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Technical Support Agent

Job Details

Location

Remote United States

Employment Type

Full time

Location Type

Remote

Department

Services & Support

Compensation

  • USD$19 – $21 per hour
  • CADCA$19 – CA$22 per hour
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Customer Support Specialist I

Job Details

SQUIRE is the leading business management system designed for the needs of barbers, shop owners, and their communities. We believe the pursuit of artistry and autonomy should not be restricted by the complexities of running a business. With SQUIRE, we provide custom-branded tools, resources, and guidance to help barbers of all stages and experience levels attract and retain more customers, efficiently manage their shop operations, and increase their revenue.

 

Founded in 2015, SQUIRE is trusted by more than 30,000 barbers across 5,000+ shops in more than a thousand cities worldwide. From streamlined booking and opening new shops to real-time earning dashboards and building lasting customer relationships, SQUIRE supports shop owners in seamlessly bridging the gap between their personal craft and business goals. SQUIRE enables barbers everywhere to unlock their full potential both as artists and as entrepreneurs.

 

For more information, please visit getsquire.com or download the SQUIRE app from the App or Play Store.

 

 

SUMMARY

The Customer Support Specialist I is the first point of contact for our Customers and their clients, providing timely assistance, troubleshooting basic issues, and helping shops and barbers succeed using the SQUIRE platform. This position may work shifts between Monday – Friday,  7:00 am EST – 9:00 pm EST to support SQUIRE’s global customer base.

 

REPORTS TO

Manager, Customer Support

JOB DUTIES AND RESPONSIBILITIES

  • Respond promptly to customer inquiries through chat, email, and phone.
  • Troubleshoot and resolve common technical and account-related issues.
  • Escalate complex cases to Tier II or other departments as needed.
  • Maintain accurate and detailed records of customer interactions and resolutions.
  • Develop a strong understanding of SQUIRE’s products and services to provide effective support.
  • Deliver excellent service by ensuring a positive and professional customer experience.
  • Identify recurring issues and share feedback with the team to improve processes.
  • Contribute to maintaining and updating internal knowledge base articles.

 

The duties and responsibilities outlined above are not a comprehensive list and additional tasks may be assigned from time to time based on business needs.

REQUIREMENTS AND QUALIFICATIONS

  • 1+ years of technical support experience.
  • Prior experience and understanding of Android, Apple, Mac, PC technology and operating systems.
  • An outside-the-box thinker and problem solver, able to diagnose problems even when there isn’t a manual.
  • Ability to work 40 hour work-week.
  • Excellent oral and written communication skills.
  • Understanding of Payment Processing and Payment devices.
  • Flexibility to work weekends/evenings.

WHAT WE OFFER

  • Base Salary ($52,000)
  • New hire stock grant
  • 100% employer paid medical, dental, and vision insurance for you and your dependents
  • 401K plan with company contribution
  • Generous PTO and Parental Leave policies

Interview Accommodations

SQUIRE is committed to working with and providing reasonable assistance to individuals with physical and mental disabilities. If you are an individual with a disability requiring an accommodation to apply for an open position, please email your request to recruiting@getsquire.com and someone on our team will respond to your request.

 

EEO Provision

SQUIRE provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state or local laws.

 

This policy applies to all terms and conditions of employment, including recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation, and training.

 

Pay Transparency Nondiscrimination Provision

SQUIRE will not discharge or in any other manner discriminate against employees or applicants because they have inquired about, discussed, or disclosed their own pay or the pay of another employee or applicant. However, employees who have access to the compensation information of other employees or applicants as a part of their essential job functions cannot disclose the pay of other employees or applicants to individuals who do not otherwise have access to compensation information, unless the disclosure is (a) in response to a formal complaint or charge, (b) in furtherance of an investigation, proceeding, hearing, or action, including an investigation conducted by the employer, or (c) consistent with the contractor’s legal duty to furnish information.

 

E-Verify Participation

SQUIRE participates in E-Verify. Learn more about E-verify here.

We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.

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Customer Support Representative (Multi Channel)

Job Details

The Mission: Eliminate Fear

Health insurance is complicated, expensive, and intimidating. At SimplyInsured, we are on a mission to eliminate that fear. We empower small business owners—the backbone of the economy—by making the enormous task of providing health insurance transparent, accessible, and dead-simple.

Born in Y-Combinator and backed by top-tier investors like Bessemer Venture Partners, we are disrupting a convoluted industry. We aren’t just a platform; we are a lifeline for over 20,000 customers.

The Role: The Face of the Mission

As a Customer Support Representative, you are on the front lines of our mission. You are the voice of calm in a confusing industry. You won’t just be “processing tickets”—you will be guiding real people through some of the most important decisions they make for their families and employees.

This is a multi-channel role (Phone, Chat, Email) where your empathy, speed, and problem-solving skills will directly impact our growth and customer loyalty.

How You’ll Make an Impact

  • Be a Trusted Guide: Help potential customers navigate our online shopping experience, helping them find the perfect health insurance quotes for their teams.
  • Solve Real Problems: Resolve administrative and billing questions with urgency and clarity. Your goal is to turn a “stressful question” into a “seamless resolution.”
  • Master the Stack: Use industry-leading support tools and CRMs to document interactions and ensure no customer is left behind.
  • Advocate for Change: You have a front-row seat to our customers’ challenges. You are empowered to propose product and process improvements directly to our leadership team.
  • Deliver “Delight”: Maintain high productivity in a fast-paced, high-volume environment while keeping a “people-first” attitude.

What You’ll Bring

  • Experience: 1-2 years in a customer-facing role (Support, Retail, or Sales) in a remote, startup environment. 
  • Communication: Exceptional oral and written skills. You can explain complex topics in a way that is easy to understand.
  • Tech-Savvy: Familiarity with support ticketing systems (like Zendesk, Freshdesk, or Salesforce) and the ability to multitask across several tabs and tools.
  • Empathy: A genuine passion for helping people and a desire to support small business owners.
  • Reliability: Ability to work a consistent schedule of 8:30 am – 5:00 pm CST, Monday through Friday.

 

What We Offer

  • World-Class Benefits: 100% Company-paid Medical, Dental, and Vision coverage for you and your dependents. This is a rare benefit that ensures your family is as protected as our customers.
  • Work from Anywhere: This is a 100% remote position (must be based in the U.S.).
  • Generous Time Off: “Take what you need” vacation policy to ensure you stay refreshed.
  • Growth Culture: A values-based environment where your “obligation to dissent” and your ideas for improvement are actually heard.

Compensation

Starting Base Salary: $15.00 per hour Note: This is the base hourly rate. We offer a robust benefits package that significantly increases the total value of your compensation.

Our Commitment to Diversity

We are driven by the diversity of our backgrounds. Research shows that candidates from underrepresented backgrounds—including women and people of color—often apply only if they meet 100% of the criteria.

At SimplyInsured, we want to change that. If you are passionate about our mission and have a heart for service, we want to hear from you—even if you don’t check every single box.

SimplyInsured is an equal opportunity employer. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.

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Customer Support Specialist – USA

Job Details

Join the leading independent rail vacation provider in North America and beyond! Railbookers Group, home to both Railbookers and Amtrak Vacations, is passionate about delivering unforgettable train travel experiences. We take pride in crafting seamless, personalized itineraries for our guests and travel advisors, offering the largest selection of independent rail vacations worldwide. If you have a passion for travel and a knack for sales, we invite you to be a part of our growing team. 


POSITION PURPOSE  

The Customer Support Specialist for Railbookers and Amtrak Vacations is a crucial front-line position responsible for providing exceptional support and service to our valued guests primarily through inbound phone calls, emails, and web inquiries. This role focuses on assisting customers with existing reservations, resolving issues, and ensuring a positive and memorable travel experience. The ideal candidate is a proactive problem-solver with a strong customer service orientation and a genuine passion for travel. 


RESPONSIBILITIES  

  • Serve as the primary point of contact for customer inquiries regarding existing Railbookers and Amtrak Vacations bookings via phone, email, and online channels. 
  • Provide comprehensive support for itinerary changes, cancellations, modifications, and special requests, ensuring accuracy and adherence to company policies. 
  • Troubleshoot and resolve a wide range of customer service issues, including but not limited to booking discrepancies, ticketing concerns, payment issues, and in-travel support. 
  • Liaise effectively with internal departments (e.g., Sales, Operations, Finance) and external partners (e.g., Amtrak, hotel suppliers, transfer companies) to resolve complex issues and facilitate smooth customer journeys. 
  • Process payments, issue refunds, and manage billing inquiries with attention to detail and accuracy. 
  • Proactively communicate with guests about potential itinerary changes or disruptions, offering suitable alternatives and solutions. 
  • Document all customer interactions accurately and thoroughly in the CRM system. 
  • Identify opportunities to enhance the guest experience and provide feedback to management for continuous improvement. 
  • Maintain a high level of product knowledge regarding Railbookers and Amtrak Vacations packages, train routes, destinations, and amenities. 
  • Handle customer complaints and challenging situations with empathy, professionalism, and a calm demeanor, aiming for first-contact resolution whenever possible. 
  • Collaborate with team members and contribute to a positive and supportive contact center environment. 
  • Adhere to all company policies, procedures, and service level agreements. 
  • Perform other duties as assigned to support the Guest Experience team and overall business objectives. 
  • Demonstrate strong organizational skills to manage daily tasks efficiently and consistently. 
  • Remain adaptable and open to change in a fast-paced, growing organization, with a mindset that embraces new challenges and opportunities. 

  

CORE COMPETENCIES 

  • Customer Focus: Acts with the customer in mind, building trust and using feedback to improve service and experience. 
  • Functional/Technical Skills: Applies strong technical knowledge and expertise to consistently perform at a high level. 
  • Interpersonal Savvy: Builds effective, respectful relationships across all levels using empathy, tact, and diplomacy. 
  • Drive for Results: Delivers strong outcomes by consistently exceeding goals and pushing for high performance. 
  • Written Communications: Communicates clearly and effectively through written messages tailored to the audience and purpose. 

Qualifications

  • Minimum of 2 years of experience in a high-volume customer service contact center environment, preferably within the travel, hospitality, or transportation industries. 
  • Exceptional verbal and written communication skills with a clear, concise, and professional telephone manner. 
  • Strong active listening skills and the ability to empathize with customer needs. 
  • Proven problem-solving abilities and a resourceful mindset to find effective solutions. 
  • Excellent organizational skills and attention to detail, especially when managing multiple tasks and complex itineraries. 
  • Proficiency with CRM software and Microsoft Office Suite (Outlook, Word, Excel). 
  • Ability to work independently as well as collaboratively in a team-oriented, remote environment. 
  • Comfortable working in a fast-paced and dynamic environment, adapting to changing priorities. 
  • A genuine passion for travel and a desire to create unforgettable experiences for guests. 
  • Flexibility to work varied shifts, which may include evenings, weekends, and holidays, as required by business needs. 
  • High school diploma or equivalent required; Bachelor’s degree or relevant certifications in Hospitality or Travel are a plus. 

 

What we Offer:  

  • Work from Home  
  • Generous PTO Package  
  • Bonus and Incentive Plans  
  • Medical, Dental, and Vision Insurance Including Optional HSA, Gym Membership Contributions and Healthy Actions incentive (sponsored by Cigna)  
  • Employee Assistance Program  
  • Short-term/Long Term disability Plan  
  • Employer sponsored Life Insurance  
  • Employer-Matched 401(k)  
  • Familiarization Trips (Get paid to experience our vacations!)  
  • Employee and Family/Friend Travel Discounts  
  • Corporate Discounts through Working Advantage  
  • Employee Referral Bonus  
  • Cross-Departmental and Advanced Training Opportunities  
  • Anniversary, Birthday, and Recognition Perks  
  • Years of Service Awards  
  • Annual Reimbursements for Home Office (office expenses, phone, internet)  
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