
Paddle · Toronto
What do we do? Paddle offers digital product companies a completely different approach to their payment infrastructure. Instead of assembling and maintaining a...
What do we do?
Paddle offers digital product companies a completely different approach to their payment infrastructure. Instead of assembling and
maintaining a complex stack of payments-related apps and services, we're a Merchant of Record for our customers. That means we
take away 100% of the pain of payment fragmentation. It's faster, safer, cheaper, and, above all, way better.
We're backed by investors including KKR, FTV Capital, Kindred, Notion, and 83North and serve over 6,000 software sellers in 245
territories globally.
We’re hiring a Customer Marketing Lead to own Paddle’s customer storytelling, advocacy, and community-building efforts, supporting
both our PLG and sales-led motions. This role turns customer success into scalable proof, and customer engagement into long-term
advocacy that drives acquisition, conversion, and expansion.
You’ll develop high-impact customer stories, commercial insights, and references, while also building community connections that
fuel events, ABM, campaigns, and content. Crucially, you’ll act as a conduit for customer insights, capturing and surfacing key
feedback themes from our most engaged customers to influence GTM strategy, messaging, and product development.
You’ll operate across marketing, sales, product, and customer success to ensure that the voice of our customer is not only heard
but leveraged to accelerate growth.
campaigns, PLG sign-up flows, and sales conversations.
for different personas, stages, and regions.
marketing, and product initiatives.
and Revenue Marketing to sharpen ICP understanding, campaign messaging, and product prioritisation.
events, campaigns, or outbound ABM plays.
messaging.
accelerate deals.
ownership of post-sale outcomes such as adoption, retention, or expansion
not just content libraries or asset counts
marketing can influence outcomes at every stage
signals, and behavioural data to prioritise activity and report ROI to senior leadership
design a retention strategy
opinions about how they should reshape customer marketing from research and writing to personalisation and signal monitoring
insight synthesis, agent-assisted lifecycle triggers, or similar
landscape evolves
including executive sponsors and champions
marketing
Everyone is welcome at Paddle
At Paddle, we're committed to removing invisible barriers, both for our customers and within our own teams. We recognise and
celebrate that every Paddler is unique and we welcome every individual perspective. As an inclusive employer we don't care if, or
where, you studied, what you look like or where you're from. We're more interested in your craft, curiosity, passion for learning
and what you'll add to our culture. We encourage you to apply even if you don't match every part of the job ad, especially if
you're part of an underrepresented group.
Please let us know if there's anything we can do to better support you through the application process and in the workplace. We
will do everything we can to support any accommodations needed. We're committed to building a diverse team where everyone feels
safe to be their authentic self. Let's grow together.
Our Values
Paddle Together - "None of us, is as smart as all of us"
Paddle Simply - "Simple can be harder than complex: you have to get your thinking clean to make it simple"
Paddle for others - "We can realise our wildest dreams, so long as we help enough other people to realise theirs"
Why you'll love working at Paddle
We are a diverse, growing group of Paddlers across the globe who pride ourselves on our transparent, collaborative and respectful
culture.
We are a 'digital-first' company, which means you can work remotely, from one of our stylish hubs, or even a bit of both! We offer
all team members unlimited holidays and 4 months paid family leave regardless of gender. We invest in learning and will help you
with your personal development via constant exposure to new challenges, an annual learning fund, and regular internal and external
training.
Upwork Inc.’s (Nasdaq: UPWK) family of companies connects businesses with global, AI-enabled talent across every contingent work type including freelance, fractional, and payrolled. This portfolio includes the Upwork Marketplace, which connects businesses with on-demand access to highly skilled talent across the globe, and Lifted, which provides a purpose-built solution for enterprise organizations to source, contract, manage, and pay talent across the full spectrum of contingent work. From Fortune 100 enterprises to entrepreneurs, businesses rely on Upwork Inc. to find and hire expert talent, leverage AI-powered work solutions, and drive business transformation. With access to professionals spanning more than 10,000 skills across AI & machine learning, software development, sales & marketing, customer support, finance & accounting, and more, the Upwork family of companies enables businesses of all sizes to scale, innovate, and transform their workforces for the age of AI and beyond. Since its founding, Upwork Inc. has facilitated more than $30 billion in total transactions and services as it fulfills its purpose to create opportunity in every era of work. Learn more about the Upwork Marketplace at Upwork.com and follow us on LinkedIn, Facebook, Instagram, TikTok, and X; and learn more about Lifted at Go-Lifted and follow on LinkedIn. ---------------------------------------------------------------------------------------------------------------------------------- Upwork’s Marketing Analytics team is focused on optimizing our growth engines through rigorous experimentation and data-driven decision making. This role sits at the intersection of product and marketing, driving measurement and experimentation across the customer funnel to improve acquisition, engagement, and conversion. You will partner cross-functionally with product, marketing, SEO, and data science teams to design experiments, analyze user behavior, and build frameworks that inform growth strategy. This role also supports understanding organic discovery, including traditional search and emerging AI-driven discovery surfaces. YOUR RESPONSIBILITIES: * Organic & AI Discovery Analytics: Support analysis of organic channels, including SEO and emerging AI-driven discovery (e.g., ChatGPT, Gemini). Evaluate performance signals such as engagement, traffic, and visibility. * Strategic Communication: Present insights and recommendations to marketing leadership, influencing growth strategy and prioritization. * Experimentation & Testing: Design, execute, and analyze A/B and incrementality tests. Define hypotheses, success metrics, and test duration, and conduct deep post-test analysis to inform decisions. * Drive insights that improve conversion, engagement, and overall growth. * Data Extraction & Technical Analysis: Extract and analyze large datasets using SQL, Python, or R to support experimentation, user behavior analysis, and growth initiatives. * Experimentation Tooling: Utilize platforms such as Statsig, Optimizely, VWO, or similar tools to implement and monitor experiments across experiences. * SEO Tooling: Leverage tools such as Google Search Console, SEMrush, Ahrefs, or similar to explore keyword performance and on-site engagement trends. WHAT IT TAKES TO CATCH OUR EYE: * A degree in Mathematics, Statistics, Economics, Computer Science, or a related quantitative field. * Proven experience designing and executing experiments (A/B, multivariate, incrementality), including hypothesis development, metric definition, sample sizing, and post-test analysis. * Experience in marketing or growth analytics, with a strong focus on customer funnels, acquisition, and conversion optimization. Experience with organic search and SEO analytics. * Technical Proficiency: Strong SQL skills and proficiency in Python or R for analyzing large datasets and supporting experimentation and analytics workflows. * Experimentation Tools: Experience with platforms such as Statsig, Optimizely, VWO, or similar tools used to run and monitor experiments. * BI tools such as Looker or Tableau. (SEO-specific tools are a plus, e.g., Google Search Console, SEMrush, Ahrefs, Botify, Screaming Frog) * Testing & Statistical Knowledge: Strong foundation in experimental design, statistical significance, and methods to measure incremental impact. * Marketplace Context: Previous experience in a two-sided marketplace or consumer tech environment will be highly regarded. ---------------------------------------------------------------------------------------------------------------------------------- Come change how the world works. Upwork is establishing an operational hub in Toronto, Canada. The new office is expected to be fully operational by Q4 2026. This role will require 3 days in office once we have an office open. This position will initially be employed through a partner to ensure a seamless hiring process while we establish the hub. Once the hub is established, there may be opportunities to transition to employment with Upwork, depending on business needs and other requirements. While employed by the partner, you’ll work as part of Upwork’s team, with access to our resources, culture, and growth opportunities. Our partner will offer competitive benefits. When Upwork’s hub is established, we will be excited to offer employment and benefits directly as business needs require. Upwork is committed to building a diverse, inclusive, and equitable workforce. Employment decisions are made without regard to race, color, religion, gender, sexual orientation, gender identity, national origin, disability, or any other status protected by applicable law. We use BrightHire, an AI-enabled tool, to record interviews and summarize interview transcripts. The tool allows the interviewer to focus on the discussion and does not score or evaluate candidates or make recommendations. The interview transcripts are reviewed, and decisions are only made by humans. Candidates who prefer not to have their interview recorded through BrightHire can opt out when the interview is scheduled. To learn more about how Upwork processes and protects your personal information as part of the application process, please review our Global Job Applicant Privacy Notice and the Applicant Privacy Addendum (Canada). The annual base salary range for this position is displayed below. The range displayed reflects the minimum and maximum salary for this position, and individual base pay will depend on your skills, qualifications, experience, and location. Additionally, this position is eligible for the annual bonus plan or sales incentive plan and eligibility to participate in our long term equity incentive program. Annual Base Compensation $135,500—$212,000 CAD To learn more about how Upwork processes and protects your personal information as part of the application process, please review our Global Job Applicant Privacy Notice
What do we do? Paddle offers digital product companies a completely different approach to their payment infrastructure. Instead of assembling and maintaining a complex stack of payments-related apps and services, we're a Merchant of Record for our customers. That means we take away 100% of the pain of payment fragmentation. It's faster, safer, cheaper, and, above all, way better. We're backed by investors including KKR, FTV Capital, Kindred, Notion, and 83North and serve over 6,000 software sellers in 245 territories globally. The Role We're looking for a Senior Product Marketing Manager to own the positioning, messaging, and go-to-market strategy for core areas of Paddle's product suite. This is a high-impact individual contributor role at the heart of our marketing function. You will be the connective tissue between Product, Sales, and Marketing translating deep customer and market insight into commercially sharp narratives that drive awareness, conversion, and revenue. You'll shape how we go to market, how we equip our sales teams to win, and how we position Paddle for differentiation. The most successful candidate will be a master at aligning launch objectives to commercial value, connecting every GTM motion directly to business outcomes. Operating with a high degree of autonomy, you'll lead complex cross-functional workstreams, use data and AI-powered tools to accelerate your craft, influence strategic decisions, and mentor peers across the team. This role is ideal for someone who thrives at the intersection of strategy and craft: a rigorous thinker who can also write a killer one-pager, run a crisp competitive briefing, and land a product launch with measurable impact. WHAT YOU'LL DO Own positioning and messaging - Develop and maintain differentiated positioning and messaging for key product areas, grounded in deep customer, market, and competitive insight. - Translate complex product capabilities into clear, compelling narratives tailored to distinct buyer segments and personas. - Ensure message consistency across all touchpoints website, sales collateral, campaigns, and executive communications. Drive go-to-market strategy and execution - Lead end-to-end GTM strategy for major product launches, from discovery and segmentation through to launch and post-launch measurement. - Define launch objectives, success metrics, and cross-functional plans in partnership with Product, Sales, and Marketing teams always anchored to commercial & business outcomes - Tie every launch plan directly to commercial value: align messaging, timing, and channel mix to where deals are won and revenue is made. - Continuously improve GTM playbooks based on performance data, win/loss signals, and pipeline impact learnings. Enable the commercial team - Create high-impact sales enablement materials including pitch decks, battlecards, objection-handling guides, demo narratives, and ROI tools that equip Sales and Customer Success to win, expand, and defend revenue. - Run training sessions and competitive briefings to keep the commercial team sharp and confident on product differentiation. - Measure enablement effectiveness through content adoption, win rate trends, and deal velocity and use those signals to sharpen the assets over time. - Partner with Revenue Operations to embed commercial messaging into the sales process and CRM workflow. Be the voice of the customer and market - Design and run qualitative and quantitative research programmes (win/loss interviews, customer surveys, persona studies) to develop a deep understanding of buyer motivations, pain points, and decision-making. - Own competitive intelligence for your product area, tracking competitor moves, synthesising insights, and equipping the business to respond. - Surface customer and market insights to influence product strategy and roadmap prioritisation. Shape category and brand narrative - Contribute to Paddle's broader category positioning and thought leadership strategy in collaboration with Brand and Content teams. - Partner with the executive team on key narratives for analyst relations, investor communications, and major industry moments. Measure and prove commercial impact - Own the PMM measurement framework for your area: define success metrics for positioning work, product launches, and sales enablement that connect directly to business outcomes - Leverage data to track launch performance, content usage, win/loss trends, and competitive displacement and use those insights to make better decisions faster. - Work with Revenue Operations and Analytics to model the commercial impact of GTM initiatives and clearly articulate the ROI of positioning and research programmes to senior stakeholders. - Bring a data-first mindset to every strategic decision: use quantitative signals alongside qualitative insight to prioritise, adjust, and prove impact. Accelerate with AI and agents - Use AI tools and agents actively to compress research cycles from competitive monitoring and win/loss synthesis to persona development, message testing, and brief generation. - Build AI-assisted workflows that accelerate content creation and sales asset production without sacrificing quality or strategic rigour. - Experiment with emerging agentic tooling to automate repeatable PMM tasks, freeing capacity for higher-leverage strategic work. - Share AI workflows, prompts, and best practices with the wider PMM team to raise productivity and capability across the function. Mentor and raise the bar - Act as an informal leader and mentor to more junior PMMs, sharing frameworks, reviewing work, and helping the team grow. - Contribute to the development of team processes, playbooks, and standards that improve the quality and velocity of PMM output. We'd love to hear from you if you are - An experienced product marketer with 8+ years in B2B SaaS product marketing, ideally in payments, fintech, or developer/platform tooling. - A masterful storyteller who can distil complex, technical concepts into messaging that resonates with both technical and business buyers. - Commercially sharp, with strong instincts for how product positioning translates into pipeline and revenue and a proven track record of tying GTM strategy to measurable commercial outcomes. - A master at aligning launch objectives to commercial value: you connect positioning decisions to where deals are won, where revenue is lost, and what moves the number. - A confident cross-functional operator who can align and influence Product, Sales, and Marketing leaders without formal authority. - Highly autonomous and structured, able to manage multiple complex workstreams simultaneously and deliver to a high standard with limited oversight. - Experienced in running customer research and using insight to inform strategy, not just validate it. - A skilled writer who takes genuine pride in the quality of the work from a one-page positioning brief to a full sales deck. - Data-fluent and analytically rigorous: able to build and interpret PMM dashboards, model GTM impact, and connect marketing activity directly to pipeline, revenue, and retention outcomes. Comfortable working with tools like Salesforce, Amplitude, or similar to pull and synthesise commercial insight. - A practitioner-level user of AI tools and agents actively using them to accelerate competitive research, win/loss synthesis, content generation, and brief creation. Not just curious about AI; building with it every day to move faster and smarter. - Experienced with agentic workflows and prompt engineering as a craft, and enthusiastic about sharing those capabilities to raise the ceiling of what the PMM team can produce. Everyone is welcome at Paddle At Paddle, we're committed to removing invisible barriers, both for our customers and within our own teams. We recognise and celebrate that every Paddler is unique and we welcome every individual perspective. As an inclusive employer we don't care if, or where, you studied, what you look like or where you're from. We're more interested in your craft, curiosity, passion for learning and what you'll add to our culture. We encourage you to apply even if you don't match every part of the job ad, especially if you're part of an underrepresented group. Please let us know if there's anything we can do to better support you through the application process and in the workplace. We will do everything we can to support any accommodations needed. We're committed to building a diverse team where everyone feels safe to be their authentic self. Let's grow together. Our Values Paddle Together - "None of us, is as smart as all of us" Paddle Simply - "Simple can be harder than complex: you have to get your thinking clean to make it simple" Paddle for others - "We can realise our wildest dreams, so long as we help enough other people to realise theirs" Why you'll love working at Paddle We are a diverse, growing group of Paddlers across the globe who pride ourselves on our transparent, collaborative and respectful culture. We are a 'digital-first' company, which means you can work remotely, from one of our stylish hubs, or even a bit of both! We offer all team members unlimited holidays and 4 months paid family leave regardless of gender. We invest in learning and will help you with your personal development via constant exposure to new challenges, an annual learning fund, and regular internal and external training.
Reddit is a community of communities. It’s built on shared interests, passion, and trust, and is home to the most open and authentic conversations on the internet. Every day, Reddit users submit, vote, and comment on the topics they care most about. With 100,000+ active communities and approximately 126 million daily active unique visitors, Reddit is one of the internet’s largest sources of information. For more information, visit www.redditinc.com. We are looking for a Senior Client Account Manager to join the Retail vertical of our Large Customer Sales team in Canada. This person will closely collaborate with a Client Partner on campaign execution and optimizations to help agencies and advertisers achieve their marketing objectives on the fast-growing Reddit platform. This role is required to be based in Toronto, Ontario. Responsibilities: * Collaborate closely with Client Partners to meet and exceed your client's marketing goals * Proactively manage and deepen relationships with existing advertising partners, both with agencies and directly with clients to drive year-over-year Reddit revenue growth * Lead and execute campaign launches from start to finish, delivering insightful optimization recommendations to agency and client partners * Act as the primary point of contact for internal account operations, including managing revenue delivery, troubleshooting issues, and escalating when necessary * Educate brands and media agencies, effectively communicating Reddit’s value proposition and best practices for advertising on the platform * Consult clients on their awareness and direct response objectives, partnering closely with Client Partners to craft thoughtful and creative media plans * Collaborate with Ad Ops to ensure effective campaign delivery and resolve any technical hurdles * Dive deep into campaign performance data, audience and competitor insights, seasonality, and market and performance trends to develop KPI-driven campaign recommendations * Proactively seek and represent client needs and asks to cross-functional stakeholders * Shape Reddit’s native ads product roadmap by aggregating and sharing client feedback and campaign metrics with cross-functional stakeholders Required Qualifications: * 7-12 years of experience in advertising sales and account management * Experience working with Enterprise Retail brands * Strong understanding of customer marketing funnel and traditional marketing ecosystem * Expertise with performance/direct response campaigns * Comfortable with problems of diverse scope where analysis of data requires evaluation of identifiable factors * Understanding of Digital measurement, tracking fundamentals and mobile measurement partners * Tenacious and entrepreneurial approach to working through product, process, and client challenges * Experience cultivating strong relationships with external partners * Exceptional communication and interpersonal skills * Ability to work in a fast-paced and unstructured work environment * High attention to detail * Proficiency in Excel preferred * BA / BS degree or equivalent work experience Benefits: * Global Benefit programs that fit your lifestyle, from workspace to professional development to caregiving support * Family Planning Support * Gender-Affirming Care * Mental Health & Coaching Benefits * Comprehensive Medical Benefits & Health Care Spending Account * Registered Retirement Savings Plan with matching contributions * Income Replacement Programs * Flexible Vacation & Paid Volunteer Time Off * Generous Paid Parental Leave #LI-Hybrid #LI-ES1 #LI-onsite In select roles and locations, the interviews will be recorded, transcribed and summarized by artificial intelligence (AI). You will have the opportunity to opt out of recording, transcription and summarization prior to any scheduled interviews. During the interview, we will collect the following categories of personal information: Identifiers, Professional and Employment-Related Information, Sensory Information (audio/video recording), and any other categories of personal information you choose to share with us. We will use this information to evaluate your application for employment or an independent contractor role, as applicable. We will not sell your personal information or disclose it to any third party for their marketing purposes. We will delete any recording of your interview promptly after making a hiring decision. For more information about how we will handle your personal information, including our retention of it, please refer to our Candidate Privacy Policy for Potential Employees and Contractors. Reddit is proud to be an equal opportunity employer, and is committed to building a workforce representative of the diverse communities we serve. Reddit is committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. If, due to a disability, you need an accommodation during the interview process, please let your recruiter know.