IT Operations Administrator

Posted 6 Hours Ago
Hiring Remotely in USA
Remote
Senior level
Artificial Intelligence • Professional Services • Conversational AI
The Role
Senior IT Operations Administrator responsible for end-to-end administration of multiple SaaS and B2B platforms, triaging support tickets to SLA, auditing and maintaining property/listing systems, developing SOPs, onboarding users, managing vendor relationships, and overseeing basic SMB cybersecurity and system reliability in a high-autonomy remote role.
Summary Generated by Built In

This is a remote position.

We are hiring immediately — this is an urgent opening and we are ready to move fast for the right candidate.


About the Role


We are a growing U.S.-based property management company seeking an experienced IT Operations and Business Systems Administrator to join our remote team. This is a full-time, senior-level position that owns the day-to-day administration of a broad suite of third-party SaaS and B2B software platforms that power our daily operations.

This is not a helpdesk or entry-level IT role. We need someone who is genuinely comfortable owning a wide range of operational systems independently, building and following SOPs, and solving problems across multiple platforms without being walked through every step. You will report directly to our executive leadership team and be trusted to keep our technology ecosystem running smoothly, securely, and at scale.

If you have a strong IT operations or systems administration background and you thrive in a high-autonomy remote environment — we want to hear from you right away.


Schedule & Work Arrangement


Full-time — 40 hours per week

Remote — work from home

Hours: U.S. business hours (availability and responsiveness during core U.S. time zones required)

Start: As soon as possible — this role is open now and we are actively interviewing



What You Will Do


Daily

Monitor and triage shared company inboxes, routing messages per established procedures

Complete internal IT support tickets within a 24-hour SLA, including:

Sending e-signature documents to clients and team members

Monitoring and resolving booking platform support cases

Deactivating listings and cancelling associated reservations

Creating user accounts for new clients and team members

Recording and approving PTO and overtime submissions

General troubleshooting across company software systems


Administer DocuSign end-to-end: distribute completed documents and maintain records in Airtable

Provide general oversight, maintenance, and monitoring of company software systems

Three Times Per Week (Monday / Wednesday / Friday)


Review accounting reporting to identify delinquent accounts; take appropriate action on associated listings and coordinate with account managers

Coordinate the new listing review process: confirm readiness, audit setup across platforms for compliance with company standards, and resolve issues before go-live


Weekly

Review and resolve listing issues flagged by team members across booking and internal platforms

Audit listings pending deactivation for outstanding reservations

Resolve system notifications regarding listing issues

Download performance data, update internal pricing database, and upload pricing adjustments across pricing platforms


Bi-Weekly

Audit key platforms for setup accuracy, organization, and common configuration issues

Review future calendar availability to confirm booking windows are operating correctly


Quarterly

Audit listing booking-window settings and confirm configuration with account managers


As Needed

Develop new SOPs and systems to support company growth

Own vendor relationships and manage software vendor accounts

Onboard new employees: provision accounts and provide basic training on company systems

Maintain oversight of team member hardware

Oversee cybersecurity practices: manage spam and phishing reporting, educate team members on best practices, and advise leadership on appropriate SMB cybersecurity standards



Systems You Will Work In

You do not need to know every system on day one — but you need to be the type of person who picks up new platforms quickly and independently. Prior experience with any of the following is a strong advantage:

Booking & Distribution: Airbnb, Vrbo, Homes & Villas by Marriott Bonvoy

Property Operations: Hostaway (core property management system), Operto, PriceLabs, Buildium, Safely Portal

Database & Automation: Airtable (hands-on experience required), Make (Make.com)

Finance & Accounting: QuickBooks, Stripe

Communication & Productivity: Google Workspace (GSuite), DocuSign, Glue, Fathom

Sales & Marketing: Google Ads, Meta Ads Manager, Vintory, Instantly

Website: WordPress, SiteGround

HR & Workforce: Workyard


A Note on Communication and Multitasking

These are non-negotiable for this role. This position requires constant coordination across approximately 15 team members who are each handling different tasks at any given point in time. You will be the connective tissue between those moving parts. Candidates who struggle with juggling multiple priorities simultaneously, or who are not confident and clear communicators across all channels, will not be successful here. If you are excellent at both, you will thrive.



Requirements

Required Qualifications


5 or more years of experience in an IT operations, systems administration, or software/database administration role

Hands-on experience with Airtable or similar database-driven platforms — this is required, not preferred. Comfort with linked records, views, and structured data is essential

Demonstrated ability to independently learn, configure, and administer a wide range of SaaS platforms without formal vendor training

Strong troubleshooting skills with the ability to manage a high volume of support requests and consistently meet SLA deadlines

Excellent written English communication skills — you will regularly coordinate across account managers, regional managers, and executive leadership

Comfortable working independently in a high-autonomy remote role with minimal day-to-day supervision

Basic cybersecurity awareness including phishing and spam identification and SMB best practices

Available and responsive during core U.S. business hours

Preferred Qualifications


Experience in the short-term rental, hospitality, or property management industry — this is a strong plus

Familiarity with vacation rental software such as property management systems, channel managers, or dynamic pricing tools (Hostaway, PriceLabs, Vrbo/Airbnb professional tools, Operto)

Experience with no-code/low-code automation platforms such as Make.com





Technical Requirements:

*Internet speed: Minimum 50 Mbps upload and download (wired connection strongly preferred).

*A verified backup internet connection is required — mobile phone hotspots are not acceptable as backup.

*Dedicated wireless dongles or secondary ISP connections are acceptable backup solutions.

*Backup power source required (UPS or generator) to maintain connectivity during outages.

*Quiet, professional workspace suitable for voice work — free from background noise and interruptions.

*Noise-canceling headset required.

*Reliable computer with sufficient processing power to run software systems and softphone simultaneously.

*You must have Windows 11 or the most recent Apple OS / Update



Benefits

Compensation & Payments


Competitive hourly rate

On-time payments, every time

Payments processed via Wise


Training & Support

Direct client training provided — you are never thrown in blind

Dedicated Account Manager as your point of contact

Stable, long-term placement with a growing U.S.-based company

Exposure to a wide range of modern SaaS platforms

Potential for increased responsibilities as the company scales

Tenure recognition for long-term team members

Clear escalation paths — you always know who to go to


Work Environment

100% remote — work from home

U.S.-based company with structured operations

Stable, long-term account placements (not gig-style work)

Supportive team culture across all accounts

Growth & Experience

Build your U.S. industry experience

Exposure to multiple practice types and platforms

Potential for increased hours or additional accounts based on performance

Strengthen your resume with verified, legitimate U.S. client experience


Recognition

Tenure recognition for long-term team members

We value loyalty and recognize those who grow with us



Skills Required

  • 5+ years experience in IT operations, systems administration, or software/database administration
  • Hands-on experience with Airtable (linked records, views, structured data)
  • Ability to independently learn, configure, and administer a broad range of SaaS platforms
  • Strong troubleshooting skills and ability to meet 24-hour SLA for support tickets
  • Excellent written English communication and cross-team coordination skills
  • Available and responsive during core U.S. business hours
  • Basic cybersecurity awareness (phishing/spam identification and SMB best practices)
  • Experience administering DocuSign and maintaining records in Airtable
  • Reliable high-speed internet (minimum 50 Mbps up/down) and verified backup internet connection (no phone hotspots)
  • Backup power source (UPS or generator) and quiet professional workspace suitable for voice work
  • Noise-canceling headset and reliable computer (Windows 11 or recent macOS)
  • Experience in short-term rental, hospitality, or property management
  • Familiarity with vacation rental software (Hostaway, PriceLabs, Vrbo/Airbnb professional tools, Operto)
  • Experience with no-code/low-code automation platforms such as Make.com
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The Company
75 Employees
Year Founded: 2015

What We Do

HelpSquad is a business process outsourcing (BPO) company providing managed customer service, 24/7 live chat, call-center, and virtual assistant solutions. Its remote teams handle customer-facing and administrative tasks such as emails, phone calls, scheduling, CRM updates, and support requests. The company serves healthcare, legal, financial services, real estate, e-commerce, and other businesses, with U.S.-based management and global delivery across multiple time zones.

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