Project Management Lead

Zip
Toronto, Canada
On-site

Who this role is best for

Aimed at senior project management professionals who thrive in high-growth B2B SaaS environments and have experience scaling PMO functions from the ground up.

Best fit for

  • Seasoned project managers with a track record of building PMO functions in fast-growing tech companies.
    — “Demonstrated success in building, launching, or significantly up-leveling a PMO function within a fast-growing B2B SaaS environment.
  • Leaders who balance strategic vision with hands-on execution in complex enterprise implementations.
    — “Hands-On Project Execution: Directly own and drive the end-to-end delivery of high-priority, complex enterprise implementations.

Things to consider

  • This role requires direct people management experience and mentoring a team of project managers.
    — “3+ years of direct people management experience, with a proven track record of growing and mentoring technical implementation teams.
  • The position involves managing executive escalations and ensuring high client satisfaction.
    — “Executive Escalations: [REDACTED] the primary escalation management point for enterprise client implementations.

How to stand out

  • Highlight specific instances where you established or matured a PMO in a similar environment.
    — “Build and Mature the PMO: Architect and implement Zip’s project management standards, methodology templates, and tooling.
  • Showcase your ability to influence decision-making and push back constructively at the executive level.
    — “Outstanding communication, negotiation, and relationship skills; expert ability to influence decision-making and push back constructively at the executive level.
  • Demonstrate your experience with enterprise financial systems or procurement workflows in your resume.
    — “Deep familiarity with enterprise financial systems, procurement workflows, or large-scale ERP implementation methodologies.
Pace · SteadyCollaboration · HighAutonomy · MediumDecision Impact · TeamLevel · Lead

Derived from job-description analysis by Serendipath's career intelligence engine.

What success looks like

  • builds and matures the PMO
  • leads and mentors a team of project managers
  • drives high-priority enterprise implementations
Typical background
8+ years of experience in enterprise software implementation3+ years of direct people management experience

Skills & requirements

Required

Project ManagementPeople ManagementEnterprise Software ImplementationDelivery FrameworksCross-functional Collaboration

Preferred

Enterprise Financial SystemsProcurement WorkflowsERP Implementation Methodologies

Stack & domain

Project ManagementEnterprise Software ImplementationTechnology ConsultingComplex Project ManagementCommunicationNegotiationRelationship BuildingEnterprise ProcurementAI

About the role

Original posting from Zip via Ashby

ABOUT ZIP

Zip is the AI platform for enterprise procurement — built for humans and agents working together. By orchestrating procurement across teams, tools, and suppliers with the help of AI agents, companies can secure the resources they need to innovate faster than ever before.

The world’s most influential enterprises trust Zip, including T-Mobile, OpenAI, AMD, Mars, Dollar Tree, and more. Together they’ve saved over $8 billion and processed over $500 billion in spend. Zip’s team includes product leaders from Apple, Airbnb, and Meta, as well as former procurement leaders from United Health, Sanofi, MGM Resorts, Discover, and NASA.

Backed by Adams Street, Alkeon, BOND, CRV, DST, Tiger Global, and Y Combinator, Zip has raised $371 million, most recently at a $2.2 billion valuation and has been recognized by Forbes Fintech 50, Fast Company's Most Innovative Companies, Inc. Best in Business, and LinkedIn Top Startups.

YOUR ROLE

We are seeking a visionary and operationally strong Project Management Lead to establish, scale, and mature our Project Management Office (PMO) from the ground up. In this role, you will be responsible for defining the governance models, standard methodologies, and delivery frameworks that power Zip's enterprise deployments. Beyond establishing the infrastructure, you will lead, mentor, and coach a growing team of high-performing project managers. You will collaborate cross-functionally with Product, Engineering, and Customer Success leadership to optimize our delivery lifecycle and accelerate time-to-value for strategic global clients.

YOU WILL

  • Build and Mature the PMO: Architect and implement Zip’s project management standards, methodology templates, and tooling to create a scalable delivery practice.
  • People Management & Leadership: Directly manage, mentor, and hire a team of project managers, establishing clear performance expectations and supporting career pathing.
  • Hands-On Project Execution: Directly own and drive the end-to-end delivery of high-priority, complex enterprise implementations, balancing team leadership with active, on-the-ground execution.
  • Portfolio Governance: Oversee the global portfolio of active enterprise onboardings, proactively monitoring resource constraints, capacity planning, and target delivery timelines.
  • Metrics & Continuous Improvement: Define and track operational metrics (e.g., project velocity, milestones hit, time-to-value) to continuously optimize post-sales execution.
  • Cross-Functional Collaboration: Partner closely with Product and Engineering leadership to communicate enterprise deployment needs, streamline feedback loops, and shape product readiness.
  • Executive Escalations: Act as the primary escalation management point for enterprise client implementations, resolving complex delivery blockers and ensuring high client satisfaction.

QUALIFICATIONS

  • 8+ years of experience in enterprise software implementation, technology consulting, or complex project management.
  • 3+ years of direct people management experience, with a proven track record of growing and mentoring technical implementation teams.
  • Demonstrated success in building, launching, or significantly up-leveling a PMO function within a fast-growing B2B SaaS environment.
  • Deep familiarity with enterprise financial systems, procurement workflows, or large-scale ERP implementation methodologies.
  • Outstanding communication, negotiation, and relationship skills; expert ability to influence decision-making and push back constructively at the executive level.
  • Thrives in high-growth startup conditions, possesses excellent analytical problem-solving skills, and demonstrates a strong bias for action.

PERKS & BENEFITS

At Zip, we’re committed to providing our employees with everything they need to do their best work.

  • 📈 Start-up equity
  • 🦷 Health, vision & dental coverage
  • 🍽️ Catered lunches & dinners
  • 🚍 Commuter benefit
  • 🚠 Team building events & happy hours
  • 🌴 Flexible PTO
  • 💻 Apple equipment plus home office stipend

Source: Zip careers (Ashby)

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