Sr. Director, Product Pricing and Monetisation (Product Led Pricing)

HighLevel; United States; Remote; USD 250,000 - 350,000; Full time

Job summary

HighLevel is seeking a Sr. Director of Product Pricing & Monetization to lead pricing, packaging, monetization, and customer research across the platform.

You will sit at the intersection of Product, Finance, Data, Growth, Sales, Success, Marketing and Operations, shaping the company’s commercial strategy. You will develop recommendations, drive alignment, support implementation, measure results, and iteratively improve decisions based on learnings.

Qualifications

• Lead pricing strategy and monetization framework across products and services.
• Build and manage a continuous customer-research program.
• Design and run pricing experiments with clear hypotheses and metrics.
• Translate insights into product strategy, roadmaps, and GTM decisions.
• Collaborate with Finance, Data, Growth, Marketing, Sales and Success teams to execute pricing initiatives.

Responsibilities

• Develop company-wide pricing and packaging strategy for subscriptions, bundles, add-ons and usage-based models.
• Model revenue and customer impact with cross-functional partners.
• Create rolled-out monetization roadmaps and guardrails for discounts and promotions.
• Establish post-launch measurement plans to learn from pricing decisions.
• Monitor metrics like trial conversion, plan mix, ARPU, churn, and margin.

Skills

Pricing strategy

Customer research

Experimentation

Market intelligence

Cross-functional leadership

Job description

About HighLevel: HighLevel is an AI-powered business operating system that gives agencies, entrepreneurs and SMBs the infrastructure to build, automate and scale. Today, HighLevel supports SMBs across 150+ countries, fueling community-driven growth rooted in real customer outcomes. To date, businesses operating on HighLevel have generated over $7 billion in ecosystem value, demonstrating the impact of shared infrastructure at scale. By centralizing conversations, automation and intelligence into one system, we help businesses move faster, reduce complexity and execute efficiently. Behind the platform, HighLevel powers more than 4 billion API hits and 2.5 billion message events daily. With 250 terabytes of distributed data, 250+ microservices and over 1 million domain names supported, our architecture is built for performance, resilience and long-term scalability.

Our People: With over 2,000 team members across 10+ countries, HighLevel operates as a global, remote-first organization built for speed and ownership. We value initiative, clarity and execution, creating space for ambitious people to build systems that support millions of businesses worldwide. Here, innovation thrives, ideas are celebrated and people come first, no matter where they call home.

Our Impact: Every month, HighLevel enables more than 1.5 billion messages, 200 million leads and 20 million conversations for the more than 1 million businesses we support. Behind those numbers are real people building independence, expanding opportunity and creating measurable impact. We’re proud to be a part of that.

Learn more about us on our YouTube Channel or Blog Posts

About the role :

HighLevel is hiring a Sr.Director of Product Pricing & Monetization to lead our company-wide approach to pricing, packaging, monetization, and customer research.

This person will help HighLevel answer four critical questions:

• Who are our most important customer segments, and what outcomes are they trying to achieve?

• Which products, capabilities, and services do those customers value most?

• How should we package and price our offerings to align customer value with sustainable company growth?

• How do we create a continuous customer-learning system that improves product, go-to-market, and strategic decisions?

You will sit at the intersection of Product, Finance, Data, Growth, Sales, Customer Success, Marketing, and Operations. You will combine customer research, behavioral data, market intelligence, financial analysis, and experimentation to shape HighLevel’s commercial strategy.

This is not an advisory-only role. You will be expected to develop recommendations, build alignment, support implementation, measure results, and improve decisions based on what we learn.

The role reports to the Chief of Staff and will have significant exposure to HighLevel’s executive leadership team.

What you will own

Pricing and packaging strategy

• Develop a clear, company-wide pricing and packaging strategy across subscription plans, product bundles, add-ons, usage-based capabilities, services, and new product launches.

• Evaluate how HighLevel’s pricing architecture should evolve as the platform expands into new products, customer segments, and monetization models.

• Identify the most appropriate value metrics for different parts of the platform, including where subscription, usage-based, account-based, feature-based, or hybrid pricing models may be appropriate.

• Assess opportunities to improve plan differentiation, feature entitlements, upgrade paths, product bundling, and add-on attachment.

• Build business cases for pricing and packaging changes, including expected impact on acquisition, trial-to-paid conversion, average revenue per customer, expansion, retention, gross margin, and lifetime value.

• Develop principles and guardrails for discounts, promotions, trials, grandfathering, migrations, and price increases.

• Partner with Finance and Data teams to model revenue impact, customer impact, adoption scenarios, and potential risks.

• Create a prioritized monetization roadmap rather than treating pricing as a series of isolated decisions.

Customer research and insights

• Build a continuous customer research program covering prospects, trial users, paying customers, expanded customers, churned customers, agency owners, affiliates, and the businesses operating within agency sub-accounts.

• Establish a clear segmentation framework based on customer needs, behaviors, maturity, business models, use cases, value realization, and willingness to pay.

• Lead qualitative and quantitative research, including customer interviews, surveys, concept testing, win/loss analysis, churn research, behavioral analysis, and willingness-to-pay studies.

• Understand the jobs customers hire HighLevel to perform, the outcomes they value, the alternatives they consider, and the barriers that prevent them from adopting or expanding.

• Create a centralized customer-insights repository so that research is accessible, reusable, and connected to company decisions.

• Develop a regular cadence for sharing insights with Product, Marketing, Sales, Customer Success, and executive leadership.

• Translate research into clear implications for product strategy, roadmap prioritization, positioning, onboarding, customer education, and go-to-market execution.

Experimentation and implementation

• Design pricing, packaging, positioning, and offer experiments with clearly defined hypotheses, target segments, success metrics, and decision criteria.

• Partner with Product, Growth, Engineering, Billing, Legal, Finance, Marketing, Sales, and Customer Success to operationalize approved changes.

• Develop rollout strategies that account for existing customers, new customers, channel partners, affiliates, billing complexity, communications, and customer support.

• Establish guardrails to ensure that monetization initiatives improve business performance without creating unacceptable deterioration in customer trust, conversion, adoption, or retention.

• Build post-launch measurement plans and ensure that each major pricing or packaging decision generates reusable learning.

• Monitor performance across metrics such as trial-to-paid conversion, plan mix, average revenue per customer, add-on attachment, expansion, downgrade rates, churn, net revenue retention, gross margin, and customer lifetime value.

Market and competitive intelligence

• Maintain a structured view of pricing, packaging, positioning, and monetization trends across relevant SaaS, agency technology, CRM, marketing automation, communications, AI, and adjacent software categories.

• Identify changes in customer expectations, competitive offers, business models, and emerging value metrics.

• Distinguish between competitive signals that require action and those that should not influence HighLevel’s strategy.

• Use market intelligence as one input alongside customer value, product strategy, economics, and HighLevel’s long-term differentiation.

Decision-making and organizational leadership

• Establish a