Senior Director, Network Reliability

Five9 is rebuilding leadership for its network function and needs a senior technical leader to take ownership of the entire environment. 

The right candidate will have led production networks at scale, built teams that engineer and operate those systems, and helped organizations evolve from click-ops into true engineering-driven operating models. If you have not done that work yourself, this is not the right role. 

Modernization is already underway, but the current team is short-handed and lacks several key skills. The person stepping into this role should expect that situation, stabilize the urgent work quickly, and begin rebuilding both the team and the operating model against clear and measurable timelines. 

This is a player-coach role. You should stay close enough to the work to keep your judgment sharp and the team accountable and be willing to set the standard by example when needed. At the same time, you must step out of the critical path quickly enough that the team is not dependent on one person to make decisions or push changes forward. Carrying part of the senior technical load at the outset is expected, still operating that way six months in is not. 

What success looks like in your first 120 days 

• A working map of the network estate across our DCs and our cloud footprint, plus a clear-eyed read on the team you inherited
• A personnel evaluation and a tech roadmap that show how we move from manual ops to network as code, automation, and drift control, sequenced against budget and the work that’s already running
• The first wave of new engineers landed, with retained engineers in active upskilling
• Modernization visible in production, on-call and incident load redistributed across the team, you start stepping out of the critical path 

What you bring to Five9

• A track record of rebuilding teams, raising engineering standards, and moving organizations from reactive operations to engineering-led execution 
• Experience stabilizing under-resourced organizations during periods of organizational and technical change  
• Strong executive communication skills backed by operational data, clear risk articulation, and measurable outcomes  
• Proven ability to build trust, accountability, and a high-performance engineering culture across globally distributed teams  
  
• Strong cross-functional leadership skills with experience partnering across infrastructure, software engineering, security, SRE, and executive leadership organizations  
• Ability to mentor and develop senior technical leaders, driving accountability while creating clear ownership, operational discipline, and career growth pathways for engineering teams 
• Strong decision-making and prioritization skills in high-pressure production environments with competing operational demands  
  
• Demonstrated ability to lead through ambiguity, drive organizational alignment, and execute large-scale operational and technical transformations
• Effective conflict resolution and stakeholder management skills with the ability to influence technical and business decisions at all levels of the organization
• Strong operational judgment in network security and ability to build clear partnership boundaries with Security teams 

What We Require

• 10+ years leading global teams in multi-DC, mission-critical production environments
• 10+ years experience with modern DC networking, including OSPF, EVPN, VXLAN, Cisco Nexus, and NX-OS
• Experience in a hybrid cloud environment with special focus on GCP workloads
• Proven success building network automation and IaC using tools such as Ansible, Terraform, Python, Git, and CI/CD
• Experience modernizing legacy network environments by introducing config management, drift detection, network observability, and policy-based ops where they didn’t exist before
• In depth knowledge of network observability using tools such as Thousand Eyes, Grafana, Loki, Netflow and Netscout to obtain “full pane of glass” for network health
• Experience supporting Kubernetes workloads, AI and GPU workloads
• Bachelor's degree in computer science, engineering or related field