Join us in revolutionizing how the world is built!

At Trestle, we're solving problems that have been entrenched at the intersection of communication and data connectivity in the construction industry for decades. We’re on a mission to improve collaboration and streamline workflows, so projects can be done faster and more cost efficiently.

We work hard, are mission driven, and love rising to a challenge. If you are looking to be part of a fast paced environment with lots of growth and want to build something that literally transforms how the world is built, come on down to Trestleland!

As Chief of Staff, you will work directly with the CEO to keep the company operating smoothly, decisively, and efficiently. This is a high-trust, high-impact role focused on execution, coordination, and operational excellence, freeing the CEO to focus on customers, strategy, and enterprise sales.

This role is ideal for someone who thrives at the center of a fast-moving organization and enjoys turning direction into action.

This position is based full-time in New York, New York, with 3 days in the office per week in Long Island City.

About the Role

We are seeking a highly organized, proactive, and execution-focused Chief of Staff to act as an extension of the CEO across the company. You will own follow-through on key initiatives, manage operational workflows, and ensure cross-functional alignment as Trestle scales.

Trestle is at a critical inflection point. We are validating product-market fit while actively selling into large, complex enterprise accounts. The CEO’s highest leverage is setting direction, engaging customers, and closing strategic deals.

This role exists to maximize CEO effectiveness by translating intent into execution, ensuring the company operates cleanly, decisively, and without unnecessary friction.

This is a Chief of Staff role that:

• Absorbs operational, administrative, recruiting, and cross-functional execution work
• Turns CEO priorities and decisions into clear plans, ownership, and follow-through
• Keeps the company running smoothly so the CEO can stay focused on external impact and strategic leadership

This is a high-trust, high-impact position with direct exposure to company strategy, customers, investors, and leadership.

Responsibilities

CEO Support & Company Execution

• Act as the CEO’s operational extension across the company
• Own follow-through on CEO decisions and commitments
• Translate high-level direction into clear actions, timelines, and owners
• Proactively identify and resolve execution gaps
• Protect the CEO’s time by absorbing operational and coordination work

Operations & Company Infrastructure

• Manage core operational workflows including:
  • Billing, invoicing, expenses, and payment tracking (with external finance support)
  • Vendor management (legal, accounting, payroll, benefits, IT)
  • Business formation, compliance, and cross-border operations (U.S. & Canada)
• Maintain and administer internal systems
• Ensure the company operates cleanly, legally, and predictably

Recruiting Operations & People Support

• Manage recruiting pipelines and candidate tracking
• Schedule interviews and coordinate interview loops
• Send candidate communications (rejections, next steps, offer process)
• Own onboarding and offboarding logistics
• Maintain employee documentation and systems
• Support performance review and separation processes

Cross-Functional Coordination

• Act as connective tissue between engineering, sales, and operations
• Maintain Linear and Notion hygiene for company initiatives
• Track priorities, dependencies, and execution status
• Run internal meetings, follow-ups, and action tracking
• Prepare concise execution updates for leadership

Customer Onboarding & Support Operations (Short-Term)

• Own post-sale customer onboarding until a dedicated customer success role is hired
• Run onboarding meetings, follow-ups, and action item tracking
• Ensure customer commitments are tracked and delivered
• Coordinate technical questions and requests with engineering leadership
• Maintain clear communication with customers around timelines and next steps

Requirements

• Exceptionally strong organizational and execution skills
• Excellent written and verbal communication abilities
• Comfortable working directly with executives and senior stakeholders
• Ability to manage multiple workstreams in a fast-changing environment
• Strong sense of ownership and follow-through
• High discretion and comfort handling sensitive information
• Calm, thoughtful, and proactive under pressure
• Experience working cross-functionally with technical and non-technical teams

Nice to Have

• Experience in a Chief of Staff, operations, or early-stage startup role
• Familiarity with SaaS or enterprise customers
• Past experience specifically in the heavy construction industry (infrastructure, industrial, commercial, multi-family)

What Success Looks Like

At 1 Month

• Strong understanding of how Trestle operates and how teams work together
• Trusted execution partner to the CEO
• Core operational workflows running smoothly
• Customer onboarding and follow-ups are organized and professional

At 3 Months

• No operational or coordination work bottlenecked on the CEO
• Clear visibility into priorities and execution across the company
• Recruiting and people operations running smoothly
• Customers feel supported and well-managed post-sale

At 6 Months and Beyond

• The company feels calmer, faster, and more focused
• Leadership has confidence that nothing important is slipping through the cracks
• The CEO is spending the majority of time on enterprise sales and strategic leadership

What We Offer

• Comprehensive medical, vision, and dental health plans
• Competitive equity options
• Flexible vacation policy
• A central role in building Trestle’s culture and operating cadence
• A dynamic work environment where you’ll never be bored

Commitment to Equal Employment Opportunity

Trestle is an equal opportunities employer, committed to building an inclusive culture where everyone feels welcomed and supported. We embrace uniqueness and believe our diverse, values-driven culture makes us stronger. This commitment extends to all aspects of employment, including recruiting, hiring, compensation, promotion, and professional development.