Hey there! We’re ContactMonkey 👋

Our mission? To power measurable employee engagement worldwide. And we’d love for you to join us!

About the job - Principal Product Marketing Manager

ContactMonkey is repositioning from the best internal email tool to an intelligent communication effectiveness platform — with AI capabilities (ConfidenceCheck, CoAuthor, Audience Preview, Insights Assistant) that are genuinely first in the category. To carry that story to market with the depth it deserves, we’re creating a dedicated, senior product marketing role reporting directly to the CPTO. You won’t be starting from a blank page or working alone. Our team has already done real groundwork — a clear strategic narrative, shipped differentiators, an active launch process, and a healthy content and demand-gen engine — and you’ll build on it. You’ll also partner closely with a dedicated marketer who knows our audience and brand voice inside out. Product marketing is a distinct craft, and we’re now investing in it as a dedicated, senior discipline; your job is to bring that depth and take the story the rest of the way. This is a super-IC role for someone who wants maximum scope and autonomy, not headcount. You’ll operate as a peer to product and sales leadership, working through a virtual team (PMs, sales enablement, content marketing, design) rather than direct reports.

What you’ll own

Positioning & messaging. Drive our positioning evolution to completion: new messaging architecture, persona and segment narratives, stop / start language for GTM, and a single current source of truth that replaces our legacy messaging guide. You own how the company talks about the product — internally and externally. A seat inside the product team. You’re not a downstream recipient of the roadmap — you’re a core member of the product group, shaping strategy, prioritization, and feature definition with a market and customer lens. When we decide what to build, how to sequence it, and how to package it, you’re in the room. Customer & market insight. Own the qualitative and quantitative work — customer conversations, win / loss, competitive dynamics, market trends — that tells us what’s actually true about our buyers, and feed it into both positioning and the roadmap. You’re the closest person to the buyer who isn’t carrying a quota. (Analyst relations is nascent for us — an area to grow into over time, not a day-one mandate.) Competitive strategy. Build the competitive program: battlecards for our full competitor set, win / loss analysis, talk tracks by buyer (comms leaders vs IT / InfoSec vs execs), and comparison content. Today this work is scattered across sales, sales engineering, and product — you’ll consolidate it under one owner with one standard. Launch & commercialization. Own the GTM layer of our launch process (the tiering playbook and launch infrastructure already exist). Partner with the marketing team on launches and commercialize what’s already shipped — several flagship capabilities are live but commercially invisible. “Built but untold” is the first backlog you’ll inherit. Sales & CS readiness. Partner with marketing to create decks, one-pagers, objection handling, demo narratives, enablement sessions — built around buyer pain and our narrative spine, not feature lists. Partner with sales enablement on delivery; you own the content and the story. Pricing & packaging narrative. Partner with the CPTO and RevOps on packaging decisions and own how tiers and value are communicated to buyers, customers, and internal teams. Cross-functional partnership. Keep positioning consistent, differentiated, and grounded in product truth across product, design, engineering, and the rest of marketing. You’ll lead without authority — influence, not org chart, is how the job gets done.

What you won’t own

Demand generation, SEO, paid, brand, and the content calendar — we have a marketing team that runs that engine well. You’ll feed it positioning and product stories; they’ll amplify them.

First two quarters, concretely

Ship the new positioning and messaging house; retire the legacy guide; train GTM on the new language. Stand up the competitive program — primary competitors covered, single battlecard standard, win / loss loop running. Take our pre-send AI story to market properly: category framing (“the only native pre-send quality layer”), comparison assets, updated landing pages and sales deck. Commercialize the shipped-but-untold features with deck sections, one-pagers, and 2–3 customer proof stories. Build the differentiator one-pager library and close out pricing collateral gaps.

About you

8+ years in B2B SaaS product marketing, mid-market / enterprise sales-led motions; you’ve been the most senior PMM in a company before, ideally the only one. You’ve personally led a repositioning (point solution → platform) and lived with the results — not just shipped the deck. Deep positioning craft (Dunford-style), strong competitive instincts, and a portfolio of sales-facing work that reps actually used. You’ve marketed AI capabilities credibly — narrative and sequencing, not buzzwords. Operate autonomously from a strategic brief; communicate at SLT level; comfortable influencing without authority across product, sales, and marketing. Bonus: internal comms / employee experience / HR tech market exposure; experience with pricing & packaging work.

Why this role is rare

Most senior PMM roles are either strategy-without-access or execution-without-influence. This one reports to the CPTO, inherits a written strategic direction with executive sponsorship, and has visible, high-leverage gaps to close in the first 90 days. The wins are sitting on the shelf.

What we bring to the table

🏥 100% employer-paid benefits and a Health Spending Account from day one 🌎 Work from anywhere in the world for up to 4 weeks 💰 Stock option plan—own a piece of our success 💲 RRSP Group Savings Plan to plan for your future 🏝 Generous vacation package to recharge and relax 📚 Personal development budget to fuel your growth 🧖 One personal day and two volunteering days to give back 🎂 Your Birthday off—celebrate on us! 🍎 Five health days per year to stay at your best 💼 Beautiful downtown Toronto office for hybrid work—fully stocked with all the best snacks Compensation & Work Details The salary range for this role is $175,000-$200,000+ CAD. Compensation is thoughtfully determined based on your experience, skill set, and alignment with our internal compensation framework and internal equity. We’re always happy to answer questions about compensation throughout the hiring process. This is a net new position based out of our downtown Toronto office, at King and Spadina. Our team works in the office 3x per week to promote collaboration Who We Are Imagine being part of a team of brilliant minds, all shaping the future of workplace communication. Here at ContactMonkey, we’re not just sending out traditional emails with our internal comms software; we’re changing the way companies connect and communicate with their people. Brands like IKEA, Roku, KMPG, and countless others are using our solution to transform employee engagement. Our all-in-one platform—featuring a drag-and-drop email builder, engagement tools, and analytics—makes it easy for businesses to create, send, and measure their internal email campaigns directly within Outlook or Gmail. This way, internal communications go from being ignored to binge-worthy, sparking more opens, clicks, and conversations. We’ve been on an explosive growth streak over the past few years, and we’re not slowing down anytime soon. Here’s a bit of what we’re proud of: Ranked by the Globe & Mail as one of Canada’s fastest-growing companies Recognized in 2023, 2024 and 2025 Deloitte Technology Fast 50™ awards for revenue growth over the past four years Recognized in 2023, 2024 and 2025 Deloitte Technology Fast 500™ as one of the fastest-growing companies in North America Raised $55 million Series A financing in 2023 Diversity is our strength At ContactMonkey, we are building diverse products and we need a diverse team to do that. We strongly encourage applications from everyone regardless of race, religion, colour, national origin, gender, sexual orientation, age, marital status, or disability status. We are committed to creating an accessible experience for all candidates. If you require any accommodations or adjustments during the interview process or beyond, please inform us, and we will work with you to ensure the necessary support is in place. We are continually striving to enhance our accessibility practices and welcome any feedback or suggestions on how we can better serve candidates with accessibility.

AI Disclosure

We use AI to take notes during our interview. Applications and interviews are reviewed by our Talent Acquisition team. Our applicant tracking system utilizes AI for workflows and hiring process efficiencies.