Jayson Ambrose, Product Manager in Ottawa, ON, Canada
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Jayson Ambrose

Verified Expert  in Product Management

Product Manager

Ottawa, ON, Canada
Toptal Member Since
November 11, 2020

Jayson's approach to product engineering is systems-driven. Whether it is OKRs to communicate and measure goals, JTBD and ODI to identify the most valuable opportunities, or design thinking to develop the most innovative solutions, good systems allow disciplined teams to focus their talent where it is most effective at all times. He has a diverse background delivering technology solutions for digital advertising, user-generated content, financial services, emergency response, and telehealth.

Project Highlights

Audience Segmentation Tool for Digital Ad Targeting
Led the design and development of an audience segmentation and media planning platform that led to an acquisition.
User and Revenue Growth for Photography Marketplace
Led a growth team at a VC-backed startup resulting in significant increases to sign-up and subscription conversion rates.
Adding Data Integration Capabilities (iPaaS) for Financial Services Platform
Led the analysis of data integration needs, vendor selection, and implementation of an integration platform-as-a-service (iPaaS) for cloud-based financial services products.


Work Experience

Fractional CPO

2021 - PRESENT
  • Worked with the senior leadership team to refine the product and engineering roadmap.
  • Hired and led the product management and engineering functions.
  • Implemented product development frameworks and engineering processes, including Scrum and DevOps.

VP Product Management and Development

2017 - 2020
Xtiva Financial Systems
  • Revitalized the development of cloud-based strategic initiatives, resulting in product delivery to first enterprise customers in less than one year.
  • Created and led strategy and roadmap that included buy-vs-build recommendations to optimize resource allocation and support revenue objectives.
  • Managed and grew remote product development teams in Canada, the US, and Colombia.
  • Launched the company’s first mobile experience for financial advisors.

Director, Product Management

2015 - 2017
Audience Partners (Acquired by Altice USA)
  • Launched the company’s first B2C product from prototype to revenue in seven months. It was a self-serve ad-buying application that drove $1.5 million in revenue in its first year.
  • Delivered multiple products to the enterprise market, including Time Warner and Charter Communications.
  • Designed and implemented custom user analytics with Segment, AWS, and Confluence.

Senior Product Manager

2014 - 2014
500px (Acquired by Visual China Group)
  • Led the core application development team through UX research, design, development, and deployment of new features and improvements.
  • Led a growth team that increased visitor to sign-up conversion rate by 20%, sign-up to upgrade conversion rate by 30%, and revenue by 66% in Q2 2014.
  • Improved agile processes and communication which led to manageable and predictable sprints.

Product Manager

2007 - 2014
Filemobile (Acquired by Newzulu)
  • Launched 15 cross-platform products, including web, mobile, hyper-local, and flagship CMS.
  • Managed products that established market leadership and delivered consistent revenue growth, including 50% in FY 2013.
  • Improved project capacity over 100+ campaigns, reducing the average project time by up to 75%.
  • Deployed projects for major broadcasters and media brands, including CBC, CTV, and FOX.

Audience Segmentation Tool for Digital Ad Targeting

Led the design and development of an audience segmentation and media planning platform that led to an acquisition.

As director of product, I led the development of an audience segmentation system that made our unique home address to IP matching technology easily available to media planners. Traditional media planning software is notoriously difficult to use, and our goal was to dramatically improve non-technical users' experience.

Our initial focus was on political campaign managers—a savvy group of operators, but not technical power users.

We conducted interviews that quickly produced a prioritized list of valuable, measurable outcomes that we believed could significantly improve our product.

Next, we mapped specific product metrics to those outcomes and partnered with engineering to quickly iterate on designs. We created low-fidelity prototypes to validate key assumptions and refined the experience through interactive usability tests. We discovered a significant unmet need in the market that we were uniquely positioned to solve through this process.

Focusing on specific high-value outcomes, a disciplined approach to design and tight collaboration with engineering resulted in a clearly differentiated product that was immediately successful in the marketplace and ultimately led to an acquisition.

User and Revenue Growth for Photography Marketplace


Led a growth team at a VC-backed startup resulting in significant increases to sign-up and subscription conversion rates.

"500px is the premier community and social network for aspiring and practicing photographers. Over 15 million creatives from 195 countries come to 500px to discover and share incredible photos and gain global exposure."

As a senior product manager, I led a small team with the mandate of increasing user sign-ups and upgrades to paid memberships. Experiments included CTA position and copy to increase CTRs, improved onboarding process to increase engagement, and targeted emails to resurrect churned users.

Our process included:

• Analytics tooling in core application
• Configuration of Google Analytics and Mixpanel for funnel and cohort analysis
• Baseline reporting and analysis to produce hypotheses
• Experiment design and prioritization
• Implementation of Optimizely to conduct A/B testing

The result was a significant increase in our target metrics, including the new MRR.

Adding Data Integration Capabilities (iPaaS) for Financial Services Platform

Led the analysis of data integration needs, vendor selection, and implementation of an integration platform-as-a-service (iPaaS) for cloud-based financial services products.

Xtiva Financial Systems provides the leading and most respected sales performance management (SPM) and incentive compensation management (ICM) technology systems for the financial services industry. As the VP of product management and development, my team was tasked with increasing the speed at which we could offer new data integrations while minimizing the cost to maintain and manage those integrations.

After assessing our current and future data needs, the pace of change in standards, and considering the opportunity cost of developing and maintaining ETLs in code, the decision was made to integrate a full-featured service with our core platform. This would allow us to focus on leveraging our differentiated skills to take advantage of valuable opportunities.

With a robust integration sub-system in place, we used our deep knowledge of industry data to add dozens of new sources to support new customers while committing the bulk of our engineering team to work on our core technology.

OTT Sports Video App - Omniplatform


Led the design and development of sports streaming app for web, iOS, Android, AppleTV, GoogleTV, Amazon FireTV, and Roku.

Reporting to the SVP and GM, I was responsible for delivering a new cross-platform streaming video platform to market. Worked with internal stakeholders and technology vendors to define core features, financial model, analytics pipeline, infrastructure requirements, user experience design, and roadmap. Targeting web, iOS, Android, AppleTV, GoogleTV, Amazon FireTV, and Roku.

Scrum Product Owner Certified (SPOC)

Scrum Alliance


Practical Product Management

Pragmatic Marketing


New Product Development Certificate

Schulich Executive Education Centre


Marketing Management Certificate

Schulich Executive Education Centre


Atlassian Suite, Jira, Google Analytics, Optimizely, GIS, Web GIS, ETL


Usability Testing, Agile Software Development, Agile Product Management, Agile, Scrum, Agile Project Management, Rapid Prototyping, Requirements Analysis, B2B2C, Business to Business to Consumer (B2B2C), Design Thinking, B2C, Gamification, Key Performance Metrics, Conversion Rate Optimization (CRO)


Mixpanel, Apple TV, Android TV

Industry Expertise

High-tech Startups, Professional Services, Sports, iPaaS, Financial Services


Product Strategy, Process Improvement, Agile Product Delivery, Jobs to be Done (JTBD), Outcome-driven Innovation (ODI), Product Analytics, Team Leadership, Product Roadmaps, Product Development, User Experience (UX), B2B, SaaS, Product Management, Project Reporting, Software Implementation, Documentation, Product Owner, Analytics, Agile Leadership, Client Management, Communication, Key Performance Indicators (KPIs), Roadmaps, Technical Support, Technical Project Management, Product Launch, Mapping, Business to Business (B2B), Certified Scrum Product Owner (CSPO), Product Requirements Documentation (PRD), Minimum Viable Product (MVP), Product-market Fit, Use Case Analysis, Use Cases, User Interviews, Wireframe to Product, Wireframing, Social Networks, Social Networking, Social Media, Product Ownership, Cost Estimation, Digital Project Management, Project Budget Management, Project Planning, Remote Team Leadership, Resource Allocation, Project Management, Hiring, Multimedia, Web Platforms, Prototyping, Scope, Scope of Work, Software Consulting, B2B Product Management, SaaS Product Management, App Product Management, Business Process Re-engineering, Journey Mapping, Media, Story Mapping, Requirements & Specifications, User Stories, Videos, Websites, Feature Roadmaps, Software as a Service (SaaS), Software Project Management, Estimation & Planning, Estimations, Project Estimation, Feature Planning, User Flows, App UX, Customer-centered Product Development, Product Discovery, Strategy, Product Operations, SWOT Analysis, User Feedback, Business Transformation, Business Consulting, Structure & Organizational Design, Organizational Development, Dashboards, Data Analysis, Client Relations, Customer Journeys, Process Mapping, Workflow, Leadership, Business Operations, Enterprise, Vendor Selection, Segment.io, Product Marketing, Growth, Marketing, APIs, Integration, Vendor Management, Business Analysis, IT Business Analysis, Product Design, UX Design, REST APIs, Technical Direction, Technical Leadership, Technical Product Management, Technical Requirements, Process Analysis, Process Flows, Business Process Analysis, Process Design, Business Modeling, Business Process Modeling, Systems Analysis, Business Systems Analysis, Business Development, New Business Development, Startups, Early-stage Startups, Startup Consulting, Lean Startups, Discovery Workshops, Market Research, Market Strategy and Research Product Manager, Mobile Apps, Mobile, Technical Hiring, Go-to-market Plans, Monetization, Technical Architecture, Two-sided Marketplaces, SEO Tools, Search Engine Optimization (SEO), Video Streaming, Advertising, Business Intelligence (BI), Data Analytics, Engineering Management, Business to Consumer (B2C), Interim CPO, Management Consulting, Operational Efficiency Improvement, Operations Management, Operations Research, DataViz, Data Visualization, SQL, Cohort Analysis, Growth Hacking, Growth Strategy, Optimization, Email Marketing Automation, A/B Testing, Multivariate Testing, User Onboarding, Onboarding, Lean Experiments, Data Reporting, UX Testing, Funnel Analysis, Databases, MySQL, PostgreSQL, Vue, Business Process Automation, Business Models, Business Model Canvas, Lean Canvas, Team Management, Data Integration, Cloud Platforms, Social Media Marketing (SMM), Fintech, iOS, Google TV, Roku, Android, Cryptocurrency, Dashboard Development

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