Senior IT Telephony Engineer Outbound Specialist Five9 Platform

Franklin, Tennessee
Wesley Group
Job DescriptionJob Description

Senior IT Telephony Engineer – Outbound Specialist Five9 Platform

Wesley LLC Franklin, TN Full-Time, Exempt

About Wesley LLC

Wesley LLC is a high-growth company headquartered in Franklin, Tennessee. We operate a specialized sales organization with 90 setters, 30 closers, and over 200 corporate users executing over 1.1 million outbound calls annually. Our team moves fast, sets high standards, and invests in the tools and talent needed to win.

We are building out our telephony infrastructure for the long term and are looking for the right person to own it.

The Opportunity

We are looking for a high-impact Lead Telephony Engineer to own the buildout and long-term operation of our Five9 platform. This is a greenfield implementation. Wesley is migrating from Dialpad and needs someone who can start up Five9 from the ground up, replicate and improve our existing functionality, then drive continuous optimization from there.

Reporting directly to the CTO, you will be the technical authority on all things Five9. You will also mentor and level up a small supporting team of 2-3 engineers with varying degrees of telephony depth.

This is an individual contributor role with real technical authority, not a management track. The right person wants to go deep on the platform, not up the org chart.

Key Responsibilities

• Five9 Platform Ownership: Lead the full migration from Dialpad to Five9. Greenfield buildout, feature parity, then optimization. Own all administrative and technical configuration of the platform long-term.
• Migration Execution: Translate existing Dialpad workflows, routing logic, and outbound cadences into Five9. Identify gaps and improvements in the process rather than copying problems forward.
• Infrastructure & Carrier Management: Manage the technical relationship with our dedicated carriers to ensure Tier-1 voice quality, high answer rates, and consistent deliverability.
• System Integration: Build and maintain deep integrations between Five9 and Salesforce, NetSuite, and Zapier to ensure clean data flow, accurate lead attribution, and automated workflows.
• Outbound Cadence Engineering: Design and iterate on complex outbound sequences blending voice, SMS, and digital touchpoints. You are optimizing connect rates and agent efficiency, not just keeping the lights on.
• Compliance & Deliverability: Own STIR/SHAKEN compliance, 10DLC registration for SMS, and ongoing reputation management to protect deliverability at scale.
• Team Mentorship: Work alongside and actively develop a team of 2-3 supporting engineers: one solid mid-level and one to two engineers with adjacent technical backgrounds building their telephony depth.
• Executive Collaboration: Serve as the technical advisor to senior leadership on platform performance, translating Five9 metrics and operational data into clear business decisions.

The Ideal Candidate

• Deep, hands-on Five9 expertise. You have built, administered, and optimized Five9 environments in high-volume outbound contexts. Certifications are not the signal; demonstrated platform mastery is.
• Has executed a platform migration before and knows where the friction hides-routing logic, data mapping, agent workflow disruption.
• Fluent in SIP trunking, WebRTC, and API-driven workflow design.
• Understands dialer modes (Predictive, Progressive, Power) and can make intelligent decisions about when and why to use each.
• Comfortable with the full regulatory landscape, not just aware of it: TCPA, TSR, STIR/SHAKEN, 10DLC.
• Thinks in systems: can hold a deep technical conversation with network engineers and then pivot to a strategy discussion with senior leadership without losing altitude in either direction.
• Enjoys testing assumptions-whether a text-first cadence outperforms a call-first approach is a real question you want to answer with data.
• Collaborative by default. You will be elevating teammates, not gatekeeping expertise.

Technical Environment

Wesley’s stack is Apple hardware, Google Workspace, Slack, and Salesforce as the primary business platform. Five9 will integrate into this ecosystem. Candidates should be adaptable to this environment-deep prior experience in each tool is not required, but comfort operating in it is.

Qualifications

• Experience: 5+ years in high-volume Contact Center (CCaaS) engineering, with meaningful Five9 depth.
• Migration Experience: Demonstrated experience leading or owning a CCaaS platform migration in a production environment.
• Integrations: Proven experience integrating Five9 or comparable platforms with Salesforce and NetSuite. Proficiency with Zapier for automation and integration workflows.
• Outbound Expertise: Deep understanding of dialer modes and the regulatory landscape governing outbound contact operations (TCPA, TSR).

Perks & Benefits

Compensation & Financial

• Competitive salary commensurate with experience
• Weekly pay schedule
• 401(k) with company match

Health & Wellness

• Medical, Dental, and Vision Insurance
• Employer-funded Health Savings Account (HSA)
• Access to on-site fitness center and wellness facilities
• In-office massage chairs

Time Off

• 9 Paid Holidays + 2 Floating Holidays
• Paid Time Off (PTO)
• Outstanding work/life balance

Culture & Growth

• MacBook provided for work
• Leadership training and advancement opportunities
• Continuous coaching from industry professionals
• Robust employee recognition programs
• Company-wide community outreach programs
• Fun, engaging company events and activities
• Spirited team environment with core values of teamwork and integrity

Awards & Recognition

• USA TODAY Top Workplace 2025
• The Tennessean Top Workplaces 2024
• Great Place to Work Certified (2023, 2024)
• INC 500 Fastest Growing Company
• 75+ business awards since 2020

Location

This role is based at Wesley’s headquarters in Franklin, TN. We are ideally looking for someone who can work in the office, but we are open to hybrid or fully remote arrangements for the right candidate.

Remote/Hybrid Eligibility: Wesley is currently set up to hire remote and hybrid employees in the following states only: AL, FL, GA, KS, KY, NC, NV, OH, TN, TX, VA, and WV.

Regardless of location, quarterly travel to Franklin, TN headquarters is required.

How to Apply

If this sounds like you, we’d love to hear from you. Apply with your resume and a brief note on the most complex Five9 environment you’ve built or managed.