Executive Assistant/Operations & Systems Coordinator

WHO WE ARE

About CPLL & the RETAIN Coaching Hub The Center for Parental Leave Leadership (CPLL) is a small and growing mission-driven organizations helping companies build parental leave cultures that work—for employees, managers, and organizations. Our RETAIN Coaching Hub is a dynamic online platform that, through a major strategic partnership, will expand dramatically beginning in 2026. We’re building the team that will support a smooth go-to-market and the future of our growing community.

THE OPPORTUNITY

We are looking for an exceptional Operations & Executive Support Lead to serve as the vital “right hand” to our Founder and Leadership Team. This is not a behind-the-scenes support role; it is a high-trust, high-impact position at the center of our expansion.

You are the person who thrives in the “engine room”—someone who finds genuine satisfaction in turning chaos into order and ensuring that as we scale, nothing slips through the cracks. You will protect leadership’s time, manage the backend of our customer service and technical systems, and bring an anticipatory mindset that keeps the entire organization one step ahead.

WHAT YOU WILL OWN

• Executive & Leadership Support: Total mastery of the Founder’s calendar, communications, and meeting preparation. You will own the “rhythm of business,” ensuring leadership is briefed, prepared, and focused on high-value tasks.
• Financial Operations: Full ownership of the “money-in/money-out” process. This includes managing contracts, generating invoices, tracking payments, and coordinating with our external accounting team to ensure flawless financial hygiene.
• Systems & IT Architecture: Serve as one of the team of internal experts on our backend tech stack. You will improve and manage our CRM, file organization, and specialized platforms, ensuring our systems are optimized for a 2026 scale-up.
• Accountability & Cadence: Attend leadership meetings to capture action items and follow through with team members to ensure commitments are met. You are the “closer” for internal tasks (particularly supporting our Founder and CEO so they don’t drop anything).
• Internal Communications: Anticipate and provide initial drafts of required communications to the internal team, outside partners, vendors, and clients in a professional, clear style.
• Special Projects: From researching new partnerships to scoping out a new workflow, hopping on urgent customer success logistics, you will take on ad-hoc initiatives with a bias for action and total ownership.

QUALIFICATIONS

• 6+ years of professional experience, with at least 3 years supporting senior leadership in a fast-growing environment.
• Technical Fluency: High comfort level with digital tools (G-Suite, Slack, Notion, CRM systems). Experience with membership platforms or financial/billing processes is a significant plus.
• Precision Communication: Polished, warm, written and verbal skills. You can draft executive-level correspondence and interact with Fortune 500 stakeholders with total professionalism while enhancing relationships.
• Operational Mindset: Proven ability to build or refine processes that increase efficiency. You don’t just follow a workflow; you improve it.

WHO YOU ARE

• A Proactive Architect: You don’t wait for a task list. You see a gap in a process or a conflict in a schedule and you fix it before leadership even notices.
• Relentlessly Detail-Oriented: You have an eye for excellence and hold yourself to a high standard, while also holding that we are all human and kindness is imperative. You understand that in a high-growth organization, the small things are the big things.
• Emotionally Intelligent: You read the room, understand the pressures on leadership, and act as a calm, steadying force during high-intensity periods.
• Service-Oriented: You take genuine pride in making others more effective. You find fulfillment in knowing that your excellence allows all of us working together to change the world.

DETAILS

• Fully Remote Contract Position: We operate as a high-performing fully remote distributed fractional team. Hybrid optional for Portland, OR hires.
• Pay: ~$25-35/hr, based on skill and experience.
• Availability: 20-30 hours a week, depending on the person’s availability and needs. Business hours to be determined collaboratively based on the chosen person. Broadly, team overlaps work hours are at a minimum 10-2pm Pacific, with occasional after-hours availability for time-sensitive scaling needs.
• Culture: We are a heart-centered team of passionate, driven, and visionary professionals who work together to deliver field-defining solutions to the complex problem that is parental leave in the United States, while delivering a life-improving experience for our clients.

WHY CPLL?

This is a seat at the table during the most exciting chapter in our company’s nearly two-decade history. You will work shoulder-to-shoulder with our founder and recognized industry pioneers and be rewarded as an essential part of growing CPLL. If you want to do meaningful work that changes the lives of working parents while operating at the highest level of professional excellence, this is your place.

TO APPLY

Submit your resume and cover letter to info@cplleadership.com. Use the subject line “[JOB TITLE] – [YOUR FULL NAME]”

 *******************************************************************

Content & Community Manager

WHO WE ARE

About CPLL & the RETAIN Coaching Hub The Center for Parental Leave Leadership (CPLL) is a small and growing mission-driven organizations helping companies build parental leave cultures that work—for employees, managers, and organizations. Our RETAIN Coaching Hub is a dynamic online platform that, through a major strategic partnership, will expand dramatically beginning in 2026. We’re building the team that will support a smooth go-to-market and the future of our growing community.

THE OPPORTUNITY

This is the most central hire on our growing concierge support team. As our Content & Community Manager, you’ll be the primary steward of everything that lives inside the RETAIN Coaching Hub: the content, the community, the voice, and the experience that keeps members engaged and coming back. You’ll work directly with our Director of Product & User Experience and CEO, and engage with our rapidly growing community day to day.

This role is ideal for someone who deeply understands the RETAIN methodology and framework—ideally a certified RETAIN Parental Leave Coach—who is equally comfortable writing compelling content, moderating a community with warmth and confidence, and showing up live to support community office hours and events.

WHAT YOU WILL OWN

Content Creation & Management

• Support with refreshing and maintaining existing content within the RETAIN Coaching Hub, ensuring it stays current, accurate, and aligned with CPLL’s methodology
• Support with the creation of new hub content, including resources, guides, discussion prompts, and member-facing materials
• Write and schedule community posts collaboratively that drive engagement, spark conversation, and reflect CPLL’s voice
• Support content development for external marketing purposes, including blog posts, social content, and articles (as needed)

Community Management

• Serve as the primary day-to-day moderator and community host inside the RETAIN Coaching Hub
• Welcome new members, facilitate introductions, and create a culture of connection and psychological safety
• Monitor community activity, flag issues, and maintain community guidelines with consistency and care
• Respond to member questions and comments in a timely, thoughtful, and on-brand manner

Concierge Support

• Monitor and respond to support tickets and member inquiries in collaboration with the broader concierge team
• Escalate technical or platform-related issues to the appropriate team member
• Contribute to onboarding materials and member welcome sequences

Live Events Support

• Attend live events (office hours, webinars, community calls) and support hosts with logistics, chat moderation, and real-time member engagement as needed
• Serve as a backup event lead or co-host for orientation calls, office hours, and community calls when the primary host is unavailable
• Eventually, serve as a primary (co-)host for live orientation calls and office hours

QUALIFICATIONS

• RETAIN Coach certification strongly preferred. Familiarity with the RETAIN framework and methodology is essential.
• Experience in community management, content creation, or a similar role.
• Excellent written communication skills with a warm, professional, and mission-aligned voice.
• Comfortable showing up live on video for community events and office hours.
• Highly organized, self-directed, and able to manage multiple priorities without hand-holding.
• Familiarity with Mighty Networks or similar online community platforms a strong plus.
• Experience with Canva, Slack, Zoom, and similar tools.
• Reliable internet connection with availability during normal working hours in the US.

DETAILS

• Type: Independent Contractor
• Commitment: Minimum 20 hours/week, up to 40 hours/week
• Availability: Must be available during core hours for live events and collaboration; schedule otherwise flexible
• Location: Fully remote; Contractor provides own equipment and tools
• Rate: $28–$35/hour depending on experience and certification status
• Retainer Option: Hourly rate with opportunity to convert to a monthly retainer based on consistent commitment (typically after 60–90 days)
• Tools Provided: Access to CPLL’s team Zoom, Slack, and Canva accounts

WHY CPLL?

This is a seat at the table during the most exciting chapter in our company’s nearly two-decade history. You will work shoulder-to-shoulder with our founder and recognized industry pioneers and be rewarded as an essential part of growing CPLL. If you want to do meaningful work that changes the lives of working parents while operating at the highest level of professional excellence, this is your place.

TO APPLY

Submit your resume and cover letter to info@cplleadership.com. Use the subject line “[JOB TITLE] – [YOUR FULL NAME]”