[Hiring] Senior Customer Delivery Manager @HerculesAI

Role Description

We’re looking for a rare blend of operator and strategist—someone who can own the full Customer lifecycle from first deployment to long-term success, and who is energized by the challenge of doing it better every time. This is not a siloed role. You will serve as the single point of accountability across project delivery, technical deployment, customer success, and frontline support for your portfolio of enterprise accounts.

This role was intentionally designed to consolidate what have traditionally been four separate functions—Project Management, Implementation/Deployment Engineering, Customer Success, and Technical Support—into one senior individual contributor who can move fluidly across all of them.

You’ll plan the project, configure the deployment, train the users, monitor adoption, and troubleshoot issues—all while continuously identifying ways to automate and improve the process through AI tooling and operational excellence.

What you'll do

• Project Governance & Delivery
  • Own the end-to-end onboarding journey for enterprise Customers, ensuring AI deployments are delivered on time, within scope, and aligned with Customer requirements.
  • Build and maintain project plans, timelines, baselines, and risk registers.
  • Lead weekly cadence meetings with executive stakeholders and provide dashboard summaries on project and portfolio progress.
  • Manage internal and external resource coordination, meeting scheduling, agendas, and detailed post-meeting minutes across all active engagements.
  • Maintain the Hercules Enterprise Playbook, including review of implementation guides, user manuals, and internal process documentation.
• Customer Deployment and Configuration
  • Lead AI Assisted Customer Post Sales Discovery sessions to uncover gaps with current onboarding plans.
  • Act as the technical liaison between our engineering teams and DevOps Team for our SAAS based solution and the Customer’s IT organization.
  • Work with Customer to understand their desire for specific configuration options and provide insight to Product on any changes that may be required.
  • Coordinate deployment timelines between the Customer’s team and internal DevOps/engineering resources.
  • Own the UAT and acceptance testing process with the Customer, ensuring validation criteria are met before go-live.
• Customer Success & Adoption
  • Serve as the trusted advisor for your accounts post-deployment—monitoring adoption metrics, conducting health checks, and building joint success plans with Customers.
  • Proactively identify adoption gaps through usage data analysis and develop targeted intervention strategies.
  • Create and deliver Quarterly Business Review packages, including usage analytics, technical improvement roadmaps, and strategic recommendations.
  • Act as the primary liaison between the Customer and our Product team, translating user feedback into actionable insights.
  • Facilitate virtual and on-site training sessions tailored to diverse user groups.
• AI Assisted Customer Support & Issue Resolution
  • Directly manage the support queue for accounts in your portfolio during onboarding and beyond.
  • Leverage internal Hercules AI Agents to perform initial ticket triage.
  • Track issues through to resolution within agreed SLAs.
• Process Improvement & AI-Driven Automation
  • Continuously identify opportunities to streamline and automate administrative tasks.
  • Design and implement process improvements for onboarding playbooks, support triage, and internal documentation.
  • Champion the use of AI to augment your own work.
  • Develop and maintain standard operating procedures and best practices documentation.
  • Contribute to a culture of operational excellence by measuring your own processes.

Qualifications

• 7–12 years of combined experience spanning at least two of the following: project management, technical implementation/deployment, customer success, or technical support in an enterprise SaaS environment.
• Demonstrated track record managing complex enterprise onboarding engagements.
• Hands-on experience deploying or supporting enterprise software.
• Experience building and executing customer success strategies.

Requirements

• A functional understanding of how LLM-based software operates.
• Advanced proficiency in project management and collaboration tools (e.g., Smartsheet, Jira, MS Project, MS Teams, Slack).
• Comfort navigating enterprise IT environments.
• Firm understanding of cloud-based SaaS architecture and delivery models.
• Ability to independently produce high-quality training materials and client-facing presentations.
• Experience building automation using AI/LLM tools for operational workflows.

Benefits

• This is a fully remote position, however periodic travel to Customer sites and company offices will be required.
• Salary Range: $140,000 - $180,000.
• The company does not currently match RRSP contributions.