Sr. Manager, Web Strategy and Growth

The Role 

As Pilot's Sr. Manager, Web Strategy and Growth, you will own the design, strategy, performance, and optimization of Pilot’s most important marketing asset—our website. Your mission will be to drive organic traffic growth, optimize conversion rates, and deliver an exceptional user experience for visitors to pilot.com.   This position requires a strategic thinker and hands-on executor who thrives at the intersection of data-driven decision-making, user-centric design, and business impact. You’ll be responsible for managing our Webflow instance and collaborating across teams to build a website that scales Pilot’s growth to $100M ARR and beyond.

Key Responsibilities

• Website Strategy and Ownership:
• Develop and execute a comprehensive web strategy that supports Pilot’s growth and brand goals.
• Own Pilot’s Webflow instance, ensuring its functionality, scalability, and alignment with business objectives.
• Drive the vision for the evolution of pilot.com, incorporating best practices in UX/UI, SEO, CRO, and analytics.
• Performance and Conversion Optimization:
• Use data and insights to optimize the website for key metrics, including traffic, engagement, and conversions.
• Continuously improve conversion rate optimization (CRO) through A/B testing, personalization, and iterative enhancements.
• Monitor and report on website performance, identifying areas for improvement and delivering measurable results.
• Optimize the use of machine learning tools, AI and AI agents / automation to enhance team efficiency across all parts of the website optimization workflow.
• Organic Traffic Growth:
• Partner with content and SEO agencies to implement strategies that drive sustainable growth in organic search traffic.
• Stay up-to-date with industry trends, algorithm updates, and emerging tools to maintain Pilot’s competitive edge in search rankings.
• Cross-functional Collaboration:
• Work closely with marketing, product, and sales teams to align website strategies with broader company goals.
• Partner with content and design agencies and internal teams to ensure the website reflects Pilot’s brand and resonates with target audiences.
• Implement tracking, reporting, and technical improvements.
• Product Management and Execution:
• Write up requirements and work with web agency and/or Growth Engineer on scope necessary to develop website features (MVP, trade-offs, balance short- and long-term). 
• Manage the end-to-end development of new website features, page designs, and updates, ensuring timely and high-quality delivery.
• Oversee web agency, freelance resources, and tools to maximize impact on Pilot’s goals.
• Assist with QA and UAT, ensuring consistency of customer experience.

About You

• Experience: 5-8 years of experience in web strategy, as part of an agency team or an in-house marketing team, with expertise in managing websites and CRO. 
• Web Expertise: Proficient in Webflow or similar CMS platforms, has led web development projects and built web experiences that motivate users to move through the funnel. 
• SEO: Demonstrable knowledge of SEO fundamentals and how they interplay with website technology, architecture, and content.
• Analytics Savvy: Strong knowledge of web analytics, and goal setting, including experience with tools like Google Analytics, Amplitude, Google Tag Manager, and heat-mapping software to analyze performance and optimize results.
• Strategic and Tactical: Able to balance long-term strategy with day-to-day execution, keeping business impact at the forefront. Experience with sprint planning and roadmapping is a plus.
• Collaborative: Proven ability to work cross-functionally with marketers, designers, and engineers to deliver seamless web experiences.
• Fast-paced: Thrive in a dynamic startup environment, managing multiple priorities and driving measurable results.
• Communicative: Excellent written and verbal communication skills, with the ability to articulate complex ideas to stakeholders at all levels.

Join us at Pilot and help transform our website into a growth engine that scales with our ambitious goals. Your expertise and creativity will play a critical role in shaping the future of pilot.com and accelerating our path to success. 

About Pilot

Pilot launched in 2017 to bring the back office into the modern era. Pilot provides small businesses with dedicated finance experts - which Pilot hires as full-time, U.S.-based employees - who learn the ins-and-outs of their business. Pilot integrates directly with the billing, banking, expense, and payroll systems customers already use. With a special blend of custom software and expert bookkeepers, Pilot delivers accurate, consistent bookkeeping and financial management and tax services that give entrepreneurs the freedom to focus on their business.

Pilot has over 1,000 customers and has raised over $170 million in financing from Sequoia, Index Ventures, Stripe, Bezos Expeditions, and Whale Rock.  Our investors also include a long list of world-class entrepreneurs, including Patrick and John Collison, Drew Houston, and Diane Greene.  Our most recent funding round doubled our valuation to $1.2 billion – Meet Fintech’s Newest Unicorn.

Why Pilot?

• We invest in our employees’ development and happiness because our employees are the keys to our success and ensuring happy customers
• The opportunity to join a seasoned founding team that has led companies through two prior successful startups and acquisitions (by Oracle and Dropbox).
• Flexible vacation/time-off policy
• All federal holidays are observed
• Competitive benefits package including wellness benefits such as Modern Health, Headscape, One Medical, Aaptiv and Rightway
• Parental leave for birthing or non-birthing parents – 100% pay for 12 weeks
• 401(k) plan

The base pay range target for the role seniority described in this job description is $106k - $215k in most remote locations, and between $133k - $215k in San Francisco, CA and New York City, NY. Final offer amounts depend on multiple factors such as candidate experience and expertise, geographic location, total compensation, and market data. In addition to cash pay, full-time regular positions are eligible for equity, 401(k), health benefits, and other benefits; some of these benefits may be available for part-time or temporary positions.

Pilot commits to provide a work environment free of discrimination and harassment, as well as equal employment opportunity regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity or Veteran status. We also consider qualified applicants regardless of criminal histories, consistent with legal requirements. You may view all of Pilot’s recruiting notices here, including our EEO policy, recruitment agency policy, recruitment scam notice, and important E-Verify information. You may view our job candidate privacy policy here.

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