Special Assistant to Chief Executive Officer
Company Description
Tax & Contracts is a Chicago-based legal services company dedicated to supporting small and family business owner-operators, social enterprises, nonprofit founders, and the international startup community. The firm provides low volume high-touch, bespoke legal services tailored to the needs of CEOs, founders, and owner-operators. Core practice areas include business formation and reorganization, company governance, partnership and equity agreements, federal regulatory compliance and intellectual property protection. Tax & Contracts focuses on delivering strategic, proactive guidance that offers legal clarity and confidence. The team helps clients launch, grow, and restructure their organizations while scaling with integrity. Role Description Tax & Contracts is a tech-forward law firm. We have been embracing technology since ColecoVision and Atari 5200, and our CEO/Managing Attorney has been working with AI since 2022, when ChatGPT, whom we call Chad, first arrived. Yes, our AI employees have names. With the arrival of AI, the traditional assistant role built on mundane, repetitive tasks is nearly obsolete for those who embrace technology, and we do. So we are reimagining company roles: less 1980s just-in-time industrial operations standard, and more tech-forward with 2030 in mind, and with the realization that people will always need people. The Special Assistant to the CEO/Managing Attorney is the secretary of old, reborn for a modern firm. It is a full-time remote, strategic role. The Special Assistant will drive the firm's strategic initiatives, as set by the CEO/Managing Attorney, from initiation through execution. Those initiatives span strategic legal, marketing, organizational, and implementation work. The CEO/Managing Attorney is both the firm's chief executive and its managing attorney, and this role gives the CEO/Managing Attorney the room to do the visionary work of the CEO and the critical work of the managing attorney, ensuring compliance and stellar service delivery. The firm has set an ambitious goal: to serve 1,000 small and family businesses over the next four years. Aggressive goals call for commitment to purpose, capacity for deep research and a solid knowledge base to match. This role is pivotal in the firm's growth, and as such is eligible for parallel profit share. We use AI daily to support research and the timely delivery of strategic initiatives, and AI can be wrong. Therefore, a central part of this role is catching AI hallucinations by validating every output against primary sources before it reaches a client, a filing, or a decision. Those sources include the United States Code, the Code of Federal Regulations, state and local law, international law and treaties, and the regional compliance requirements of the jurisdictions where our clients operate. The Secretary of Old, the Special Assistant we seek The special assistant we have in mind is the secretary of the 1700s. The title comes from the Latin secretarius, a person entrusted with secrets. In an era when business was intensely personal and built on relationships, the secretary guarded the executive's trade secrets, ledgers, and strategic intentions. Secretaries wrote the formal letters, proposals, and inquiries, which demanded rare literacy and care, and they kept the records: ledgers, receipts, bills of exchange, and contracts. They also stood in for the principal, corresponding, negotiating deals, and handling disputes on the principal's behalf. Above all, the role was an apprenticeship to power. An educated person learned the mechanic directly from a prominent executive, at the executive's elbow, in the room where decisions were made. The room where it happened. Internationally, the word has kept that weight. A secretary of state, a secretary-general, a cabinet secretary, and a company secretary are all officers of trust, responsible for records, governance, compliance, and carrying out the principal's decisions. This role draws on both traditions: keeper of the firm's confidences and records, and a trusted officer who moves the executive's agenda from decision to done. We are reviving that role for a firm that serves small owner-operated and family-owned businesses, with modern tools in hand. The Special Assistant works beside the CEO/Managing Attorney, to launch the strategic initiatives that help us serve this mission critical segment of our economy. The role combines several positions that were previously separate: the assistant to the CEO/Managing Attorney, the executive assistant, the research assistant, the analyst, and the secretary of old. Technology absorbs the repetitive and mundane tasks that once defined those positions, which frees this role for strategic work. It is a strategic role, not an operations role, and it does not manage a team. The Special Assistant will Work collaboratively with the CEO/Managing Attorney. Own and drive the firm's strategic legal, marketing, organizational, and implementation initiatives, as set by the CEO/Managing Attorney, translating strategy into scoped projects, milestones, owners, and deadlines, and holding the work to completion. Drive the firm's growth goals, supporting the execution of quarterly and annual strategic plans, including goals, metrics, and reporting. Drive the firm's external-facing strategic work forward independently, bringing forward only the risks, decisions, and approvals that require the CEO/Managing Attorney's attention. Validate AI-assisted work against primary sources, including the United States Code, international law, and regional compliance requirements, and identify hallucinations before they reach a client, a filing, or a decision. Conduct legal, tax, and business research from primary sources, and produce research memos and decision-ready recommendations that identify legal and regulatory risks early. Research clients, markets, partners, and competitors to inform the firm's business development and strategy. Document and keep the record of the firm's strategic initiatives, decisions, and commitments, so that nothing the CEO/Managing Attorney has set in motion stalls. Draft and review sensitive communications, briefing memos, white papers, proposals, reports, and presentations on the CEO/Managing Attorney's behalf, in the firm's voice. Sit in on and prepare for high-stakes engagements alongside the CEO/Managing Attorney, with briefing materials, research, and talking points. Apply the judgment of a professional to the firm's documents, correspondence, and matter files, while technology handles routine preparation, formatting, and filing. Direct the firm's AI-enabled tools and automation, which handle routine scheduling and coordination, toward the firm's strategic priorities. Serve as keeper of the firm's confidences, handling privileged and confidential information with sound judgment and complete discretion. How We Use AI Tax & Contracts is a heavy user of AI, and the Special Assistant will use it every day. AI is a lever, not a substitute for skill. You must be able to do the work without AI first, including the research, the writing, the analysis, and the quality check. Only then can you use AI strategically. We are a law firm. Use of primary sources are mission critical. Using AI without a keen eye towards the desired output is contrary to the essence of the tool. The work product delivered in execution of the initiatives is what you own, regardless of which tool helped produce it.
Qualifications
Proven ability to run complex initiatives independently, with strong project management skills, prioritization, follow-through, and ownership of outcomes. Consultant experience, with the ability to diagnose problems, structure solutions, and deliver recommendations to senior decision-makers. Legal research experience, including research in statutes, regulations, case law, and official agency guidance, and the knowledge base to recognize when an AI-generated answer is wrong. Experience in primary-source validation, including the United States Code, international law, and regional compliance. Experience as a secretary, paralegal, research assistant, analyst, or similar role, with an exemplary command of executive document delivery. Excellent writing skills, including experience drafting executive-level correspondence, research memos, white papers, briefing memos, and presentations. Strong research, analytical, and synthesis skills, with the ability to turn complex information into concise recommendations. Demonstrated ability to perform core research, writing, and analysis without AI, paired with working fluency in AI tools to extend that work. AI use without knowledge of the result is not acceptable. Sound judgment and demonstrated discretion with sensitive, confidential, and privileged information. Experience as a special assistant, strategy lead, or similar trusted advisor to senior leadership, ideally in a legal, professional services, or consulting environment. Genuine curiosity about how a business is built, led, and grown, and the ambition to learn it from the inside. Comfort with automation and modern productivity and document platforms. Proactive communicator who is comfortable working independently and remotely across time zones.
Nice to Have
A JD, A master's in Divinity, History, Political Science, or another discipline that demands extensive writing and research skills. Interest in or familiarity with small business, startup, or nonprofit ecosystems A Note to Liberal Arts Graduates We may be looking for a unicorn, but we believe you are out there. If you have just 60% of what we are looking for, we are willing to train. If you have one of those amazing liberal arts degrees that you were told would never we want to hear from you. Profit share available.