Senior Director of Tax Strategy & Systems
Cynch AI, Pleasanton, CA, United States
Please note:
We discovered a technical error in our original application link from last week's post (originally titled Head of Tax Operations) and have reposted here. If you saw the earlier listing and intended to apply, please do. We're looking forward to hearing from you. About Aardvark Tax Advisors
Aardvark Tax Advisors is an AI-native tax, accounting, and advisory firm that combines startup speed with enterprise-grade rigor.
We are the accounting arm of Cynch AI, the AI-native platform democratizing access to financial expertise for small businesses and entrepreneurs. The Opportunity
This is a builder role.
We're looking for a senior leader who brings deep technical expertise, strong client instincts, and a genuine interest in building something new: someone comfortable operating at multiple altitudes, from advising clients on complex tax matters to designing the workflows and systems that make consistent, high-quality delivery possible at scale. What You\'ll Do
Drive Practice Innovation and Growth
Partner with the Tax & Accounting Leader to hire, develop, and manage a high-performing team delivering tax and accounting services to a diverse client base Help shape how we work by contributing to the automation tools, planning systems, and technology behind our AI-native approach to tax and accounting Design and implement scalable workflows that reduce variability, improve quality, and enable team leverage Identify breakdowns in current processes and rebuild them into repeatable systems Translate complex tax work into standardized, auditable workflows Contribute to firm strategy around client experience and how we scale service delivery Own Client Relationships
Serve as a strategic advisor to a portfolio of clients, including high-net-worth individuals, entrepreneurs, and closely held businesses Deliver proactive tax planning, compliance, and advisory services Build client relationships that are genuinely personal, with deep understanding of their business, goals, and history. About you
You're motivated by building a firm that can scale rapidly without breaking, where quality, consistency, and client experience improve as we grow, not degrade. Core Qualifications
CPA or Enrolled Agent (EA) required; Master\'s in Taxation or related field preferred 10+ years of leadership experience, including managing other managers and building high-performing teams 12+ years total experience in tax and accounting, managing complex client engagements Strong technical command of individual, partnership, and corporate taxation Experience with high-net-worth clients, entrepreneurs, or complex equity, real estate, or investment structures Experience in trust and estate taxation is a plus Leadership & Work Style
Natural team leader: builds high-performing teams and establishes culture and expectations in newly acquired practices Exceptional communicator: able to translate complex tax and financial matters into clear, actionable guidance for non-expert clients Process-oriented: has redesigned workflows around new tools Self-directed: able to make sound decisions in a fast-moving environment where processes are still being built Why Join Us
We\'re building something rare: a firm that honors the rigor of traditional accounting while embracing the speed and tools of the future. Work with proprietary AI systems that automate the most error-prone parts of tax preparation and reporting, producing consistent, reliable outputs Join a small, senior team with direct access to firm leadership: your decisions shape how we grow, how we serve clients, and how we build the practice Solve a real, industry-wide problem: millions of small businesses are losing their trusted advisors Neuro-symbolic AI with purpose: our AI creates auditable, repeatable, and explainable results Want to help define how a modern, AI-native tax firm operates at scale. Career opportunities grow with the firm, and we\'re growing fast. Hybrid based in Cupertino or Pleasanton, CA (3+ days/week in office) Occasional extended hours during peak periods; occasional local travel California Salary Range:
$195,000 - 265,000
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We discovered a technical error in our original application link from last week's post (originally titled Head of Tax Operations) and have reposted here. If you saw the earlier listing and intended to apply, please do. We're looking forward to hearing from you. About Aardvark Tax Advisors
Aardvark Tax Advisors is an AI-native tax, accounting, and advisory firm that combines startup speed with enterprise-grade rigor.
We are the accounting arm of Cynch AI, the AI-native platform democratizing access to financial expertise for small businesses and entrepreneurs. The Opportunity
This is a builder role.
We're looking for a senior leader who brings deep technical expertise, strong client instincts, and a genuine interest in building something new: someone comfortable operating at multiple altitudes, from advising clients on complex tax matters to designing the workflows and systems that make consistent, high-quality delivery possible at scale. What You\'ll Do
Drive Practice Innovation and Growth
Partner with the Tax & Accounting Leader to hire, develop, and manage a high-performing team delivering tax and accounting services to a diverse client base Help shape how we work by contributing to the automation tools, planning systems, and technology behind our AI-native approach to tax and accounting Design and implement scalable workflows that reduce variability, improve quality, and enable team leverage Identify breakdowns in current processes and rebuild them into repeatable systems Translate complex tax work into standardized, auditable workflows Contribute to firm strategy around client experience and how we scale service delivery Own Client Relationships
Serve as a strategic advisor to a portfolio of clients, including high-net-worth individuals, entrepreneurs, and closely held businesses Deliver proactive tax planning, compliance, and advisory services Build client relationships that are genuinely personal, with deep understanding of their business, goals, and history. About you
You're motivated by building a firm that can scale rapidly without breaking, where quality, consistency, and client experience improve as we grow, not degrade. Core Qualifications
CPA or Enrolled Agent (EA) required; Master\'s in Taxation or related field preferred 10+ years of leadership experience, including managing other managers and building high-performing teams 12+ years total experience in tax and accounting, managing complex client engagements Strong technical command of individual, partnership, and corporate taxation Experience with high-net-worth clients, entrepreneurs, or complex equity, real estate, or investment structures Experience in trust and estate taxation is a plus Leadership & Work Style
Natural team leader: builds high-performing teams and establishes culture and expectations in newly acquired practices Exceptional communicator: able to translate complex tax and financial matters into clear, actionable guidance for non-expert clients Process-oriented: has redesigned workflows around new tools Self-directed: able to make sound decisions in a fast-moving environment where processes are still being built Why Join Us
We\'re building something rare: a firm that honors the rigor of traditional accounting while embracing the speed and tools of the future. Work with proprietary AI systems that automate the most error-prone parts of tax preparation and reporting, producing consistent, reliable outputs Join a small, senior team with direct access to firm leadership: your decisions shape how we grow, how we serve clients, and how we build the practice Solve a real, industry-wide problem: millions of small businesses are losing their trusted advisors Neuro-symbolic AI with purpose: our AI creates auditable, repeatable, and explainable results Want to help define how a modern, AI-native tax firm operates at scale. Career opportunities grow with the firm, and we\'re growing fast. Hybrid based in Cupertino or Pleasanton, CA (3+ days/week in office) Occasional extended hours during peak periods; occasional local travel California Salary Range:
$195,000 - 265,000
#J-18808-Ljbffr