Senior Technical Program Manager, Engineering at Faire

Toronto, Ontario, Canada -

Full Time

Start Date

Immediate

Expiry Date

30 Jan, 26

Salary

214500.0

Posted On

01 Nov, 25

Experience

5 year(s) or above

Remote Job

Yes

Telecommute

Yes

Sponsor Visa

Skills

Technical Program Management, Cross-Functional Leadership, Strategic Planning, Risk Management, Data-Driven Insights, Communication Skills, Systems Thinking, Execution Strategies, Program Management Practices, Technical Fluency, Organizational Skills, Influencing Skills, Problem Solving, Alignment, Business Impact, Milestones

Industry

Software Development

Description

About Faire Faire is an online wholesale marketplace built on the belief that the future is local — independent retailers around the globe are doing more revenue than Walmart and Amazon combined, but individually, they are small compared to these massive entities. At Faire, we're using the power of tech, data, and machine learning to connect this thriving community of entrepreneurs across the globe. Picture your favorite boutique in town — we help them discover the best products from around the world to sell in their stores. With the right tools and insights, we believe that we can level the playing field so that small businesses everywhere can compete with these big box and e-commerce giants. By supporting the growth of independent businesses, Faire is driving positive economic impact in local communities, globally. We’re looking for smart, resourceful and passionate people to join us as we power the shop local movement. If you believe in community, come join ours. About this role: Faire is seeking Senior Technical Program Managers to lead some of the company’s most critical and cross-functional initiatives. As part of a highly leveraged TPM team, you’ll work across domains—spanning infrastructure, data, AI/ML, product engineering, and platform efficiency—to accelerate execution, improve alignment, and deliver measurable business impact. You’ll partner with senior leaders across Engineering, Product, and Business to define strategy, translate technical complexity into clear plans, and drive programs from concept to completion. This role requires strong technical aptitude, systems thinking, and the ability to quickly understand new domains to guide teams toward successful outcomes. What you’ll do: Lead high-impact, cross-functional programs that span multiple technical and business areas—from planning through delivery. Partner with engineering and product leadership to define goals, milestones, and success metrics aligned with company priorities. Develop clear execution strategies, manage dependencies, and proactively surface risks and tradeoffs. Establish and evolve scalable program management practices that increase delivery speed and quality. Contribute to strategic planning and prioritization through data-driven insights and structured execution frameworks. Qualifications: 5+ years of relevant technical program or project management experience driving cross-functional initiatives in software or platform engineering environments. Proven track record delivering large-scale, complex programs with measurable business outcomes. Strong technical fluency and ability to quickly understand new systems, architectures, and problem spaces. Excellent communication and influencing skills across technical and non-technical stakeholders. Highly organized, execution-oriented, and skilled at bringing clarity and alignment to ambiguity. Salary range: Canada: the pay range for this role is $156,000 - $214,500 per year. This role will also be eligible for equity and benefits. Actual base pay will be determined based on permissible factors such as transferable skills, work experience, market demands, and primary work location. The base pay range provided is subject to change and may be modified in the future. Hybrid Faire employees currently go into the office 2 days per week on Tuesdays and Thursdays. Effective starting in January 2026, employees will be expected to go into the office on a third flex day of their choosing (Monday, Wednesday, or Friday). Additionally, hybrid in-office roles will have the flexibility to work remotely up to 4 weeks per year. Specific Workplace and Information Technology positions may require onsite attendance 5 days per week as will be indicated in the job posting. Applications for this position will be accepted for a minimum of 30 days from the posting date. Why you’ll love working at Faire We are entrepreneurs: Faire is being built for entrepreneurs, by entrepreneurs. We believe entrepreneurship is a calling and our mission is to empower entrepreneurs to chase their dreams. Every member of our team is taking part in the founding process. We are using technology and data to level the playing field: We are leveraging the power of product innovation and machine learning to connect brands and boutiques from all over the world, building a growing community of more than 350,000 small business owners. We build products our customers love: Everything we do is ultimately in the service of helping our customers grow their business because our goal is to grow the pie - not steal a piece from it. Running a small business is hard work, but using Faire makes it easy. We are curious and resourceful: Inquisitive by default, we explore every possibility, test every assumption, and develop creative solutions to the challenges at hand. We lead with curiosity and data in our decision making, and reason from a first principles mentality. Faire was founded in 2017 by a team of early product and engineering leads from Square. We’re backed by some of the top investors in retail and tech including: Y Combinator, Lightspeed Venture Partners, Forerunner Ventures, Khosla Ventures, Sequoia Capital, Founders Fund, and DST Global. We have headquarters in San Francisco and Kitchener-Waterloo, and a global employee presence across offices in Toronto, London, and New York. To learn more about Faire and our customers, you can read more on our blog. Faire provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, sex, national origin, age, disability, genetics, sexual orientation, gender identity or gender expression. Faire is committed to providing access, equal opportunity and reasonable accommodation for individuals with disabilities in employment, its services, programs, and activities. Accommodations are available throughout the recruitment process and applicants with a disability may request to be accommodated throughout the recruitment process. We will work with all applicants to accommodate their individual accessibility needs. To request reasonable accommodation, please fill out our Accommodation Request Form (https://bit.ly/faire-form) Privacy For information about the type of personal data Faire collects from applicants, as well as your choices regarding the data collected about you, please visit Faire’s Privacy Notice (https://www.faire.com/privacy)

Responsibilities

Lead high-impact, cross-functional programs that span multiple technical and business areas. Partner with engineering and product leadership to define goals, milestones, and success metrics aligned with company priorities.