Jobs at Prospr

Chief Operating Officer

Full time - Hybrid Toms River NJ / Remote

We are looking for a high-impact COO / Implementation Lead to serve as the operational architect and strategic #2 to our Founder. This is an intense, entrepreneurial environment where the pace is relentless and the expectations are high.

Your primary objective is to turn visionary concepts into a structured, revenue-generating engine. You will be the bridge between “what if” and “how to” taking high-level frameworks
and building the rigorous systems, protocols, and teams necessary to bring them to market. This role requires a leader who is bold enough to challenge ideas and flexible enough to pivot as the business evolves.

Key Competencies

● Translational Leadership: The ability to take abstract, high-level visions from a founder
and translate them into concrete, practical execution plans.
● Systems Architecture: A natural tendency to see the world in workflows. You don’t just solve a problem once; you build a protocol so it never becomes a problem again.
● Emotional Resilience: The “grit” to handle the pressures of a fast-paced startup. You remain calm under fire, accept feedback without ego, and lead with a steady hand.
● Strategic Boldness: You are proactive and decisive. You don’t wait for permission to move things forward; you take ownership and drive results.
● Tech-Forward Mindset: While you don’t need to code, you must be “tech-fluent”—understanding how data, platforms, and automation integrate to create business value.

Key Responsibilities

Operational Systemization & Scaling

● Protocol Development: Design and document end-to-end systems for operations, product delivery, and customer success to ensure 100% scalability.
● Execution Engine: Convert the Founder’s roadmap into actionable sprints, ensuring every project has a clear owner, timeline, and ROI.
● Monetization Strategy: Audit current and future offerings to identify gaps in revenue and implement structured monetization paths.

Technical & Data Oversight

● Tech Stack Management: Act as the primary liaison between the business and external developers/consultants to ensure technical builds align with commercial goals.
● Data-Driven Decision Making: Build and maintain sophisticated dashboards to track KPIs, ensuring the business moves based on facts rather than feelings.

Leadership & Accountability

● Team Architecture: Hire, manage, and mentor a high-performance team (local, remote, and offshore) across technical and concierge/coaching functions.
● Visionary Partnership: Work in lockstep with the Founder, providing the organizational structure that allows their vision to thrive while maintaining the “checks and balances” of
a sound business.

Qualifications & Requirements

The “Builder” Track Record: Proven experience taking early-stage or “messy” concepts and turning them into structured, profitable business units.
● Tech Savviness: High proficiency in navigating tech-enabled platforms, CRM systems, and automated workflows. You should be comfortable discussing technical logic with developers.
● High-Growth Experience: You have thrived in an entrepreneurial setting where you had to build the plane while flying it.
● Leadership Maturity: Significant experience managing people and projects with a focus on emotional intelligence and radical candor.
● Local Presence: Must be able to commute to the New Jersey office initially for deep-dive integration, moving to a hybrid schedule thereafter.

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.