Weekend Creative Jobs in Toronto, ON (NOW HIRING)

We're looking for a Creative Director to lead a full rebrand of PolyAI and establish a creative function that can scale with the company.
This is a rare opportunity: a category-defining AI company at an inflection point, with the resources to do it right. You'll build from a strong foundation — proven technology, marquee customers, and a product that genuinely changes how enterprises serve their customers — but the visual identity, brand voice, and design system haven't kept pace with our growth or our ambitions.
You'll own everything from brand strategy and visual identity to campaign creative and product design language. You'll hire and manage a distributed creative team, set the creative bar across the company, and act as a strategic partner to Marketing, Product, and Executive leadership.
This role reports to the Head of Brand and sits on the Marketing leadership team.
What You'll Do:
Brand Overhaul

• Lead a comprehensive rebrand of PolyAI — from positioning and visual identity to brand voice, messaging architecture, and design system — fit for a Series D enterprise AI company competing with Salesforce, Genesys, and Five9 in the boardroom

• Develop a brand that makes the abstract tangible: helping enterprise buyers (CX leaders, IT executives, CFOs) understand, trust, and feel excited about voice AI

• Build and maintain a scalable brand system — guidelines, component libraries, templates — that enables consistency across a fast-moving, globally distributed org

• Own the creative expression of PolyAI across all touchpoints: website, sales collateral, product UI, events, analyst presentations, social, and video

AI-Augmented Design Practice

• Build an AI-forward creative team and workflow — using generative AI tools (Midjourney, Runway, Adobe Firefly, and emerging tools) to accelerate production, expand creative range, and prototype faster without sacrificing quality

• Develop standards and guardrails for AI-assisted creative work: when to use it, how to quality-control it, and how to maintain brand integrity as tooling evolves

• Stay at the leading edge of AI-in-design: evaluate new tools continuously and bring your team along as the field moves

• Translate PolyAI's core technology — human-sounding AI, natural conversation, real-time dialogue — into visual and conceptual metaphors that resonate with enterprise buyers who've never seen it before

B2B and Enterprise Creative

• Develop campaign creative for complex, multi-stakeholder B2B buying journeys — from awareness through to late-stage sales enablement

• Partner with Product Marketing to translate technical capabilities (ASR, LLM hallucination reduction, Agent Studio) into compelling, buyer-relevant narratives

• Create high-impact sales assets: pitch decks, one-pagers, case study formats, RFP-response templates, and executive-level leave-behinds

• Build the creative foundation for PolyAI's presence at industry conferences and tradeshows (CCW, Enterprise Connect, Gartner, etc.) — from booth design to keynote decks

Team Building and Leadership

• Hire, build, and manage a remote-first creative team across design, copy, motion, and video — including a mix of FTEs and agency/freelance relationships

• Establish creative operations infrastructure: briefing process, asset management, review cadence, and production workflows that keep a lean team moving fast

• Mentor and develop individual contributors; build a team culture that prizes both craft and velocity

• Act as creative partner and thought leader to the wider business — running creative reviews, presenting work to executives, and pushing back when business needs and creative quality are in tension

What We're Looking For:
Experience

• 10+ years in brand design, creative direction, or integrated marketing — with at least 3 years in a senior leadership role

• Demonstrable experience leading a rebrand or brand transformation at a B2B technology, SaaS, or enterprise software company

• Portfolio that shows both strategic thinking and executional range: brand systems, campaign creative, digital, and content

• Experience managing distributed or fully remote creative teams across time zones

• Track record of building creative functions at scale: hiring, process-setting, vendor management

Skills

• Expert in Figma and Adobe Creative Cloud; fluent in the broader design toolchain (motion, video, web)

• Hands-on experience integrating AI tools into creative workflows — not just awareness of them

• Strong written communication: able to write a creative brief, a brand voice guide, and an exec summary with equal clarity

• Comfortable presenting work at board level and influencing without authority across Product, Sales, and Engineering

Mindset

• A systems thinker who also sweats the details — you can zoom out to brand architecture and zoom in to kerning

• Genuinely curious about AI and what it means for how brands communicate, not just for how creative teams work

• Comfortable with ambiguity; energised by a blank canvas more than daunted by it

• Strong point of view — you know what good looks like and can defend it — but ego-light enough to take feedback and build collaboratively

Nice to Have:

• Experience at a voice AI, conversational AI, or contact center technology company

• Background in or strong exposure to enterprise CX, contact center, or fintech/hospitality verticals

• Motion design or video direction experience

• Experience with analyst relations creative (Gartner, Forrester, IDC briefings)

We provide a competitive salary range for this role - which is $220,000-$255,000 base salary plus an annual bonus - depending on level and experience. Please note this range is intended as a guide, not a guarantee. Final compensation will be based on individual qualifications, relevant experience, and the scope of the role.
In addition to salary, this position includes equity in the business, giving you the opportunity to share in the company's long-term success.

Benefits
💰 Participation in the company's employee share options plan
🏥 100% of Single Cost (employee) and 70% of Dependent for medical, dental & vision
👪 Life Insurance
◻️ STD and LTD
💰 The opportunity to contribute to the company's 401k plan
🏝 Flexible PTO policy + 11 designated company holidays
📚 Annual learning and development allowance
🏡 We're all about making WFH work for you - that's why we offer a one-off WFH allowance when you join. Offering perks like noise-cancelling headphones or a comfortable desk chair to boost your comfort and focus!
🧡 Enhanced parental leave
👨‍👩‍👧 Company-funded fertility and family-forming programmes
🌸 Menopause care programme with Maven