Chief of Staff / Head of Business Operations | Cubyl Co | Handshake

Cubyl Chief of Staff / Head of Business Operations Reports to: CEO / Founder | Full-time | Remote What You’ll Own This role has five core pillars. You are expected to own outcomes in each of them — not just support others who do. 1. CEO Support

• Serve as a trusted proxy for the CEO — represent their priorities in meetings, decisions, and communications
• Own the company’s OKR process end-to-end: facilitation, tracking, and accountability reporting
• Run the leadership operating cadence
• Filter and triage competing priorities so the founder stays focused on the highest-leverage work
• Act as a sounding board and thought partner on strategy, hiring decisions, and company direction
• Own financial planning and monitoring — budget management, cash flow tracking, burn rate oversight, and flagging variances before they become problems
• Prepare financial summaries and internal spend reviews that give leadership a clear picture of company health at any point in time

2. GTM & Early Sales Strategy

• Own and evolve the go-to-market strategy in partnership with the CEO
• Build and run early sales cycles — outreach, qualification, demos, and closing alongside the founders
• Develop the sales playbook: ICP definition, messaging, outreach sequences, and objection handling
• Bring a working knowledge of how sales cycles operate in B2B environments — understanding deal stages, buyer psychology, multi-stakeholder dynamics, and what moves a deal forward vs. stalls it
• Establish the feedback loop between customers and product to inform roadmap and positioning
• Help hire and onboard the first dedicated sales or revenue hire when the time comes

3. Special Projects & Operations Builds

• Lead one-off strategic and operational projects
• Build internal processes and playbooks where none exist — from hiring workflows to market analysis
• Own cross-functional initiatives that require coordination across engineering, product, and business
• Conduct market and competitive research to inform strategic decisions
• Take ambiguous problems from ‘undefined’ to ‘solved’ with minimal hand-holding
• Serve as the operational hub for all hiring – from identifying team needs, job specs, recruitment, and hiring in partnership with relevant stakeholders/leads

4. Company Rhythm & OKR Management

• Design and run the company’s goal-setting and tracking process (OKRs or equivalent)
• Facilitate quarterly planning cycles — aligning the team on priorities before each quarter begins
• Own strategic meetings — agenda, format, and follow-through
• Ensure decisions made in leadership meetings are documented and actioned

5. Product & Engineering Partnership

• Feed structured customer and market insight back into product conversations — you are the bridge between what the market needs and what the team is building
• Partner with the PM on go-to-market readiness for new features and launches
• Build credibility with the engineering team as a business operator who understands the product deeply and respects the technical culture

What We’re Looking For We care far more about the quality of your thinking and your track record of owning outcomes than your exact background. That said, the following profiles tend to succeed in this role: Background

• 3–7 years of experience in a high-performance environment — early-stage startup, venture capital, investment banking, management consulting, or a growth-stage technology company
• Direct experience working with founders or C-suite executives in an operator or strategic capacity
• Experience working with or embedded alongside Product and Engineering teams
• A working understanding of how B2B sales cycles operate — deal stages, buyer dynamics, pipeline management, and what separates deals that close from deals that stall
• Domain knowledge of financial markets strongly preferred — familiarity with how equity analysts work, what portfolio specialists bring to institutional conversations, and the language and priorities of the investment management world.
• CAPM, PMP, or other project management certification preferred

What You Bring

• Structured thinking. You can take a messy, ambiguous problem and bring clarity to it quickly. You write well and communicate precisely.
• Bias to action. You move fast, make decisions with incomplete information, and course-correct as you learn.
• Builder mentality. You are energised, not intimidated, by the absence of process. You build things from scratch and leave them better than you found them.
• High EQ. You can read a room, manage up and across without authority, and build relationships with engineers, customers, and C-suite alike.
• Financial acumen. You can read a P&L, track a budget, and hold your own in a conversation about cash flow, burn, and unit economics. Numbers inform your decisions and you know when to flag what you’re seeing.
• Commercial instinct. You understand how customers buy and why deals move or stall. You’re comfortable in a sales conversation and can think clearly about pipeline, positioning, and revenue levers.

Hard Requirements

• Exceptional written and verbal communication — you will represent the company and the founders externally
• Comfort with ambiguity and rapid context-switching — no two weeks look the same in this role
• Ability to work in a small, fast-moving team where titles matter less than output
• Based in the United States, ideally East Coast, or able to work East Coast hours for a remote team

Why This Role We know this kind of role is rare, and we want to be honest about what it is — and what it isn’t. What makes this a great opportunity

• You will have more ownership and exposure at this company than you would get in years at a larger one
• You’ll work directly with the founder on the most important decisions the company makes — commercial, strategic, and operational
• You’ll be one of the most senior business operators at the company — the decisions you make will be visible and consequential

What to expect (honestly)

• This is an early-stage company. Things move fast and change direction. Comfort with that is a prerequisite, not a bonus
• The team is mostly engineers. You will need to build relationships and credibility in a technical culture without a ready-made peer group on the business side
• There is no playbook yet. You’re writing it. That’s the job
• The role will evolve quickly. What you own in month 3 may look very different from month 12 as the company grows and hires around you

If you’re looking for a clearly defined remit, a team of peers to benchmark against, and a role where impact is measured quarterly — this probably isn’t the right fit.

How to Apply

Send a short note to [[email protected]] with the subject line “CoS / Head of Biz Ops”. Tell us:

• What you’ve worked on that’s most relevant to this role — be specific about what you owned and what happened
• Why this company and this stage interest you
• CV

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