Director, Product Pricing and Monetisation
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Job Description
Director shaping pricing, packaging, and monetization for HighLevel’s AI-powered business operating system. Leading customer research, experimentation, and commercial strategy across the company.
Responsibilities:
- Develop a company-wide pricing and packaging strategy across subscription plans, product bundles, add-ons, usage-based capabilities, services, and new product launches
- Evaluate and evolve pricing architecture across products, customer segments, and monetization models
- Identify value metrics and improve plan differentiation, feature entitlements, upgrade paths, bundling, and add-on attachment
- Build business cases and model revenue, customer impact, adoption scenarios, risks, and financial outcomes
- Develop principles for discounts, promotions, trials, grandfathering, migrations, and price increases
- Create a prioritized monetization roadmap
- Build and lead continuous customer research across prospects, trial users, paying customers, expanded customers, churned customers, agency owners, affiliates, and sub-accounts
- Establish customer segmentation and lead qualitative and quantitative research
- Create a centralized customer-insights repository and share insights with cross-functional teams and executives
- Translate research into product strategy, roadmap prioritization, positioning, onboarding, customer education, and go-to-market decisions
- Design pricing, packaging, positioning, and offer experiments
- Partner with Product, Growth, Engineering, Billing, Legal, Finance, Marketing, Sales, and Customer Success to implement approved changes
- Develop rollout strategies and guardrails that protect customer trust, conversion, adoption, and retention
- Build post-launch measurement plans and monitor conversion, plan mix, revenue per customer, expansion, churn, retention, gross margin, and lifetime value
- Maintain competitive intelligence across SaaS, agency technology, CRM, marketing automation, communications, AI, and adjacent software categories
- Establish cross-functional pricing and monetization governance, decision rights, approval processes, and measurement standards
- Present commercially grounded recommendations to senior leaders
- Build alignment, challenge assumptions, and surface trade-offs
- Initially operate as a hands-on leader and help build the pricing, monetization analytics, and customer insights team
- Raise organizational capability in customer research, pricing strategy, experimentation, and value-based decision-making
- Report to the Chief of Staff and work closely with executive leadership
Requirements:
- 12+ years of experience across SaaS pricing, monetization, product strategy, customer insights, growth strategy, management consulting, corporate strategy, or related roles
- Significant direct experience leading pricing and packaging decisions for a B2B SaaS, platform, or technology company
- Demonstrated experience translating customer research and data into changes in product, pricing, packaging, or go-to-market strategy
- Strong understanding of SaaS business models, including subscription economics, usage-based pricing, expansion revenue, retention, gross margin, and customer lifetime value
- Experience working with multi-product or multi-tier offerings and navigating pricing changes for existing and new customers
- Strong quantitative and financial modeling skills
- Experience with qualitative and quantitative research methods, including customer interviews, segmentation, surveys, willingness-to-pay analysis, concept testing, conjoint analysis, and behavioral data analysis
- Strong commercial judgment
- Excellent executive communication skills
- Highly collaborative working style and experience influencing Product, Finance, Data, Engineering, Marketing, Sales, and Customer Success leaders
- Comfort operating in a fast-moving environment where the operating model and analytical foundation may still need to be built
- Player-coach mentality, comfortable defining strategy, conducting customer interviews, reviewing analyses, building business cases, and supporting execution
- Preferred: experience with product-led growth, free trials, self-serve acquisition, or hybrid product-led and sales-assisted models
- Preferred: experience with agency software, SMB software, CRM, marketing automation, communications, payments, AI products, or vertical SaaS
- Preferred: experience with white-label products, reseller models, marketplaces, channel partners, or multi-sided platforms
- Preferred: experience launching usage-based products or monetizing high-variable-cost capabilities
- Preferred: familiarity with SQL, experimentation platforms, business intelligence tools, or product analytics systems
- Preferred: experience building a pricing, customer insights, or monetization function from an early stage
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