Jobs – Executive Assistant

Executive Assistant (EA) & Marketing Generalist

We are seeking a proactive, highly organized, and execution-oriented Executive Assistant (EA). You will report directly to the CEO/Founder to provide operational relief and streamline everyday workflows.

This role serves as a key operational lever for the company. It combines executive administration with hands-on marketing support to reduce task fragmentation across the team. You will help centralize administrative, copywriting, and social media tasks. This will allow the CEO to step back from day-to-day management to focus on high-value scaling initiatives.

Key Responsibilities

1. Executive Support & Operational Coordination
  • Manage the CEO's administrative workflow, calendar, and task tracking.
  • Act as a central communication link between the CEO and internal team contractors.
  • Screen and manage inbound candidate flows and applicant tracking.
  • Establish, standardize, and document internal processes to eliminate role confusion.
  • Organize project dependencies to optimize overall business scalability.
2. Marketing & Content Execution
  • Centralize marketing execution under a single, highly accountable function.
  • Write and distribute clear marketing copy, email newsletters, and drip campaigns.
  • Publish, schedule, and monitor quality control across corporate social media platforms.
  • Coordinate digital assets, video content, and online brand presentation materials.
  • Consolidate and monitor performance metrics across all active marketing channels.
3. Workflow & Technical Alignment
  • Own day-to-day work systems within Asana for task execution and reminders.
  • Manage inbound pipeline workflows and notification routing inside Gmail and Asana.
  • Interface with the internal IT support team to resolve system tech bottlenecks.
  • Explore and implement AI automation tools for drafting emails and improving operational workflows.

Required Core Attributes & Experience

Critical Competencies
  • Execution Focus: Thrives on clear direction, details, and consistent daily execution over high-level strategic driving.
  • Extreme Organization: Natural inclination toward organizing information, building schedules, and cleaning up administrative overlap.
  • Thorough Communication: Clear, proactive, and prompt verbal and written communication styles.
  • Adaptability: Calm, composed, and comfortable balancing a hybrid mix of administrative and marketing tasks.
  • Rapid Learner: Possesses a positive learning attitude and a strong aptitude for mastering new business processes quickly.
Ideal Technical Skill Sets
  • Proven proficiency using Asana or equivalent robust project management software platforms.
  • Experience utilizing Google Workspace environments, specifically advanced Gmail filtration and workflows.
  • Hands-on familiarity with basic graphic design or UI/UX tools for social media and marketing layouts.
  • Experience writing short-form or long-form copy for digital marketing and drip campaigns
  • Comfort navigating data structures, basic budgets, and performance metric tracking sheets.

Chava Caplan

Financial Coach

Chava brings warmth, clarity, and practical tools to her role as a Financial Coach at PROSPR. She works with individuals and couples to help them feel more confident and empowered with their money, especially during times of change.

She is a Certified Life Coach (Darco Coaching) and Certified Mesila Financial Coach, combining her financial training with a compassionate, client-centered approach. Her background in grief support allows her to guide clients with sensitivity through emotionally charged financial decisions.

Chava creates a supportive space where clients can feel safe, seen, and successful in their financial journeys.

Milena

Concierge Coach

Milena supports day-to-day operations at PROSPR as our Concierge Coach, working closely with founder Simi Mandelbaum to keep clients organized and on track. She keeps your financial plan running smoothly: handling updates, tracking transactions, and offering real-time support so nothing falls through the cracks.

She holds a BA in Business and is currently pursuing further studies while working full-time. Outside of work, she enjoys reading, snowboarding, and spending quality time with friends over coffee.

Shira Rubinstein

Tech & Concierge Lead

Shira leads PROSPR’s tech operations and concierge services, combining her background in Computer Science with a thoughtful, people-first approach. She’s passionate about making systems more efficient and ensuring every client has a seamless, supportive experience.

Shira loves family safaris and staying closely connected to her roots. She brings warmth, precision, and care to every aspect of her work.

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Kimberly Olson, AFC Candidate

Financial Coach

Kimberly brings her many years of experience as an analyst and accountant to the PROSPR Coaching team. Her desire to help others overcome their obstacles and achieve financial freedom has led her to pursue financial coaching with PROSPR.
Kimberly has passed the rigorous Accredited Financial Counselor® exam and is in the process of completing her certification. In her spare time, she volunteers at a number of community centers helping those in need of financial counseling. She enjoys spending time outdoors with her family and dog in her home state of Minnesota.

Meir Neiman, MBA

Financial Coach

Meir has been the recipient and received the benefit of PROSPR financial coaching. He has a deep passion for passing those benefits on to others.
Meir earned his MBA in Business Administration with a concentration in Finance from Bellevue University. He has 10+ years of experience in the financial services area, specifically in the complex Home Buying or Mortgage process.
Meir lives in New Jersey with his wife and 6 children.

Ariella Gofman, FFC

Lead Financial Coach

As PROSPR’s Lead Financial Coach, Ariella blends strategic insight with a deep understanding of human behavior. She helps clients build money systems that reflect their values, reduce stress, and support long-term growth, using the PROSPR Plan Software as a guide.

Ariella is a Certified Family Financial Coach (Esh Lidor) and Certified Financial Literacy Educator (Mesila International). She also teaches at Michlalah College for Women in Jerusalem, where students describe her classes as “life-changing,” “practical,” and “transformative.”

She’s the founder of My Sister’s Closet, a nonprofit clothing boutique that supports women in need with dignity and care. Across all her work, Ariella is driven by one goal: helping people live more intentionally, with clarity and alignment. She brings a heartfelt and grounded energy that makes big ideas feel manageable and achievable.

Simi Mandelbaum CFT™, AFC®, FBS®

Founder & CEO

Simi is the Founder and CEO of PROSPR Financial Wellness. She launched PROSPR after experiencing firsthand the stress and confusion that often comes with managing money—and made it her mission to help others find clarity, confidence, and calm.

A Certified Financial Therapist (CFT™), Accredited Financial Counselor (AFC®), and Financial Behavior Specialist (FBS®), Simi has helped hundreds of clients reduce debt, grow income, and align their finances with their values. She’s also the creator of The PROSPR Plan Software™, a cash flow management tool designed for both ADHD and non-ADHD users.

Simi has been featured on Kosher Money, Nerd Wallet, The Voice of Lakewood, Ami Living, Mishpacha Magazine and various other podcasts and publications. She has spoken at national conferences including the 2024 International ADHD Conference, the AFCPE National Convention, and the Financial Therapy Association Annual Conference.

Christopher Stuart

Software Specialist

Chris is PROSPR’s all-around Software Guru. He is certified in a number of technologies and specializes in Data Architecture, Zapier, Web Design, Google Workspace Administration, JavaScript, Node.js, GitHub, WordPress, and Google Apps Script, among others.
Chris brings his skills as a former Firefighter at Elk Creek Fire Protection District, with expertise in Problem Solving and Incident Management, to his position at PROSPR. He is always up to the challenge of solving any IT crisis the Company may face.