Strategic Pricing & Monetization Lead

Block•Bay Area, CA, United States of America, CA

5d•$207,900 - $311,900•Remote

About The Position

Block is looking for a Strategic Pricing & Monetization Lead to shape how Block creates, captures, and grows value across its sales-driven channels. This role will lead a team of strategic pricing partners who support complex commercial decisions and help Sales achieve strong outcomes for Block and our customers. The role sits within Strategic Finance and partners closely with Sales, Product, Engineering, Legal, Risk, and Revenue Operations. You will provide thoughtful commercial guidance while establishing the frameworks, tools, and guardrails needed to support consistent, well-informed pricing and deal decisions. This leader will build on Block’s existing Deal Desk capabilities by expanding the use of automation, AI, data, and scalable processes. The role will also extend the team’s impact beyond individual opportunities by using insights from complex upmarket deals to inform broader pricing, packaging, monetization, and portfolio-level initiatives.

Requirements

12+ years of experience in strategic pricing, monetization, Deal Desk, commercial strategy, revenue operations, finance, consulting, or a related field, with a track record of translating transaction-level insights into broader commercial strategy.
Experience leading and developing a high-performing team in a complex, cross-functional environment.
Experience supporting enterprise or upmarket sales motions, including complex pricing negotiations.
Experience developing pricing frameworks, discounting approaches, approval processes, commercial policies, or related governance.
Strong financial acumen and an analytical and data-informed approach, with the ability to turn complex analysis into clear recommendations and evaluate trade-offs across different business outcomes.
Experience using technology, automation, AI, or data to increase the scale and effectiveness of commercial work.
Comfort operating at both the strategic and tactical levels—from advising on individual opportunities to shaping broader commercial initiatives.
Excellent judgment and the ability to make principled decisions in ambiguous or high-stakes situations.
Clear, concise communication and strong executive presence.

Responsibilities

Lead and develop a team of strategic pricing partners who support complex commercial decisions across Block’s sales-driven channels.
Partner with Sales on the most complex and strategically important opportunities, helping teams structure deals that balance customer value, revenue quality, profitability, ROI, risk, and growth.
Build trusted relationships with Sales leadership and cross-functional partners to evaluate revenue, margin, customer economics, and long-term business impact, while informing packaging, offers, launches, and commercial models.
Establish clear, thoughtful frameworks for pricing, deal structuring, approvals, exceptions, and commercial risk that enable timely, well-informed decisions while maintaining appropriate financial and commercial guardrails.
Build on Block’s existing Deal Desk capabilities by increasing the team’s leverage through automation, AI, data, and scalable processes.
Use insights from individual opportunities and customer negotiations to identify broader pricing, packaging, monetization, and portfolio-level opportunities.
Establish reporting and operating rhythms that improve visibility into pricing performance, discounting, deal economics, and commercial outcomes.
Create practical tools, playbooks, and guidance that help Sales navigate pricing and negotiations with confidence.
Identify opportunities to simplify and scale commercial processes while preserving the judgment required for complex deals.