Technical Project Manager – Team Lead

Job Title: Technical Project Manager – Team Lead
Department: Professional Services
Reports to: General Manager
Term: Full-Time Permanent
Primary Location: Remote in Canada
Salary range: $90,000 – $110,000

Help us build a better way for associations with the world’s first Member Data Platform.

Associations create communities and advocate for progress. They deserve best-in-class software so they can focus more on making our world stronger. Come build it with us! 

About Us

We’re one of Canada’s fastest growing startups with a world-class SaaS product and in-house professional services team. Our roots are in Ottawa, Ontario, but we’re remote, so our team works from all across Canada. We’re creating new roles and adding to our team of developers, data analysts, product owners, UX researchers, project managers, sales, marketing, and customer experience specialists. Our customer base continues to grow throughout Canada and the US – we doubled last year and will again this year. We’re always on the lookout for our next new Wicketeer to join and grow with us.

Learn about Wicket’s culture, benefits, hiring process, and other opportunities at

Wicket is looking for an experienced Technical Project Manager – Team Lead to join our Professional Services team to oversee a wide variety of projects from conceptual design through implementation. Reporting directly to the General Manager, the ideal candidate will have a minimum of 5 years experience in Technical Project Management within an IT role or digital/technical agency environment. You’re an empowering people manager, have a high EQ, and you naturally roll up your sleeves alongside your team. Lastly, you’re at home interacting with all levels of the organization from entry-level to C-Suite executives. 

Job Responsibilities

Project Management – 

  • Manage projects with top-down oversight throughout the entire execution to ensure success as defined by adherence to standards of scope, budget, and timeline.
  • Develop comprehensive project plans that involve multiple vendors and merge customer requirements with company goals, coordinate various managers and technical personnel during all project phases, from initial development through implementation.
  • Monitor project progress continuously and make detailed scheduled reports on measurable items, such as milestones and deliverables.
  • Communicate proactively with all involved personnel to provide encouragement, identify problems, create solutions, and implement efficiency improvements.
  • Analyze economics of project plans and provide actionable feedback relating to cost benefit and return-on-investment standards.
  • Serves as a focal point for a number of technical projects, providing project planning, execution, timing, resource planning, and risk and cost management services. 
  • Motivates the project team, ensuring project deliverables and schedules are met. 
  • Identify and/or resolve project-related issues and barriers to success
  • Ensure all stakeholders are provided with timely and accurate project information and status updates
  • Facilitate project meetings

Leadership – 

  • Oversee and manage the Project Managers by way of their: 
    • Project priorities
    • Quality of work
    • Train and maintain on our processes
    • 1:1 bi-weekly check-ins
    • Quarterly performance reviews
  • Contribute to the planning, implementation and commitment to the overall project delivery process
  • Contribute to the definition of roles and responsibilities related to Wicket project management and implementation across teams
  • Aid in the recruitment process for hiring new team members
  • Tracking and reporting on KPIs related to project delivery
  • Work closely with other Team Leads to ensure the success of overall project delivery

What you’ll need to be successful:

  • You are a proven leader and motivator, with deep experience building and leading technical project teams
  • You do not shy away from mediating conflict and fostering honest dialog in difficult conversations
  • You’re ready to step into a role to take action, ask where the fires are and help figure out what needs to be done to put them out 
  • You have experience in organizations with a complex, strategic sale, where best practices and technology define a customer’s success 
  • You have the ability to create structure in ambiguous situations, design effective processes, and hold customers and internal stakeholders accountable 
  • You’re comfortable in developing and maintaining strong relationships with customers and can quickly establish trust
  • You know when to pull in a subject matter expert and when you can handle the conversation on your own
  • You have a demonstrated understanding of Project Management processes, strategies and methods
  • You are aware that not everything on a project will go as planned. Mistakes are to be expected, however, you always accept when you are wrong, hold yourself accountable to your team and learn from your mistakes.
  • You realize that issues with external constraints and complexities, resource limitations, conflict and ambiguity and other uncertainties will almost certainly be encountered – you understand this, embrace it, and build elements of uncertainty into your project plans.
  • You have experience mentoring, coaching and developing rising talent 
  • You have a level of data-savvy and familiarity with data analytics, BI, and cloud data 
  • You have excellent time management and organizational skills and experience establishing guidelines in these areas for others
  • Process, plans, budgets and scope are your life! You are not afraid to remind stakeholders of deadlines, what it means when a deadline gets missed and quite frankly, we’re all a little bit afraid of you 😉

 Familiarity with any of the following would be considered an asset:

  • Basecamp
  • Harvest
  • AirTable
  • ClickUp
  • Miro
  • Zendesk
  • Accessibility standards
  • PHP
  • WordPress CMS
  • WooCommerce

Skills & Qualifications:

  • 5+ years of Technical Project Manager experience with gradually increasing responsibilities and a demonstrated understanding of Project Management processes, artifacts and tools
  • Professional Project Management Certification from an accredited institution preferred
  • Experienced Project Manager in B2B IT Software environment
  • The ability to thrive and collaborate with colleagues and customers in a remote environment
  • Superb communication and interpersonal skills
  • A passion for data and technology with proven technical aptitude
  • The ability to engage remotely in strategic conversations with senior leaders
  • Eligible to work in Canada

What we offer:

  • The opportunity to work remotely from anywhere in Canada
  • Competitive salary
  • Competitive health benefits (dental, vision, paramedical, prescriptions, out-of-country care) that extend to programs including mental health, employee family assistance, virtual health care services, and Best Doctors
  • An annual wellness stipend towards gym memberships, fitness equipment, sports fees, etc.
  • An annual professional development stipend and dedicated time for professional development
  • Highly intentional, progressive practices around feedback, team-building, skills and career development, and peer-to-peer recognition
  • Equal opportunity employer who prioritizes diversity and inclusion 
  • Awesome culture and growing team that has been around for over 20 years!
  • Certified Great Place to Work
  • Paid vacation time, paid personal “life leave” and your birthday off
  • We love dogs, trivia, and wine/beers/soda on Friday

We are accepting applications for remote workers from anywhere in Canada. 

When you apply please provide a cover letter clearly explaining how your background is a good fit for this position.

Wicket is committed to creating a diverse environment and is proud to be an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, colour, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, or age.

More about Wicket and the problem we solve

We build and sell the world’s first Member Data Platform (MDP). Not only are we building a new product, but we’ve created a new software category.

Our customers are associations which are membership-based organizations and nonprofits. They provide services and benefits to a specific group, profession, or community. Nearly every industry you can think of has an active association, so our reach is vast and diverse. For example, we have a customer who serves as a think tank for better public policies in Canada, and another who acts as a voice for renewable energy and storage solutions to power Canada’s future.

Until Wicket, associations were stuck managing their data through antiquated Association Management Software (AMS). Worse, this software tries to do it all – data, content management, email marketing, event management, e-commerce and so on – but one software can’t be the best at everything.

We knew there had to be a better way, so we reinvented how associations manage and engage with their members. Wicket frees association’s data to integrate with best-in-class software including MailChimp, WordPress, WooCommerce and Tableau. The list goes on and we’re always adding to it.

Wicket also has a very strong Professional Services Team, which originated as an independent digital web agency, with 20+ years of experience building and maintaining web solutions. The services team is a very important part of Wicket and is made up of experienced UX researchers, designers, developers and project managers, designing and building powerful websites using WordPress and WooCommerce. The Wicket Services Team collaborates very closely with the product team, tightly integrating the web solutions we build with Wicket’s platform. 

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