About the role
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, developing an intimate understanding of each customer’s technical capabilities, and constraints.
- 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, ensuring environment readiness and smooth handoffs at each stage of the implementation.
- Own the UAT and acceptance testing process with the Customer, ensuring validation criteria are met before go-live and that any gaps are resolved collaboratively with engineering.
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 to maximize the value Customers derive from the platform.
- 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 and friction points into actionable insights for the AI roadmap.
- Facilitate virtual and on-site training sessions tailored to diverse user groups and their specific workflows.
AI Assisted Customer Support & Issue Resolution
- Directly manage the support queue for accounts in your portfolio during onboarding and beyond, ensuring prompt resolution of technical and functional issues.
- Leverage internal Hercules AI Agents to perform initial ticket triage, ensuring issues are categorized and routed efficiently before hands-on resolution.
- Track issues through to resolution within agreed SLAs, and follow up to ensure systems are fully functional post-fix.
Process Improvement & AI-Driven Automation
- Continuously identify opportunities to streamline and automate administrative tasks across all four functional areas using AI tools, scripting, and workflow automation.
- Design and implement process improvements for onboarding playbooks, support triage, adoption reporting, and internal documentation—reducing manual effort and increasing quality.
- Champion the use of AI to augment your own work: automated meeting summaries, intelligent ticket routing, predictive adoption analytics, self-service training content, and more.
- Develop and maintain standard operating procedures, desk procedures, and best practices documentation for the consolidated role.
- Contribute to a culture of operational excellence by measuring your own processes and iterating toward faster, more reliable Customer outcomes.
Qualifications
Experience & Background
- 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 involving multiple stakeholders, IT security reviews, and corporate change management.
- Hands-on experience deploying or supporting enterprise software
- Experience building and executing customer success strategies including health scoring, adoption analysis, QBR programs, and retention plays.
Technical Aptitude
- A functional understanding of how LLM-based software operates. You don’t need to be a data scientist, but you must be able to explain how our models process data and deliver value to non-technical stakeholders.
- Advanced proficiency in project management and collaboration tools (e.g., Smartsheet, Jira, MS Project, MS Teams, Slack).
- Comfort navigating enterprise IT environments—you understand networking basics, SSO configurations, API integrations, and can hold your own in a technical conversation with a Customer’s IT team.
- Firm understanding of cloud-based SaaS architecture and delivery models, including multi-tenant environments and API-driven integrations.
- Serve as the final quality gate for client-facing technical documentation and help desk materials, providing actionable feedback to product and engineering teams and contributing content enhancements when needed.
- Ability to independently produce high-quality training materials and client-facing presentations tailored to diverse audiences and workflows.
- Experience building automation using AI/LLM tools for operational workflows (e.g., automated reporting, intelligent ticket triage, self-service content generation).
Mindset & Soft Skills
- You are a self-starter who thrives in ambiguity and takes ownership without being asked.
- Exceptional verbal and written communication skills with the ability to manage executive-level expectations and high-pressure situations with composure.
- A genuine drive to improve processes—you see friction and think “how do I automate this?” before “that’s just how it works.”
- Comfortable interfacing directly with complex, multi-divisional, multi-geographical enterprise Customers at the C-suite and director level but equally so with individual job specific contributors
- Willing to travel to Customer sites as required for go-lives, training, or critical escalations (up to 25%).
Nice to Have
- Experience in staffing, insurance, government, financial services
- Familiarity with containerized deployment models (Kubernetes, Docker)
- PMP, CSM, or equivalent certification.
- Experience with Salesforce, Zendesk, Totango, or similar CRM/CS platforms.
- Some past experience operating in a high stakes customer support organization
Location & Logistics
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.