[Hiring] Project Manager @Leena AI

Role Description

As a Project Manager, you will be entrusted with leading the end-to-end client engagement, from the initial planning stages to the successful completion of a project. This pivotal role demands exceptional leadership and communication skills to facilitate collaboration among all members of the Implementation team. You will be accountable for the timely delivery of all contracted scope and will be expected to consistently exceed client expectations to ensure complete satisfaction and success.

We are seeking a proactive, results-driven professional to orchestrate complex AI and digital transformation initiatives for our enterprise clients. This is an exciting opportunity to drive strategic outcomes at the intersection of B2B SaaS, AI, and enterprise-level client success.

Key Responsibilities

• Strategic Project Leadership & Execution: Lead and manage the comprehensive client engagement lifecycle, from initial planning and project kick-off to full execution and successful go-live. This includes developing robust, strategic project plans and proactively allocating resources to ensure efficient delivery and adherence to scope, schedule, and budget.
• Concurrent Portfolio Delivery: Manage a portfolio of simultaneous client onboardings and implementations at varying stages, sizes, and complexity levels. Prioritize competing demands across engagements, coordinate shared delivery resources, and sustain quality and momentum on every account rather than trading one engagement's health for another's.
• High-Stakes Client & Stakeholder Management: Serve as the primary point of contact for client teams, managing expectations and cultivating strong, lasting relationships with both enterprise and mid-level clients. Ensure clear and consistent communication with all internal and external stakeholders, presenting project updates and key metrics to senior leadership on both the client and Leena AI teams.
• Technical Implementation Oversight: Oversee the execution of complex AI and digital projects, including critical system integrations. Work closely with our Product and Technical teams to drive project engagements forward and swiftly resolve any technical challenges.
• Hands-On Product Fluency: Serve as a credible technical voice in client conversations. Independently demo core product capabilities and triage integration issues in the product's admin and backend layers — without requiring an engineer or solutions engineer to be pulled in.
• Risk Mitigation & Delivery Governance: Proactively manage and ensure the timely delivery of all contracted scope. Identify, assess, and mitigate project risks to maintain project timelines and objectives, ensuring project integrity and successful outcomes.
• Process Improvement: Champion best practices in project management and implementation methodologies to optimize delivery efficiency and client experience.

Qualifications

• Education: BS or BA Degree from an accredited University.
• Professional Experience:
  • 7+ years in a client-facing project management capacity in a B2B SaaS company.
  • Proven track record leading enterprise and mid-market client engagements — including AI and digital projects with heavy system integration — while managing concurrent onboardings and implementations at different lifecycle stages without loss of delivery quality or client confidence.
  • Demonstrated experience in presenting to and communicating effectively with senior internal and client stakeholders (C-suite, VPs, Directors).
• Technical Fluency:
  • Demonstrated experience delivering B2B SaaS implementations with real system integrations (HRIS, ITSM, identity providers, ticketing, or similar).
  • Comfort working in a product's configuration and backend layers — the "plumbing." You can navigate admin settings, workflow logic, integration setup, and logs to diagnose an issue before escalating it.
  • Working understanding of APIs and how enterprise systems talk to each other: REST endpoints, JSON payloads, webhooks, and authentication (SSO, SAML, OAuth). No coding required — but you should be able to read a payload, follow an auth handshake, and explain what broke and why.
  • Ability to demo high level product features end-to-end to a client audience independently.
• Communication & Leadership:
  • Exceptional verbal and written communication skills are essential for this role, with a proven ability to lead and motivate cross-functional teams.
  • Ability to negotiate and persuade without formal authority — you can hold a scope line with a client, push back on an unreasonable timeline, and bring stakeholders along on a technical recommendation they didn't originally want.

Preferred Qualifications

• Prior experience with AI/ML products or technologies is a significant advantage.
• Familiarity with modern project management tools (e.g., Jira, Rocketlane).
• Product obsession — a habit of going deep into the product to find the answer yourself rather than waiting for someone to explain it.

Benefits

• Work at the forefront of enterprise AI and automation with a company that is defining the trends in this space - not following.
• Influence how the world’s biggest companies transform their employee experience.
• Partner with a global team of innovators building industry-defining technology.
• Be part of a dynamic, innovative, and high-growth company.
• Competitive compensation, meaningful equity, and opportunities for rapid career growth.