Live Chat Support Specialist – SaaS Construction Software – Contract‑to‑Hire (2‑4 Openings, Full‑Time, Remote)

About arenaflex

arenaflex is a fast‑growing provider of cloud‑based software solutions that empower construction firms to streamline estimating, invoicing, and project management. Our platform is trusted by hundreds of contractors nationwide to deliver accurate, on‑time financial documents and to keep projects moving forward. As a leader in the SaaS construction space, arenaflex combines cutting‑edge technology with a customer‑first mindset, ensuring that every interaction—whether via chat, ticket, or phone—adds real value to our clients’ businesses.

Why This Role Matters

Our customers rely on arenaflex for mission‑critical tasks that affect their bottom line. When a contractor encounters a hiccup while creating an estimate or generating an invoice, they turn to our support team for immediate, knowledgeable assistance. As a Live Chat Support Specialist, you will be the front line of that assistance, providing real‑time guidance that helps users stay productive and confident in their use of our software.

Role Overview

This contract‑to‑hire position is designed for experienced live‑chat professionals who thrive in a fast‑paced SaaS environment. You will join a collaborative support team that handles inbound chat, ticket, and email inquiries using arenaflex CRM, arenaflex Desk, and arenaflex SalesIQ. Your primary focus will be to resolve technical and functional questions, guide users through complex workflows, and ensure every interaction meets our high standards for speed, accuracy, and customer delight.

Key Responsibilities

• Respond to live chat inquiries from construction professionals, delivering clear, concise, and solution‑oriented assistance within established SLAs.
• Log and manage support tickets in arenaflex Desk, ensuring each case is documented, prioritized, and escalated when necessary.
• Utilize arenaflex CRM to track customer histories, identify recurring issues, and provide personalized follow‑up.
• Collaborate with product, engineering, and QA teams to reproduce bugs, verify fixes, and communicate status updates to customers.
• Maintain and continuously improve the knowledge base, adding new articles, screenshots, and video tutorials that empower users to self‑serve.
• Identify trends in support requests and proactively suggest product enhancements or training resources.
• Participate in daily stand‑ups, weekly retrospectives, and quarterly performance reviews to align with team goals.
• Provide occasional email support for customers who prefer written communication, ensuring consistency across channels.
• Adhere to best‑practice chat etiquette, including proper greetings, tone, and problem‑resolution techniques.
• Achieve individual and team performance metrics, such as chat volume, first‑contact resolution rate, and customer satisfaction scores.

Essential Qualifications

• Minimum 2 years of live‑chat support experience in a SaaS environment, preferably serving subscription‑based customers.
• Proficiency with arenaflex (formerly QuickBooks) for handling financial software queries, including invoicing and estimate creation.
• Hands‑on experience with CRM and ticketing platforms (e.g., arenaflex CRM, arenaflex Desk, arenaflex SalesIQ).
• Demonstrated ability to follow structured chat scripts while adapting to unique customer scenarios.
• Excellent written communication skills, with a focus on clarity, empathy, and professionalism.
• Strong multitasking abilities—capable of handling multiple chats, tickets, and internal communications simultaneously without sacrificing quality.
• Self‑motivated mindset with a track record of setting personal performance goals and exceeding them.
• Critical thinking and problem‑solving skills that enable rapid identification of root causes and creative solutions.
• Reliable high‑speed internet connection, a dedicated workspace, and a willingness to use a second monitor for increased productivity.

Preferred Qualifications & Additional Knowledge

• Familiarity with construction industry terminology and workflows (e.g., project estimating, job costing, subcontractor invoicing).
• Experience editing or creating knowledge‑base articles, tutorials, or FAQ content.
• Exposure to other financial platforms such as arenaflex (formerly Xero) or similar accounting software.
• Basic understanding of computer hardware assembly, troubleshooting, or repair.
• Experience with website management tools like arenaflex (formerly WordPress) for updating support portals.
• Familiarity with collaboration tools such as arenaflex (formerly ClickUp, Asana, Monday), and communication platforms like arenaflex (formerly Slack, Teams).
• Prior exposure to phone support, QA testing, or server/hosting management.

Core Skills & Competencies

• Chat Etiquette: Ability to greet, listen, diagnose, and resolve issues with a friendly, professional tone.
• Goal Orientation: Comfortable setting measurable objectives (e.g., chats per hour, CSAT targets) and tracking progress.
• Detail Orientation: Precision in documenting interactions, updating tickets, and following up on open items.
• Quick Learning: Ability to absorb new product features, updates, and internal processes with minimal guidance.
• Responsibility: Ownership of tasks from start to finish, including escalation when needed.
• Communication: Clear, concise writing and the ability to convey technical concepts to non‑technical users.
• Performance Mindset: Drive to exceed expectations, earn positive customer reviews, and contribute to team success.

Work Environment & Culture at arenaflex

arenaflex embraces a remote‑first culture that values flexibility, autonomy, and continuous learning. Our support team operates across multiple time zones, but core hours are anchored at 7 AM EST to ensure coverage for our North American client base. We provide:

• A collaborative Slack‑style channel for real‑time peer support and knowledge sharing.
• Weekly virtual coffee chats and quarterly team‑building events to foster camaraderie.
• Access to a learning budget for certifications, webinars, or courses related to SaaS support, customer experience, or construction technology.
• Regular feedback loops, one‑on‑one coaching sessions, and clear career pathways.

Compensation, Perks & Benefits

arenaflex offers a competitive hourly rate that reflects your experience and the high‑impact nature of the role. In addition to base pay, you will be eligible for:

• Performance bonuses ranging from $100–$400 per month, tied to chat volume and 5‑star customer reviews.
• Comprehensive health, dental, and vision coverage (for full‑time employees after the probationary period).
• Retirement savings plan with company matching contributions.
• Generous paid time off, sick days, and holidays.
• Equipment stipend for a second monitor, ergonomic accessories, or a high‑quality headset.
• Remote‑work allowance to cover internet, coworking space fees, or home office upgrades.

Career Growth & Development

Starting as a Live Chat Support Specialist, you will have clear pathways to advance into senior support, team lead, or even product‑focused roles such as Customer Success Manager or Implementation Specialist. arenaflex encourages internal mobility, and we regularly promote high‑performing team members into leadership positions.

Application Process

To be considered, please submit a resume that highlights your live‑chat experience, SaaS background, and any construction‑industry exposure. In your cover letter, address the following:

• Confirm you have read the full job posting by including the phrase “I reviewed the bid details” at the top of your response.
• Provide a brief overview of the SaaS companies you have supported, focusing on subscription‑based customer interactions.
• Detail how your unique skills—beyond job titles—will add value to arenaflex’s support team.
• Indicate your preferred weekly hours (40 – 60) and your availability within the 7 AM – 7 PM EST window.
• State whether you have a second monitor and a secure private Wi‑Fi connection.

Join arenaflex Today

If you are passionate about delivering exceptional customer experiences, love solving technical puzzles, and thrive in a dynamic SaaS environment, we want to hear from you. Become part of a forward‑thinking company that values your expertise, rewards your performance, and invests in your professional growth.

Apply Job!