Role: Chief of Staff

Location: Remote (East Coast Hours) | Full-Time

Salary: $150-175K

Our client is a mission-driven, innovative company focused on supporting working parents through a comprehensive paid parental leave insurance program. Their insurance-based solution covers salary expenses during leave for all parents (birth, adoption, foster), offers administrative simplicity with a concierge team managing leave processes and compliance, and provides unlimited personalized coaching before, during, and after leave. With five years in the market, they have a proven track record:

• Currently closing funding round to double team size from 11 to ~22 employees
• Transforming how companies support working parents through comprehensive insurance-based solutions
• Addressing the 43% of highly-skilled women who leave the workforce after becoming mothers, representing $12 trillion in lost global economic growth

Position Overview:

They are seeking a strategic, financially-savvy Chief of Staff to work directly with our Founder & CEO, as we scale our innovative paid parental leave insurance solution. This is a unique opportunity to join a mission-driven company that enables employers to retain and elevate working parents, particularly working mothers, while making a significant impact on workplace equity and economic growth.

As Chief of Staff, you will be a critical extension of the CEO, owning financial operations, analytics, project management, and investor relations functions during a pivotal growth phase. With our team doubling following our current fundraising round, you'll play an instrumental role in building the operational foundation that will support Parento's continued success.

Key Responsibilities:

• Financial Operations (40%):
• Rebuild and maintain our financial model (currently 4 months behind)
• Manage A/R, billing, and revenue recognition processes for multiple revenue streams (commissions and annual fees paid quarterly)
• Identify, select, and implement new financial tools to improve tracking and reporting
• Oversee financial performance tracking and analytics
• Bridge the gap between finance, tech, and underwriting teams on integrated systems
• Performance Analytics (30%):
• Track and report on marketing performance metrics
• Monitor sales pipeline by channel
• Analyze insurance performance data
• Create and maintain dashboards for key business metrics
• Develop data-driven insights to guide strategic decision-making
• Project Management (20%):
• Lead implementation of new tools and systems to integrate disparate operations
• Create structure and urgency around key projects
• Ensure cross-functional alignment on strategic initiatives
• Drive projects independently with minimal guidance
• Establish processes where none currently exist
• Investor & Executive Support (10%):
• Prepare investor materials and meeting agendas
• Support fundraising and strategic partnership efforts
• Handle administrative functions currently managed by the CEO
• Participate in strategic planning and execution

Qualifications:

Must-Haves

• 5-7 years of professional experience with background in management consulting, investment banking, or startup operations
• Strong financial modeling and Excel skills with demonstrated ability to build and maintain comprehensive financial models
• Experience with data analytics and establishing performance tracking systems
• Proven track record of successfully managing complex projects independently
• Previous work in a fast-paced, resource-constrained startup environment
• Exceptional self-direction and ability to solve problems with minimal oversight
• Ability to work remotely during East Coast business hours
• Strong attention to detail and ability to drive projects to completion
• Experience implementing systems and processes from scratch
• Bachelor's degree in Finance, Economics, Business, or related field

Non-Negotiables

• Must be comfortable working in a remote-first environment
• Must be able to handle multiple competing priorities
• Must be able to receive direct feedback without taking it personally
• Must be tenacious and able to figure out solutions independently
• Must be able to balance strategic thinking with tactical execution

Nice-to-Haves

• Experience preparing investor materials or supporting fundraising efforts
• Understanding of insurance industry or benefits administration
• Experience with revenue recognition in complex business models
• Previous Chief of Staff or similar role working directly with founders/executives
• MBA or advanced degree in Finance or related field
• Experience with sales or marketing operations and performance tracking
• Background in implementing financial or operational systems
• Professional certifications (CFA, etc.)