Chief of Staff

About Parento

Parento is the first provider for paid parental leave, distributing the first and only paid parental leave insurance and parental support program. Our holistic program enables companies to offer paid maternity and paternity leave to all employees.

Designed to support working parents while alleviating HR’s workload, Parento’s white glove leave concierge handles the complexities of leave management, payroll calculations, compliance, and claims, while providing emotional and parent coaching for employees. Our proprietary program boasts a 95% return-to-work rate and guides employees through the process before, during, and after leave to ensure a seamless re-onboarding.

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.

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

Must-Haves

• 5-7 years of professional experience with background in management consulting, investment banking, or startup operations - or former startup found
• Strong financial modeling and Excel skills with demonstrated ability to build and maintain comprehensive financial models, preferred
• 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
• Experience with sales or marketing operations and performance tracking
• Background in implementing financial or operational systems