Contextere is an Ottawa-based AI company helping industrial and defence organizations transform
operational data into actionable intelligence for technicians, operators, maintainers, and leaders.
We work with global organizations including defence agencies, aerospace leaders, transportation
providers, and industrial enterprises to deploy practical AI solutions that deliver measurable
operational impact. As demand for our platform grows, we are seeking a Project Manager to help
coordinate strategic customer programs, strengthen delivery discipline, and support successful
execution across Contextere’s most important initiatives.
Contextere is seeking a Project Manager to support the planning, coordination,
reporting, and delivery of strategic customer and product initiatives, including
iMAPLE, DrivePilot, and MADISON-related deployments.
The successful candidate will bring project management discipline, strong communication skills,
and the ability to coordinate across business development, product, engineering, finance,
customer success, and executive leadership. This role requires someone who can bring structure
to complex initiatives, support proposal and reporting activities, and help Contextere deliver high-
quality outcomes for customers and partners.
The Opportunity
This is a high-impact coordination and execution role for someone who wants to help scale a
Canadian AI company working at the intersection of industrial innovation, national security, and
frontline workforce transformation.
As Project Manager, you will help Contextere manage strategic programs from planning through
delivery, ensuring projects remain organized, visible, and aligned with customer expectations,
internal priorities, budgets, schedules, and contractual commitments.You will work closely with cross-funtional teams while coordinating with technical, commercial,
and delivery teams. The ideal candidate is organized, proactive, comfortable operating in a fast-
moving environment, and able to translate ambiguity into practical plans, clear communications,
and measurable progress.
KEY RESPONSIBILITIES
- Program and Project Management: Manage project planning, coordination, scheduling, execution
tracking, and reporting for strategic initiatives including iMAPLE, DrivePilot, and MADISON-related
customer programs.
- Cross-Functional Coordination: Coordinate activities across Business Development, Product,
Engineering, Finance, Customer Success, and executive leadership to ensure alignment on priorities,
milestones, risks, and deliverables.
- Project Governance: Establish and maintain project plans, workback schedules, action registers,
risk logs, decision records, status reports, and governance routines that improve visibility and
accountability.
- Customer and Partner Coordination: Support communications with customers, partners, and
stakeholders to ensure project expectations, timelines, responsibilities, and next steps are clearly
understood.
- Project Reporting and Financial Coordination: Support project reporting, budget tracking, invoicing
inputs, milestone documentation, and financial visibility in coordination with Finance and
leadership.
- Proposal and Bid Support: Support RFP responses, proposals, innovation challenges, statements of
work, and strategic bids aligned with Contextere’s defence, industrial, transportation, and public-
sector growth objectives.
- Delivery Support: Help ensure that implementation activities, proof-of-concepts, customer
onboarding, and deployment milestones are coordinated, documented, and completed on schedule.
- Security Administration: Administer and coordinate personnel security clearances, facility security
requirements, customer security documentation, and related compliance records.
- Regulatory and Standards Compliance: Coordinate activities related to the Controlled Goods
Program, ITAR, export controls, SOC 2, ISO 27001, and other applicable governance requirements.
- Audit and Assessment Readiness: Coordinate audits, assessments, and compliance reviews to
ensure Contextere maintains the security and compliance posture required by customers, partners,
and regulatory stakeholders.
- Executive Communications: Prepare concise updates, dashboards, briefing materials, meeting
notes, and decision summaries for internal leadership and external stakeholders.
- Process Improvement: Identify opportunities to improve project delivery discipline, reporting
consistency, internal workflows, customer handoVs, and operational maturity.
What We’re Looking For
REQUIRED
- 5+ years of experience in project management, program coordination, operations, customer delivery,
professional services, or a related role.
- Strong organizational skills with the ability to manage multiple initiatives, deadlines, stakeholders,
and priorities simultaneously.• Excellent written and verbal communication skills, with the ability to prepare clear updates, reports,
meeting notes, and executive-ready materials.
- Experience coordinating cross-functional teams in a fast-moving business, technology, consulting,
defence, industrial, or enterprise software environment.
- Ability to create and maintain project plans, schedules, status reports, risk logs, decision records,
and action registers.
- Strong attention to detail and comfort managing documentation, reporting, follow-ups, and project
administration.
- Ability to work independently, anticipate needs, and bring structure to ambiguous or evolving
priorities.
- Comfortable engaging with customers, partners, executives, technical teams, and internal
stakeholders.
- Proficiency with Microsoft OVice and Microsoft 365 collaboration tools, including Word, PowerPoint,
Excel, Teams, and SharePoint.
- Strong judgment, professionalism, and discretion when handling sensitive customer, partner,
commercial, or security-related information.
PREFERRED
- Experience in defence, aerospace, industrial technology, transportation, manufacturing, critical
infrastructure, enterprise software, or AI-related environments.
- Experience supporting government procurement processes, proposals, RFPs, statements of work, or
funded innovation programs.
- Familiarity with security, compliance, and controlled programs, including Controlled Goods, ITAR,
export controls, SOC 2, ISO 27001, or related frameworks.
- Experience working with project management tools, CRM systems, collaboration platforms, or
reporting dashboards.
- Experience supporting contract milestones, customer reporting, invoicing inputs, or budget tracking.
- Familiarity with agile delivery environments, software implementation projects, proof-of-concepts,
or customer onboarding.
- Security clearance eligibility or an existing security clearance is considered an asset.
Success Measures
Within the first 12 months, the successful candidate will be expected to:
- Establish consistent project management routines across key strategic initiatives.
- Improve visibility into project milestones, risks, decisions, dependencies, and action items.
- Support successful execution and reporting for iMAPLE, DrivePilot, and MADISON-related customer
programs.
- Strengthen project reporting, budget tracking, and coordination with Finance and leadership.
- Improve Contextere’s readiness for customer, partner, security, and compliance reviews.
- Support higher-quality proposals, bids, statements of work, and customer-facing documentation.
- Reduce execution risk by improving coordination between commercial, product, engineering, and
delivery teams.
- Build trust as a reliable internal coordinator and external-facing project representative.
Why Join Contextere?
At Contextere, you will not just help manage projects - you will help put practical AI into the hands
of the people who keep critical operations moving. This is an opportunity to work at the intersection
of industrial innovation, national security, and frontline workforce transformation.
- Shape the future of AI for the technicians, operators, maintainers, and mission teams who power the
physical world.
- Work directly with the CEO and leadership team in a high-trust, high-visibility role where your
organization, judgment, and execution discipline will matter.
- Engage with world-class defence, aerospace, transportation, and industrial organizations solving real
operational problems.
- Help turn complex programs into coordinated plans, measurable progress, and successful customer
outcomes.
- Join a Canadian AI company at a pivotal growth stage, with the opportunity to help define a category
and build lasting enterprise value.
- Make a measurable impact in a role that blends project execution, customer coordination,
operational discipline, and meaningful career growth.
