Managing Director - Head of Sales Enablement

About Clear Street: 

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.

 

The Role

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.

Key Responsibilities

Executive GTM & Revenue Strategy

• 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
  
  

Institutional Demand Generation & Pipeline Ownership

• 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
  
  

Revenue Operations & Process Leadership

• 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
  
  

Revenue Analytics, Forecasting & Performance Management

• 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
  
  

Revenue Technology & CRM Ownership

• 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
  
  

Cross-Functional Leadership & Enterprise Alignment

• 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
  
  

Qualifications

Required Experience

• 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
  
  

Core Skills & Expertise

• 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
  
  

Preferred Attributes

• 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
  
  

Personal Attributes

• 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

 

We Offer: 

The Base Salary Range for this role is $200,000-$265,000. This range is representative of the starting base salaries for this role at Clear Street. Where a candidate falls in this range will be based on job related factors such as relevant experience, skills, and location. This range represents Base Salary only, which is just one element of Clear Street's total compensation. The range stated does not include other factors of total compensation such as bonuses or equity.

At Clear Street, we offer competitive compensation packages, company equity, 401k matching, gender neutral parental leave, and full medical, dental and vision insurance. Our belief has always been that we are better as a business when we are all together in person. As such, we are requiring employees to be in the office 4 days per week. In-office benefits include lunch stipends, fully stocked kitchens, happy hours, a great location, and amazing views.

Our top priority is our people. We’re continuously investing in a culture that promotes collaboration. We help each other through challenges and celebrate each other's successes. We believe that modern workplaces succeed by virtue of having high-performance workforces that are diverse — in ideas, in cultures, and in experiences. We put in the effort to make such a workplace a daily reality and are proud to be an equal opportunity employer.