Head of Communications

Paddle; Toronto; Remote; CAD 80,000 - 110,000; Full time

Job summary

A technology company in Toronto is seeking a Head of Communications to lead its global communications strategy across various audiences. This role involves managing media relations, overseeing internal communications, and developing strategies to build Paddle's reputation. Candidates should have strong communication skills and experience in PR and social media management. The company offers a remote-first work environment with generous benefits including unlimited holidays.

Benefits

Unlimited holidays

Paid family leave

Annual learning fund

Private healthcare

Qualifications

• Experience in PR, internal, and social media communications.
• Ability to translate complex ideas into clear messages.
• Calm under pressure with strong judgement.

Responsibilities

• Define and execute Paddle’s integrated communications strategy.
• Build relationships with media, analysts, and influencers.
• Manage internal and external communications effectively.

Skills

Strategic communication

Storytelling

Crisis management

Social media management

Relationship building

Job description

Location

Toronto

Employment Type

Full time

Location Type

Remote

Department

Commercial Marketing

What do we do?

Paddle offers SaaS 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 3000 software sellers in 245 territories globally.

The Role:

We’re looking for a Head of Communications to lead Paddle’s global communications strategy — internal, external, and social.

This role is about shaping how Paddle shows up across every audience: employees, media, analysts, influencers, and the broader SaaS community. You’ll balance proactive storytelling with reputation management, building credibility and preference for Paddle as the growth platform for modern software companies.

You’ll oversee media and analyst relations, social media strategy, and internal communications, working closely with executives to ensure every message — from product news to leadership updates — lands with clarity, confidence, and consistency.

You’ll manage our PR agency, coach spokespeople, and partner across the business to integrate storytelling into everything we do. It’s a hands‑on leadership role suited to a strategic operator who can think fast, write clearly, and act decisively under pressure.

What you'll do:

• Define and execute Paddle’s integrated communications strategy (internal, external, and social).
• Build and maintain strong relationships with tier‑one media, analysts, and influencers.
• Lead the social media direction, ensuring tone, cadence, and content reflect our brand voice.
• Manage the day‑to‑day press office, overseeing coverage, message pull‑through, and issues management.
• Partner with executives on visibility and thought leadership programmes — from media briefings to keynote amplification.
• Oversee internal comms to keep employees informed, inspired, and aligned to company priorities.
• Anticipate risks, own crisis and issue comms, and ensure preparedness with clear playbooks and templates.
• Manage agency partners and collaborate with Content, Creative, and Product Marketing to align storytelling.
• Track and report on share of voice, sentiment, and engagement across earned and owned channels.

We'd love to hear from you if you are:

• A strategic communicator with experience spanning PR, internal, and social media.
• A natural storyteller who can translate complex ideas into clear, compelling messages.
• Confident managing external agencies and building trusted relationships with journalists and analysts.
• Calm under pressure, with strong judgement and credibility when representing leadership.
• Skilled at integrating brand, content, and comms for consistent narrative execution.
• Experienced in using social as a reputational channel — not just a marketing one.
• A proactive planner who thrives in a fast‑paced, scaling environment.
• Excited by the opportunity to help define a company’s public voice at a pivotal moment of growth.

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.

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 live and breathe our values, which are:

Exceptional Together

Execute with impact

Better than Yesterday

We offer a full suite of benefits, including attractive salaries, stock options, retirement plans, private healthcare and well‑being initiatives.

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 of 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.