Agent Strategist

Jobtailor; New York (NY); On-site; USD 110,000 - 160,000; Full time

Job summary

Jobtailor in New York is seeking a seasoned Customer Success professional to own and grow a portfolio of enterprise accounts. You will build trusted relationships with senior stakeholders, deeply understand deployment architectures, and audit health metrics to guide renewal and expansion decisions.

You will collaborate across FDE, CSE, Sales, and Product to prioritize deployments, establish regular syncs, and implement proactive health monitoring.

Qualifications

• 5+ years in customer success, technical account management, or solutions consulting.
• Experience managing a portfolio of enterprise accounts ($100K+ ACV) with complex deployments.
• Strong stakeholder management with VP and C-level executives.
• Technically fluent in APIs, integrations, deployment workflows, and architecture.
• Renewal and expansion motions experience; able to build commercial narratives.
• Highly organized with CRM hygiene and documentation habits.
• Comfortable operating in ambiguity in a high-growth environment.
• Bonus: experience in voice, conversational AI, telephony, contact center technology, or AI/ML products.

Responsibilities

• Take ownership of a portfolio of enterprise accounts and build trusted relationships with key stakeholders.
• Deeply understand each customer’s deployment architecture, use cases, and success criteria.
• Audit current health metrics, renewal timelines, usage patterns, and engagement cadence.
• Align with FDE, CSE, Sales, and Product on open workstreams and deployment priorities.
• Establish a structured cadence of weekly, biweekly, or monthly syncs based on account tiering.
• Implement proactive health monitoring using usage data, stakeholder engagement, and sentiment signals.
• Begin identifying renewal risks and expansion signals across your portfolio.
• Deliver structured QBRs for Tier 1 and Tier 2 accounts with executive-ready reporting.
• Drive renewal conversations beginning 120 days out and partner with AEs on commercial strategy.
• Surface qualified expansion opportunities supported by usage data and deployment success metrics.
• Enforce service tier boundaries and protect the integrity of the engagement model.
• Contribute to refining post-sales playbooks, documentation standards, and tooling as the function scales.

Skills

Stakeholder management

Account management

B2B SaaS

Renewal & expansion

Technical fluency

Executive communication

Tools

CRM software

APIs & integrations

Job description

Overview

• Take ownership of a portfolio of enterprise accounts and build trusted relationships with key stakeholders.
• Deeply understand each customer’s deployment architecture, use cases, and success criteria.
• Audit current health metrics, renewal timelines, usage patterns, and engagement cadence.
• Align with FDE, CSE, Sales, and Product on open workstreams and deployment priorities.
• Establish a structured cadence of weekly, biweekly, or monthly syncs based on account tiering.
• Implement proactive health monitoring using usage data, stakeholder engagement, and sentiment signals.
• Begin identifying renewal risks and expansion signals across your portfolio.
• Deliver structured QBRs for Tier 1 and Tier 2 accounts with executive-ready reporting.
• Drive renewal conversations beginning 120 days out and partner with AEs on commercial strategy.
• Surface qualified expansion opportunities supported by usage data and deployment success metrics.
• Enforce service tier boundaries and protect the integrity of the engagement model.
• Contribute to refining post-sales playbooks, documentation standards, and tooling as the function scales.

Requirements

• 5+ years in customer success, technical account management, or solutions consulting at a B2B SaaS or API-first company.
• Experience managing a portfolio of enterprise accounts ($100K+ ACV) with complex deployments and integrations.
• Strong stakeholder management skills with the ability to engage VP and C-level executives.
• Technically fluent enough to discuss APIs, integrations, deployment workflows, and architecture without needing to write code.
• Experienced in renewal and expansion motions and comfortable building commercial narratives.
• Highly organized with strong CRM hygiene, documentation habits, and follow-through.
• Comfortable operating in ambiguity and helping build process in a high-growth environment.
• Bonus: Experience in voice, conversational AI, telephony, contact center technology, or AI/ML products.