Managing Director - Head of Sales Enablement

Clear Street•New York, NY

7h•$200,000 - $265,000•Onsite

About The Position

Clear Street is modernizing the brokerage ecosystem. Founded in 2018, Clear Street is a diversified financial services firm replacing the legacy infrastructure used across capital markets. We started from scratch by building a completely cloud-native clearing and custody system designed for today’s complex, global market. Clear Street’s proprietary prime brokerage platform adds significant efficiency to the market, while focusing on minimizing risk, redundancy, and cost for clients. Our goal is to create a single source-of-truth platform for every asset class, in every country, and in any currency. By combining highly-skilled product and engineering talent with seasoned finance professionals, we’re building the essentials to compete in today’s fast-paced markets. We are seeking a Managing Director of Revenue Operations & Go-To-Market Strategy to lead and optimize the firm’s end-to-end revenue engine. This executive role is responsible for defining and scaling the GTM operating model, owning revenue operations, pipeline governance, and sales-driven demand generation across the organization. The Managing Director will partner closely with Sales, Marketing, Finance, Product, and Executive Leadership to ensure predictable revenue growth, data-driven decision-making, and operational excellence. This role carries enterprise-level accountability for pipeline performance, forecasting accuracy, and the systems and processes that enable efficient revenue execution.

Requirements

10–15+ years of progressive experience in revenue operations, go-to-market strategy, sales operations, or growth leadership roles
Demonstrated success leading revenue operations and pipeline strategy in high-growth environments, ideally within FinTech, Financial Services, or enterprise technology
Proven ownership of enterprise forecasting, pipeline governance, and GTM execution
Experience operating as a senior leader partnering directly with executive teams
Executive-level GTM and revenue operations leadership
Enterprise demand generation and pipeline strategy
Revenue forecasting, modeling, and analytics
Salesforce and modern RevOps technology ecosystems
Process design, automation, and systems integration
Cross-functional leadership and executive communication

Nice To Haves

Strategic executive mindset with the ability to move seamlessly between vision and execution
Strong commercial intuition and understanding of institutional buyers and complex sales cycles
Highly analytical with the ability to translate data into decisive action
Comfortable leading in ambiguity and building scalable systems in growth-stage environments
Executive presence with a bias toward accountability and outcomes
Curious, adaptable, and energized by building and scaling revenue engines
Collaborative and empathetic leader who elevates teams and cross-functional partners
Passion for leveraging technology, automation, and AI to drive operational excellence and growth

Responsibilities

Define and own the firm’s global go-to-market operating model, aligning sales execution, demand generation, and revenue operations with strategic growth objectives
Serve as a senior advisor to executive leadership on pipeline health, revenue performance, and growth opportunities
Translate corporate strategy into scalable GTM processes that drive predictable, repeatable revenue growth
Present revenue insights, forecasts, and strategic recommendations to senior leadership and executive stakeholders
Oversee sales-driven demand generation strategy, including outbound prospecting, account-based targeting, and pipeline acceleration initiatives
Establish and govern account prioritization frameworks, lead scoring models, and qualification standards
Ensure seamless handoff of qualified opportunities across GTM teams to maximize conversion and velocity
Partner with sales leadership to refine messaging, targeting, and engagement strategies for institutional and enterprise buyers
Architect and continuously optimize scalable workflows for lead management, pipeline progression, forecasting, and quota attainment
Own the design and governance of revenue processes to improve efficiency, visibility, and execution quality
Lead automation and systems integration initiatives across the GTM ecosystem to eliminate friction and improve scalability
Establish best practices for pipeline inspection, deal hygiene, and revenue governance
Own enterprise revenue forecasting and pipeline modeling end to end
Define and track key performance indicators including pipeline velocity, conversion rates, forecast accuracy, and revenue attainment
Deliver actionable insights through executive dashboards and reporting frameworks
Ensure data integrity, accuracy, and consistency across all revenue and CRM systems
Provide executive ownership of Salesforce and the broader revenue technology stack, including tools such as Clari, Groove, LeanData, ZoomInfo, and future platforms
Evaluate, select, and implement technologies that materially improve GTM efficiency, insight, and scalability
Ensure seamless data flow, automation, and system adoption across sales, marketing, and finance functions
Act as a connective leader across Sales, Marketing, Finance, Product, and Operations
Partner with Finance on revenue planning, forecasting, and long-range growth modeling
Support executive decision-making with data-driven analysis and scenario planning
Drive organizational alignment around revenue priorities, execution standards, and accountability