Chief of Staff

Chief of Staff to the CEO

The Role

This is a Chief of Staff / Founder's Associate role for a high-trajectory operator, not an administrative position. You will function as the CEO’s master organizer, communications lead, and change agent, multiplying the CEO’s effectiveness from day one while helping the company move faster, stay aligned, and execute at a high bar.

Your job is simple to state and hard to do:
Take as much as possible off the CEO’s plate, turn relationships into outcomes, and convert priorities into closed deals and real progress.

Growth Trajectory

This role is designed for someone who wants to level up extremely fast.

You will start as a day-one force multiplier for the CEO and executive team, then grow into a true thought partner, taking on larger strategic initiatives, shaping execution, and expanding scope as the company scales.

Cyvl is one of Boston’s fastest-growing venture-backed startups, founded by three Forbes 30 Under 30 Gen Z founders, and is leading the transformation of civil engineering. Our mission is to help every town and city in the U.S (and eventually the world) build better roads and sidewalks faster, cheaper, and safer than ever before.

We believe we are ushering in the golden age of transportation infrastructure, and we intend to lead the entire category.

This is a rocket ship.
We hire killers.
We move fast.
We have fun while doing meaningful work.

Who You Are

• Exceptionally organized with strong instincts for prioritization and timing

• Strong writer and presenter; able to produce clean, persuasive decks and proposals

• Comfortable operating in CRM and turning relationship data into action

• Confident communicator with executives, customers, investors, and government officials

• Proactive, high-energy, and motivated to grow into a long-term thought partner

What You’ll Own

CEO Leverage & Time Optimization

• Own scheduling and calendar strategy so the CEO can focus on the highest-impact work

• Prioritize and sequence meetings based on revenue, strategic value, and timing

• Prepare the CEO for priority meetings with context, objectives, and follow-ups

Enterprise Deal Acceleration & Relationship Intelligence

• Accelerate enterprise deals by pairing the CEO’s relationships with the right timing, narrative, and materials

• Produce and customize high-quality decks, proposals, and written materials to advance or close deals

• Maintain rigorous CRM visibility (HubSpot): notes, momentum, next steps, blockers

• Proactively identify: Who we should be reaching out to now, which deals are stuck and how to unstick them, where warm introductions can accelerate progress

• Treat the CEO’s network (government officials, industry executives, senior advisors, investors) as a strategic asset

• Sequence outreach and meetings to open new deals, accelerate active ones, and close faster

Communications & Information Flow

• Manage and draft executive-level communications so the CEO focuses only on high-leverage comms

• Research, synthesize, and present information needed for fast, confident decisions

• Act as a trusted filter and amplifier for inbound requests

Execution, Change & Accountability

• Track strategic initiatives across the company and provide a real-time pulse on progress

• Help drive change by holding leaders accountable to commitments and timelines

• Turn CEO priorities into action and ensure nothing falls through the cracks

Delegation & Force Multiplication

• Take ownership of the CEO’s to-do list, executing directly or drafting first passes for review

• Proactively delegate work to the right people and follow through to completion

• Build systems and use AI tools to automate low-level work and increase leverage

Who You’ll Work With & Learn From

You will work directly and daily with Cyvl’s Cofounder & CEO, Daniel, and operate in tight collaboration with Cyvl’s executive leadership team, including their:

• CFO

• VP of Sales

• VP of Product

• VP of Operations

• VP of Engineering

This role gives you front-row access to how a fast-scaling, venture-backed company is built—across revenue, product, engineering, operations, and finance.

Operating Expectations

• In-office as much as possible in Somerville; occasional travel for business trips

• High agency, high-trust role with availability outside normal hours when needed

• Expected to exercise judgment independently and move fast without constant direction

• Primary optimization goal for the next 12 months: CEO leverage and revenue growth

Benefits

• Equity: meaningful, early-stage equity (just raised Series A)

• 4 weeks PTO

• Generous company holidays

• Monthly location bonus if you live within 1 mile of the office

• 401(k) with company match

• Health, dental, and vision insurance

• Ongoing talent development programs to accelerate your career now and long term

At Cyvl, we welcome and celebrate diversity in all its forms. We do not discriminate based on race, color, religion, sex, gender identity or expression, sexual orientation, age, national origin, disability, veteran status, or any other protected characteristic. Your unique perspective is valued here.