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The Senior Digital Experience Lead defines digital journey strategies for AI, IT, Employee Experience, and CRM audiences, collaborating with product marketing and executing integrated marketing campaigns.
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Who we are:
Alignable is the largest online network of small business owners in North America, with over 10 million members. We help entrepreneurs grow through trusted relationships, referrals, and partnerships—not ads alone.
We are entering a defining chapter: transforming Alignable into the first AI-powered relationship intelligence and introduction engine for small businesses. Central to this evolution is our AI Networking Coach, which guides business owners toward revenue-producing networking behaviors in real time.
This role exists to ensure that marketing, lifecycle, and sales convert our member product usage into revenue at scale.
We are looking for a senior marketing and growth leader on a VP trajectory to own Alignable’s product-led sales and lifecycle revenue motion, establish our AI-first market position, and build a repeatable system that turns free usage into durable, compounding revenue.
This is not a product management role, but a commercial growth leadership role for a builder who wants to architect how an AI-powered platform markets, converts, retains, and expands its customer base. Importantly, you will be responsible for lifecycle strategies and tactics aligned with activation, conversion, and retention but without sales-led functions such as business development and direct sales.
What you will be doing:
You will own Alignable’s end-to-end revenue growth motion, with product-led growth serving as the primary sales and conversion strategy, not a product development function.
This is a player–coach role, with a strong emphasis on hands-on execution. You’ll be deeply involved in lifecycle design, messaging, conversion optimization, and monetization—operating directly in growth, CRM, lifecycle, and experimentation systems.
You will sit at the intersection of:
- Growth & Lifecycle Marketing
- Product-Led Sales & Monetization
- AI-Driven Retention & Expansion
- Category, Positioning & Revenue Narrative
You’ll lead growth and lifecycle marketing functions, report directly to the Chief Revenue Officer, and partner closely with Product, Sales, and Data.
This role is intentionally designed to scale into VP of Marketing.
What you will own:
1) Product-Led Sales & Revenue Growth (Core Mandate)
You will design and operate Alignable’s product-led sales motion, ensuring that free usage reliably converts into paid revenue and long-term customer value.
This includes ownership of:
- Free → Paid conversion strategy across self-serve and assisted motions
- Lifecycle-driven revenue: activation, retention, reactivation, expansion, and upsell
- Monetization strategies tied to demonstrated customer ROI
- Sales enablement narratives that leverage product usage and AI insights
- Expansion paths that move members from single-product usage to multi-product adoption
Product usage is the signal. Marketing and sales are the conversion engines.
2) Lifecycle Marketing & Revenue Orchestration
You will own the funnel-driven lifecycle marketing system across:
- Email, notifications, and application experience.
- In-app messaging and prompts (in partnership with Product)
- AI-driven member communications
- Community, events, and high-intent moments
Your mandate is to:
- Move members from first value to consistent ROI
- Reduce churn by reinforcing outcomes, not features
- Identify expansion moments based on behavioral and revenue signals
- Ensure lifecycle programs are measurable, repeatable, and revenue-driven
This is lifecycle marketing as a revenue discipline, not a communications function.
3) AI as a Commercial Growth Engine
You will be the commercial owner of the AI Networking Coach, ensuring it directly supports revenue, retention, and expansion goals.
This includes:
- Defining how AI conversations and insights support conversion and upsell
- Translating AI engagement into monetization opportunities
- Partnering with Product and Engineering to ensure AI outputs align with sales and lifecycle needs
- Ensuring AI strengthens Alignable’s value story in marketing and sales contexts
You do not manage AI development; you ensure AI drives revenue outcomes.
4) Brand, Positioning & Revenue Narrative
You will lead Alignable’s market narrative with a clear commercial lens.
This includes:
- Owning positioning, messaging, and value propositions across the funnel
- Defining Alignable’s differentiation as an AI-powered relationship and referral engine
- Building category credibility with buyers, not just users
- Ensuring marketing, sales, and lifecycle touchpoints tell a single, economically coherent story
Brand here exists to accelerate conversion and expansion, not just awareness.
5) Growth Velocity, Experimentation & Commercial Rigor
You will set the operating cadence for revenue-focused experimentation:
- Clear KPI ownership across conversion, retention, and expansion.
- Rapid testing of messaging, offers, pricing, packaging, and lifecycle programs
- Tight feedback loops between data, insight, and execution
- Strong prioritization around initiatives that materially move revenue
Speed, discipline, and accountability are non-negotiable.
What you will bring:
- 8–15 years of experience in growth marketing, lifecycle marketing, revenue marketing, or product-led sales
- Proven ownership of conversion, monetization, and expansion, not just acquisition
- Experience operating in high-growth SaaS, marketplace, or network-effect businesses
- Strong intuition for how usage signals translate into sales opportunity
- Experience working alongside and influencing Product
- AI-fluent: comfortable using AI systems as commercial leverage
- Exceptional storyteller with strong economic and buyer-centric framing
- Data-driven, experiment-oriented operator
- Builder mindset with a bias toward action and accountability
- Founder or zero-to-one experience a strong plus
What success looks like (12-18 months):
- Product-led sales is Alignable’s dominant revenue motion
- Free-to-paid and tier-to-tier conversion materially outperform historical benchmarks
- AI-driven lifecycle programs measurably increase retention and expansion
- Marketing and lifecycle are viewed as revenue infrastructure, not support functions
- You are operating at VP-level scope and impact
Why Alignable?
- Impact & Mission: Help millions of small businesses grow through trusted relationships while owning a pivotal moment in Alignable’s evolution toward AI-powered, product-led sales.
- Team & Environment: Partner with a founder-led, cross-functional leadership team with deep experience in SMB, SaaS, and growth-driven businesses.
- Compensation & Benefits: Competitive salary, meaningful equity, flexible work, comprehensive benefits, and long-term ownership upside.
- Diversity & Inclusion: We celebrate diverse perspectives and believe they create stronger businesses and better outcomes.
Our culture in action:
- 🎉Enjoy the Journey: We're passionate about our mission but don't take ourselves too seriously. We celebrate customers, teammates, and key moments.
- 🤝 Be Stronger Together: We combine strengths, build trusted relationships, and treat everyone as partners. No egos welcome.
- 🌈Be Different Together: We create space for everyone to show up as their truest selves and seek diverse perspectives.
- 👑Act Like an Owner: We proactively act on behalf of the entire company and customers, not just ourselves. No passing the buck.
- 🎯Change the Game: We start with first principles, assume nothing is impossible, and go after 10x outcomes relentlessly.
- 📈Adapt & Evolve: We accept we won't be right every time and create an environment where people feel safe to admit failure and lean into learning.
- 🧠 Exercise Excellent Judgment: We turn knowledge into understanding based on equal parts data and intuition.
- ⚡Profound Bias for Action: Speed matters. We value calculated risk-taking while avoiding one-way doors.
- ❤️ Be Customer Obsessed: We work vigorously to earn and keep customer trust in everything we decide to work on and how we do it.
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.
Alignable Boston, Massachusetts, USA Office
Boston, Massachusetts, United States
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