Our History

Following a successful career in the corporate sector, Challenge Factory’s founder and president, Lisa Taylor, was called to focus full-time on shaping the Future of Work and Canada’s approach to career development.

Revolutionary change across workforces is here

As a technology strategy consultant in the 1990s, Lisa was actively involved in the early stages of Internet disruption. By the mid-2000s, she noticed the same type of early unrest that had occurred in the mid-90s was beginning to re-emerge. Workforce systems and processes weren’t working the way they used to, and new questions were being asked of leaders—who didn’t have good answers.

At the time, Lisa managed a team of more than 120 staff. The team’s average age was 48 years, and their average length of employment at the company was 17 years. As she conducted regular career conversations with her staff, she was appalled to discover that many of them were “successful, but not satisfied.” They were good at their jobs, but bored. Yet they weren’t interested in any of the new opportunities Lisa could offer. They were waiting for a life milestone—their final mortgage payment, or their last child graduating from university—before they would be willing to discuss their future. For many, the amount of time they “just had to get through” before making a change was longer than Lisa’s entire career had been at that point.

Lisa became curious about the impact and costs associated with entire workforces “just passing time.” It led her to the study of demographics, labour market dynamics, and career life-stage theory. Lisa realized the next wave of disruption was not going to be technology-led. It was going to be led by the changing nature and needs of the workforce and how people work—including the norms, values, and activities that the workforce wants in exchange for their labour, across a much longer working life.

Challenge Factory is founded to fill unmet workforce needs

Lisa quit corporate life and founded Challenge Factory to address the workforce and career needs of an emerging market: older workers. The company focused on shifting demographics, career transitions, and tools for workforce managers. She identified the need and opportunity to get ahead of baby boomers approaching the traditional age of retirement without new career systems, structures, and expectations in place that will ensure careers can grow through an individual’s late 40s, 50s, 60s, 70s, and beyond.

This was in 2012, well before the conversations that are common today about ageing populations, gig economies, and hybrid work.

Challenge Factory’s focus on hidden talent has evolved from this thinking. Better than anyone in Canada, we see and understand workers who are not well served by traditional hiring methods, such as Legacy Career® seekers, older workers, and military Veterans. Recognizing that services delivered to these individuals (labour supply-side solutions) will fall flat unless employers restructure talent and training programs (labour demand-side solutions), Lisa identified a need for a systems approach to address changing labour dynamics.

Today, our work is in use around the world by leaders, educational institutions, and governments as new workforce programs, training paths, and policies are formed.

What drives Challenge Factory today?

  • Wasted workforce potential is wasted impact.
  • The Future of Work is human. People are at the centre of work, and technology is there to enable them.
  • Seismic shifts in human and technology-driven innovation have made change a constant in today’s workplace, and organizations now must learn how to work within this new normal.
  • Business can be a force for good.

Challenge Factory’s timeline



Challenge Factory is incorporated and Lisa Taylor, founder and president, hires the company’s first staff member. We launch a career test-drive service that provides a guided “day-in-the-life” experience to executive leaders and other clients going through career transitions. Over 70 jobs are available to test-drive.

This unique offering recognizes that adult career transitions need to tap into instinct and “gut-feel,” which is different from how students might make career choices. Later-life change requires tailored approaches that differ from general career or job search services. This understanding distinguishes Challenge Factory’s services and leads to the development of the term Legacy Career®.



Challenge Factory is invited to meet with General (Ret’d) Walt Natynczyk, Deputy Minister, Veterans Affairs Canada (VAC), to discuss the impact of identity on career change generally and implications for the Department to consider as new approaches to military-to-civilian career transition supports are developed.

Except for the Life After Service Survey (conducted by Statistics Canada in collaboration with VAC and the Department of National Defence), there is very little information about Veterans’ work and career experiences when they transition into post-service civilian life.

Challenge Factory identifies the similarities between the career transitions that older workers and military Veterans go through. We begin to develop deep expertise in how to close the gap between employers and the hidden talent pool of Canada’s military Veterans. Explore the full timeline of Challenge Factory’s work with Veterans and employers across Canada.



Challenge Factory begins helping organizations address their workforce needs. Our consulting services focus on how ageing workforces will impact workplaces. Projects include helping private and non-profit sector organizations with issues that require workforce modelling, new Legacy Careers® paths and programs, alumni programs, and leadership support for better career conversations and approaches with staff.

Often, the senior leader hiring us to help with workforce planning also wants support in their own career and future. Lisa and other Challenge Factory team members become advisors to these leaders on topics that bridge professional and personal concerns. Challenge Factory also becomes known for creative, strategic approaches to connecting hidden talent to the labour market.

Notable work includes:

  • Toronto Community Housing Corporation: The development of an onboarding program that helps its Board of Directors understand the complexity of day-to-day challenges faced by frontline staff in six key roles.
  • Ontario Nurses Association: The development of an intergenerational career and learning program for labour negotiators in anticipation of future workforce shortages.


Challenge Factory’s work and impact begin to receive exciting recognition.

Our unique career transition service delivery is featured in a CBC Television documentary called The Boomer Revolution. The work-related segment follows a transitioning executive leader who, following a 25-year financial services career, goes on a Challenge Factory test-drive to own a Bed & Breakfast. It explores how demographic change is impacting the lives and lifestyles of boomers. Challenge Factory’s President, Lisa Taylor, discusses the career development of Canadians in mid and later stages of life.

The Urban Land Institute selects Lisa as one of the Top 100 Women in Canada for her work in leadership, employment, and city building. This recognition acknowledges the importance of work and careers in building sustainable cities.

Lisa also wins the Career Professional of the Year, awarded by the Career Professionals of Canada (CPC) and voted by her peers in the career development sector. Recipients are selected for the contribution their work makes to advancing the future of the sector.



Challenge Factory wins a major contract with ArcelorMittal to reimagine the Future of Work within Canada’s steel manufacturing industry.

We develop a comprehensive HR strategy to help address and leverage the industry’s ageing workforce, for the first time developing our Broken Talent Escalator® model. This becomes a foundational tool and thought leadership piece for understanding outdated workplace structures, programs, and approaches to intergenerational workforces.



Funded and published by national charitable organization CERIC, Lisa authors Retain and Gain: Career Management for Small Business.

The playbook identifies 40+ low-cost tips, activities and actions that small business can take right now (some in only 10 minutes a day) to attract, engage, and retain staff. Written in an innovative “travel guide” format, Retain and Gain includes special sections on new graduates, the aging workforce, and family enterprises, and provides planning templates and links to unique resources. It also features research, facts, and statistics that shed new light on Canada’s small business economy and workforce.



Challenge Factory leads a National Conversation on the Future of Work with more than 1,000 participants across Canada. We take the project to Cannexus18, Canada’s national career development conference, and film a documentary that showcases the hopes, fears, and ideas that Canada’s employment services and career development professionals have for the Future of Work. The film is part of a professional development program, with a companion conversation guide to spark meaningful future-focused discussion on issues related to employment, jobs, skills, and careers in workplaces across Canada.

This work is supported by the Ontario Centre for Workforce Innovation, a project of Ryerson University, with partial support from the Government of Ontario and Government of Canada.



After the wonderful reception of Retain and Gain: Career Management for Small Business, CERIC funds Challenge Factory to write a second playbook for a different sector. Lisa authors Retain and Gain: Career Management for Non-Profits and Charities. It focuses on providing managers with practical career management tools to use with employees in ways that advance thriving careers and build the capacity of the non-profit and charitable sector.



Challenge Factory undergoes exciting international growth.

We are nominated by the World Trade Centre Toronto to take part in its Trade Accelerator Program (TAP) through the Toronto Region Board of Trade. The program recognizes businesses, with a focus on women-owned businesses, that are ready to enter new international markets. It provides supports to build an export strategy and the resources required to find success.

Leveraging our TAP program participation, Lisa is selected to be one of five members of Team Canada to attend the International Centre for Career Development & Public Policy (ICCDPP) Symposium in Norway. Lisa is also selected to be one of three speakers to address the ICCDPP’s 33 member countries.

The symposium catapults Challenge Factory onto the international stage as policymakers, career development professionals, researchers, and employer and workplace representatives gather to discuss the way forward for global career development, with a focus on how governments can support citizens to build fulfilling careers.



Lisa co-authors The Talent Revolution: Longevity and the Future of Work with Fern Lebo. Published by the University of Toronto Press, this seminal book exposes work-life longevity as the most influential driver transforming today’s workplacesa competitive edge for organizations smart enough to capitalize on it.

For the first time, The Talent Revolution explains the five drivers that are shaping the Future of Work and provides a lens through which we can understand, prioritize, and better advance the work of creating sustainable and responsive workplaces, workforces, and labour markets where no one is left behind.

Lisa embarks on a cross-Canada book tour.



The COVID-19 pandemic hits and Challenge Factory implements key business decisions to ensure its growing staff is well supported and the company is responsive to new challenges and opportunities:

  1. All regular contractors are offered employment contracts.
  2. All staff are provided health, dental, and life benefits.
  3. An immediate pivot to support public sector workforce needs brings Challenge Factory’s expertise to new clients and audiences.


Challenge Factory begins a years-long collaboration with the Labour Market Information Council (LMIC).

We become a strategic and trusted advisor, community animator, and project manager for LMIC during the creation of the LMIC Data Hub, a central data repository that hosts labour market information (LMI) from vetted sources across Canada.

This is a technology project focused on LMI, but the central challenge is not only technical. Adoption of any technology requires strong buy-in and support from the intended user community. Challenge Factory leads activities related to identifying end-user needs and engaging different and diverse community representatives from Canada’s hidden career development sector. Challenge Factory’s role emerges from our unique expertise at the intersection of career development, technology change, and community engagement.



Challenge Factory kicks off a new period of growth when Emree Siaroff joins Challenge Factory as the Vice President of Consulting and Leadership. With more than 30 years of global and domestic human resources experience, Emree’s past as a CHRO expands Challenge Factory’s consulting capabilities and the advisory role that we have been playing for senior leaders is formalized into our Trusted Advisor Leadership Counsel.

We also launch Workforce Architecture, a new and unique digital magazine. Workforce Architecture applies career development, Future of Work, and revolutionary change thinking to today’s workforce needs in order to create a future that advances the prosperity and well-being of individuals, organization, and communities.



CERIC sees the potential to expand the Retain and Gain series to include a third playbook focused on executives and managers in the public sector (encompassing all levels of government and jurisdictions across Canada). Lisa authors Retain and Gain: Career Management for the Public Sector.

This playbook includes a lens on diversity, equity, and inclusion (DEI) and recognizes the unique context of public sector workplaces. It also provides planning templates and links to additional resources. Challenge Factory presents the playbook’s research and contents to departments and communities across the Government of Canada, and media attention for the Retain and Gain series continues to increase.



Challenge Factory’s curriculum development work enters a new phase. Building on the platform and expertise that began in 2015 with the launch of the Centre for Career Innovation, Challenge Factory undertakes new learning mandates. We partner with the Information Communications and Technology Council (ICTC) on two projects.

The first project is the development of an online asynchronous training program to help youth apply career development practices and reflection techniques during their internship experiences.

The second project is the creation of a series of bilingual videos for youth that showcases elements of Canadian culture and workplace behaviours beyond basic etiquettes and norms. It includes the development of a facilitator’s guide so that the video content can become standalone.



Challenge Factory’s leadership in topics related to intergenerational workforces and ageism in the workplace is recognized and advanced when Lisa becomes an Associate Fellow with the National Institute on Ageing. She is also recognized as one of Canada’s Most Powerful Women by the WXN Top 100 Awards.



After a years-long process, Challenge Factory successfully becomes a Certified B Corporation. This difficult and thrilling achievement helps us better align our values and mission to make business a force for good. It supercharges our purpose, impact, and the future we want to shape for Challenge Factory and the people, organizations, and clients we help.

Did you know? A B Corporation is a type of for-profit business that is also committed to meeting rigorous standards of social and environmental performance, accountability, and transparency. B Corps are distinct from traditional businesses in that they are legally required to consider the impact of their decisions not only on shareholders but also on workers, customers, the community, and the environment.



The deep expertise in military Veterans’ career transitions that Challenge Factory has cultivated since 2012 is recognized when our president, Lisa Taylor, is invited to appear before the House of Commons Standing Committee on Veterans Affair as an expert witness. She provides three recommendations to the Committee:

  1. Use a career development model when designing the National Strategy for Veterans Employment After Service, and adhere to Canada’s national Competency Framework for Career Development Professionals when outlining any service or intervention to be included in the strategy.
  2. Focus on equipping Veterans with career agency rather than identifying specific jobs or career paths for them.
  3. Make it easier for small- to medium-sized enterprises (SMEs) in the private and non-profit sectors to hire Veterans through employer-focused supports and incentives.

The Committee is conducting a consultation process to inform a National Strategy for Veterans Employment After ServiceThe final report is published in October 2023.



Working across North America, Challenge Factory’s consulting group helps leaders and organizations address a range of workforce challenges, including:

  • Women’s leadership in male-dominated industries
  • Succession planning and leadership in the mining and engineering industries
  • Return-to-work policy and culture implications in professional service firms

Demand for Challenge Factory’s Trusted Advisor Leadership Counsel services continues to grow. We bring on new Trusted Advisors based in Canada and the United States.



Challenge Factory publishes a new report called Hidden Sector, Hidden Talent: Mapping Canada’s Career Development Sector. This is a first-of-its-kind evidence base about the size, membership, and impact of Canada’s career development sector. It is launched at Cannexus24, Canada’s career development conference, including a main stage presentation by Lisa Taylor, Challenge Factory’s president.

The report’s reception exceeds all our expectations. We see community in action, the power of research to excite and motivate, and a sector’s intense commitment to helping Canadians shape their own Future of Work. Media attention is high and enthusiastic, reflecting the public interest in changing workforces and careers.

Project partners include CERIC and the Canadian Career Development Foundation.