Senior Delivery Project Manager

Conquest Planning is a leading financial planning software company with a purpose-driven approach to delivering financial advice. Established in 2018, Conquest Planning was founded by a team of financial technology veterans whose track record of success spans over 30 years in the financial planning software space. The company’s mission is to ensure that everyone has access to great financial advice, transforming the financial planning landscape and improving outcomes for all clients. Users of Conquest Planning leverage its intuitively designed product, simple onboarding process, and data-driven artificial intelligence to accelerate the delivery of beautifully designed, hyper-personalized financial plans. We are based out of Winnipeg, Manitoba and have team members located across Canada, the United States, and United Kingdom. We are seeking a Senior Delivery Project Manager to join our dynamic team! The Senior Delivery Project Manager is accountable and owns project delivery at Conquest Planning. Being an accountable ownership role, the Project Manager takes a project from the moment scope is handed off through to production, closure, and retrospective — and is answerable for how it runs, how it is governed, how it is reported, and when it deploys for the client. The Senior Delivery Project Manager sets the direction for the project. They define how the project will be governed, convert high-level scope into a client-facing Statement of Work, call for the solutioning resources the work demands, drive milestones and dependencies to closure, and own the truth of status — internally and externally. When a project is at risk, the Senior Delivery Project Manager owns the recovery plan, not just the escalation. This role runs multiple concurrent projects across Conquest’s delivery engagements, applying best practices in project governance and change management. The Senior Delivery Project Manager is a highly organized, detail-oriented leader who is trusted to make decisions, hold internal and external stakeholders to commitments, and deliver Conquest solutions into client environments with a high standard of quality, efficiency, and customer satisfaction. This is a remote / work from home opportunity. Duties of the role include: The Senior Project Manager is the single accountable owner for the following, end to end: End-to-end ownership . The project runs from initiation to production and closure under the Project Manager's ownership. Governance definition . A detailed project charter is authored up front, establishing how projects will be governed. Define within the charter: objectives and success criteria, scope boundaries, governance and decision rights, escalation paths, meeting and reporting cadence, roles and responsibilities, assumptions, constraints, and change control. Secure alignment and sign-off on the charter from internal leadership and the client before execution begins, so that governance is agreed rather than improvised. Maintain the charter as the governing reference for the life of the program, updating it through formal change control as the program evolves. Statement of Work . High-level scope from the Sales Engineer and Solutions Consultant is converted into a Statement of Work and submitted to the external client. Define deliverables, milestones, timelines, dependencies, assumptions, exclusions, acceptance criteria, and client responsibilities with enough precision to hold up through delivery. Partner with Solutions Consultants to validate feasibility ad effort before the SOW is issued. Present the SOW to the client, resolve questions, and drive it to client acceptance. Own change control against the SOW: identify scope change as it emerges, quantify its impact, and manage it formally rather than absorbing it silently. Resourcing advocacy . Solutioning resource needs are identified early and escalated with a clear case for what is required and why. Assess the skills, capacity, and specialist solutioning support each project requires, and surface those needs early. Make the case for solutioning resources with clear justification: what is needed, when, for how long, and what the consequence is if it is not provided. Partner with the VP Global Delivery to secure the right people at the right time, and flag contention across concurrent projects. Continuously monitor whether the resourcing in place still matches the work, and re-raise the need as scope, complexity, or timelines shift. Execution control . Milestones, dependencies, blockers, action items, and change requests are tracked and driven to closure throughout the program. Partner with Solution Consultants who are responsible for requirements while retaining accountability for the project plan itself. Author and own the status report for every assigned program, for both internal leadership and the external client. Report accurately and candidly: progress against plan, upcoming milestones, risks and issues with owners and mitigations, decisions required, and changes to scope, schedule, or cost. Set and hold a predictable reporting cadence so stakeholders are never guessing at program health. Facilitate effective communication across technical and non-technical audiences, ensuring shared understanding and alignment. Escalate to senior leadership early and with a recommendation attached, not simply a problem statement. Act as the primary liaison between internal product leaders, development teams, and the client. Build and nurture trusted relationships with internal and external stakeholders to foster collaboration and long-term success. Status reporting . Internal and external status reporting is authored and owned by the Project Manager. Hold all parties accountable to agreed commitments, dates, and quality standards. Own the decision path for the project: escalate what genuinely requires senior input, and decide what does not. Act as the hub of communication and accountability across clients, internal teams, and stakeholders — the person who knows the state of the project at all times. Closure . The program is formally closed once delivered into production. Confirm all deliverables are complete and accepted, all acceptance criteria are met, and all open items are resolved or formally transferred with a named owner. Secure client sign-off and confirm the transition to production support, ensuring the receiving team has what it needs. Finalize and archive comprehensive project documentation, including plans, workflows, decisions, risks, changes, and lessons learned. Retrospective . A retrospective is conducted, documented, and converted into actions that improve future projects. Champion continuous improvement across project governance and seek efficiencies. Portfolio management . Multiple concurrent projects are owned and balanced without loss of quality or visibility. Maintain consistent governance, documentation, and reporting standards across every project, so quality does not vary with volume. Recognize and raise cross-project dependencies, resource contention, and cumulative risk that would not be visible from any single project. Qualifications required: 5-10 years of PM experience Demonstrated ownership of complex delivery projects end to end, in a client-facing environment. Proven ability to author project charters, Statements of Work, and executive-level status reporting. Strong command of Agile, software development lifecycles, and change management practices. Hands-on proficiency with JIRA and Confluence for program planning, tracking, and reporting. Confidence holding internal and external stakeholders accountable to commitments, with credibility rather than escalation. Clear, direct communication across technical and non-technical audiences. Comfort owning several concurrent projects without losing rigour. Current awareness of trends in FinTech, program management methodologies, and software delivery best practices. How Success Is Measured: Projects delivered on schedule, in scope, and to defined quality standards. Every project governed by an agreed charter and an accepted Statement of Work. Risks and blockers raised early, with mitigation owned and resolved before they affect commitments. Status reporting delivered on cadence, accurate, and trusted by internal leadership and clients alike. Projects formally closed with client sign-off and a clean transition to production BAU. Retrospectives completed for every project, with improvement actions owned and implemented. Client satisfaction sustained across a portfolio of concurrent projects. What to expect: An inclusive culture comprised of extremely talented individuals. A leadership team with a proven track record of success. The opportunity to join a company as it expands across the globe. Competitive compensation and generous benefits. Next steps: If this exciting opportunity is of interest to you, please apply to the Senior Delivery Project Manager job posting via the Bamboo link below by September 4, 2026. https://conquestplanning.bamboohr.com/careers/27 We thank all applicants for their interest. Only those invited for an interview will be contacted. Conquest Planning Inc. is an equal opportunity employer. Our inclusive work environment welcomes diversity and supports accessibility. If you require accommodation at any time during the recruitment process, please contact [email protected] .