Riley B.
Pricing Strategy & Consulting | Monetizing innovation
I'm a SaaS pricing and monetization operator. I've spent more than a decade helping software companies take innovative products to market with innovative pricing & packaging. I work with companies at every stage - from founders who are just getting started, to growth-stage teams, to the larger incumbents. A summary of the work I do: - Pricing model design: seat-based, usage-based, consumption, hybrid, and outcome-based models for AI products - Pricing agents: build AI agents that do monetization work, or act as your all-in-one Pricing function - Pivots: seat-based to usage- or outcome-based pricing, including the billing infrastructure, sales motion, and customer migration those pivots require - Packaging architecture: tier design, feature gating, add-on strategy, and the upgrade paths that turn a free user into an enterprise account - Pricing research: customer interviews, surveys, financial modeling, market research, competitive teardowns, experimentation, and deeep data analysis - Customer migrations: segmenting the base, sequencing communication, and moving large installed bases through major pricing changes without blowing up retention - Governance and ops: approval frameworks, cross-functional pricing rituals, product catalog governance - Proserv and CX: packaging and monetizing the value of helping customers optimize their deployments I live and work in Brooklyn, NY, and I like to enjoy my time away from work exploring the city with my partner, curling up with a good book in a local park, and traveling the world for the best beaches and waves.
Earnings and projects
Last 6 months ÷ 2, the fewest it counts (since Oct 2026)
Read daily since Oct 13, under 30 days
Billed in all: $14,839$15k
$12k in the last 6 months
Earnings, last 30 days
Tracked from Oct 13, 2026.
Skill rankings: #1 in 1 skill of 11
Rarest: top 0.66% in Pricing Research, of 152. Ranked by MRR among everyone on Upwork with the skill.
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