Sr. Manager, Web Strategy and Growth
Pilot.com📌 Core Information
🔹 Job Title: Sr. Manager, Web Strategy and Growth
🔹 Company: Pilot.com
🔹 Location: Manitoba, Canada
🔹 Job Type: Full-time
🔹 Category: 🚀 Growth Marketing
📌 Essential Job Details
🚀 Job Overview
As Pilot.com's Sr. Manager of Web Strategy and Growth, you'll take ownership of the company's website - their most critical marketing asset. You'll drive organic traffic growth, optimize conversion rates, and enhance user experience while managing the Webflow instance. This strategic role sits at the intersection of data-driven decision making, user-centric design, and business impact, with the mission of scaling Pilot's growth to $100M ARR and beyond.
ASSUMPTION: The role is full-time based on the comprehensive responsibilities, senior title, and inclusion in the company's benefits package information which references full-time positions.
📋 Key Responsibilities
✅ Website Strategy and Ownership: Develop and execute comprehensive web strategy supporting growth goals, manage Pilot's Webflow instance, and drive the evolution of pilot.com
✅ Performance and Conversion Optimization: Use data to optimize website metrics, implement CRO through A/B testing, monitor performance, and leverage AI/ML tools to enhance team efficiency
✅ Organic Traffic Growth: Partner with content and SEO agencies to drive sustainable organic search traffic growth and stay current with industry trends
✅ Cross-functional Collaboration: Work with marketing, product, and sales teams to align website strategies with company goals and partner with agencies to reflect Pilot's brand
✅ Product Management and Execution: Create requirements, manage web development features, oversee resources and tools, and ensure consistent customer experience through QA and UAT
🎯 Required Qualifications
Education: Not specified
Experience: 5-8 years in web strategy (agency or in-house marketing team), expertise in website management and CRO
Skills:
- Proficiency in Webflow or similar CMS platforms
- Web development project leadership
- SEO fundamentals knowledge
- Strong analytics skills (Google Analytics, Amplitude, GTM, heat-mapping)
- Strategic thinking balanced with tactical execution
- Cross-functional collaboration abilities
- Thrives in fast-paced environments
- Excellent written and verbal communication
💰 Compensation & Benefits
Salary Range: $106K - $215K in most remote locations; $133K - $215K in San Francisco, CA and New York City, NY
Benefits:
- Flexible vacation/time-off policy
- All federal holidays observed
- Wellness benefits (Modern Health, Headscape, One Medical, Aaptiv, Rightway)
- Parental leave - 100% pay for 12 weeks (birthing and non-birthing parents)
- 401(k) plan
- Equity for full-time positions
- Health benefits
Industry Comparison: The salary range is competitive for senior marketing positions in tech companies, particularly for a unicorn-status startup with significant funding.
📌 Applicant Insights
🔍 Company Context
Industry Position: Pilot.com is a fintech unicorn providing bookkeeping, financial management, and tax services for small businesses.
Company Size: Over 1,000 customers with significant growth trajectory
Company Stage: Growth-stage startup with unicorn status ($1.2 billion valuation)
Funding: Raised over $170 million from prominent investors including Sequoia, Index Ventures, Stripe, Bezos Expeditions, and Whale Rock
ASSUMPTION: While exact employee count isn't provided, based on the funding amount, valuation, and customer base, Pilot likely has between 100-500 employees typical of a growth-stage fintech at this valuation level.
📊 Role Analysis
Career Level: Senior management (strategic leadership position)
Reporting Structure: Not explicitly stated, but likely reports to a Director or VP of Marketing/Growth
Team Size/Composition: Not specified, but indicates working with agencies, freelancers, and cross-functional teams
Growth Opportunities: Potential path to Director or VP level as the company scales toward $100M ARR
ASSUMPTION: The reporting structure and growth path are inferred based on the senior manager title and typical org structures in growth-stage startups.
🌍 Location & Work Environment
Office Type: Remote position in Manitoba, Canada
Geographic Context: Manitoba offers a lower cost of living compared to major tech hubs while providing access to Canada's growing tech ecosystem
Work Schedule: Not explicitly mentioned, but likely standard business hours with flexibility
Regional Considerations: Working remotely for a US-based company from Canada may involve cross-border considerations for taxes and benefits
ASSUMPTION: This appears to be a remote role based on the location being in Canada while Pilot is a US-based company, and the salary information mentioning "remote locations." The work schedule assumption is based on standard practices for senior marketing roles.
💼 Interview & Application Insights
Typical Process: For senior marketing roles at tech startups, expect multiple rounds including:
- Initial screening with a recruiter
- Technical/strategy interview with marketing leadership
- Case study or presentation on web strategy
- Cross-functional interviews with stakeholders (product, design, sales)
- Final interview with executive leadership
Key Assessment Areas:
- Strategic thinking and business impact orientation
- Technical knowledge of Webflow, SEO, and CRO
- Data analysis capabilities and results orientation
- Collaborative approach and communication skills
- Experience managing and scaling websites
Application Tips:
- Highlight measurable website performance improvements you've driven
- Demonstrate both strategic vision and hands-on execution abilities
- Showcase cross-functional collaboration examples
- Emphasize experience with similar tech stacks, especially Webflow
ATS Keywords: Webflow, CRO, conversion rate optimization, SEO, web strategy, growth marketing, A/B testing, web analytics, Google Analytics, Amplitude, heat-mapping, user experience, product management, cross-functional collaboration
ASSUMPTION: These insights are based on industry standards for senior marketing roles at growth-stage tech companies and the specific requirements mentioned in the job posting.
🛠️ Tools & Technologies
Explicitly mentioned:
- Webflow (CMS/website platform)
- Google Analytics
- Amplitude
- Google Tag Manager
- Heat-mapping software
- AI/ML tools for website optimization
Commonly used in similar roles:
- SEO tools (e.g., Ahrefs, SEMrush, Moz)
- A/B testing platforms (e.g., Optimizely, VWO)
- Project management tools (e.g., Asana, Jira)
- Conversion tracking tools
ASSUMPTION: Additional tools listed beyond those explicitly mentioned are industry-standard for web strategy and growth roles but would need to be confirmed during the interview process.
👔 Cultural Fit Considerations
Company Values: While not explicitly stated, the job description suggests these values:
- Innovation and modernization (bringing the "back office into the modern era")
- Employee development and happiness ("employees are the keys to our success")
- Ambitious growth mindset (scaling to "$100M ARR and beyond")
- Data-driven decision making
- Work-life balance (generous parental leave, flexible time off)
Work Style: The role requires a blend of strategic thinking and hands-on execution in a fast-paced startup environment. Collaboration across teams is emphasized, indicating a highly cross-functional culture.
Self-Assessment: Candidates should consider:
- Do you thrive in environments requiring both strategy and execution?
- Are you comfortable working with both technical and non-technical stakeholders?
- Can you balance multiple priorities while maintaining focus on key metrics?
- Do you enjoy the pace and ambiguity of a scaling startup?
ASSUMPTION: Company values are inferred from the job description and company information provided. The work style is based on explicit mentions of "fast-paced" environment and cross-functional collaboration needs.
⚠️ Potential Challenges
- Broad scope: Owning both strategy and execution across multiple web disciplines (SEO, CRO, UX, analytics) could be demanding
- Ambitious growth targets: Scaling to $100M ARR indicates high-pressure performance expectations
- Managing agencies and internal stakeholders: Balancing external resources with internal team needs
- Technical complexity: Need to balance technical implementation with marketing strategy
- Cross-border remote work: Working remotely from Canada for a US company may present logistical challenges
ASSUMPTION: These challenges are inferred from the comprehensive responsibilities and company context provided. The actual difficulty would vary based on team structure and support resources.
📈 Similar Roles Comparison
This role combines elements of several positions that might be separate in larger organizations:
- Web Manager/Director: Similar focus on website strategy but this role has broader growth marketing responsibilities
- SEO Manager: This role includes SEO but extends to full website experience and conversion
- Growth Marketing Manager: Similar growth focus but more specifically centered on the website as the primary channel
- Product Marketing Manager: Shares the product management aspects but with website as the product
ASSUMPTION: This comparison is based on standard industry role definitions and how this position appears to combine elements from multiple traditional marketing functions.
📝 Sample Projects
- Developing a comprehensive website roadmap aligned with company growth targets and marketing strategy
- Implementing a structured A/B testing program to optimize conversion rates across key landing pages
- Working with SEO agency to restructure website architecture for improved organic visibility
- Creating a web analytics dashboard integrating multiple data sources for performance tracking
- Managing the redesign of high-traffic conversion pages to improve user experience and conversion rates
- Implementing AI-powered personalization to deliver customized content based on visitor behavior
ASSUMPTION: These projects are illustrative examples based on the responsibilities described in the job listing and represent typical initiatives for this type of role.
❓ Key Questions to Ask During Interview
- What are the most significant challenges or opportunities for the Pilot.com website in the next 12 months?
- How do you measure success for this role, and what key metrics will I be responsible for improving?
- Can you describe the working relationship between this role and the agencies or freelancers currently supporting the website?
- What is the current tech stack and martech ecosystem supporting the website, and are there any planned changes?
- How does website strategy integrate with the broader marketing and growth initiatives at Pilot?
- What resources (team, budget, tools) will be available to support the ambitious growth goals?
ASSUMPTION: These questions are suggested based on the role description and would be helpful for understanding expectations, resources, and challenges. They should be adapted based on interview context and the candidate's specific interests.
📌 Disclaimer
⚠️ This enhanced job description was AI-generated based on the original job listing. Information has been organized and supplemented with industry-standard insights where details were not provided. All assumptions are explicitly labeled. Applicants should verify all details directly with the employer before making decisions based on this content.
📌 Next Steps for Applicants
- Customize your resume: Highlight experience with Webflow, web optimization, and measurable growth results. Incorporate the ATS keywords mentioned above.
- Prepare a portfolio: Gather examples of websites you've managed, with before/after metrics showing improvements in traffic, conversion, or user experience.
- Research Pilot.com: Study their website, understand their product offerings and target audience, and be prepared to discuss specific improvement opportunities.
- Connect with employees: Reach out to current team members on LinkedIn to learn more about company culture and the marketing department.
- Prepare for technical questions: Be ready to discuss specific strategies for SEO, CRO, and web analytics, particularly as they relate to B2B SaaS companies.
- Consider the remote aspect: If you're in Manitoba, be prepared to discuss how you've successfully managed remote work, particularly cross-border collaboration.