Lead Product Manager – Product-Led Growth (Freemium Conversion)

AlignableBoston, MA

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Job Description

Who we are:

Alignable is the largest online network of small business owners, with over 9 million members across North America. Our mission is to empower small businesses by helping them build trusted relationships and grow through referrals, connections, and community.

We don’t just connect business owners—we unlock the hidden potential in their existing networks by revealing second- and third-degree relationships that drive real business growth. With 20,000+ new freemium members joining each week, we're entering a new phase of scale where product-led growth (PLG) is core to our transformation.

Why this role matters:

This scale puts us at an inflection point. With our user volume, we have an unprecedented opportunity to unlock significant revenue growth through conversion optimization. The challenge? Most of these business owners haven't yet experienced the full power of their network—that's where you come in.

We’re hiring an experienced PLG Product Manager to lead the strategy and execution behind Alignable’s free-to-paid user journey. In this high-impact role, you'll own the product experience that converts free users into paying members, defining what users experience in their first few visits and how that experience turns curiosity into commitment.

You’ll be responsible for identifying the most valuable elements of the premium offering, then shaping how they’re surfaced—or simplified—for freemium users. The impact potential is massive—small improvements in activation and conversion at our scale translate to millions in additional ARR.

Your north star: drive activation, conversion, and revenue by making early product experiences more engaging and outcome-driven.

What you will do:

Own the free-to-paid journey: Build and optimize in-product flows that highlight premium value early and create natural upgrade moments. You'll design conversion touchpoints that feel helpful, not pushy.
Prioritize premium visibility: Evaluate and elevate paid features that best represent Alignable’s core value; strategically deprecate or redesign those that don't. Make data-driven decisions about what freemium users see and when.
Lead cross-functional execution: Partner with UX, Engineering, Data, Marketing, Customer Success, and Sales to align on goals and build seamless, measurable experiences. Drive product decisions that support shared growth objectives.
Run data-informed experiments: Launch and iterate on onboarding, matchmaking, and engagement features using behavioral analytics and cohort performance. Build a continuous testing culture focused on activation and conversion improvements.
Optimize for the right users: Design personalized experiences for high-intent cohorts and “hot leads” that signal greater likelihood to convert or retain. Use behavioral data to identify and nurture your highest-value segments.
Collaborate with Growth Marketing: Build unified user journeys, blending your product experiences with their personalized lifecycle messaging and campaign timing. Share insights and coordinate experiments for maximum conversion impact.

What success looks like:

Significant improvement in activation rate and first 14-day engagement—new users quickly discover core value and establish usage patterns that predict long-term retention.
Measurable lift in free-to-paid conversion among new and existing high-value Lead segments—your product optimizations drive more qualified users through the upgrade funnel with higher conversion rates.
Frictionless onboarding and early product experience—users complete key setup actions faster, with reduced drop-off rates and clearer paths to value realization.
Premium value is obvious and compelling across the freemium experience—free users understand upgrade benefits without feeling restricted, leading to natural conversion moments.
Seamless cross-functional execution with product, marketing, UX, and engineering teams working in sync toward shared conversion goals and celebrating joint wins.
Efficient funnel experimentation process running continuously with reliable results and actionable insights.

What you will bring:

5+ years of product management experience with demonstrated PLG success, ideally in freemium SaaS environments with a high-volume of weekly new users and measurable conversion improvements.
Proven track record of driving activation and monetization through strategic in-product experiences.
Strong understanding of user behavior, conversion funnels, and iterative testing.
Experience launching and scaling high-value onboarding, lifecycle, or freemium monetization flows.
Clear communicator with strong cross-functional collaboration instincts, especially with Growth or Lifecycle Marketers.
Familiarity with tools like Amplitude, AB Tasty, AppCues, or equivalent.
Genuine passion for small business success and empathy for time-strapped entrepreneurs.
Bonus: AI/ML experience for personalization, lead scoring, or funnel conversion optimization.

Why you’ll love Alignable:

Make a meaningful impact at a mission-driven company.
Own a high-leverage product pillar that drives revenue and user success.
Work with seasoned leaders from companies like Vistaprint, Constant Contact, and Invisalign.
Competitive compensation, equity, and full benefits.
Remote-first culture with flexible, people-first values.

Alignable is an equal opportunity employer and encourages all applicants from every background and life experience without attention to race, color, religion, sex, sexual orientation, gender identity, national origin, veteran or disability status.

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