📌 Core Information
🔹 Job Title: Senior Content Writer
🔹 Company: Willful
🔹 Location: Toronto, Ontario, Canada (Remote)
🔹 Job Type: Full-Time
🔹 Category: Content & Writing
🔹 Date Posted: April 10, 2025
🔹 Experience Level: Mid-Senior level (4-6 years)
🔹 Remote Status: Fully Remote (Canada only)
🚀 Job Overview
Key aspects of this role include:
- Leading Willful’s content strategy across multiple channels
- Developing compelling copy for email campaigns, long-form content, and in-app messaging
- Collaborating with cross-functional teams to ensure a consistent brand experience
- Refining and maintaining Willful’s voice and brand guidelines
- Partnering with Product, CRM, and other stakeholders to improve user journeys and drive conversions
ASSUMPTION: This role requires a balance of strategic thinking and hands-on execution. The ideal candidate will be comfortable working independently and collaboratively, with a strong understanding of both content strategy and tactical writing.
📋 Key Responsibilities
✅ Own the brand voice: Refine and maintain Willful’s voice across all communications, from product tooltips and marketing assets to customer support resources. Train and support cross-functional teams to ensure every written asset aligns with brand guidelines.
✅ Email and direct response copy: Develop compelling email and direct response ad copy that reaches users at various touchpoints, driving engagement and conversion.
✅ Long-form content: Research and write in-depth articles and guides that educate and empower readers to plan their futures while employing SEO best practices. Collaborate with the PR team to support thought leadership initiatives, industry reports, and earned media opportunities.
✅ In-app copy: Partner with the Product team to craft user-centric messaging that resonates with users at various stages of their journey.
✅ Collaborate across teams: Work with content, product, customer success, PR, and design stakeholders to align messaging and campaign goals.
ASSUMPTION: This role involves a mix of creative and analytical tasks. The ideal candidate will be comfortable using data and feedback to inform content decisions and continuously improve performance.
🎯 Required Qualifications
Education: Bachelor's degree in English, Journalism, Marketing, or a related field (or equivalent experience)
Experience: 4-6 years of professional writing experience in B2C tech, SaaS, digital marketing, or media/editorial publishing
Required Skills:
- Proven track record in email, direct-response, editorial, and in-app copy
- Strong storytelling, editing, and SEO skills
- Customer-centric mindset with a deep understanding of customer needs and aspirations
- AI-native mindset, seeing AI and emerging technology as creative tools
- Collaborative spirit, thriving in cross-functional environments
- Analytical mindset, eager to use data and experimentation to improve content performance
- Curiosity and empathy, valuing diverse perspectives and collaboration
Preferred Skills:
- Experience with estate planning or related topics
- Familiarity with marketing automation tools and email service providers
- Portfolio showcasing a range of writing styles and formats
ASSUMPTION: While industry-specific experience is not required, a strong understanding of Willful’s mission and target audience is essential for success in this role.
💰 Compensation & Benefits
Salary Range: CAD 80,000 - 120,000 per year (Based on industry standards for mid-senior level content roles in Toronto)
Benefits:
- Competitive salary and participation in employee stock option plan (ESOP)
- Comprehensive benefits plan, including health, dental, and vision
- Flexible perks including the choice of a health spending account (HSA) or RRSP matching
- A CAD 500 wellness budget to support physical, mental, and emotional health
- Monthly meal and entertainment budget
- 4.5-day work week and flexible work hours
- Company-wide “recharge” days off in December in addition to vacation time
- Competitive parental leave policy
- Fun and inclusive virtual team events
- In-person team and company-wide events
Working Hours: Full-time (35-40 hours per week, flexible schedule)
ASSUMPTION: The salary range provided is an estimate based on market research and may vary depending on the candidate’s experience and skills.
📌 Applicant Insights
🔍 Company Context
Industry: Software Development (Estate Planning)
Company Size: Small (11-50 employees) – Offers a close-knit, collaborative work environment with ample opportunities for growth and impact.
Founded: 2017 – Willful is a relatively young company with a strong focus on innovation and continuous improvement.
Company Description:
- Willful is on a mission to make estate planning simple, affordable, and accessible for Canadians.
- Since 2017, they’ve helped over 300,000 people create wills and powers of attorney documents through an intuitive online platform and support from human estate planning experts.
- Willful partners with Canada’s most trusted brands, including Wealthsimple, Scotiabank, CIBC, and Amazon, to bring estate planning within reach for every Canadian.
Company Specialties:
- Wills
- Wills and Estate Planning
- Living Wills
- Power of Attorney
Company Website: willful.co
ASSUMPTION: Willful’s focus on innovation and user-centric design makes it an attractive employer for candidates seeking to make a meaningful impact in the tech industry.
📊 Role Analysis
Career Level: Mid-Senior level – This role offers significant growth potential for the right candidate, with opportunities to shape Willful’s content strategy and grow within the organization.
Reporting Structure: The Senior Content Writer will report directly to the Marketing Director and collaborate with various teams, including Product, CRM, Customer Success, PR, and Design.
Work Arrangement: Fully Remote (Canada only) – Willful offers a flexible, remote-first work environment with in-person team and company-wide events a few times a year.
Growth Opportunities:
- Potential to grow into a leadership role, such as Content Manager or Director of Content, as the company expands
- Opportunities to collaborate with cross-functional teams and gain exposure to various aspects of the business
- Chance to make a significant impact on Willful’s content strategy and brand voice
ASSUMPTION: This role offers a unique opportunity for a mid-senior level content writer to join a growing company and make a significant impact on its content strategy and brand voice.
🌍 Location & Work Environment
Office Type: Remote – Willful is a fully remote company with no physical office location.
Office Location(s): N/A
Geographic Context:
- Toronto, Ontario, Canada – Willful’s target market is primarily Canadian, with a focus on urban and suburban areas.
- Canada-wide – While Willful is based in Toronto, it serves customers across Canada and has a remote workforce.
- North America – Willful may consider expanding its services to the United States in the future.
Work Schedule: Full-time (35-40 hours per week) with a 4.5-day work week and flexible hours
ASSUMPTION: The remote work environment offers candidates the flexibility to work from anywhere in Canada, with the convenience of avoiding a daily commute.
💼 Interview & Application Insights
Typical Process:
- Initial screening with the hiring manager
- At-home assignment to assess writing skills and strategic thinking
- Final interview with the Marketing Director and other team members
- References and background check
- Meet the Marketing Team
- Job offer
Key Assessment Areas:
- Writing skills and ability to maintain a consistent brand voice
- Strategic thinking and content strategy development
- Collaboration and communication skills
- Understanding of Willful’s mission and target audience
- Cultural fit and alignment with Willful’s core values
Application Tips:
- Tailor your resume and cover letter to highlight your relevant experience and skills for this role
- Include a brief, engaging cover letter that explains why you’re excited about Willful and how your experience aligns with their needs
- Submit 2-3 writing samples, including at least one email or direct-response piece, to demonstrate your versatility and ability to maintain a consistent brand voice
- Prepare thoughtful questions to ask during the interview, demonstrating your understanding of Willful’s mission and target audience
ATS Keywords: Senior Content Writer, Content Strategy, Email Copywriting, Direct Response Copy, Long-form Content Writing, SEO, User-Centric Messaging, Collaboration, Storytelling, Editing, Customer-Centric Mindset, AI-Native Mindset, Empathy, Inclusivity, Estate Planning, Willful
ASSUMPTION: The interview process is designed to assess both the candidate’s technical skills and cultural fit with Willful’s mission and values.
🛠️ Tools & Technologies
- Content Management System (CMS) – Willful uses a custom-built CMS for its website and content management
- Email Marketing Platform – Willful uses a third-party email marketing platform for email campaigns and automation
- Project Management Tool – Willful uses a project management tool (e.g., Asana, Trello, or Jira) to collaborate and track progress
- Communication Platform – Willful uses a communication platform (e.g., Slack or Microsoft Teams) for internal communication and collaboration
ASSUMPTION: The ideal candidate will be comfortable learning and adapting to new tools and technologies as needed.
👔 Cultural Fit Considerations
Company Values:
- Empowering Canadians to take control of their futures
- Simplifying complex processes through intuitive design and user-centric thinking
- Fostering a collaborative and inclusive work environment
Work Style:
- Remote-first, with a focus on asynchronous communication and flexible work hours
- Data-driven, with a commitment to continuous improvement and experimentation
- Collaborative, with a strong emphasis on cross-functional teamwork and open communication
Self-Assessment Questions:
- How do you align with Willful’s mission to empower Canadians to take control of their futures?
- How do you approach simplifying complex processes through intuitive design and user-centric thinking?
- How do you foster a collaborative and inclusive work environment, both within your team and with external stakeholders?
ASSUMPTION: Willful values candidates who are passionate about its mission and committed to fostering a collaborative, inclusive work environment.
⚠️ Potential Challenges
- Managing multiple content channels and stakeholders simultaneously
- Balancing strategic thinking and tactical execution in a fast-paced, growing company
- Adapting to a remote work environment and maintaining a consistent brand voice across various touchpoints
- Keeping up with industry trends and best practices in content marketing and estate planning
ASSUMPTION: The ideal candidate will be proactive, organized, and comfortable working in a dynamic, fast-paced environment.
📈 Similar Roles Comparison
- Unlike traditional content marketing roles, this position requires a strong understanding of estate planning and a customer-centric mindset focused on empowering Canadians to take control of their futures
- Willful’s focus on user-centric design and intuitive user experiences sets it apart from other content marketing roles in the tech industry
- This role offers significant growth potential for the right candidate, with opportunities to shape Willful’s content strategy and grow within the organization
ASSUMPTION: Candidates with experience in estate planning or related fields may find this role particularly appealing, as it offers a unique opportunity to make a meaningful impact on a growing company’s content strategy.
📝 Sample Projects
- Developing a comprehensive content strategy for Willful’s email marketing campaigns, driving user engagement and conversions
- Collaborating with the Product team to craft user-centric messaging for Willful’s in-app onboarding and user journey
- Researching and writing long-form content pieces that educate and empower readers to plan their futures while employing SEO best practices
ASSUMPTION: These sample projects demonstrate the breadth of responsibilities and the strategic, collaborative nature of the Senior Content Writer role at Willful.
❓ Key Questions to Ask During Interview
- How does Willful plan to expand its services and reach new audiences in the coming years?
- What are the key priorities for the first 90 days in this role, and how can I make the most significant impact on Willful’s content strategy?
- How does Willful support the professional development and growth of its content team members?
- What are the most challenging aspects of working in a remote, fully distributed team, and how does Willful address these challenges?
- How does Willful measure the success of its content marketing efforts, and what key performance indicators (KPIs) does it track?
ASSUMPTION: Asking thoughtful, insightful questions demonstrates your understanding of Willful’s mission and commitment to driving its content strategy forward.
📌 Next Steps for Applicants
To apply for this position:
- Submit your application through this link
- Tailor your resume and cover letter to highlight your relevant experience and skills for this role
- Submit 2-3 writing samples, including at least one email or direct-response piece, to demonstrate your versatility and ability to maintain a consistent brand voice
- Prepare thoughtful questions to ask during the interview, demonstrating your understanding of Willful’s mission and target audience
- Follow up with the hiring manager one week after submitting your application to express your continued interest in the role
⚠️ This job description contains AI-assisted information. Details should be verified directly with the employer before making decisions.
