Customer Success Specialist I

Greater Chicago AreaFull-Timemid

Customer SuccessCustomer Success Specialist

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Requirements Summary

You are a technically curious, customer-focused problem solver who enjoys working in enterprise customer support within a telecommunications and platform operations environment.

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You are a technically curious, customer-focused problem solver who enjoys working in enterprise customer support within a telecommunications and platform operations environment. You thrive in a fast-paced setting, can manage multiple priorities at once, and take pride in delivering excellent service while solving technical issues.

As a Customer Success Specialist I, you will serve as the primary technical point of contact for a portfolio of enterprise customers using Vail’s Routing and Call Control (RACC) platform. You will support customers throughout their lifecycle by troubleshooting technical issues, monitoring customer traffic and platform health, maintaining strong customer relationships, and working with internal engineering and product teams to help ensure long-term customer success.

Serve as the primary day-to-day technical contact for assigned customer accounts utilizing the RACC platform
Build and maintain strong customer relationships through proactive outreach, regular communication, and ongoing support
Review monitoring pages and system dashboards throughout the day to identify, investigate, and resolve customer-impacting issues
Troubleshoot call routing, provisioning, and platform issues using SIP call logs, call detail records (CDRs), and internal monitoring/reporting tools
Work closely with software developers, network/operations engineers, project managers, and business analysts to resolve customer issues
Document troubleshooting steps, technical findings, customer environments, and operational procedures in internal knowledge bases such as Confluence/Jira
Support onboarding and provisioning efforts by attending implementation meetings, tracking progress, and assisting with technical readiness activities
Manage inbound customer communications through email, ticketing systems, and phone while meeting internal response expectations
Participate in team meetings to provide customer/project updates, escalate blockers, and align on weekly priorities
Provide after-hours support as needed for emergency customer-impacting incidents
Identify opportunities for process improvements, documentation updates, and operational efficiencies across the team

Bachelor’s degree in Business, Telecommunications, Computer Science, Information Technology, or related field, or equivalent practical experience is required
1+ year of experience in technical support, technical customer success, implementation, IT support, or another customer-facing technical role is required
Strong analytical and troubleshooting skills with the ability to diagnose and resolve technical issues are required
Excellent written and verbal communication skills, including the ability to explain technical concepts to non-technical audiences, are required
Strong organizational and time management skills, with the ability to manage multiple priorities effectively, are required
Able to learn complex technical platforms and internal systems quickly is required
Proficiency with Microsoft Office Suite and general business software tools is required
Experience in telecommunications, VoIP, SIP, call routing, or contact center technologies is preferred
Familiarity with SIP call flows, SIP logs, call detail records (CDRs), or telecom troubleshooting tools is preferred
Experience using Jira, Confluence, or similar documentation/ticketing platforms is preferred
Experience supporting enterprise/B2B customers in a SaaS, telecom, or technical services environment is preferred
Exposure to cloud contact center platforms such as Genesys, Five9, Amazon Connect, Twilio, or similar technologies is preferred

At Vail, we believe in the unique power of voice interactions to create more expressive, more intimate, and more efficient interpersonal interactions. Using Vail technology, we make millions of voice interactions better every day. We process around 10% of all toll-free call traffic in the U.S.; 1 in 10 times, when someone calls a customer support hotline, Vail is routing or interacting with that call.

We are rapidly growing across multiple dimensions, including our customer base, the scope of products we offer, and the size of our team. Now is the right time for a strong candidate to join and grow with us. We have a supportive culture where employees are encouraged to achieve both personal and team goals because we believe growth leads to both business impact and personal fulfillment.

We offer competitive compensation and affordable benefits with flexibility and choice to meet individual and family (including Domestic Partnerships) needs, including:

Multiple medical, dental, and vision plan options
Company-paid life insurance, short and long-term disability
401(k) savings plan with company match (50% on first 6% of employee contribution)
35 days total annual PTO
Annual Bonus Program
Paid maternity and paternity leave
Relocation allowance
Employee referral bonus
Gym membership
Technical and Professional Development stipend

We are striving to implement and sustain an inclusive and equitable work environment for all employees by sourcing underrepresented groups and continually empowering those individuals within our organization to further enrich Vail’s communication solutions. We recognize that equitable and unique individuals benefit our teams’ problem-solving, innovation, and development efforts.

Our offices are located in Deerfield and Chicago, IL. Interviews and onboarding are conducted in our offices when possible. We observe a hybrid work format that provides employees with the flexibility to collaborate with team members based on business needs.