Head of Operations

Streetsense; Washington (District of Columbia); On-site; USD 180,000 - 280,000; Full time

Benefits offered by this job

Medical, Dental, Vision Insurance

401k match

Wellbeing resources

Job summary

Streetsense is seeking a Head of Operations to serve as the senior operational leader, uniting people, process, technology, and performance management to scale the business while preserving its entrepreneurial culture. Reporting to the Board, you will drive planning, forecasting, and cross-unit collaboration to enhance profitability and resource use.

The role requires a proven operator with experience in design, architecture, or professional services, strong financial acumen, and the ability to

Qualifications

• Strategic thinker and disciplined executor
• Emotionally intelligent and highly effective communicator
• Collaborative, pragmatic, and low-ego leader
• Comfortable operating in a Board-led environment
• Data-driven, with an appreciation for creativity and design
• Curious and committed to continuous improvement
• Effective coach, mentor, and developer of talent
• Entrepreneurial and comfortable navigating ambiguity and change

Responsibilities

• Partner with the Board and business-unit leaders to translate strategic priorities into measurable operating plans
• Lead annual planning, quarterly priority-setting, and execution reviews
• Establish clear goals, ownership, accountability, and firm-wide operational reporting
• Develop resourcing and performance benchmarks informed by industry best practices
• Improve profitability, margins, and operating efficiency in collaboration with Finance and unit leaders
• Establish disciplined monitoring of utilization, project profitability, backlog, forecasting, and resource allocation
• Develop reporting systems that provide timely, actionable visibility into operating performance
• Oversee and continuously improve the firm’s core operating infrastructure and workflows
• Improve the quote-to-cash process, including scoping, staffing, project setup, delivery, billing, and collections
• Establish scalable operating standards across service lines while preserving entrepreneurial flexibility
• Define and lead the firm’s operational technology roadmap
• Evaluate and implement AI, automation, and workflow tools that improve productivity and service delivery
• Improve integration among project management, CRM, finance, and resource-planning platforms
• Drive adoption, governance, and continuous improvement of operating systems
• Partner with business-unit leaders on organizational design and workforce planning
• Build leadership capacity, succession pipelines, and meaningful career-development pathways
• Strengthen goal-setting, feedback, performance management, and leadership accountability
• Reinforce Streetsense’s culture and entrepreneurial spirit while advancing a “One Streetsense” mindset across offices, disciplines, and business units

Skills

Strategic thinker

Disciplined executor

Emotionally intelligent communicator

Collaborative leadership

Data-driven

Continuous improvement

Coach and mentor

Entrepreneurial mindset

Job description

Description

Streetsense is a multidisciplinary design and strategy company that helps create places and brands people love. Our work sits at the intersection of strategy, design, branding, real estate, and experience. Through our three integrated business units—Place Consulting, Interior Architecture, and Creative Agency—we help owners, developers, institutions, and cities create destinations that drive economic, social, and cultural value.

As Streetsense enters its next phase of growth, we are seeking a Head of Operations who can help transform strategy into execution, strengthen operational performance, and build the systems, processes, and accountability necessary to scale the business while preserving the entrepreneurial culture that defines Streetsense.

Position Overview

The Head of Operations serves as Streetsense’s senior operational leader and chief integrator, bringing together people, process, technology, and performance management to create a more connected, efficient, and scalable business. Reporting directly to the Board of Directors, this leader oversees day-to-day operations, aligns the business units, improves profitability and resource utilization, and drives execution of the firm’s strategic priorities. Success requires equal parts operator, coach, and change agent, along with a visible organizational presence and periodic travel to support teams, clients, and company initiatives.

What Success Looks Like

Within the first 12 months, the Head of Operations will have:

• Established a disciplined operating cadence and improved visibility into staffing and financial performance
• Strengthened forecasting, resource planning, and cross-business-unit collaboration
• Reduced friction and administrative burden in core workflows
• Advanced the use of technology and AI-enabled tools to improve productivity
• Developed emerging leadership capacity and strengthened organizational accountability
• Reinforced a unified “One Streetsense” culture that supports growth without sacrificing creativity

Key Responsibilities, Strategy & Execution

• Partner with the Board and business-unit leaders to translate strategic priorities into measurable operating plans
• Lead annual planning, quarterly priority-setting, and execution reviews
• Establish clear goals, ownership, accountability, and firm-wide operational reporting
• Develop resourcing and performance benchmarks informed by industry best practices

Financial Performance

• Partner with Finance and business-unit leaders to improve profitability, margins, and operating efficiency
• Establish disciplined monitoring of utilization, project profitability, backlog, forecasting, and resource allocation
• Develop reporting systems that provide timely, actionable visibility into operating performance

Operations & Delivery Excellence

• Oversee and continuously improve the firm’s core operating infrastructure and workflows
• Improve the quote-to-cash process, including scoping, staffing, project setup, delivery, billing, and collections
• Establish scalable operating standards across service lines while preserving appropriate entrepreneurial flexibility

Technology & Innovation

• Define and lead the firm’s operational technology roadmap
• Evaluate and implement AI, automation, and workflow tools that improve productivity and service delivery
• Improve integration among project management, CRM, finance, and resource-planning platforms
• Drive adoption, governance, and continuous improvement of operating systems

Talent & Organizational Development

• Partner with business-unit leaders on organizational design and workforce planning
• Build leadership capacity, succession pipelines, and meaningful career-development pathways
• Strengthen goal-setting, feedback, performance management, and leadership accountability
• Reinforce Streetsense’s culture and entrepreneurial spirit while advancing a “One Streetsense” mindset across offices, disciplines, and business units

Ideal Candidate:

The ideal candidate is a proven operator with experience leading a creative, consulting, design, architecture, or other professional-services organization. This person understands that great firms are built through people, process, accountability, and culture—not bureaucracy.

• Strategic thinker and disciplined executor
• Emotionally intelligent and highly effective communicator
• Collaborative, pragmatic, and low-ego leader
• Comfortable operating in a Board-led environment
• Data-driven, with an appreciation for creativity and design
• Curious and committed to continuous improvement
• Effective coach, mentor, and developer of talent
• Entrepreneurial and comfortable navigating ambiguity and change

Requirements

• 10+ years of operational leadership experience within a professional services organization
• Previous experience in a comparable executive-level operational leadership role
• Demonstrated success improving profitability, operational discipline, and organizational performance
• Experience leading across multiple disciplines, offices, or business units within a complex organization
• Strong financial acumen, including experience with forecasting, utilization, project economics, and resource planning
• Experience implementing operating systems, technology platforms, and performance-management frameworks
• Experience managing through growth and organizational change

Streetsense is committed to creating a diverse environment and is proud to be an equal opportunity workplace. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, or veteran status.

This job operates in a professional office environment and involves regular computer use, communication, and occasional travel.

Base salary is just one component of Streetsense's total rewards philosophy. We offer a wide range of benefits and perks that appeal to the variety of needs across our diverse employee base. This may include Medical Dental & Vision Insurance, paid time off, 401k match, wellbeing resources, and more.