Founder's Office

Kastle AI Inc

$100K — $150K *
Business Services
Less than 5 years of experience
Job Overview by Ladders

Qualifications

  • 3-7 years in fast-paced environments like startups or consulting.
  • Strong writing skills for memos and project plans.
  • Experience with enterprise customers and regulated workflows preferred.
  • Analytical skills, including KPI design and basic modeling.
  • Ability to manage stakeholders, both internal and external.

Responsibilities

  • Own and manage the CEO's operational cadence and tracking systems.
  • Turn leadership conversations into actionable plans with clear owners.
  • Prepare and execute briefs, agendas, and follow-up materials for meetings.
  • Run multiple cross-functional special projects across various departments.
  • Build scalable systems including dashboards, templates, and playbooks.
  • Support enterprise deal execution with thorough documentation and coordination.
  • Operationalize compliance and maintain change management discipline.

Benefits

  • Opportunity to work closely with the CEO and leadership team.
  • Impact on key company operations and strategic projects.
  • High agency role with a focus on execution, not just coordination.
  • Fast-paced environment ideal for learning and growth.
  • Potential for career advancement in a founder-led structure.
Full Job Description
About The Role

You'll sit in the Founder's Office and act as force-multiplier to the CEO and leadership team. This is not a coordination role - this is an execution role. You'll take ambiguous, cross-functional problems (GTM, product ops, customer delivery, hiring, internal cadence) and drive them to crisp plans, clear owners, and shipped outcomes.

What You'll Do
CEO & Founder Enablement
  • Own the CEO's operating cadence: weekly priorities, KR tracking, meeting hygiene, decision logs, follow-ups.
  • Turn leadership conversations into action: write crisp memos, capture decisions, assign owners, drive closure.
  • Prepare internal and external meetings: briefs, stakeholder maps, agendas, talking points, post-meeting execution.
Strategic & Cross-Functional Execution
  • Run special projects across Product, Engineering, Sales, and Customer Success - often simultaneously.
  • Build lightweight systems: dashboards, templates, playbooks, and operating routines that scale.
  • Drive 01 initiatives: customer onboarding plans, KPI frameworks, pricing analyses, process redesigns.
GTM & Customer Delivery Ops
  • Support enterprise deal execution: proposal/SOW hygiene, pricing models, redline coordination, mutual action plans.
  • Create customer-ready artifacts: exec updates, ROI/KPI reporting, launch comms, rollout plans.
  • Own the details on high-stakes timelines: dependencies, risk flags, escalation paths.
Compliance, Quality & Governance
  • Help operationalize compliance: tracking policy updates, QA workflows, audit-ready documentation, evidence collection.
  • Maintain discipline around change management: what changed, why, who approved, what the rollout plan is.
Internal Operations
  • Improve internal throughput: planning rituals, meeting structures, hiring process upgrades, tooling choices.
  • Partner with Finance/BizOps on budgeting, vendor management, and operational metrics as needed.
What Success Looks Like (First 90 Days)
  • You've built a reliable founder/leadership operating cadence: priorities, KPIs, decision logs, follow-up system.
  • 2-4 cross-functional projects are moving faster because you're driving alignment and execution.
  • Leadership is spending less time on coordination and more time on decisions.
  • Customer launches and deliverables are cleaner: clearer owners, fewer surprises, tighter comms.
Who You Are
  • High-agency operator: you proactively diagnose problems and drive solutions end-to-end.
  • Structured thinker: you write clearly, make crisp plans, and turn ambiguity into concrete next steps.
  • Low ego, high standards: you do what it takes, and you care about quality.
  • Fast learner: you can ramp quickly in complex, regulated domains.
  • Trustworthy: you handle sensitive information with discretion.
  • Comfortable with intensity: early-stage pace, shifting priorities, and high expectations.
  • Founder energy: you're a past founder, or have ambitions of becoming one.
Preferred Background (not required)
  • 3-7 years experience in a demanding environment: startup ops, consulting, banking/fintech ops, product ops, investment/strategy, or founder-led roles.
  • Prior work with enterprise customers and/or regulated workflows (finance, mortgage, insurance, healthcare).
  • Strong writing: memos, project plans, customer updates, specs.
Skills We Care About
  • Project management (real execution, not just status updates)
  • Exceptional written and verbal communication
  • Analytical ability (Excel/Sheets, basic modeling, KPI design)
  • Stakeholder management (execs and ICs, internal and external)
  • Operational rigor (process, documentation, follow-through)
How to Apply

Email with your resume or LinkedIn and a few sentences on the most operationally complex thing you've owned end-to-end.

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