Chief of Staff

Crane Venture Partners; New York (NY); Hybrid; USD 270,000 - 300,000; Full time

Benefits offered by this job

Stock options

Home office stipend

Learning & development budget

Phone and international data plan

Job summary

Gigs is building the operating system for mobile services. As Chief of Staff to the CEO, you accelerate decision-making, align leadership, and drive critical initiatives from strategy to execution.

You’ll own communications, board materials, and cross-functional programs that move the company faster while maintaining a founder-driven culture. You’ll work closely with the leadership team, preparing narratives, shaping the fundraising story, and ensuring follow-through on high-priority projects.

Qualifications

• 8+ years across strategy, ops, or senior strategy/ops in high-growth tech
• Executive-style writing and slide delivery
• Ability to make progress with imperfect information and shifting priorities
• Comfort with financial modeling, cap tables, and board narratives
• High ownership, discretion, and deadline-driven work

Responsibilities

• Be the CEO's thought partner with structured analysis and clear recommendations
• Build and run the founders' transmission layer across the company
• Own board and investor materials and fundraising narratives
• Write in the founders' voice for decks and memos across the organization
• Lead cross-functional, confidential projects end to end
• Act as proxy for founders in meetings and unblock teams

Skills

Senior generalist

Executive communication

Judgment under ambiguity

Business & financial fluency

Ownership & discretion

Job description

About Gigs

At Gigs, we're building the operating system for mobile services—a platform that lets tech companies embed global connectivity into their products effortlessly.

Just as Stripe lets any business add a payment button in seconds, Gigs empowers platforms to weave in connectivity—bridging the traditional world of telecom with modern tech. From fintechs launching mobile services to HR platforms offering work phone plans, we automate provisioning and remove telecom complexity.

Our team of around 150 people across the US and Europe, backed by nearly $100 million in funding from Ribbit Capital, Google, and Y Combinator. As one of the fastest-growing tech companies, bringing together early-stage engineers, product builders, and business athletes from companies like Stripe, Airbnb, and Shopify. We’re tackling deep technical and regulatory challenges to make connectivity truly seamless.

If you’re driven by curiosity, creativity, and the chance to shape the future of telecom, we’d love to hear from you.

Things We Care About

We are building in a highly complex space and tackling a massive problem. We want people who lean in when things get hard.

• Speed. We move and we ship. We set bold deadlines and treat every week like it matters.
• Ownership. If you see something broken, fix it. We don't wait for permission.
• Customer Obsession. Our customers' product is our product.
• Ambiguity. We're building frontier technology in a complex domain. You'll need sound judgement and good instincts to make decisions without complete information.
• First principles. We don't ask how things have been done before. We ask why they were done that way at all.

The Role

As Chief of Staff to the CEO, you are our CEO's force multiplier. You make the CEO and the company move faster and decide better.

You work at the center of Gigs: strategy, the leadership team's operating cadence, board and investor work, and the highest-priority projects in the company. You take first cuts on ambiguous problems, turn rough direction into sharp narratives, and build the mechanisms that keep a fast-scaling company aligned as it grows. When something matters and has no owner, you own it.

This is a senior role. You will sit in rooms with the leadership team, the board, and investors, and you will be trusted to act on the CEO's behalf. It is also a role of high leverage and low ego: your job is to make other people's output better, often without your name on it.

Salary range: $270K - $300K

What You Will Do

• Be the CEO's thought partner. Take structured first cuts on the hardest questions. Synthesize context, run the analysis, frame the options and trade-offs, and recommend a path. Give our CEO a sharper starting point than a blank page.
• Build and run the founders' transmission layer. Turn the founders' priorities into execution across the company. Capture decisions, drive follow-ups, close loops, and make sure nothing important waits on them. This is the operational spine of the founders' office, and you own it.
• Own board and investor work. Build board decks and investor materials that tell a clear, honest story. Shape the fundraising narrative and the numbers behind it. Prepare the founders for every board meeting and investor conversation so they walk in ready.
• Write in the founders' voice. Turn rough storylines into polished decks and memos for all-hands, builder meetings, leadership reviews, and external moments.
• Lead special projects end to end. Take on the urgent, cross-functional, often confidential work: fundraising, org design, new market entry, key hires, the occasional fire. Drive them to done.
• Act as proxy. Represent the founders in meetings when they can't be there. Carry decisions, unblock teams, and be a reliable channel between the founders and the company.

What We Are Looking For

• Senior generalist track record. 8+ years across strategy consulting, banking, VC, or senior strategy/ops roles in high-growth tech. You have run workstreams, teams, or functions, and people trust your judgment.
• Executive-grade communication. Writing and slides that tell a clear story and drive a decision. You can brief a board and rally a room of builders with the same material.
• Sound judgment under ambiguity. You make progress with imperfect information and competing priorities. You make the call and own it.
• Business and financial fluency. You are comfortable with a model, a cap table, a board narrative, and the metrics that run the business. You can hold your own with Finance and investors.
• High ownership and discretion. Deadline-driven, detail-obsessed, able to run many workstreams without dropping balls. Trusted with the company's most sensitive information.

Work At Gigs

At Gigs, we value in-person collaboration. We believe the best ideas, decisions, and relationships are built when teams spend meaningful time together, and our culture is designed around that belief. We support flexibility where it makes sense. Some focused work can be done remotely, and not every role or week looks the same. You should expect regular time in one of our hubs, as well as occasional travel for team workshops, customer meetings, and Gigs Republic, our bi-annual company off-site. Our offices are designed to feel like home-inspired workspaces, with plants, thoughtful tools, and small, tight-knit teams that make collaboration feel natural, energizing, and effective.

What We Offer

At Gigs, we believe in rewarding excellence. We offer competitive compensation and stock options because we see you as a true partner in our growth. We also provide stipends for your home office or work setup, a budget for learning and development to fuel your career, and of course, a free phone and international data plan

Want to learn more about our benefits, hubs, and what it’s like to work at Gigs? Check out our Careers page.