Head of Marketing

Hybrid (3 days/week) – Toronto, ON

$140,000 - $150,000 base / $200,000 - $220,000 OTE + 0.1 - 0.25%

Your opportunity

This is a confidential search for a venture-backed, early-stage Canadian software company building an AI-enabled security and compliance platform.

The company combines software with hands-on expertise to help businesses meet complex regulatory requirements, implement and monitor security controls, manage evidence, and prepare for third-party assessments. Its customers operate in highly regulated industries where compliance is increasingly tied to their ability to win and retain valuable commercial and government contracts.

The business has established meaningful early traction and is now concentrating its go-to-market efforts on a large, underserved North American market shaped by new regulatory requirements. The company has strong customer relationships, growing website demand, productive sales and partnership motions, and a collection of specialist marketing resources already in place.

What is missing is a cohesive strategy for turning that foundation into a predictable pipeline.

You’ll lead the marketing function, reporting to the CEO and operating as a peer to the company’s sales and customer leaders. You’ll inherit a small internal team, external agencies and contractors, an established technology stack, and a meaningful budget.

The mandate is broad. You’ll own marketing strategy, product marketing, demand generation, brand, lifecycle programs, partner marketing, customer marketing, sales enablement, and performance reporting.

The company sells into industries that have historically received less attention from modern B2B software marketers. Buyers are actively searching for solutions, respond to direct engagement, and can be reached through a mix of digital, field, partner, and traditional channels.

Your job will be to understand the business deeply, identify the highest-value customer segments, determine which opportunities deserve investment, and convert a large number of promising initiatives into a focused and measurable marketing system. You should be comfortable challenging founders, setting priorities, rejecting distractions, and remaining close enough to execution to ensure the work gets done.

Key responsibilities

  • Marketing strategy: Build a cohesive plan connecting customer segments, positioning, channels, budget, pipeline, and company objectives

  • Pipeline generation: Create a more predictable contribution from marketing by improving how demand is identified, captured, qualified, nurtured, and converted

  • Go-to-market development: Build distinct but coordinated marketing motions for the company’s priority market and its more established customer base

  • Market segmentation: Use customer, sales, website, and market data to identify repeatable customer cohorts and prioritize valuable accounts

  • Product marketing: Own positioning, messaging, competitive differentiation, audience definition, launches, and commercial storytelling

  • Lifecycle marketing: Develop nurture programs across email, content, paid media, retargeting, events, and sales outreach

  • Conversion optimization: Improve website conversion, landing pages, calls to action, lead scoring, follow-up workflows, and meeting generation

  • Partner marketing: Activate relationships with service providers, advisory firms, industry groups, and strategic corporate partners

  • Sales enablement: Equip the revenue team with effective presentations, customer proof, competitive intelligence, proposals, and industry content

  • Customer marketing: Turn customer outcomes, testimonials, implementation insights, and product feedback into credible marketing assets

  • Brand and content: Establish a consistent point of view across the company’s website, content, social channels, events, announcements, and executive communications

  • Channel experimentation: Test account-based campaigns, direct mail, field marketing, associations, telephone outreach, and other channels suited to the target audience

  • Performance management: Define and report on qualified pipeline, customer acquisition cost, conversion, campaign effectiveness, and marketing-attributed revenue

  • Budget ownership: Allocate spend across internal hires, agencies, contractors, media, events, partnerships, software, and experimental programs

  • Agency management: Evaluate external partners and determine which capabilities should be retained, replaced, expanded, or brought in-house

  • Executive partnership: Turn a large volume of ideas into a focused sequence of priorities and clearly explain what the company should not pursue

  • Team building: Lead the existing marketing resources and build a small, high-output internal function as the business scales


Tech stack

  • CRM & Lead Management: HubSpot, Salesforce

  • Prospecting & Data Enrichment: Clay, LinkedIn Sales Navigator

  • Sales Engagement & Email Outreach: Unify GTM, Instantly

  • Calling: CloudTalk

  • Buyer Intent & Website Intelligence: G2, RB2B

The company is not committed to preserving its current GTM stack for its own sake. You’ll have the authority to consolidate, replace, or expand these systems based on the strategy you develop.


Your know-how

  • You have experience leading marketing within B2B SaaS, enterprise software, developer tools, cybersecurity, fintech, or another complex technology category

  • You have a strong demand-generation foundation and a track record of producing qualified pipeline

  • You have the breadth, mental flexibility and desire to own product marketing, brand, demand generation, lifecycle, partnerships, customer marketing, sales enablement, reporting, and team development

  • You have experience operating within a seed, Series A, Series B, or similarly formative company where strategy and execution cannot be separated into different jobs

  • You have experience building a marketing function within a business previously reliant on founder activity, outbound sales, referrals, or disconnected campaigns

  • You have strong commercial judgment and the ability to connect marketing activity to pipeline, conversion, customer acquisition cost, and revenue

  • You have experience developing segmentation, account-based marketing, and multi-channel strategies for distinct industries or customer cohorts

  • You have practical familiarity with CRM systems, marketing automation, enrichment, paid acquisition, content distribution, nurture programs, website analytics, and sales-engagement tools

  • You have the analytical depth to investigate customer, funnel, website, and campaign data and turn it into clear decisions

  • You have strong product-marketing instincts and the ability to communicate complex technical or regulatory capabilities in straightforward commercial language

  • You have experience working closely with sales leadership and creating productive tension between marketing and revenue objectives

  • You have the confidence to disagree with founders, reject low-priority initiatives, and explain the sequence of work you recommend

  • You have a hands-on operating style and a willingness to build campaigns, inspect data, review copy, develop collateral, brief agencies, and configure tools

  • You have an experience managing agencies, contractors, and specialists without surrendering strategic ownership

  • You are comfortable operating in an environment where priorities, customer segments, and channels continue to evolve


It’s a bonus if

  • You have marketed B2B technology to industrial businesses, professional-services firms, government contractors, or industry associations

  • You have built a partner or channel motion involving service providers, consulting firms, audit firms, resellers, or strategic alliances

  • You have marketed products that combine software with expert services, implementation, or managed delivery

  • You have worked in cybersecurity, compliance, governance, risk, infrastructure, or another trust-sensitive category

  • You have developed account-based programs for clearly identifiable customer universes

  • You have used direct mail, events, field marketing, telephone outreach, or associations to reach audiences outside conventional technology circles

  • You have improved conversion within a business that already had strong traffic and lead quality but lacked effective nurture and follow-through

  • You have repositioned a company toward a new vertical or customer segment without abandoning an existing revenue motion

  • You have built a marketing function from an initial collection of individual contributors, contractors, and agencies


Interested in learning more? 

Because this is a confidential search, the company’s identity and additional information about its product, customers, team, compensation, and growth plans will be shared with qualified candidates during the process.