Complex challenges need different ways of working.
We bring together strategy, lived experience, community knowledge and diverse expertise to find thoughtful ways forward.
We Bring People, Ideas and Possibility Together
We work on the kinds of challenges that don't have simple answers. The issues are often connected, the people involved bring different experiences and perspectives, and the systems around them can make change difficult. We bring together strategy, research, community engagement, policy and facilitation, drawing on the right combination of approaches to understand what is getting in the way, identify where there is opportunity, and create practical ways forward.
Our work goes beyond any one service. We work alongside the people closest to the issues, building from the knowledge, relationships and work that already exist. We connect people, ideas and existing efforts, creating the relationships and momentum needed to move from understanding a challenge to building something different.
Why 'Pineapple Flags'
The pineapple is a symbol of welcome. Shared around the table and offered to guests as a gesture of hospitality, it says: you are important, you are welcome here, and there is a place for you.
Flags tell us what matters. They make the unseen visible, mark a direction and give people something to move toward together.
Together, that is the spirit behind Pineapple Flags. We create space for people and ideas to come together, make what matters visible and move toward meaningful change.
How We Show Up
We believe meaningful change starts with relationships and a deeper understanding of how people experience systems differently. Our work is grounded in feminist leadership, intersectionality, lived experience and shared power, helping organizations see beyond silos, surface overlooked perspectives and create solutions that are practical, equitable and grounded in the people they serve.
Care is central to how we work because the way change happens matters as much as the change itself. So much so that we developed CARE, our approach to putting these principles into practice.
Our CARE Infrastructure
At the heart of Pineapple Flags is CARE Infrastructure, our approach to building care into how organizations, communities and systems work. CARE is how we move from values to action, shaping how we listen, collaborate, design solutions and move ideas forward. Adaptive and connected, it helps us respond to what we learn, strengthen the work as it develops, and create practical pathways toward meaningful change.
CARE brings together four connected practices: Connect, Analyze, Reimagine and Embed. Together, they provide a way to move from understanding complex challenges to creating and sustaining change.
Connect brings people, relationships, lived experience, community knowledge and different forms of expertise into the work. We look for the connections that already exist and create space for new ones to develop.
Analyze looks beneath the surface. We examine the systems, structures, relationships, evidence and experiences that shape an issue, building a fuller picture of what is happening and where change may be possible.
Reimagine creates space to think differently about what could be possible. We bring people together to develop ideas, strategies and solutions that respond to what we have learned and to the realities of the people involved.
Embed moves ideas into practice and creates the structures that allow them to take hold. We support implementation, measure and learn from impact, adapt as needed, and identify what needs to change for progress to last.
Come and Meet Our Ecosystem of Expertise
Pineapple Flags takes a networked approach to consulting, bringing different kinds of expertise into the work around a shared challenge. We build ongoing relationships with people across the fields and practices that shape social change, allowing us to bring fresh perspectives and relevant expertise to each project. Depending on the work, this can include consultants, strategists, systems thinkers, academics, topic experts and people with deep implementation experience from years of working within a sector.
Bringing these perspectives together allows us to look at a project from different points along the path from theory and strategy to implementation. For each project, Pineapple Flags brings the right combination of people and expertise together around the client's goals. We create space for different perspectives to inform one another, challenge assumptions and strengthen the work, while maintaining clear direction and coordination around the project.
Your Core Team
Jennifer Gordon (she/her)
Founder and Principal Consultant
Jen is an award-winning feminist leader, social innovation and strategy consultant, and creative systems thinker with more than 15 years of experience working across community, government and social change. Jen brings extensive experience across the social sector, including senior leadership in local government, more than a decade in the YWCA movement, deep experience in housing and homelessness, and extensive work alongside survivors of gender-based violence and the organizations that support them.
As Manager of the Region of Waterloo’s Plan to End Chronic Homelessness, Jen led the implementation of a community-wide strategy with 30 strategic priorities to achieve functional zero chronic homelessness by 2030. During her tenure, the inflow rate into chronic homelessness declined by more than 60%. Her work brings together research, strategy, community engagement and systems thinking to translate complex social issues, evidence and community knowledge into practical action..
Jen holds a Master of Social Work in Macro Social Work from Wilfrid Laurier University.
Sid MacDonald (they/she)
Community Engagement Manager
Sidney is a community-informed researcher and strategist with extensive experience across housing, homelessness and gender-based violence. Sidney brings deep expertise in relationship-based engagement, creating spaces where diverse perspectives, lived experience and community knowledge can meaningfully shape the work. Their experience with multiple YWCAs, collaborative research projects, service providers, municipalities and grassroots organizations has given them a strong understanding of the systemic barriers facing women and gender-diverse people, as well as the ways equity-led organizations work to address gaps in policy and systems.
Sidney brings a macro-level perspective grounded in trust, accessibility and meaningful participation, with experience in strategic planning, policy development, research and collaborative engagement. They recently completed the Broadbent Institute’s Emerging Leaders Program.
Sidney holds a Master of Social Work from Wilfrid Laurier University.
Strategy and Implementation Advisors
Sara Escobar
(she/her)
Sara, co-founder of Peregrine Outreach Waterloo Region, brings more than 25 years of social justice and street outreach experience, providing trusted insight to community partners and multiple levels of local government on issues affecting people experiencing homelessness and street involvement.
Marjorie Knight (she/her)
Marjorie is an anti-poverty advocate and community outreach worker whose lived experience with homelessness informs her work supporting families and children facing poverty and housing insecurity, while bringing the realities of people experiencing homelessness directly into government and policy conversations through advocacy and community leadership.
Consulting Collaborators
Scaled Purpose
A social innovation partner, led by Sean Campbell, with affordable and supportive housing expertise, supporting governments, non-profits, and social enterprises through research, program design, financial modelling, and implementation.
Dumbo Octopus Consulting
A grassroots-focused consulting partner. led by Robyn Schwarz, supporting community-led organizations and equity-seeking groups through capacity building, strategic interventions, and collaborative systems change.
Social Innovation Research Group
A research partner, led by Ginette Lafrenière, based at Wilfrid Laurier University, specializing in gender-based violence, outcome evaluation, and community-based research to strengthen programs and advance social change.
GroupThink Labs
A collective intelligence and participatory decision-making partner that uses participatory budgeting, digital polls, and inclusive group processes to help communities and organizations make decisions about how resources are allocated.
What Our Partners Are Saying
Elizabeth Clarke
CEO YW Kitchener-Waterloo (2002-2022)
I’ve worked with Jen for more than a decade and have marvelled at her skill in all phases and aspects of project design, development, delivery and evaluation. She is a diligent researcher, a persuasive grant-writer and a creative thinker, who has successfully brought many project ideas-especially in the areas of human services, advocacy, and the arts- to fruition.
Maria Huijbregts
Director of Knowledge Building- Family Services Toronto
I am very thankful for Jennifer’s contributions to our work around peer support and gender-based violence. Jennifer made a strong contribution in her energy and creative ideas. I also really appreciate her facilitation style. It truly made a difference.
Ginette Lafreniere
Director, Social Innovation Research Group (SIRG); Former Director, Manitoulin Centre for Community Health Research (MCCHR), Wilfrid Laurier University.
If you are looking for a community-based researcher who understands the ethos of working with equity-seeking populations and more importantly knows how to walk with individuals in ways which are respectful, Jen fits the bill. Moreover, she is also estraordinarily creative and can use her talents as an artist to engage in innovative ways in community development strategies both within and outside of research projects. She is a most talented individual with a strong work ethic who will get the job done.
15+ Years
Leading systems change projects, from front-line experience in service resolution through to research, policy and strategy.
7+ Impact Areas
We bring deep experience and practical insight to complex challenges across housing, gender equity, safety, systems and community change, and more.
Let's Build Better Systems Together
The most meaningful work begins with a conversation. Whether you’re navigating a complex community challenge, shaping policy, or exploring a new idea, we’d love to hear what’s possible.