Pilot.com
Head of Demand Generation and Growth
Pilot.com, San Francisco, California, United States, 94102
Head Of Demand Generation And Growth
At Pilot, we're building something special in the fintech spaceremoving the headache from back-office financial operations for startups and SMBs. As we scale, we're seeking a strategic and hands-on leader to build a scalable, AI-powered growth engine that fuels predictable, high-quality pipeline across self-serve and sales-led motions. This role is ideal for a senior marketing leader with a proven track record in scaling demand generation programs at fast-growing companies. You're equal parts strategist, operator, and systems thinkerAI- and data-forward, with a sharp understanding of what it takes to drive sustainable growth in a competitive market. You'll join at a pivotal moment, with strong marketing foundations in place, a highly capable team of senior marketers, and the opportunity to lead our next chapter of growth on the path to $100M in revenue. This is a hybrid position with the expectation to work in the San Francisco or Nashville office on Mondays, Tuesdays, and Thursdays. What You'll Do
Strategic Growth Leadership Develop and execute omni-channel strategies to increase brand awareness and attract new customers in the startup and small business sectors. Prioritize efficiency, experimentation, and repeatable pipeline creation across self-serve and sales-led motions. Align closely with Sales and RevOps on pipeline goals, ICP focus, and campaign strategy. Use AI, automation, and data-driven tooling to accelerate execution and scale personalization. Utilize analytics to measure the effectiveness of demand generation campaigns, identify trends, and make data-driven decisions, adjusting strategies as needed for optimal results. Acquisition Strategy And Oversight Set strategy and goals for digital acquisition across channels like Google and Bing Ads, LinkedIn, Meta, YouTube, and OTT. Drive creative testing, landing page optimization, and media mix planning in collaboration with senior marketers and agency partners. Monitor CAC efficiency and ROI, ensuring acquisition efforts are performance-driven and attributable. Build outbound programs grounded in deep buyer research and problem-based messagingnot just persona or industry assumptions. Use technographics, firmographics, and behavioral triggers to develop scalable hypotheses about customer pain points. Leverage AI and automation to generate personalized campaigns at scale while maintaining message relevance and quality. Lifecycle & Funnel Acceleration Guide full-funnel lifecycle strategy to increase conversion across all funnel stages. Oversee nurture programs, retargeting, and behavior-triggered sequences to engage and advance prospects. Own lead scoring frameworks, funnel diagnostics, and handoff processes in collaboration with Sales and RevOps. Drive measurable impact on lead-to-opportunity conversion and deal velocity. Marketing Operations & Tech Stack Oversee marketing operations and reporting infrastructure, ensuring accurate attribution and funnel visibility. Manage and optimize tools including Salesforce, Marketo, Bizible, GA4, Unify, Influ2, and others. Partner with RevOps and Data teams to ensure clean data flow, align on reporting infrastructure, funnel metrics, and automation systems. Team & Agency Leadership Lead a small but mighty team of senior marketersproviding strategic direction, coaching, and prioritization. Oversee relationships with agencies and contractors to augment execution across paid, ops, and outbound programs. Establish clear KPIs, workflows, and feedback loops across internal and external partners. Cross-Functional Collaboration Partner with the broader marketing team to activate content, campaigns, and cohesive buyer journeys. Collaborate closely with Sales, Product Marketing, RevOps, CFO Services, and R&D to align on GTM priorities and share funnel insights. Continuously refine messaging, segmentation, and positioning based on cross-functional input and performance data. About You
810+ years in B2B demand generation with 2+ years managing teams Proven track record of developing and executing successful marketing strategies that drive growth - scaling organizations from $25M > $50M > $100M ARR Deep understanding of startup ecosystems and the specific challenges of selling to small businesses. Highly analytical and data-drivencomfortable using metrics to guide strategy, forecast performance, and optimize programs. Experienced in building, mentoring, and influencing senior marketers in a collaborative environment. Fluent in modern demand gen approaches including ABM, intent-based targeting, trigger-based messaging, personalization, and predictive analytics. Excellent communicator and cross-functional leaderyou collaborate effectively with Sales, RevOps, Data, and R&D. AI-forward mindsetyou leverage automation to scale quality, reduce manual lift, and move fast. Ready to build a modern demand engine with precision, velocity, and buyer-first strategy? Join us.
At Pilot, we're building something special in the fintech spaceremoving the headache from back-office financial operations for startups and SMBs. As we scale, we're seeking a strategic and hands-on leader to build a scalable, AI-powered growth engine that fuels predictable, high-quality pipeline across self-serve and sales-led motions. This role is ideal for a senior marketing leader with a proven track record in scaling demand generation programs at fast-growing companies. You're equal parts strategist, operator, and systems thinkerAI- and data-forward, with a sharp understanding of what it takes to drive sustainable growth in a competitive market. You'll join at a pivotal moment, with strong marketing foundations in place, a highly capable team of senior marketers, and the opportunity to lead our next chapter of growth on the path to $100M in revenue. This is a hybrid position with the expectation to work in the San Francisco or Nashville office on Mondays, Tuesdays, and Thursdays. What You'll Do
Strategic Growth Leadership Develop and execute omni-channel strategies to increase brand awareness and attract new customers in the startup and small business sectors. Prioritize efficiency, experimentation, and repeatable pipeline creation across self-serve and sales-led motions. Align closely with Sales and RevOps on pipeline goals, ICP focus, and campaign strategy. Use AI, automation, and data-driven tooling to accelerate execution and scale personalization. Utilize analytics to measure the effectiveness of demand generation campaigns, identify trends, and make data-driven decisions, adjusting strategies as needed for optimal results. Acquisition Strategy And Oversight Set strategy and goals for digital acquisition across channels like Google and Bing Ads, LinkedIn, Meta, YouTube, and OTT. Drive creative testing, landing page optimization, and media mix planning in collaboration with senior marketers and agency partners. Monitor CAC efficiency and ROI, ensuring acquisition efforts are performance-driven and attributable. Build outbound programs grounded in deep buyer research and problem-based messagingnot just persona or industry assumptions. Use technographics, firmographics, and behavioral triggers to develop scalable hypotheses about customer pain points. Leverage AI and automation to generate personalized campaigns at scale while maintaining message relevance and quality. Lifecycle & Funnel Acceleration Guide full-funnel lifecycle strategy to increase conversion across all funnel stages. Oversee nurture programs, retargeting, and behavior-triggered sequences to engage and advance prospects. Own lead scoring frameworks, funnel diagnostics, and handoff processes in collaboration with Sales and RevOps. Drive measurable impact on lead-to-opportunity conversion and deal velocity. Marketing Operations & Tech Stack Oversee marketing operations and reporting infrastructure, ensuring accurate attribution and funnel visibility. Manage and optimize tools including Salesforce, Marketo, Bizible, GA4, Unify, Influ2, and others. Partner with RevOps and Data teams to ensure clean data flow, align on reporting infrastructure, funnel metrics, and automation systems. Team & Agency Leadership Lead a small but mighty team of senior marketersproviding strategic direction, coaching, and prioritization. Oversee relationships with agencies and contractors to augment execution across paid, ops, and outbound programs. Establish clear KPIs, workflows, and feedback loops across internal and external partners. Cross-Functional Collaboration Partner with the broader marketing team to activate content, campaigns, and cohesive buyer journeys. Collaborate closely with Sales, Product Marketing, RevOps, CFO Services, and R&D to align on GTM priorities and share funnel insights. Continuously refine messaging, segmentation, and positioning based on cross-functional input and performance data. About You
810+ years in B2B demand generation with 2+ years managing teams Proven track record of developing and executing successful marketing strategies that drive growth - scaling organizations from $25M > $50M > $100M ARR Deep understanding of startup ecosystems and the specific challenges of selling to small businesses. Highly analytical and data-drivencomfortable using metrics to guide strategy, forecast performance, and optimize programs. Experienced in building, mentoring, and influencing senior marketers in a collaborative environment. Fluent in modern demand gen approaches including ABM, intent-based targeting, trigger-based messaging, personalization, and predictive analytics. Excellent communicator and cross-functional leaderyou collaborate effectively with Sales, RevOps, Data, and R&D. AI-forward mindsetyou leverage automation to scale quality, reduce manual lift, and move fast. Ready to build a modern demand engine with precision, velocity, and buyer-first strategy? Join us.