Chief of Staff / Strategic Finance / BizOps

We need to output HTML fragment with sections: About the role? Actually we need headings for sections like About the role, Responsibilities, Requirements, Qualifications, Skills, Benefits, Pay, Schedule. Use

for each heading only if there is real content. We must not repeat job title. We need to preserve all substantive info, remove boilerplate. We need to parse the posting. Content: - About Freehand (company description) maybe not needed as heading? Could be "About the role"? Actually "About Freehand" is company overview. Could be placed under a heading like "About the company"? Not in list. The instruction: use

for section headings (e.g. About the role, Responsibilities, Requirements, Qualifications, Skills, Benefits, Pay, Schedule). So we should map content to those headings if applicable. We have: - About Freehand: description of company. Could be placed under "About the role"? Not exactly. Maybe we can treat as "About the role" includes role description and company context. But we have separate sections: "The Role", "How We Think About The Business", "What You'll Do", "Ideal background", "Working at Freehand", "Compensation Range". Also "Equal Opportunity" boilerplate to remove. We need to produce sections: maybe "About the role" (includes role description and company context), "Responsibilities" (What You'll Do), "Requirements" (Ideal background), "Qualifications" maybe overlapping, "Skills" maybe not explicit, "Benefits" (Working at Freehand benefits), "Pay" (Compensation Range), "Schedule" not present -> omit. We must not create sections with filler. So we include only those with real content. We need to use

• for any list of duties/requirements/benefits. So for responsibilities list, we need to convert bullet points into
  • . Similarly for requirements list (ideal background). Benefits list also. We need to preserve all substantive info, not invent or summarize away detail. So we need to keep the exact sentences? Probably we can keep them as is, but we can format as paragraphs or list items. We must remove cookie/navigation/legal/EEO/equal-opportunity/scam-warning boilerplate, duplicated lines, and application instructions. So remove "Equal Opportunity" paragraph and the "If you meet most of the criteria..." etc. Also remove "We proudly offer the following Benefits to all our full-time employees:" maybe keep as intro but not boilerplate? It's part of benefits section; we can keep but maybe it's okay. The instruction: remove boilerplate; that line is not boilerplate but part of benefits intro. Could keep. We must not repeat job title as heading. No job title given explicitly; it's "Founder's Office roles". Not needed. We must not put Job ID/requisition numbers as headings; none. Now craft HTML. Structure:

    About the role

    About Freehand Freehand (freehand.ai) is building autonomous AI agents for enterprise spend management, replacing internal and outsourced (BPO) headcount and shared service centres with "AI Employees" across procure-to-pay and order-to-cash workflows, selling to Global 2000 CFOs. Freehand counts Apple, Meta, J&J, Pfizer, Cardinal Health, Dunkin', and Samsara among its customers. We're now scaling the team across GTM, product, and operations. The Role We're hiring two Founder's Office roles to take on the highest-leverage strategic projects across the company: fundraising, board and investor comms, org design, key customer expansions, revenue operations, cost optimization, and special initiatives that don't yet have an owner. You'll work directly with the CEO and leadership team, with end-to-end ownership of workstreams that shape how Freehand scales. This is a front-row seat to building a category-defining enterprise AI company in San Francisco.

    But we might split company description and role description. However it's okay. Next,

    How We Think About The Business

    maybe not in list but could be considered part of responsibilities? But we could include as its own section if content present. The instruction says use headings e.g. About the role, Responsibilities, Requirements, Qualifications, Skills, Benefits, Pay, Schedule. It doesn't forbid other headings? It says use

    for section headings (e.g. About the role, Responsibilities, Requirements, Qualifications, Skills, Benefits, Pay, Schedule). Likely they expect only those headings. But we could still include other headings if they are substantive? The instruction: "Use

    for section headings (e.g. About the role, Responsibilities, Requirements, Qualifications, Skills, Benefits, Pay, Schedule)." It suggests those are examples; we could use others but better to stick to those. However we have content like "How We Think About The Business" and "What You'll Do". Those could be mapped to Responsibilities. The "What You'll Do" is responsibilities. The "How We Think About The Business" is more like context; could be included under About the role or Responsibilities. To keep sections few, we can merge. Thus: - About the role: includes company description, role overview, how we think about business. - Responsibilities: What You'll Do list. - Requirements: Ideal background list. - Benefits: Working at Freehand benefits list. - Pay: Compensation Range. We need to ensure we don't create sections with filler like "commensurate with experience". Not present. Now format. Responsibilities list: The bullet points under "What You'll Do". Let's extract: - Build the top-down financial model of the business as the intersecting output of the five pipelines, and decompose it into functional models for sales, implementations, product, talent, and capital - Identify the dynamic binding constraint in each pipeline and at the company level; quantify the cost of each bottleneck and the ROI of unblocking it - Stand up dashboards for each pipeline and a consolidated business view, leading indicators, throughput, conversion, cycle time, unit economics - Partner with each function head to set weekly, monthly and quarterly goals tied to the model, and drive a prioritized list of debottlenecking initiatives across the company - Run weekly functional reviews and fortnightly business reviews alongside the CEO - Own strategic initiatives across customer expansion, pricing, org design, and cost optimization, and other high-leverage problems that don't yet have an owner - Run board meetings end-to-end: materials, narrative, follow-ups, investor materials, modeling, process management We need to put each as

    . Requirements list: Ideal background: - CS undergrad from top tier college in India (IIT/NIT) or the US (Ivy League school) - MBA from HBS, Wharton, or Stanford - At least 2-4 years in investment banking or private equity - At least 2-4 years in an operating role (BizOps / Strategic Finance) at a consumer tech or B2B software company - Founder or very early-stage startup experience is a strong plus - Proven track record of hands on financial modelling across GTM, product, tech and ops; comfortable moving between board-level strategy, management decision making and hands-on functional execution We need to keep as list items. Benefits list: Working at Freehand benefits: - Take what you need Vacation Policy - Monthly home-internet costs - Full health coverage (with multiple gold-standard carriers across medical, dental & vision) - Life Insurance and Disability benefits - HSA/FSA Access - 401(k) with a 4% Employer Match We need to keep as list items. Pay: Compensation Range: $200K - $250K We can put in

    . Now ensure we removed boilerplate: Remove Equal Opportunity paragraph and the "If you meet most of the criteria..." etc. Also remove "We proudly offer the following Benefits to all our full-time employees:" maybe keep as intro but it's not boilerplate; but we could keep it as a

    before the list. However the instruction: "Use

    • for any list of duties/requirements/benefits, and

      for prose." So we can have a

      intro then

      . That's fine. Now produce HTML fragment. We need to output only HTML, no markdown fences. Let's craft:

      About the role

      About Freehand Freehand (freehand.ai) is building autonomous AI agents for enterprise spend management, replacing internal and outsourced (BPO) headcount and shared service centres with "AI Employees" across procure-to-pay and order-to-cash workflows, selling to Global 2000 CFOs. Freehand counts Apple, Meta, J&J, Pfizer, Cardinal Health, Dunkin', and Samsara among its customers. We're now scaling the team across GTM, product, and operations. The Role We're hiring two Founder's Office roles to take on the highest-leverage strategic projects across the company: fundraising, board and investor comms, org design, key customer expansions, revenue operations, cost optimization, and special initiatives that don't yet have an owner. You'll work directly with the CEO and leadership team, with end-to-end ownership of workstreams that shape how Freehand scales. This is a front-row seat to building a category-defining enterprise AI company in San Francisco. How We Think About The Business Freehand, like any business, runs on five pipelines: capital, talent, sales, implementations, and product. Each has its own throughput, conversion, and cycle time, and each both constrains and feeds the others, and the overall business. The Chief of Staff / Strategic Finance role is to make those interactions legible, financially, operationally, and visually, and to actively de-bottleneck them.

      Responsibilities

      • Build the top-down financial model of the business as the intersecting output of the five pipelines, and decompose it into functional models for sales, implementations, product, talent, and capital
      • Identify the dynamic binding constraint in each pipeline and at the company level; quantify the cost of each bottleneck and the ROI of unblocking it
      • Stand up dashboards for each pipeline and a consolidated business view, leading indicators, throughput, conversion, cycle time, unit economics
      • Partner with each function head to set weekly, monthly and quarterly goals tied to the model, and drive a prioritized list of debottlenecking initiatives across the company
      • Run weekly functional reviews and fortnightly business reviews alongside the CEO
      • Own strategic initiatives across customer expansion, pricing, org design, and cost optimization, and other high-leverage problems that don't yet have an owner
      • Run board meetings end-to-end: materials, narrative, follow-ups, investor materials, modeling, process management

      Requirements

      • CS undergrad from top tier college in India (IIT/NIT) or the US (Ivy League school)
      • MBA from HBS, Wharton, or Stanford
      • At least 2-4 years in investment banking or private equity
      • At least 2-4 years in an operating role (BizOps / Strategic Finance) at a consumer tech or B2B software company
      • Founder or very early-stage startup experience is a strong plus
      • Proven track record of hands on financial modelling across GTM, product, tech and ops; comfortable moving between board-level strategy, management decision making and hands-on functional execution

      Benefits

      We proudly offer the following Benefits to all our full-time employees:

      • Take what you need Vacation Policy
      • Monthly home-internet costs
      • Full health coverage (with