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Toronto, Ontario, Canada
Remote only
We're seeking a Staff Product Manager to lead a strategically important initiative: transforming Loopio into an agentic-led platform for creating high-quality proactive and solicited proposals, including RFPs, Security Questionnaires, and DDQs. You'll own the vision, strategy, and execution behind building AI agents that don't just assist users but actively complete work on their behalf.
This role is built for a builder who operates with significant autonomy. You'll take initiatives from early concept through product-market fit and into scaled adoption, working alongside our established, high-usage product.
The ideal candidate has direct experience shipping successful AI-powered Enterprise B2B SaaS experiences, a track record of launching new products and finding Product-Market Fit, and a metrics-driven approach to proving what works before scaling.
Note: This is an existing vacancy on the team
Product Vision & Strategy
Define and own the product vision for your ownership scope.
Translate company objectives, overall product vision, and market opportunity into a roadmap that sequences from early validation to scaled adoption.
Set clear success metrics for each phase of the initiative and hold the team accountable to them.
Create internal and external alignment and excitement for the exceptional future you will be creating.
Building & Execution
Collaborate closely with your partners in design and engineering to create a strongly aligned and focused team.
Drive discovery to validate problem, solution, and willingness-to-pay before over-investing in build.
Ship early, learn fast, and iterate based on real usage rather than assumption.
Navigate the specific challenge of introducing a new, agentic paradigm alongside an existing, established product, balancing cannibalization risk, migration paths, and customer trust.
Drive adoption post-launch: this role doesn't stop at shipping a v1, you fully own the realization of the customer and business outcomes we set out to achieve.
Agentic Experience Design
Develop a strong point of view on what makes an agentic experience genuinely great in a B2B SaaS context, not just technically impressive, and translate that into product decisions.
Partner closely with engineering and AI/ML on agent orchestration, model selection trade-offs, and reliability, enough to make informed product calls without needing to be talked through the fundamentals.
Design for trust and control: knowing when to let an agent act autonomously versus when a human needs to stay in the loop.
Customer & Market Focus
Deeply understand the workflows of proposal managers, sales teams, asset managers, and compliance/security teams responding to RFPs, SQs, and DDQs.
Run discovery directly with customers and prospects to validate problems and success criteria.
Track the competitive and market landscape for agentic proposal automation.
Autonomy & Influence
Operate independently, spotting gaps and opportunities without needing direction, and rallying the right people to move on them.
Communicate vision, progress, and metrics clearly to executives, cross-functional stakeholders, and customers.
Act as an internal thought leader on what great agentic product experiences look like.
Track record of building and launching new products, finding product-market fit, and driving adoption, ideally while working within or alongside an existing, established product.
Direct experience building agentic or AI-driven experiences in B2B SaaS.
We care more about this track record than a specific years-of-experience threshold; strong candidates may come from a range of tenure levels.
Experience in enterprise workflows, sales tech, or proposal/RFP automation is a plus, not a requirement.
Working knowledge of LLMs, agent orchestration, RAG pipelines, and the trade-offs involved (latency, context windows, model selection).
Comfortable enough in the technical details to be a credible thought partner to engineering, without needing to be the one writing the code.
You are already adept at using AI tools for research, artifact building, prototype building, spec building, etc., across all areas of the PM role.
You bring proven product taste - you deeply understand what matters to users and how to marry the right capabilities with an appropriate and delightful user experience.
You have strong instincts in product discovery, prioritization, and execution, especially in ambiguous, early-stage environments.
You are metrics-driven: you define what success looks like before you build, and you know how to measure it after.
You have excellent communication and stakeholder management skills, and you are able to bring people along on a new and sometimes unproven direction.
Self-directed. You don't wait for a roadmap to tell you what's next.
Entrepreneurial and comfortable with ambiguity; energized by building something that doesn't exist yet.
Results-oriented, with a bias toward shipping and learning over long planning cycles.
Loopio is a remote-first workplace because we recognize the advantages of working flexibly. We are HQ’d in Canada, with established hub regions around the world from which we hire.
Our employees (or Loopers, as we call ourselves!) live and work in 🇨🇦 Canada (British Columbia and Ontario), 🇬🇧 London, and 🇮🇳 India (specifically in Gujarat, Maharashtra, and Bengaluru).
The majority of our team is based in ON and BC, which means these employees live and work remotely within a 300km radius of Toronto (within Ontario) and Vancouver (Within BC).
We offer flexible co-working locations available to Loopers in ON and BC. Those based in ON have the option of working out of our convenient co-working space located in the heart of Downtown Toronto and a 12-minute walk from Union Station. BC Loopers have the option to work centrally in Vancouver. It is whatever works best for you!
You’ll collaborate with your teams virtually across the UK, India, and North America (we’re just a Zoom call and Slack message away!) with core sync hours and focus time for headsdown work 🙇🏾 during the workday
We encourage asynchronous collaboration to effectively work as a global #OneTeam!
Your manager supports your development by providing ongoing feedback and regular 1-on-1s, we leverage Lattice for our 1:1s and performance conversations
You will have the opportunity to elevate 🪄 your craft and the opportunity to explore your creativity, with a dedicated professional mastery allowance for more learning support! We encourage experimentation and innovative thinking to drive business impact.
We offer a wide range of health and wellness benefits to support your physical and mental well-being, starting day 1️⃣ with Loopio.
We’ll set you up to work remotely with a MacBook laptop 🍏, a monthly phone and internet subsidy, and a work-from-home budget to help get your home office all set up.
You’ll be joining a supportive culture that has thoughtfully built out opportunities for connections in a remote first environment.
Participate in 🎤 townhalls, AMA (Ask-Me-Anything), and company celebrations to celebrate the big wins and milestones as #oneteam!
Our four Employee Resource Groups offer opportunities for employees to learn and connect year-round.
You’ll be a part of an award-winning workplace 🏆with an opportunity to make a big impact on the business.
Questioning your qualifications? Read this ‼️ Hi there, we recognize that all too often, potential candidates don’t apply for a position simply because they don’t hit every single criteria included in the job description—particularly members of underrepresented groups.
Whether or not your experience ✅ checks off all the boxes on a job posting, we still encourage you to apply to ensure that your application receives a review from our team. We understand that a resume can only showcase so much during the applicant stage, so we've created prompts in the application for you to share more about yourself. If you've made a career transition (or a few!), you’re self taught in a new role, or you have skills/experience you’d like to highlight, we want to hear more about what you could bring to the table.
AI in Recruitment 👩🏻💻 At Loopio, we leverage artificial intelligence (AI) technology to enhance our recruitment process. These tools assist with tasks such as resume screening, drafting preliminary job descriptions, generating initial interview questions, transcription and occasionally sourcing prospective candidates. However, AI is never used to make final hiring decisions; our use of AI serves to support repetitive and administrative tasks in order to streamline our hiring and recruitment workflows. We are committed to the responsible use of AI in our hiring practices, prioritizing both an improved candidate experience and operational efficiency. Our standardized hiring practices remain focused on reducing biases, with all key hiring decisions solely made by our team. We continuously review and refine our hiring practices to align with industry best practices and evolving legal guidelines
AI Usage in Interviews 🤖 The Loopio interview process is designed to help us better understand your professional experiences, as well as your unique perspective and approach to delivery and collaboration. To ensure a fair and accurate assessment, we expect candidates to refrain from using AI-generated content to produce responses to our interview questions during the live interview, as our goal is to evaluate your own knowledge and problem-solving abilities - not those of an AI assistant. If AI-generated responses are identified during the interview, Loopio reserves the right to disqualify candidates from the interview process.
For specific roles that include a take-home assignment, our AI Interviewee Policy allows the use of AI for initial support; however, the final submission must be a true reflection of your personal insights, skills and decision-making.
Loopio is an equal opportunity employer that is deeply committed to building equitable workplaces that are diverse and inclusive. We actively encourage candidates from all backgrounds and lifestyles to consider us as a future employer. Please contact a member of our Talent Experience team (work@loopio.com) should you require accommodations at any point during our virtual interview processes.
