Associate Director - People Strategy

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: Associate Director, People Strategy

Clear Street is seeking an Associate Director, People Strategy to support the design, execution, and digital enablement of people programs and processes across the organization. Reporting to the HR COO, this role sits at the intersection of strategy, operations, and technology – and is built for someone who thinks rigorously, executes methodically, and connects dots across a complex, multi-workstream people function.

This is a genuinely new kind of role. We are not looking for a traditional HR business partner, a classic chief of staff, or a program manager in the narrow sense. We want someone who brings the structured thinking of a program manager, the analytical rigor of a strategist, and the product sensibility to ask “how does this scale?” at every turn. You will be a critical thought partner to the HR COO and a connective force across People Systems, People Analytics, Talent Acquisition, Total Rewards, and People Operations.

This is a high influence role for someone who wants to shape how a modern, fast-growing financial services firm runs its people function, and who finds energy in the space between strategy and execution.

Responsibilities

COO Office & Strategic Support

• Serve as a strategic thought partner to the HR COO – supporting priority-setting, decision framing, and the management of cross-functional relationships.
• Manage the operating cadence of the HR function: governance forums, leadership updates, board and executive committee materials, and cross-functional coordination.
• Prepare high-quality strategy documents, executive presentations, and business cases that communicate people strategy to senior leadership with clarity and precision.
• Track the function’s strategic commitments, surface risks, and ensure initiatives are progressing against plan.

People Program Design & Execution

• Partner with the People, Programs and Rewards COE to drive new people programs throughout the organization, from scoping and stakeholder alignment through build, launch, and measurement.
• Own program management across HR’s cross-functional initiatives: build project plans, manage workstreams, surface risks early, and drive decisions across competing priorities.
• Translate people strategy into operational reality – defining the processes, workflows, and enabling technologies needed to bring programs to life at scale.

Digital Enablement of HR Processes

• Serve as the bridge between HR strategy and HR technology: partner with the People Systems Director and People Analytics to ensure new programs are digitally enabled, automated where possible, and built on reliable data.
• Act as the product owner between HR business owners and technical teams – defining functional and process requirements, prioritizing enhancements, and ensuring solutions meet actual user needs.
• Identify opportunities to eliminate manual processes, improve the employee and manager experience, and leverage the HR tech stack more effectively across the employee lifecycle.
• Champion a design once, scale everywhere mindset: build programs and processes that hold up as the firm grows.

Insight & Analytics

• Partner with People Analytics to synthesize workforce data into strategic insights that inform program design, headcount decisions, and executive reporting.
• Build business cases for people programs using both quantitative evidence and qualitative input from stakeholders.
• Develop a consistent point of view on workforce trends, org health, and the effectiveness of people programs, and bring recommendations to the HR COO and leadership team.
• Close the loop: monitor program outcomes and use data to drive continuous improvement across the people function.

Requirements

Experience

• 8+ years of experience in a role that combines strategy, program management, and operations – management consulting, chief of staff, HR strategy, or people operations leadership in a high-growth or institutional environment.
• Proven track record of designing and executing complex, cross-functional programs from concept to operational scale.
• Experience operating at the intersection of HR and technology: whether as a product manager, HR systems owner, or digital transformation lead, you understand how people processes get systematized.
• Financial services or high-growth technology experience strongly preferred.
• Experience supporting senior executives and navigating complex, multi-stakeholder environments.

Analytical & Functional

• Strong analytical skills – comfortable building business cases, synthesizing workforce data, and communicating insights clearly to executive audiences.
• Structured problem-solver: able to take ambiguous mandates and turn them into clear project plans, process designs, and measurable deliverables.
• Ability to define process and functional requirements and work effectively with technical teams (Engineering, Systems, Analytics) to bring them to life.
• Familiarity with the HR systems landscape and the employee lifecycle — you don’t need to configure Workday, but you should understand how it works and what it enables.
• Proficiency in tools for program management, data analysis, and executive communication (e.g., Excel, PowerPoint, and project management platforms).

Mindset

• Strategic operator: equally comfortable developing a multi-year people strategy framework and managing the day-to-day execution of a complex program.
• High agency and ownership mentality: you define the scope, manage the stakeholders, and drive the work to completion without waiting to be told what to do.
• Builder mentality: energized by creating structure, process, and systems where they don’t yet exist.
• Commercial mindset, and intellectually curious about how organizations scale and how people programs drive business performance.

We Offer:

The Base Salary Range for this role is $150,000-$200,000 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. #LIHYBRID