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About Cherry Assistant

Cherry Assistant is an offshore staffing and recruiting agency that helps US and UK founders and growing teams hire vetted remote professionals. South Africa is our primary recruiting market, with additional hiring in Latin America and the Philippines.

We recruit for executive assistance, customer support, sales, marketing, bookkeeping, and operations. Choose ongoing support through Managed Hire or bring a new team member into your own operation with Direct Placement.

What Cherry Assistant does

Managed Hire

We recruit your remote team member and handle payroll and compliance workflows, with ongoing onboarding, performance, retention, and replacement support. You work directly with your hire and set their priorities, while Cherry helps with the operations around the engagement.

Explore Managed Hire

Direct Placement

We scope your role, source and screen candidates, and deliver a shortlist for you to interview. Once you hire, your team takes responsibility for payroll, onboarding, and day-to-day management, giving you recruiting support for a one-time placement fee.

Explore Direct Placement

Custom team hiring

We build a hiring plan for businesses filling several roles or combining managed staffing with direct placements. The scope, sequence, and support are tailored to the team you need and the management capacity you already have.

Discuss your hiring plan

What makes Cherry Assistant different

Month-to-month managed plans

Cherry’s standard Managed Hire plans are month-to-month. For comparison, Prialto’s published pricing FAQ specifies a 90-day minimum; Cherry’s structure gives you flexibility as your workload changes.

Support for 10, 20, or 40 hours per week

Choose the weekly capacity that matches your recurring workload. Managed plans start at $497 per month for a junior assistant working 10 hours per week, with pricing varying by experience, hours, and specialist requirements. See pricing by experience and hours.

A $3,000 direct-placement option

If you already have a manager and payroll process, Direct Placement provides recruiting support for a $3,000 one-time fee per hire. A $500 refundable deposit starts the search and is credited toward that fee if you hire; the remaining balance is due upon a successful hire. See Direct Placement details.

A vetted shortlist in about two weeks

Most searches move from kickoff to a vetted shortlist in about two weeks, with specialist roles sometimes taking longer. We screen for relevant experience, communication, and schedule fit before you interview finalists; the start date depends on interviews, candidate availability, and onboarding.

Replacement support defined by your hiring model

Direct Placement includes a six-month replacement guarantee. Managed Hire includes unlimited replacements while your monthly subscription remains active, subject to the terms of your engagement. Compare replacement support.

Who uses Cherry Assistant

We help medical practices, medspas, law firms, and businesses across a range of industries hire virtual assistants and remote support staff. Explore the roles and workflows we support in your industry.

We also support SaaS companies, startups, real estate teams, and other businesses. Browse our full directory to find virtual assistant services for your industry.

Explore All Industries

Client stories include Divisional, Reveting, and Financial Haus.

The team behind Cherry Assistant

DJ Kim, Co-Founder of Cherry Assistant

Co-Founder

DJ Kim

DJ leads go-to-market strategy and helps shape Cherry’s services around the hiring needs of business owners. His experience spans software, services, and staffing, using offshore teams and operating systems to run and grow businesses.

Ben Deckey, Co-Founder of Cherry Assistant

Co-Founder

Ben Deckey

Ben leads Cherry’s systems, product, and technical infrastructure. He holds a master’s degree in computer science from Brown University and builds the workflows and tools behind Cherry’s recruiting and operations.

Why we started Cherry

DJ and Ben used offshore talent in their own businesses before building Cherry Assistant. Their ventures include Dataghost, acquired by LeadMagic, and Marvel Maids; Cherry brings that experience to other founders who need help turning a hire into a productive part of their team.

The people supporting your hire

Our recruiting team scopes roles, sources candidates, and manages screening and interview coordination. With Managed Hire, Cherry also supports payroll, onboarding, retention, and replacements after your team member starts.

Our website received a 2026 dotCOMM Gold Award in the Professional Service category. View the award or read our announcement.

Follow Cherry Assistant on LinkedIn or hear more founder conversations on Behind the Founders.

How Cherry Assistant works

  1. Define the role with a recruitment consultant

    We discuss the responsibilities, required tools, experience level, budget, and working-hour overlap you need. This gives the search a clear brief and helps you choose between Managed Hire and Direct Placement.

  2. Review candidates and make the hiring decision

    Our recruiters source and vet candidates, focusing on South Africa with additional hiring in Latin America and the Philippines. Most shortlists are ready in about two weeks; you interview finalists and decide who joins your team.

  3. Set up the working relationship

    For Managed Hire, Cherry supports onboarding and handles payroll and compliance workflows; with Direct Placement, your team takes over those responsibilities after the recruiting handoff. Your hire works with you directly, with responsibilities and schedule defined for the role.

  4. Communicate through your existing tools

    Clients assign work through email, chat, and tools such as Slack, Asana, ClickUp, Trello, or their CRM. Working-hour overlap is part of the candidate brief so collaboration fits your business day.

More on working with your hire

Frequently asked questions

Is Cherry Assistant an AI assistant or a staffing company?

Cherry Assistant is a staffing and recruiting company that helps businesses hire human remote professionals. We source and screen candidates for roles on your team, including executive assistance, sales, support, and operations.

Where are Cherry Assistant’s candidates based?

South Africa is our primary recruiting market, and we also hire in Latin America and the Philippines. Candidate screening includes the working-hour overlap your business needs.

What is the difference between Managed Hire and Direct Placement?

Managed Hire combines recruiting with ongoing payroll, onboarding, retention, and replacement support for a monthly fee. Direct Placement provides recruiting for a one-time fee, with your team managing the hire afterward.

How much does Cherry Assistant cost?

Managed Hire starts at $497 per month for a junior assistant working 10 hours per week, with rates varying by hours, experience, and role. Direct Placement costs $3,000 per hire, including a $500 refundable kickoff deposit credited toward the total if you hire. See current pricing.

How quickly can I hire someone?

Most searches reach a vetted shortlist in about two weeks, and specialist searches can take longer. Your start date also depends on interviews, the candidate’s availability, and onboarding.

What happens if my hire is not the right fit?

Direct Placement includes a six-month replacement guarantee, while Managed Hire includes unlimited replacements during an active subscription. Cherry reviews the fit issue and coordinates the next steps under your engagement terms.

Do I need a long-term contract?

Standard Managed Hire plans are month-to-month. Direct Placement uses a one-time fee, and custom team engagements have separately scoped terms.

Tell us what you need off your plate.

We’ll help you define the role, choose the hiring model, and find candidates who fit your team.