As Pilot’s Lifecycle Marketing Manager, you will be the architect of how, when, and what we communicate to customers across their entire journey with us. You will design and implement customer programs that drive engagement, education, advocacy, and expansion — maximizing customer lifetime value while deepening customer trust in Pilot.

You will collaborate with customer success, product, content, and operations teams to define critical moments in the customer journey and build strategies to proactively support, nurture, and expand our customer relationships. You’ll help evaluate and optimize our customer lifecycle marketing systems — including identifying gaps in our tech stack (for example, CDPs or orchestration tools) and proposing solutions to close them — to ensure Pilot can deliver a seamless, personalized experience at scale.

This is a hybrid position with the expectation to work in the San Francisco or Nashville office on Monday, Tuesday, and Thursday.

Key Responsibilities

Build and own the customer lifecycle strategy

Map the full customer journey, identifying key inflection points where we can engage, educate, or expand our customers.
Define and execute customer lifecycle programs that support onboarding, product adoption, expansion (cross-sell/upsell), retention, advocacy, and win-backs.
Partner with product and operations teams to identify buying signals or key moments that indicate a customer may be ready for cross-sell, upsell, or added services — and build playbooks to capitalize on these opportunities.
Develop customer education strategies in partnership with product, customer success, and marketing teams to help customers fully realize the value of Pilot’s solutions.
You’ll manage Pilot’s customer referral program, a significant revenue driver.

Drive program execution and collaboration

Build, launch, and manage omni-channel lifecycle campaigns in partnership with creative, content, product marketing, and customer success teams.
Maintain a seasonal campaign calendar aligned with Customer Success, Sales, and Marketing initiatives.
Develop triggered campaigns, nurture programs, and playbooks that drive customer engagement and value realization.
Support customer advocacy efforts, including referral programs, reviews, case studies, and testimonials.

Implement systems and tooling

Evaluate and recommend lifecycle marketing technologies, including customer data platforms (CDPs) or orchestration tools, to support scalable and personalized customer journeys.
Partner with business systems and analytics teams to implement, measure, and optimize these tools.

Champion AI and automation

Identify and use AI-powered tools to automatically detect friction points and hidden customer segments.
Apply machine-learning models to surface propensity-to-churn, expansion, or advocacy, feeding real-time signals into campaign triggers.
Employ generative AI and dynamic content blocks to tailor messaging and educational assets per customer profile.
Explore an AI-driven orchestration layer to optimize send-times, channel selection, and content variants based on user behavior and emerging pain points.

Measure and optimize lifecycle marketing programs

Define, track, and report on key lifecycle metrics, including product adoption rates, retention/churn, cross-sell and upsell performance, and customer satisfaction/advocacy.
Partner with data and analytics teams to design experiments, interpret results, and continuously improve programs.

About You

7+ years of experience in lifecycle marketing, customer marketing, or customer engagement roles, ideally within a B2B SaaS or high-growth environment
Proven track record of designing and executing successful lifecycle programs across multiple customer segments
Familiarity with customer education, enablement, and advocacy best practices
Deep understanding of marketing automation systems, personalization tools, CDPs, triggered campaigns, and dynamic content
Able to identify, evaluate, and recommend systems or technologies to support customer marketing initiatives
Skilled at analyzing customer data and drawing actionable insights that drive revenue and loyalty
Hands-on experience collaborating with cross-functional stakeholders (product, engineering, customer success, sales)
Excellent communicator and project leader, capable of managing complex programs from strategy through execution
Data-driven mindset with a test-and-learn approach to improving program performance
Comfortable navigating a fast-paced, startup environment

Nice to Have

Experience working with Salesforce, Marketo, Looker, or similar martech tools
Familiarity with venture-backed startup environments or founder-focused customer bases
Background in building customer communities or user group programs
Exposure to account-based marketing or account-based expansion motions

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 2,000 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 $133k - $215k in San Francisco, CA. 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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