound judgment, and act as a true strategic partner, rather than waiting for instructions.
Key Responsibilities
- Strategic Calendar & Time Management: Independently own and actively manage complex, high-volume executive calendars with often overlapping priorities. Make daily, judgment-based trade-offs regarding scheduling, discerning what can move, what cannot, and what should be declined. Proactively anticipate crunch points such as travel, board meetings, conferences, deal cycles, and regulatory deadlines, and rebalance time accordingly. Prepare executives thoroughly for meetings by providing clear context, necessary materials, stakeholder insights, and desired outcomes. Act as a confident gatekeeper, saying “no” on behalf of leaders when appropriate and knowing when to escalate versus make independent decisions.
- Complex Travel & Logistics: Coordinate frequent domestic travel comprehensively, including developing contingencies and making real-time adjustments as needed. Construct realistic schedules that strategically sequence meetings and events, allowing ample time for preparation, mitigating fatigue, and ensuring the right stakeholders are engaged at optimal times. Shield leaders from disruption by meticulously managing all travel details when plans change.
- Event Planning: Take full ownership of the end-to-end planning and execution of team offsites, and collaborate on select company-wide events. This includes managing budgets, timelines, vendor relationships, and onsite logistics. Partner cross-functionally with leaders, their teams, and other internal stakeholders to ensure events and agendas are well-sequenced, aligned with organizational priorities, and run seamlessly. Capture learnings post-event to continuously refine and improve offsite and event execution processes.
- Operational Ownership: Fully manage expenses, reimbursements, invoices, and various administrative workflows with precision and without the need for reminders. Efficiently handle document preparation, slide updates, meeting notes, and follow-ups, ensuring clarity and driving progress. Track action items from key meetings and proactively ensure follow-through to prevent work from stalling.
- Executive Partner & Systems Builder: Serve as a trusted thought partner, offering insights on prioritization, workflow optimization, and operating rhythm. Collaborate closely with the Executive Support Manager to design and evolve systems aimed at enhancing SLT effectiveness. Identify patterns, risks, and inefficiencies within calendars, meetings, and workflows. Exercise consistently sound judgment and discretion, particularly when dealing with sensitive business, revenue, and regulatory information.
Required Qualifications
- 6+ years of experience supporting senior leaders (VP+) in fast-paced environments, ideally within SaaS, fintech, or regulated industries.
- Demonstrated ability to support multiple executives simultaneously in high-stakes, ambiguous settings.
- Exceptional calendar strategy skills, including proven expertise in prioritization, time optimization, and critical judgment beyond mere scheduling.
- Clear, confident, and proactive written and verbal communication abilities, with the capacity to influence without direct authority and effectively represent leaders.
- Strong judgment, keen business acumen, and comfort in making decisions with incomplete information.
- Ability to operate effectively at both strategic and tactical levels.
- Robust systems and process mindset, coupled with experience in building repeatable workflows, consistent cadences, and effective meeting hygiene.
- Proven experience owning team offsites and executive events from conceptualization to execution.
Preferred Qualifications
- Experience directly supporting revenue, go-to-market, or regulatory leaders.
- Familiarity with Google Workspace, Slack, Ramp, and Zoom.
- Experience supporting executives who frequently travel and operate across different time zones.
How Success Will Be Measured
- Executives experience reduced reactivity and increased focus.
- Calendars accurately reflect true priorities and business cadences.
- Travel, logistics, and administrative tasks function seamlessly with minimal executive involvement.
- Leaders demonstrate trust in your ability to represent them, make critical decisions, and maintain momentum.
- The SLT achieves greater clarity, efficiency, and operational rhythm through the systems you implement.
Compensation
The base salary range for this role is determined by work location and falls into one of the organization's geographic compensation zones:
- Zone 1 (San Francisco Bay Area, Seattle Metro, New York City): $120,000 – $150,000
- Zone 2 (All other U.S. locations): $105,000 – $131,000
The specific salary within this range will depend on your experience, skills, and the impact you bring to the role. In addition to base salary, this position includes equity and a comprehensive benefits package.
Why This Role
Our client is on a mission to transform one of the world's most critical and complex industries. This ambitious goal requires a team that is curious, driven, thoughtful, and pragmatic. The organization deeply values:
- Product discipline and clear reasoning.
- Deep ownership of outcomes, not just tasks.
- Straightforward, honest communication.
- Empathy for the users of its software.
Join the Team
Our client is actively expanding its product suite and the network it connects. To achieve this, they seek individuals who are excited by complexity, energized by scale, and motivated to make a tangible difference in the mortgage ecosystem. If you are eager to learn, build, and lead, you will find opportunities to do the best work of your career here. To support its valued team members, the organization offers a comprehensive and thoughtful benefits package for all full-time employees, which includes:
- Excellent medical, dental, and vision coverage.
- 401(k) with up to 4% company match.
- 16 weeks of paid parental leave.
- Flexible Paid Vacation Time Off + 10 Sick Days for exempt roles.
- Generous Accrued Paid Vacation Time Off + 10 sick days for non-exempt roles.
- Summer & Winter Break (~1-week each) + 9 Holidays per year.
- Healthcare and Dependent Care FSA.
- HSA Employer Contribution ($75-150 for individuals, $150-$250 for families).
- $15K Family Building Benefit (lifetime limit).
- Life and Disability Insurance.
- $1,500 Annual Lifestyle Stipend to support well-being.
Key skills/competency
- Executive Support
- Calendar Management
- Travel Coordination
- Event Planning
- Operational Ownership
- Strategic Thinking
- Process Improvement
- Stakeholder Management
- Discretion
- Communication
How to Get Hired at Swooped
- Research Our Client's culture: Study their mission, values, recent news, and employee testimonials on LinkedIn and Glassdoor to align with their product discipline and empathy.
- Highlight operational excellence: Customize your resume to showcase proven experience in strategic calendar management, complex travel coordination, and end-to-end event planning, specifically for VP+ leaders.
- Demonstrate proactive problem-solving: During interviews, share examples of anticipating needs, making judgment calls with incomplete information, and implementing systems that improved executive efficiency.
- Emphasize communication and discretion: Prepare to discuss how you confidently represent leaders, influence without authority, and handle sensitive business and regulatory information with utmost discretion.
- Showcase systems-thinking: Detail your experience building repeatable workflows and cadences, illustrating how you optimize processes for greater clarity and efficiency within a senior leadership team.
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