Senior Customer Support Executive – Americas | Remote SaaS & CRM Specialist (Help Scout, API & VoIP Troubleshooting)

About arenaflex

arenaflex is a bootstrapped, profitable, 100% remote company built by a thoughtful team of approximately one hundred individuals who deeply value autonomy, craftsmanship, and measurable impact. We have spent more than a decade engineering a customer relationship management (CRM) platform designed to help small and scaling businesses communicate with their customers more effectively — without the friction of manual data entry, cluttered interfaces, or steep learning curves. Our mission is ambitious yet focused: double the productivity of every sales professional who uses our software.

At arenaflex, we believe that exceptional customer support is not a cost center — it is a strategic advantage. Every conversation our support team has with a customer is an opportunity to deepen trust, unlock product value, and turn users into long-term advocates. We are now seeking a Senior Customer Support Executive to join our Americas team and help us continue delivering world-class service experiences to our growing customer base.

The Opportunity

We are hiring a Senior Customer Support Executive – Americas (100% Remote) to serve as a frontline problem-solver, product expert, and trusted advisor for our customers across North and South America. This is a high-trust, high-impact role suited for someone who thrives on independence, enjoys diagnosing complex technical issues, and takes genuine satisfaction in helping small business owners succeed.

As a fully remote member of our distributed support team, you will be responsible for managing a steady flow of customer inquiries, resolving technical problems spanning integrations, APIs, and system configurations, and delivering support experiences that embody the arenaflex philosophy: consultative, educational, and relentlessly customer-focused.

This role requires a high degree of self-direction and immediate ownership. Beyond the support queue, you will lead individual projects and contribute to initiatives that improve our products, processes, and customer outcomes.

Key Responsibilities

• Ticket Management & Resolution: Respond to customer support tickets primarily via email, with occasional live phone calls, during American business hours (Eastern, Central, Mountain, or Pacific Time). Maintain a high standard of quality, empathy, and clarity in every interaction.
• Product Expertise: Develop and maintain deep, hands-on knowledge of arenaflex features, integrations, and capabilities. Serve as a go-to resource for nuanced product questions.
• Technical Debugging: Investigate and resolve issues related to system behavior, third-party integrations, and API requests. Document findings clearly and escalate to senior support or engineering teams when appropriate.
• Escalation Handling: Identify issues that require deeper technical intervention and partner with senior staff, engineering, or product teams to drive timely resolutions.
• Fraud Prevention & Account Review: Conduct systematic, periodic reviews of new user signups to verify authenticity and prevent malicious or fraudulent account creation.
• Billing Support: Review and process billing changes, subscription updates, refunds, credits, and other account-related financial adjustments in coordination with internal stakeholders.
• Bug Identification: Detect, document, and report product bugs with sufficient detail for the engineering team to reproduce and resolve them efficiently.
• Cross-Functional Collaboration: Partner with the Customer Success team to deliver enhanced support for high-value and enterprise-tier customers, ensuring a seamless experience throughout the customer lifecycle.
• Knowledge Base Contributions: Maintain help center documentation, write new articles, and update existing content to reflect new and evolving product features.
• Project Leadership: Lead individual initiatives outside the support queue, such as process improvements, content projects, tooling evaluations, or customer research efforts.

Essential Qualifications

• Location & Time Zone: Physically based in the Eastern, Central, Mountain, or Pacific time zone of the Americas.
• Communication Skills: Highly proficient in written and verbal English, with the ability to explain complex concepts clearly and empathetically.
• Remote Work Experience: Demonstrated experience working successfully with distributed, asynchronous teams across multiple countries and cultures.
• Industry Experience: A minimum of two years of experience in a customer-facing support role at a technology company, ideally within the SaaS or CRM space.
• Product Knowledge: Familiarity with the SaaS and CRM landscape. Hands-on experience using sales platforms, help desk software, or systems commonly integrated with arenaflex is strongly preferred.

Preferred Qualifications & Bonus Skills

• Technical or coding experience, including familiarity with VoIP systems, email delivery infrastructure, network management, or RESTful APIs.
• Experience with any of the following tools: Help Scout, Sift, Stripe, Twilio, Plivo, Guru, or Asana.
• A track record of identifying process improvements and driving them to completion independently.
• Prior experience supporting small business customers or B2B SaaS users.

Skills & Competencies for Success

• Empathy & Customer Empathy: A genuine desire to understand customer pain points and advocate for their success.
• Analytical Problem-Solving: Ability to break down ambiguous problems, form hypotheses, and test solutions methodically.
• Time Management: Strong organizational skills and the ability to prioritize effectively in a fast-paced, autonomous environment.
• Written Communication: Exceptional written communication skills — our support is primarily async, so clarity in writing is paramount.
• Adaptability: Comfort with change, ambiguity, and the evolving nature of a growing SaaS company.
• Initiative: A self-starter mindset with the ability to identify opportunities and act without waiting for direction.
• Collaboration: Strong interpersonal skills and a willingness to learn from and contribute to teammates across the globe.

Career Growth & Learning Opportunities

At arenaflex, career development is not an afterthought — it is a deliberate practice. As a Senior Customer Support Executive, you will gain deep exposure to the inner workings of a profitable SaaS business, with opportunities to grow into senior support, customer success, technical writing, product, or operational leadership roles. You will receive mentorship from experienced leaders (you will report to our Manager of Customer Support), regular feedback, and the chance to lead cross-functional projects that shape the future of our support organization and product.

We invest in our people through sabbaticals, generous time off, and a culture that respects deep, focused work. Many of our team members have grown into leadership, product, and engineering roles over the years, and we actively support internal mobility.

Work Environment & Company Culture

arenaflex has been 100% remote since 2016, making us a pioneer in intentional, asynchronous workplace design. Our team spans more than 22 countries, and we are proud of the rich diversity of backgrounds, lifestyles, and cultures that shape our community. Every year, we gather in person somewhere in the world for our annual team retreat — an opportunity to strengthen the relationships that make remote collaboration feel close.

Our culture is built on a mature, adult-to-adult approach to work. We do not track hours. We trust our team members to manage their time effectively, communicate thoughtfully, and deliver high-quality work. Most teams have only two to five hours of internal meetings per week, and the rest of the time is reserved for deep, focused work.

Our core values guide everything we do:

• Build a house you want to live in — We think and act for the long term.
• No BS — We practice transparency and honesty, especially when it is hard.
• Invest in each other — We build successful relationships with our coworkers and customers.
• Discipline equals freedom — We keep our word to ourselves and others.
• Strive for greatness — We constantly challenge ourselves and others to do our best work.

Unanimously, our favorite value is “Build a house you want to live in.” We make decisions rooted in helping our customers become more successful, and we care equally about the health of our business and the wellbeing of our people.

Compensation, Perks & Benefits

• 100% Remote Work: Work from anywhere within the Americas, with flexible hours that respect your time zone and lifestyle.
• Generous Time Off: 5 weeks of paid time off plus a winter holiday break, with 2 additional PTO days for every year you are with the company.
• Sabbatical Program: 1 month of paid sabbatical leave every 5 years to recharge and pursue personal goals.
• Paid Parental Leave: Comprehensive paid leave for new parents.
• Health Benefits (US Residents): Medical, dental, and vision insurance with a Health Savings Account (HSA) option.
• Retirement Planning (US Residents): 401(k) matching at 6%.
• Dependent Care FSA (US Residents): Pre-tax savings for eligible dependent care expenses.
• Annual Team Retreats: In-person gatherings with the entire global team each year.
• Autonomy & Trust: A workplace that respects your time, your craft, and your ability to deliver impact.

How We Hire

Our application process is designed to promote equitable, unbiased hiring practices. We ask a small series of thoughtful questions that mirror what would typically be asked in a first interview. This helps us learn about you from the start, so please answer each question with care. Regardless of fit, every applicant will hear back from us with a decision.

While we are excited by the possibilities that generative AI unlocks, we kindly ask that you refrain from relying on AI tools when completing your application. We ask these questions because we want to get to know you, your experience, and your communication style. All responses are reviewed closely by multiple members of our team.

Join arenaflex

If you are a customer-obsessed problem-solver who thrives in a remote, autonomous environment and is excited about helping small businesses unlock the power of better communication, we would love to hear from you. This is more than a support role — it is an opportunity to join a profitable, bootstrapped, and intentional company where your work directly shapes customer success and product evolution.

Apply today and help us build the support experience our customers deserve.