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Executive Remote Matchmaker Jobs in Chicago, IL (NOW HIRING)

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Senior Sales Executive

Chicago, IL · Remote

Remote Get Logistics Priority, a prominent national freight broker specializing in drayage and ... Paralleled with the knowledge on how to match freight lanes with the appropriate Carrier Vendors ...

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Senior Sales Executive

Chicago, IL · Remote

Remote Get Logistics Priority, a prominent national freight broker specializing in drayage and ... Paralleled with the knowledge on how to match freight lanes with the appropriate Carrier Vendors ...

PRACTICE

Account Executive in Chicago

Chicago, IL · Remote

$70K/yr

This is a remote role! Opportunity As an Account Executive on our growing sales team, you will ... Enjoy a generous benefits package that includes medical, dental, vision, 401(k) match, paid ...

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All JobsMatchmaker JobsExecutive Remote Matchmaker JobsExecutive Remote Matchmaker Jobs in Chicago, IL

Executive Remote Matchmaker information

See Chicago, IL salary details

$27.3K

$96.4K

$189.5K

How much do executive remote matchmaker jobs pay per year?

As of Aug 19, 2026, the average yearly pay for executive remote matchmaker in Chicago, IL is $96,372.00, according to ZipRecruiter salary data. Most workers in this role earn between $59,700.00 and $124,100.00 per year, depending on experience, location, and employer.

What is an executive remote matchmaker?

An Executive Remote Matchmaker is a professional who specializes in connecting high-level executives or professionals with compatible partners for dating or relationships, often working virtually rather than in-person. They use interviews, personality assessments, and their expertise to understand clients’ preferences and values, then search for and vet potential matches. The remote aspect allows them to serve clients from various locations, leveraging technology for communication and introductions. Their goal is to facilitate meaningful relationships for busy executives who may lack the time or network to find compatible partners on their own.

What are the key skills and qualifications needed to thrive as an executive remote matchmaker?

To thrive as an Executive Remote Matchmaker, you need strong interpersonal skills, a background in relationship management or recruiting, and typically a bachelor's degree in a relevant field. Familiarity with CRM software, matchmaking platforms, and virtual communication tools is important for efficiently managing clients and candidates. Exceptional communication, discretion, and emotional intelligence help build trust and rapport with high-level clients. These skills and qualities are crucial for successfully connecting executive clients with compatible matches while maintaining a high standard of professionalism and confidentiality.

What are the main challenges executive remote matchmakers face when working with high-profile clients?

Executive Remote Matchmakers often encounter the challenge of balancing discretion with effective communication, as high-profile clients expect confidentiality and personalized attention. Additionally, understanding and managing clients' busy schedules and unique preferences can require flexibility and strong organizational skills. Building trust remotely, without in-person interactions, also means matchmakers must excel at virtual rapport-building and utilize technology effectively to ensure a seamless experience.

What is the difference between Executive Remote Matchmaker vs Remote Recruiter?

AspectExecutive Remote MatchmakerRemote Recruiter
CredentialsExperience in executive placement, industry-specific knowledgeRecruitment certifications, general HR experience
Work EnvironmentHigh-level client interactions, executive search firmsCorporate HR departments, staffing agencies
Industry UsageExecutive search, leadership rolesVarious industries, entry to mid-level roles
Search IntentMatching executives with remote leadership positionsFilling remote roles across different levels

While both roles involve remote hiring, an Executive Remote Matchmaker specializes in placing high-level executives in remote leadership positions, often within executive search firms. In contrast, a Remote Recruiter handles a broader range of roles across industries and levels, focusing on filling remote positions for various companies. The key difference lies in the seniority of placements and the scope of client engagement.

What are the most commonly searched types of Remote Matchmaker jobs in Chicago, IL?

The most popular types of Remote Matchmaker jobs in Chicago, IL are:

What cities near Chicago, IL are hiring for Executive Remote Matchmaker jobs?

Cities near Chicago, IL with the most Executive Remote Matchmaker job openings:

Executive Remote Matchmaker jobs near you
Infographic showing various Executive Remote Matchmaker job openings in Chicago, IL as of August 2026, with employment types broken down into 84% Full Time, 12% Part Time, and 4% Contract. Highlights an 84% Physical, 5% Hybrid, and 11% Remote job distribution, with an average salary of $96,372 per year, or $46.3 per hour.

Inside Sales Representative- Advertising Executive (Remote)

Guide Book Publishing

Crown Point, IN • Remote

Full-time

Medical, Dental, Vision, Life, Retirement, PTO

Posted 9 hours ago

Posted today

Job description

Location: Remote Job Type: Full-Time Compensation: Draw + Lucrative Commission + Performance Incentives

The Opportunity

Are you a self-motivated "hunter" who thrives on variety? Guide Book Publishing, an industry leader since 1991, is looking for a strategic Advertising Account Executive. Unlike traditional sales roles where you call the same list for years, our team moves to a new assignment every 2-3 weeks, helping local businesses across 24 states reach "micro-communities" through high-quality direct-mail advertising.

How it Works

  • The Workflow: You’ll switch assignments frequently, focusing on businesses within a 3-5 mile radius of a specific congregation or community center.
  • The Method: 70% of your time is spent on high-energy outreach (phone, email, and video meetings); 20% on market research; and 10% on contract execution.
  • The Flexibility: This is a remote role, but does require getting your materials back to the Post Office to return to the Home Office.

Key Responsibilities

  • New Business Development: Identify and close new advertising partnerships to meet production goals.
  • Consultative Sales: Educate local business owners on the ROI of being featured in our community guides and directories.
  • Relationship Management: Act as the primary liaison between your clients and our operations staff to ensure an excellent experience.
  • Account Growth: Nurture and maintain large-scale accounts within your metro area.
  • Administrative Precision: Manage contracts and paperwork accurately and return assignment materials via USPS upon completion.

Compensation & Benefits

We offer a structure that rewards high performers and provides security through a comprehensive benefits package via ADP TotalSource.

  • Draw & Commission: Payroll is based on "Cash In" from sales, with a Draw program available to stabilize income as you build your funnel.
  • Performance Bonuses: Additional incentive pay for hitting Assignment, Monthly, Quarterly, and Annual targets.
  • Benefits:
    • Health, Dental, and Vision Insurance
    • 401(k) with Company Match
    • Life Insurance
    • Paid Time Off (PTO)

Qualifications

  • Experience: 1-2 years of sales experience preferred (or equivalent education).
  • Mindset: A self-starter who can manage their own schedule without being micromanaged.
  • Skills: Proficient in Excel, scanning, email, and PDF management. Strong ability to calculate discounts and commissions accurately.
  • Communication: Persuasive verbal skills and clear, professional written communication.
  • Requirements: Valid Driver’s License and Auto Insurance.

Why Guide Book Publishing?

We serve the communication needs of over 800 micro-communities. If you are looking for a role that balances the freedom of remote work with the fast-paced nature of community-based sales, we want to talk to you.


Physical Demands and Work Environment:

  • Requires Valid Driver’s License and Auto Insurance
  • Frequently required to sit and utilize a keyboard and phone.


The above is intended to describe the general content of and requirements for the performance of this job. It is not to be construed as an exhaustive statement of duties, responsibilities, or physical requirements. Nothing in this job description restricts management’s right to assign or reassign duties and responsibilities to this job at any time. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.