Director, Lifecycle Marketing - PLG

The Opportunity

Seamless has historically been a sales-led company. Every customer, from an individual user to a large enterprise account, has moved through a sales-assisted motion.

As we continue scaling, we are building a stronger product-led and self-serve growth engine that allows lower-touch users to activate, convert, expand, and succeed more efficiently, while allowing Sales to focus on larger, higher-value opportunities.

We are looking for a Director, Lifecycle Marketing - PLG to help build that engine.

This is not a traditional lifecycle email role. This is a builder role for someone who understands that lifecycle marketing is the connective tissue between Marketing, Product, Sales, Customer Success, Revenue Operations, Data, and the customer experience.

You will own the journeys, systems, automation, segmentation, and product-led growth motions that help turn interest into activation, activation into revenue, and revenue into long-term expansion.

The right person has deep experience working across freemium, free trial, self-serve, sales-assisted, and hybrid PLG motions. You know how to identify friction in the customer journey, use product and behavioral data to prioritize opportunities, and partner with Product, Engineering, Sales, and Revenue Operations to improve the moments that drive conversion.

You will have the autonomy to assess what exists, identify the highest-impact opportunities, build scalable programs, and help shape how Seamless evolves from a primarily sales-led motion into a more efficient product-led and sales-assisted revenue engine.

What You'll Own

Own the end-to-end lifecycle and PLG strategy across prospect, free user, trial, customer, expansion, and retention journeys.
Build lifecycle programs that improve freemium, free trial, self-serve, sales-assisted, and hybrid PLG conversion.
Improve the path from signup to value by identifying friction, simplifying user journeys, and creating timely lifecycle touchpoints across email, in-app, SMS, and other channels.
Strengthen segmentation, lead scoring, product-qualified signals, routing logic, and behavioral triggers so Sales receives higher-quality opportunities at the right time.
Partner with Product, Engineering, UX, Data, Sales, Customer Success, Revenue Operations, Demand Generation, and Product Marketing to improve the full customer journey.
Build onboarding and engagement programs that reduce time-to-value, increase meaningful product adoption, and improve retention.
Create documented workflows, reusable playbooks, lifecycle maps, testing plans, and AI-first automations that can scale with the business.
Track lifecycle impact through activation, trial-to-paid conversion, free-to-paid conversion, self-serve revenue, MQL/PQL quality, pipeline influence, expansion, retention, and churn reduction.
Use experimentation, customer insight, and product behavior to continuously improve messaging, timing, segmentation, CTAs, journey logic, and product-led conversion.

Your Mandate

Over the next 12 to 18 months, you will help Seamless:

Build a high-performing lifecycle and customer engagement engine.
Improve freemium, free trial, self-serve, and product-led conversion.
Increase activation and reduce time-to-value for new users.
Strengthen product-qualified signals and sales handoffs.
Improve conversion across the full journey, from signup to expansion.
Build scalable automation, segmentation, and AI-enabled workflows.
Partner cross-functionally to improve not just messaging, but the product and customer experience.
Help create a more efficient go-to-market model where Sales can focus on the highest-value opportunities.

What Success Looks Like in Your First 90 Days

During your first 90 days, you will:

Complete a full audit of the current lifecycle journey across prospects, free users, trials, customers, and expansion opportunities.
Identify the biggest friction points across signup, onboarding, activation, conversion, upgrade, retention, and sales handoff.
Establish the core lifecycle metrics and reporting needed to measure performance.
Recommend immediate quick wins and longer-term structural improvements.
Build alignment with Marketing, Product, Sales, Customer Success, Revenue Operations, Data, and Engineering on lifecycle priorities.
Present a prioritized roadmap for improving PLG conversion, activation, self-serve revenue, sales efficiency, and lifecycle performance.

Responsibilities

Design, build, and optimize multi-channel lifecycle programs across email, in-app messaging, SMS, lifecycle automation, paid audience syncs, and other relevant touchpoints.
Create nurture, activation, conversion, retention, and expansion programs for prospects, free users, trials, customers, and product-qualified opportunities.
Build segmentation strategies based on persona, company size, funnel stage, use case, firmographic data, product behavior, usage signals, and revenue potential.
Develop lead scoring, product-qualified lead signals, routing logic, and sales handoff processes that improve opportunity quality and sales efficiency.
Identify friction in product flows and partner with Product, Engineering, UX, and Data to improve conversion-critical moments.
Manage lifecycle automation infrastructure, including tools such as Customer.io, HubSpot, Claude, N8N, audience segmentation, behavioral triggers, workflow logic, and documentation.
Partner with Product Marketing and Demand Generation to align lifecycle programs with acquisition strategy, messaging, positioning, conversion paths, and revenue goals.
Monitor performance across activation, engagement, conversion, trial-to-paid, free-to-paid, self-serve revenue, retention, expansion, MQL velocity, PQL quality, and pipeline influence.
Design and run A/B tests across messaging, timing, CTAs, offers, segmentation, product behavior triggers, and journey logic.
Document lifecycle journeys, automation workflows, testing plans, playbooks, and performance learnings to support long-term scalability.

Skills and Experience

We are looking for a hands-on lifecycle and PLG builder who has:

5+ years of experience in lifecycle marketing, PLG growth, CRM marketing, growth marketing, marketing automation, or demand generation within a B2B SaaS, product-led, sales technology, data, AI, or high-growth technology company.
Demonstrated experience building and optimizing lifecycle journeys from strategy through hands-on execution.
Experience working in or building freemium, free trial, self-serve, sales-assisted, or hybrid PLG motions.
Proven ability to connect lifecycle programs to revenue outcomes such as activation, conversion, pipeline, bookings, expansion, retention, or churn reduction.
Experience using product behavior, funnel data, customer insights, and experimentation to identify and improve high-impact growth opportunities.
Experience partnering cross-functionally with Product, Engineering, Sales, Customer Success, Revenue Operations, Data, Demand Generation, and Product Marketing.
Strong written communication skills with the ability to create clear, compelling lifecycle messaging.
Strong analytical skills with the ability to translate performance data into practical recommendations for Marketing, Product, Sales, Revenue Operations, Customer Success, and leadership.
A bias toward experimentation, rapid iteration, practical execution, and measurable business outcomes.
Comfort operating in ambiguity, building from scratch, and making decisions with imperfect data.

Marketing Automation and Systems

Experience with platforms such as:

Customer.io
HubSpot
Marketo
Braze
Iterable
Salesforce Marketing Cloud
N8N
Claude
Codex
Similar marketing automation, AI, CRM, or workflow tools

Technical and Data Skills

Experience with:

Salesforce or similar CRM systems
Segment or similar customer data platforms
Amplitude, Mixpanel, GA4, or similar product analytics tools
Lead scoring and routing models
Behavioral triggers and event-based journeys
Product usage data
Audience segmentation frameworks
Landing page and conversion testing tools
Workflow automation tools
AI-assisted marketing operations

Preferred Qualifications

Experience owning or influencing a digital bookings, self-serve revenue, PLG revenue, conversion, or pipeline target.
Experience improving signup, onboarding, activation, trial-to-paid, free-to-paid, upgrade, or expansion flows.
Experience working in a hybrid product-led and sales-led environment.
Experience in sales technology, revenue technology, data, AI, RevOps, or adjacent B2B SaaS categories.
Experience using AI tools to improve lifecycle marketing, automation, segmentation, analysis, messaging, or workflow efficiency.
Prior experience in a high-growth SaaS environment where Marketing, Product, Sales, and Customer Success worked closely to build a scalable revenue engine.

Benefits

At Seamless, we invest in our employees by offering a comprehensive benefits package designed to support health, financial well-being, work-life balance, and professional growth. Eligible employees have access to benefits that currently include:

Medical, dental, and vision insurance
Health Savings Account and Flexible Spending Account options
401(k) retirement plan with company matching contributions
Voluntary supplemental insurance options
Employee Assistance Program
Annual wellness reimbursement
Paid time off, company holidays, and paid parental leave for birthing and non-birthing parents
Remote-first work environment with home-office support

Benefits are subject to eligibility requirements and applicable plan documents and may be modified by Seamless at any time.

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