Executive Assistant to the CEO, Sparrow
$80-140k
Employee leave management software
Job no longer available
Employee leave management software
201-500 employees
Job no longer available
$80-140k
201-500 employees
Company mission
To take the stress out of employee leave, eliminate the associated headache of compliance for employers, and ultimately save time and money.
Role
Who you are
- 5+ years of experience supporting senior executives, ideally CEOs or founders in high-growth environments
- Exceptional written communication skills, including the ability to write clearly in another person’s voice
- Strong judgment and prioritization instincts. You know what matters most and why
- A high-ownership mindset and comfort operating independently
- Experience creating, improving, and maintaining processes
- Professionalism and confidence working with senior leaders and external stakeholders
- High emotional intelligence, discretion, and attention to detail
- Comfort supporting both professional and limited personal logistics
What the job involves
- We’re looking for an exceptional Executive Assistant / Personal Assistant to partner closely with Sparrow’s CEO during a critical phase of growth
- The CEO views her role as setting Sparrow’s vision and hiring and managing a high-performing executive team. Her time is extremely limited—and it’s essential that she spends that time only on the highest-impact work that requires her attention
- In this role, you will act as a force multiplier for the CEO and for Sparrow as a whole. You’ll help increase the velocity at which the CEO can meet, delegate, and make decisions, while ensuring strong follow-through and visibility across the executive team on CEO-dependent work
- This role is expected to be 90% Executive Assistant work and 10% Personal Assistant work, supporting both professional and limited personal logistics so the CEO can operate at her highest level
- This is a fully remote role but may require up to 25% travel to the Bay Area, where the CEO is located
- This is a role where accountability and ownership are extremely important, and at times it may require your schedule to flex with little notice
- Partner closely with the CEO on priorities and execution
- Work with the CEO to understand her highest-impact priorities and ensure her time is aligned accordingly
- Help keep Sparrow moving at high velocity by enabling faster decision-making and delegation
- Partner with the CEO to action-plan how key initiatives and tasks will be completed
- Own inbox, calendar, and communication management
- Manage a complex and fast-moving calendar, ensuring meetings are purposeful, prioritized, and sequenced effectively
- Own inbox management, including tagging, drafting emails in the CEO’s voice, and independently handling communications such as event registrations or account setup
- Ensure written communication is clear, thoughtful, and tailored to the reader’s perspective
- Prepare context and materials so meetings are efficient and effective
- Drive follow-through and executive visibility
- Track CEO-dependent projects, decisions, and action items across the executive team
- Provide visibility to relevant stakeholders on status, dependencies, and next steps
- Ensure nothing important stalls due to lack of follow-up or coordination
- Operate with a high-ownership mindset
- Take initiative to directly tackle tasks when appropriate
- When you’re not the right person for a task, proactively leverage internal partners or external resources to get it done
- Approach problems with a solutions-oriented, “figure it out” mentality
- Build and improve systems and processes
- Create and continuously improve processes that increase executive and organizational efficiency
- Stay up to date on tools and technology that improve administrative workflows
- Bring recommendations for how Sparrow’s executive operations can run more smoothly
- Provide light personal assistance
- Maintain the CEO’s personal calendar and ensure it is coordinated with work commitments
- Schedule personal appointments while avoiding conflicts with professional priorities
- Partner with the CEO to build systems that make her personal life more efficient (e.g., meal planning, wardrobe management, recurring life admin)
- What This Role Is Not:
- This is not a passive, task-only administrative role
- Success requires strong judgment, proactive ownership, and the ability to think critically about priorities—not just execute instructions
- This is not a role with rigid boundaries between responsibilities
- While the role is primarily Executive Assistant work, it includes Personal Assistant support. The goal is to enable the CEO to operate at her highest level—not to adhere to an inflexible job description
- This is not a gatekeeping or power-centered role
- The Executive Assistant is a facilitator and partner, not a blocker. The goal is to increase clarity, access, and momentum across the organization
- This is not a role for someone who prefers highly structured, static environments
- Priorities will evolve, and success requires comfort with ambiguity and change
- This is not a stepping-stone role for someone uninterested in long-term partnership
- This role is designed for someone who wants to build a trusted, enduring partnership with the CEO and grow alongside Sparrow
Our take
Taking leave from work can initially seem like an easy process, but in reality it’s often stressful and time-consuming for all involved. Employers must comply with ever-changing regulations at local, federal, and state levels which makes the leave process a legal minefield, and large quantities of paperwork must be tackled by many different departments.
Sparrow develops software that allows the HR departments of enterprises to automate the compliance and admin process of employee leave, with the ultimate aim to make taking leave stress-free for employees and employers alike.
Whilst Sparrow faces competition from similar companies, its benchmarking and consulting processes are unique and can tackle complicated and unexpected leave situations where similar products often fail. With substantial funding awarded in 2022 being used to accelerate sales, product development, and team scaling, Sparrow is retaining its edge.
Steph
Company Specialist at Welcome to the Jungle
Insights
Company
Funding (2 rounds)
Jul 2025
$35m
SERIES B
Feb 2022
$20m
SERIES A
Total funding: $55m
Company benefits
- Everyone is an Owner
- Flexible Time Off
- Paid Family & Medical Leave
- Paid Health, Dental, and Vision
- Life Insurance
- Short-Term & Long-Term Disability Benefits
- Flexible Spending Account (FSA)
- Commuter Benefits
- WFH Office Reimbursement
- Work From Anywhere
Company values
- We have limited bandwidth - Our business has grown faster than our company. Leave affects everyone. Sparrow’s market is the intersection of people who have jobs and people who take time off work. We do not just lead this market. We invented it. This means that we need to work together to ensure we clearly understand the impact each project will have before we start working.
- We don't have all the answers - The problems we’re solving are beyond our current expertise, meaning that there is incredible room for growth for everyone joining Sparrow. We are willing to give enormous responsibilities to people at any stage of their career if they demonstrate the ability to run with them.
- We build for the long-term - Building a sustainable team and product is a marathon, not a sprint. We believe in investing time in planning, communication, training, and personal growth -- so that we are all able to have a lasting impact together.
Company HQ
Rincon Hill, San Francisco, CA
Leadership
Deborah Hanus
(CEO)Started as an AI Researcher at MIT, Harvard, and Google Brain with funding from the National Science Foundation. Lived in Cambodia for a year as a Fulbright Scholar.
Samarth Keshava
(CTO)14 years at Google Search. Was a Senior Staff Software Engineer, and ran the engineering team responsible for the overall UI of the Google Search Results Page. Graduated from Yale.
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