Chief of Staff (CEO Support)

CYVL is one of Boston’s fastest-growing venture-backed startups, leading the transformation of civil engineering. The Chief of Staff will serve as the CEO’s master organizer and communications lead, helping to optimize the CEO’s time and drive strategic initiatives within the company.

Responsibilities

• 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
• 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
• 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
• 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
• 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

Skills

• 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

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

Company Overview