About Straddle

Straddle is building the trust layer for how money moves in the United States. The payments infrastructure that underpins $80 trillion in annual volume was designed for a world of batch processing and banking hours. We're replacing it with a single API that connects identity verification, bank account connectivity, and real-time payment processing across every major rail.

About the role

This role is the CEO's operating partner. You'll own the systems that make the company work: how we plan, how we execute, how we measure growth, and how we make decisions. The scope spans internal operations (planning cadence, org design, leadership alignment) and commercial operations (revenue infrastructure, GTM process, financial modeling).

You'll work across every function: engineering, product, sales, compliance, and fundraising. This isn't a support role that sits adjacent to the business. You're in the business, helping run it.

Success is measured by better decisions, fewer escalations, a revenue engine with clear visibility from pipeline to closed-won, and operating systems that run without constant intervention.

What you'll do

• Partner with the CEO to shape strategy and translate it into priorities, resource allocation, and execution plans.

• Build and refine the revenue operating model: pipeline tracking, forecasting, conversion analysis, and the reporting infrastructure that gives leadership real-time visibility into growth.

• Scope and lead strategic initiatives from ambiguity to measurable outcomes: pricing analysis, market sizing, GTM experiments, hiring coordination, organizational design, board prep.

• Act as a strategic advisor to leadership, providing guidance on decisions, trends, and growth opportunities.

• Monitor business and operational metrics and flag issues early, with a recommendation attached.

• Design, run, and continuously improve the company's operating cadence: OKRs, leadership reviews, planning cycles, and decision logs, with a focus on automation and explicit ownership.

• Prepare briefing materials that surface tradeoffs, risks, and recommended actions, not status updates.

• Track commitments across all leadership touchpoints with clear owners and deadlines.

• Own vendor relationships, tool procurement, and operational budget decisions that don't require CEO involvement.

• Build and maintain a knowledge base of SOPs, playbooks, and templates that compounds over time.

• Provide interim leadership coverage when needed, with real ownership for priorities and delivery.

• Handle confidential matters with complete discretion.

How the role grows

• Months 1-3: Company operating system installed. OKR cadence, leadership reviews, planning cycles, and decision-tracking live and running. Revenue reporting infrastructure in place.

• Months 4-6: Owning strategic projects and business-critical workstreams end-to-end. GTM process design, hiring coordination, organizational design, board prep, fundraising support. Making operational and commercial decisions independently.

• Months 7-12: Full strategic and operational partner. Driving company-level initiatives, owning the revenue operating model, and shaping how the company scales.

• Year 1+: Depending on performance and company growth, the role evolves into Chief of Staff, VP of Operations, or COO. The person who builds the operating and growth infrastructure is the natural candidate to lead it.

  
  

Who you are

• 5+ years in business operations, strategy and operations, or chief of staff roles working directly with a founder or C-level executive at a venture-backed company (Series A through C). You've been through at least one phase of meaningful scale and built process from scratch, not inherited it.

• Track record of building operational systems, not just running them. You default to investing in process so the organization doesn't depend on individual heroics.

• Experience leading or managing people, projects, or cross-functional workstreams. You've had direct ownership over outcomes, not just coordination responsibility.

• Strong written communication. You can draft an investor update, a board memo, or an internal brief and it reads like the CEO wrote it.

• Comfort making decisions with incomplete information and owning the outcome.

• Fluency with AI and automation tools to reduce planning, reporting, and synthesis load.

• Complete discretion with board materials, financial data, fundraising conversations, and personnel decisions.

Preferred qualifications

• MBA or equivalent graduate degree.

• Fintech or payments industry experience.

• Board meeting and investor relations exposure.

• Experience in regulated or service-oriented environments outside of tech.