Chief of Staff for AI Innovation

About Jobber Jobber builds technology for small businesses in the home service sector, including plumbers, painters, and landscapers. Our platform streamlines quoting, scheduling, invoicing, and payments, helping business owners deliver a smooth, professional experience to their customers. We aim to give small business owners more control over how they run their companies. Our company culture values transparency, inclusivity, collaboration, and innovation. Jobber has been recognized by Great Place to Work, Canada’s Most Admired Corporate Cultures, the Globe and Mail’s Canada’s Top Growing Companies, and Deloitte’s Technology Fast 50™. With a leadership team bringing decades of experience, we are committed to redefining what success looks like for our customers. Why Join the Fintech Team? Fintech is one of Jobber’s fastest-growing areas and a central focus for our future. By embedding financial tools into our platform, we help small business owners get paid faster, access capital, and invest in their growth. Our goal is to expand our financial offerings beyond payments and deliver new solutions that make a real difference for our users. Role Overview: Senior Manager - Fintech Innovations The Senior Manager - Fintech Innovations will lead key fintech initiatives at Jobber. This role turns ideas into business cases and launches products that drive revenue and growth. The position sits within our Fintech team, a collaborative group dedicated to building the financial tools that help small businesses succeed. Projects may include pricing strategy, partnership development, piloting new products, and more. The role bridges the gap between strategy and execution, requiring someone comfortable managing projects from start to finish. Responsibilities include analytics, pricing, go-to-market planning, product development, and risk management.

Who We AreAt Momentum Financial Services Group, we are dedicated to empowering individuals by transforming the way financial services are delivered to those in need. With over 40 years of expertise, we proudly operate Money Mart—Canada's largest non-bank branch network—leading the charge in providing financial solutions to underserved communities.Our offerings range from short-term loans to money transfers and prepaid cards, ensuring that millions of customers can access essential financial products when they need them the most.At MFSG, collaboration is at the heart of our operations. We work across various teams and functions to create impactful solutions that dismantle barriers and broaden access to financial resources. Whether you are innovating, strategizing, or problem-solving, your contributions make a difference in the lives of real people.

About Us:At Financeit, we are a dynamic fintech and enterprise services company, dedicated to empowering the largest home improvement and retail organizations across the United States and Canada. Our innovative point-of-sale financing platform enables businesses of all sizes to enhance their sales processes by providing customers with flexible and affordable monthly payment options for significant purchases, be it home improvements, vehicles, or retail items. For larger enterprises, our comprehensive suite of solutions, branded as Centah, encompasses lead management, workflow optimization, live support, financing options, promotional strategies, performance assurance, and category development.Our unique culture is a blend of agility and ambition, allowing each team member to make a meaningful impact within the organization, while also influencing the industry at large. We are committed to fostering a diverse and inclusive workplace where innovation thrives.Role Overview:As a Senior Product Manager within our Centah division, you will spearhead the evolution and success of our product offerings. This crucial position requires you to lead interdisciplinary teams in defining, designing, and delivering innovative solutions that align with client needs and drive business growth.In your role, you will report directly to the Director of Product, where you will articulate a clear product feature vision and roadmap that aligns with our strategic goals while staying ahead of market trends to identify new opportunities. As the voice of the customer, you will cultivate a culture of innovation and ensure our products effectively address real market demands. This position demands exceptional product judgment, robust cross-functional leadership, and extensive expertise in the home services sector.Your Responsibilities:Drive the product roadmap for your domain by expertly balancing immediate feature delivery with long-term platform scalability.Engage with senior leadership to present insights, trade-offs, and strategic recommendations that influence organizational objectives.Act as the primary advocate for the customer, utilizing a curious, problem-solving mindset to uncover core pain points and collaboratively develop solutions.Champion product projects from conception through launch, meticulously defining requirements, identifying edge cases, and owning delivery and outcomes.Lead development teams in an Agile environment through continuous delivery, facilitating estimations, refining scope, and making informed trade-offs to meet project deadlines.Prioritize product features based on market demand, strategic initiatives, and comprehensive risk assessments to maximize impact.Analyze product performance metrics post-release, leveraging data-driven insights to iterate and enhance product offerings.

At Relay, we empower self-made business owners through our innovative digital banking platform. Our mission is to provide the tools and knowledge needed to master their finances, bringing transparency, confidence, and control to every dollar earned. By eliminating financial uncertainties, we transform cash flow from a source of stress into a strategic asset that helps business owners operate stronger, more resilient enterprises.We are seeking a passionate Senior Manager, Brand Marketing to lead and scale Relay’s content marketing and social media strategies. You will harness the power of strategic storytelling, creative intuition, and data-driven insights to shape how Relay connects with our customers and prospects. Your leadership will build a high-performing team dedicated to enhancing brand awareness, driving organic traffic, and expanding our reach while fostering deeper audience engagement through our owned channels.As a key cross-functional collaborator, you will work alongside product marketing, performance marketing, and design teams to ensure cohesive storytelling throughout the customer journey. Partnering with Relay’s leadership team, you will define how content marketing drives business growth—enhancing brand awareness, building affinity, and generating trust and leads. You will help establish Relay’s voice within the fintech industry, transforming insights into compelling narratives that inspire, educate, and resonate with small business owners. Your curiosity, creativity, and resilience will guide your approach—striking a balance between strategic vision and practical execution, merging data with instinct to fuel meaningful growth, and thinking outside the box to bring innovative ideas to fruition. Above all, you will be a champion of Relay’s mission, values, and voice, serving as an internal storyteller and educator who brings our brand to life.Please note that we operate in a hybrid environment, collaborating in the office three days a week (Tuesday to Thursday).

At Relay, we are revolutionizing the digital banking experience for self-made entrepreneurs, equipping them with the essential tools and insights to manage their finances effectively. Our platform is designed to eliminate financial uncertainty, transforming cash flow management from a daunting task into a clear pathway for sustainable business success.As a pivotal player in our growth strategy, the Senior Demand Generation Manager will spearhead initiatives to engage and convert key partners within the accounting and bookkeeping sectors. You will be responsible for crafting and executing comprehensive demand generation programs that create awareness, stimulate engagement, and drive qualified leads from the initial touchpoint through to revenue realization.This role requires a deep understanding of our target audience and the development of innovative strategies and playbooks that resonate with this high-value segment. You will collaborate closely with Sales, RevOps, Events, and other cross-functional teams to translate our strategic vision into measurable outcomes.Key Responsibilities:Lead the full-funnel strategy, channel selection, nurturing processes, and conversion tactics for partner acquisition focused on the accounting and bookkeeping niche.Coordinate cross-departmental efforts to design, launch, and optimize multi-channel lead acquisition campaigns, including email, events, webinars, paid social, and Account-Based Marketing (ABM) initiatives.Gain in-depth knowledge of Relay's product offerings and align your demand generation initiatives with our product vision and Ideal Customer Profile (ICP).Work alongside Sales and RevOps teams to create and refine the lead handoff process, leveraging conversion data and feedback to enhance funnel efficiency and drive revenue growth.Collaborate with the Events and Community team to promote Relay's partner program and enhance the visibility of partner resources and benefits.Define metrics such as Marketing Qualified Leads (MQL) and Sales Qualified Leads (SQL), and monitor the performance of the sales-assisted channel, providing insights on effective strategies.

Join Jobber as a Senior Product Manager focusing on Payments Growth and play a pivotal role in enhancing our payment solutions. As part of our dynamic team, you will strategize and execute initiatives that drive adoption and growth of our payments products. Your insights will help shape our product roadmap and ensure we deliver exceptional value to our customers.

About Flywheel Digital Flywheel Digital partners with global brands to deliver digital commerce solutions that drive growth across major online marketplaces. Clients benefit from near real-time analytics designed to increase sales, market share, and profitability. With teams located in the Americas, Europe, and APAC, Flywheel Digital offers career paths with meaningful impact and opportunities for growth. Role Overview The AI Demand Innovation Specialist will join the Sales department in Toronto, Ontario. This role focuses on optimizing Flywheel Digital’s AI-driven technology stack, managing integrations, and supporting pipeline campaigns for the Sales team. The position also plays a key part in supporting data-driven decisions across the revenue organization. What You Will Do Optimize and manage AI-driven technology platforms and their integrations. Support sales pipeline campaigns by ensuring technology and data are aligned with business goals. Collaborate with sales, marketing, and revenue operations to improve operational processes. Promote data-driven decision-making throughout the revenue organization. Influence the way tools, data, and AI automation are used to accelerate growth. What We’re Looking For Extensive experience with Salesforce and HubSpot (both Marketing and Sales Hub). Strong background working with go-to-market technologies. Comfortable collaborating across sales, marketing, and revenue operations teams. Detail-oriented and proactive approach to building scalable processes. Interest in bridging sales and marketing through technology and AI. Location This position is based in Toronto, Ontario, Canada.

Role overview Marqeta seeks a Senior Product Manager with a focus on Tokenization to help shape payment solutions. This position is based in Toronto or Vancouver, Canada. The work centers on advancing how payments are secured and managed through tokenization technologies. What you will do Lead the development of tokenization features and improvements for Marqeta’s payment platform. Collaborate with engineering, design, and business teams to deliver solutions that address client needs. Define and guide the product strategy and roadmap for tokenization projects. Analyze market trends and gather customer feedback to inform product decisions. Ensure new features deliver clear value to clients and enhance the platform’s capabilities. What sets this role apart This position calls for strong collaboration skills, a deep understanding of the payments industry, and the ability to turn market insights into practical product plans. Success depends on connecting industry trends with client needs to drive effective product development.

Relay is a cutting-edge digital banking platform designed to empower self-made business owners with the financial tools and knowledge they need to excel. We aim to transform financial uncertainty into clear visibility, enabling our users to convert hard work into sustainable success. By providing clarity, confidence, and control over every dollar earned, we facilitate the growth of resilient businesses.As part of our dynamic Engineering team, you will play a pivotal role in developing banking products that support millions of small businesses. We are on an exciting journey to reinvent the banking experience, and we are searching for a curious and impact-driven Software Engineer to join our expanding team. This role is perfect for someone who thrives on taking calculated risks, embracing experimentation, and learning from challenges.In this position, you will confront complex challenges head-on, deliver high-quality, robust code, and contribute to systems that power our innovative products. This unique opportunity allows you to work across our entire product suite, influence technical decisions, and deliver features that our customers will love. If you are passionate about creating top-tier fintech solutions in a fast-paced and collaborative environment, this is the ideal role for you.

Resource Innovations is seeking a skilled Impact Evaluation Manager to join our dynamic team. This remote position focuses on delivering technical support and project management within our Advisory Services Group, emphasizing energy efficiency program design, execution, and assessment. You will be responsible for steering impact evaluations while providing engineering and analytical expertise.Your key responsibilities will include leading impact evaluations, supervising junior engineers and analysts, and reviewing project deliverables to maintain quality for client submissions. You will also ensure that impact evaluations and associated projects are executed on time and within financial constraints. Candidates with a minimum of 5 years of relevant professional experience are strongly encouraged to apply.At Resource Innovations, we are a women-led energy transformation enterprise dedicated to creating a significant impact. By leveraging our knowledge in energy efficiency, we continuously expand our suite of clean energy solutions, assisting utilities in addressing increasingly complex challenges such as load flexibility, electrification, and carbon reduction. We are committed to driving transformative change at every stage.

At Relay, we are on a mission to empower self-made business owners through our innovative digital banking platform. Our goal is to provide these entrepreneurs with the financial clarity, confidence, and control needed to transform their hard work into enduring success. By eliminating the uncertainties of finance, we help turn cash flow from a source of stress into a powerful tool for building robust and resilient businesses.Our Engineering team plays a pivotal role in creating banking products that drive the success of millions of small businesses. As we embark on a transformative journey in the banking sector, we are seeking a passionate and impact-oriented Senior Software Engineer to join our expanding team. We value individuals who embrace smart risks, boldly experiment, and learn from challenges.In this role, you will confront complex challenges, deliver high-quality and robust code, and help shape the systems that underpin our products. This is a unique opportunity to engage with our entire product suite, influence technical decisions, and implement features that our customers adore. If you are eager to create top-tier fintech products within a fast-paced, collaborative environment, this position is perfect for you.Key ResponsibilitiesFull-Cycle Development: Take ownership of features throughout the entire development lifecycle—from design and development to testing, deployment, and monitoring—ensuring reliability and performance at scale.Infrastructure Management: Oversee our production systems, enhance infrastructure, and contribute to the availability, scalability, and resilience of our platform.Collaborative Partnership: Work closely with Product, Design, and cross-functional teams to develop solutions that align with customer and business needs.Innovative Mindset: Proactively seek out opportunities for technical, process, and product enhancements, driving the team to elevate standards and influence long-term technical strategies.Your QualificationsA minimum of 3 years of experience in full-stack software engineering.Demonstrated leadership in developing significant components or features, successfully delivering them with minimal oversight.Experience mentoring junior engineers, sharing knowledge, and fostering the growth and skill development of the entire team.

About Us:At Financeit, we are a leading provider of point-of-sale financing, catering to some of the most prominent home improvement and retail organizations across Canada. Our innovative platform empowers businesses to enhance their sales capabilities by providing customers with attractive monthly payment options for significant purchases, whether it's a home improvement project, vehicle acquisition, or retail shopping.We foster an environment where your contributions truly matter. With a culture grounded in collaboration, inclusivity, fairness, and respect, Financeit is not just a workplace; it's a community. If you resonate with our values and are eager to make a meaningful impact, we invite you to explore this opportunity with us.Position Overview:Are you passionate about leveraging data and technology to simplify complex challenges? Do you have a keen interest in the realms of indirect consumer lending, capital markets, and fintech? If so, this role is tailored for you! As the Senior Manager of Commercial & Channel Risk Strategy, you will be pivotal in shaping risk management strategies for our key verticals, focusing on home improvement and powersports lending.Reporting to the Director of Risk Strategy, you will spearhead initiatives to develop robust channel risk management frameworks, optimize profitability, and mitigate risk across our product offerings, including multi-stage project financing. Your exceptional analytical skills and strategic mindset will be essential as you navigate this dynamic landscape.If you possess outstanding collaboration and communication skills, along with a sense of fun, we want to hear from you!

Starling Bank is the pioneering digital bank in the UK, dedicated to transforming the banking experience for over 4 million customers! Our innovative technology empowers individuals to save, spend, and manage their finances seamlessly. Introducing… Engine by Starling.Engine by Starling is our software-as-a-service (SaaS) division, designed to provide the same cutting-edge technology that drives Starling Bank. Recently established as an independent entity, we are eager to partner with forward-thinking banks globally to fuel their growth with our robust technology.This platform is now accessible to banks and financial institutions worldwide, offering them the chance to leverage innovative digital features and streamlined back-office processes that contribute to Starling's success.At Engine by Starling, we prioritize our technologists who thrive in a dynamic environment focused on innovation and collaboration. We maintain a flat organizational structure that empowers team members to make impactful decisions. In our open culture, support is always within reach, ensuring we succeed together!To excel at Engine, you must be self-motivated and take full ownership of your responsibilities—from building and designing to sharing insights and ensuring efficiency in our processes, all aimed at delivering outstanding results for our customers. Our mission is guided by five core values: Listen, Keep It Simple, Do The Right Thing, Own It, and Aim For Greatness.Hybrid WorkingWe embrace a hybrid work model at Engine, favoring team members who can commute to our Toronto office to foster in-person collaboration.About the RoleAs a Senior Solutions Engineer, you will leverage your expertise in Engine's technology and architecture to articulate our product offerings, identify client needs, and design tailored solutions.Your role will encompass both the sales and delivery phases of projects, as well as ongoing client success, collaborating with diverse teams across Technology, Delivery, Product, Client Success, and Business Development.

Join our dynamic team at oliverusa as a Senior Project Manager, where you will lead and manage high-impact projects that drive our business forward. In this role, you will collaborate with cross-functional teams to ensure successful project delivery, maintain timelines, and meet budget requirements while ensuring quality standards are upheld.

About BreeBree is an innovative consumer finance platform dedicated to transforming financial services for the over half of Canadians living paycheck to paycheck. Operating in a largely untapped market, we aim to be the leading provider of affordable short-term credit solutions for the 20 million Canadians in need. Our mission is to deliver faster, better, and more cost-effective financial services to our users.With over 600,000 satisfied customers, Bree is poised for exponential growth. We have achieved product-market fit and are on a clear trajectory to become one of Canada's most impactful FinTech companies. Currently generating 8-figure annual revenues, we are profitable and experiencing double-digit growth each month. Our exceptional work culture is evident in our low employee turnover, and we proudly participated in Y Combinator in 2021, securing a $2M seed round shortly thereafter.About the RoleWe are seeking a talented Senior Product Designer to lead the evolution of Bree’s product offerings. This pivotal role entails substantial ownership and influence, working across mobile and web platforms to define challenges, develop solutions, and implement meaningful improvements for our users. You will collaborate closely with Product and Engineering teams, applying thoughtful product judgment and clear decision-making to enhance user experiences.

About Wealthsimple Wealthsimple Technologies Inc. is a leading Canadian fintech company based in Toronto. Serving over 3 million clients and managing more than $100 billion in assets, Wealthsimple focuses on making financial services straightforward, transparent, and affordable. The team values innovation, ownership, and a genuine commitment to clients. For more about the company's values and work environment, visit the Culture Manual and careers page. Role Overview: Senior Technical Specialist - Corporate Security This full-time, on-site position is based in Toronto and requires presence in the office five days a week. The Senior Technical Specialist will lead and improve Wealthsimple’s Physical Protection System (PPS). The role centers on ensuring the effectiveness and security of all technical physical security measures, including access control, video surveillance, and intrusion detection systems. Day-to-day work involves managing technical projects from start to finish, maintaining strong partnerships with security integrators, and serving as the subject matter expert for Genetec Security Centre across all corporate locations. Staying current with security technologies, industry standards, and emerging threats is essential to proactively identify and address risks. What You Will Do Oversee all aspects of the Physical Protection System (PPS), using Genetec Security Centre as the main platform. This includes system configuration, maintenance, troubleshooting, and performance optimization across multiple sites. Serve as the primary contact for PPS issues. Conduct root cause analysis and work with the security integrator and internal IT teams to resolve defects. Manage and strengthen the relationship with Wealthsimple’s security integrator, ensuring service level agreements (SLAs) and quality standards are met. Who Thrives in This Role This position calls for a detail-oriented professional with deep technical knowledge, strong project management abilities, and clear communication skills across teams and departments.

At Veeva, we are seeking an experienced and dynamic Senior Product Manager to join our innovative team in Toronto. This role offers an exciting opportunity to lead product strategy and development, driving forward our vision in the life sciences industry. You will collaborate with cross-functional teams to define product requirements, prioritize initiatives, and ensure successful product launches.The ideal candidate is a strategic thinker with a proven track record in product management, coupled with a passion for delivering exceptional customer experiences. If you thrive in a fast-paced environment and are eager to make a significant impact, we would love to hear from you.

As a Senior Digital Account Executive at Tipalti, you will be an integral part of our vibrant sales team, driving the growth of our innovative SaaS Fintech solution. Your primary objective will be to meet revenue targets through proactive outbound sales and nurturing inbound leads generated collaboratively by our talented Sales Development Representatives (SDRs), marketing team, and strategic alliance partners.To facilitate your success, we invest significantly in our sales infrastructure, equipping you with an advanced technology stack. You will utilize tools such as Salesforce, Outreach, ZoomInfo, 6Sense, LinkedIn Sales Navigator, Chorus, and Clari to effectively engage with prospects.This role requires you to cultivate strong relationships and deliver customized solutions that cater to the distinct needs of our clients. A proactive mindset, results-driven approach, excellent communication skills, and a thorough understanding of our offerings are essential for success in this position.Why Join Tipalti?Tipalti is among the fastest-growing fintech companies globally, empowering finance professionals to excel by modernizing the entire payables operation. Backed by prestigious investors, our late-stage startup secured $270 million in our Series F funding round in 2021, valuing us at over $8.3 billion with total funding exceeding $550 million and a growing base of over 4,000 global customers. We are one of the most valuable private fintech companies in the world.At Tipalti, we celebrate a collaborative culture, high-quality products, and the exceptional capabilities of our team. Our Tipaltians are passionate about their work and committed to achieving results. We offer competitive benefits, a flexible work environment, career coaching, and a space where diverse individuals can thrive and make an impact. Our culture fosters humility and teamwork, ensuring everyone is ready to pursue success together.What You'll Do:Manage the entire sales cycle, from prospecting through to deal closure.Consistently meet or exceed sales quotas to drive revenue growth in your territory.Demonstrate a strong understanding of the value of Tipalti's products and effectively communicate their business impact to key decision-makers.Source new opportunities by meeting activity metrics.Collaborate closely with internal teams to ensure client needs are addressed.Independently create a comprehensive sales strategy leveraging ROI tools and sales plans to ensure consistent goal achievement in both the short and long term.

Join Xplor Technologies as a Senior Product Manager where you will play a pivotal role in driving the product vision and strategy. You will collaborate with cross-functional teams to develop and enhance our product offerings, ensuring they meet market demands and customer needs. Your insights will be pivotal in shaping our roadmap and influencing product features.