Part-Time Tax Director
- Work from home
- 401(k) matching
- Flexible schedule
Affinity Accounting is a modern, solutions-focused certified public accounting firm that works with forward thinking businesses looking to streamline their accounting processes. We deliver support and advice to business owners so that they can help them reach their financial goals and gain a better quality of life. Using an integrated approach, we work with their customers as a partner fueling their growth, staying connected, and providing clear answers to their client’s questions. Our core values are centered around integrity, collaboration, and commitment to our team and clients.
We’re looking for a regional but virtual Tax Director who wants to build something — a tax department that runs the way modern accounting should: efficient, tech-forward, and deeply client-focused.
You’ll have the autonomy to shape how the department operates, the tools you use, the team you hire or contract, and the way we serve clients. You’ll be the face of tax at Affinity, the person our clients trust with their most important financial decisions and planning conversations.
Schedule: 20 hrs/wk during summer months for tax planning and proactive client consulting; 30 hrs/wk November through January for planning, prep ramp-up, and client strategy sessions; 40 hrs/wk mid-January through April 15 for return preparation, review, and planning.
This role is for someone who thrives with ownership, loves client relationships, and wants to build — not just maintain.
Tax Department Leadership
- Own the tax function end-to-end; strategy, workflow, quality control, and delivery
- Build and manage a team of tax associates and/or outsourced service providers
- Establish and maintain department standards, review processes, and best practices
- Leverage AI and automation tools to increase efficiency and scale capacity
Tax Return Review & Compliance
- Review business tax returns: C-Corporations, S-Corporations, Partnerships, LLCs, and Trusts
- Review individual tax returns with business ownership and investment complexity
- Oversee multi-state tax compliance; including nexus determination, apportionment, and state-specific filing requirements
- Ensure accuracy, compliance, and quality across all tax filings
- Stay current on federal and state tax law changes impacting our client base
Tax Planning & Client Consulting
- Lead proactive tax planning consulting calls with clients throughout the year
- Develop and deliver annual and quarterly tax plans for business clients across multiple entity types
- Identify planning opportunities and communicate strategies in a way clients actually understand
- Serve as the primary tax relationship contact, building trust through proactive outreach, phone calls, and virtual meetings
- Build lasting client relationships that generate referrals and long-term retention
- Collaborate with our virtual CFO team on integrated financial advisory work
Multi-State Tax Advisory
- Guide clients through multi-state nexus exposure and registration obligations
- Advise on state income, franchise, and payroll tax implications for businesses operating or expanding across state lines
- Support clients navigating apportionment methodologies and state conformity differences
- Identify multi-state planning opportunities to minimize state and local tax burdens
Exit Planning & Business Transitions
- Support business owners navigating sales, mergers, acquisitions, and succession planning
- Structure transactions to minimize tax exposure, including multi-state implications, and maximize after-tax outcomes
- Work alongside legal, financial, and advisory professionals on client deal teams
- CPA license, active and in good standing
- 12+ years of tax experience, with meaningful time in business entity returns and client-facing leadership
- Bachelor’s Degree in Accounting; Master’s in Taxation or MBA preferred
- Strong working knowledge of C-Corp, S-Corp, partnership, and individual taxation
- Experience reviewing complex tax returns and leading client tax planning engagements
- Demonstrated ability to communicate tax concepts clearly to non-accountants
- Self-directed and comfortable working independently in a remote-first environment
- Proven track record of managing client relationships at a senior level
Strongly Preferred
- Multi-state tax experience: nexus, apportionment, and state/local tax compliance across multiple jurisdictions
- Experience with exit planning, M&A transactions, or business succession
- Familiarity with AI tools, tax automation platforms, or a genuine interest in leveraging technology
- Prior leadership or team management experience
- Experience in a virtual or distributed firm environment
- Knowledge of UltraTax software
- What interest you specifically at this position at our firm?
Associate Accountant
- Work from home
- 401(k) matching
- Flexible schedule
Affinity is growing. Our accounting managers are spending significant time on bookkeeping preparation work that pulls them away from the advisory and client-facing activities our clients value most. This role is the linchpin — by owning the day-to-day bookkeeping execution, you free up the entire team to operate at a higher level. You’ll touch every client, build real relationships, and develop a deep foundation in small business accounting.
- You love being and staying organized — clean books make your day
- You want to feel fulfilled in your work, knowing that what you’re doing makes a real difference for business owners
- You take pride in the work you put out and hold yourself to a high standard
- You value flexibility and a family-friendly, results-oriented workplace
- You prefer a mainly work-from-home environment with occasional in-person collaboration
- You want to be part of a team that’s working toward the same goal and genuinely supports each other
- You adapt well to change and embrace new technology and process improvement
- You’re eager to learn and grow — you see this as the start of a career, not just a job
- You live in or around the Milwaukee, WI area and are available for in-person meetings 1–2 times a month at our downtown office
- Accept and categorize bank feed transactions on a weekly or monthly basis
- Reconcile balance sheet accounts including accounts payable, accounts receivable, bank, credit card, and loan accounts
- Reconcile payroll accounts
- Process journal entries
- Manage source document processing — bills, invoices, and receipts
- Assist with monthly, quarterly, and year-end close processes
- Maintain the chart of accounts
- Manage several client accounts simultaneously with consistent quality and timeliness
- Support accounting managers and senior staff with additional tasks as needed across engagements
- Associate’s degree in accounting or business administration, or equivalent professional experience
- 1–2 years of professional accounting experience
- An exceptional level of attention to detail
- Comfortable adapting to new and evolving technology
- Willingness to communicate directly with clients via phone or video when needed
- A team player who thrives in a collaborative virtual environment and enjoys sharing ideas
- Knowledge of bookkeeping fundamentals and generally accepted accounting principles
- Working knowledge of QuickBooks Online and/or Xero accounting software
- Experience with small business bookkeeping and accounting
- 401(k) matching
- Flexible schedule
- Work from home
Director of Operations and Finance
- Work from home
- 401(k) matching
- Flexible schedule
Affinity Accounting is a boutique CPA firm that has served owner-led businesses in the Milwaukee area for 13 years. We specialize in tax, accounting, and CFO advisory services for service-based companies in the $1M to $10M range. We are small by design, close-knit, and at an exciting inflection point in our growth. The next chapter of the firm will be built by the leaders who step up to shape it, and we are looking for one of those leaders now.
The Director of Operations and Finance is a leadership role at Affinity Accounting. You will own the firm’s operating engine: people, processes, systems, and internal financials. You take pride in ownership, move with urgency, and drive measurable outcomes that make the firm stronger, more profitable, and a better place to work.
- Measurable improvement in firm operating profit margin against an agreed baseline.
- Strong staff retention with documented development plans for every team member.
- A client satisfaction measurement program, established and improving year over year.
- A technology stack and automation roadmap with quantified wins in hours saved.
- A monthly capacity planning rhythm that drives hiring decisions before bottlenecks emerge.
- Recognition from the team and clients as the operational leader of the firm.
Team Leadership and Culture
- Conduct weekly/bi-weekly 1:1s with all team members and serve as their primary operational leader.
- Drive performance management, professional development, and accountability.
- Build and sustain a workplace culture where people do their best work.
- Partner with our HR advisor on hiring, onboarding, and compensation reviews.
- Plan and coordinate quarterly team outings, all-staff meetings, and culture-building initiatives.
Operations and Workflow Management
- Own and continuously improve Karbon-based project management workflows.
- Manage vendor relationships, firm-level costs, and operational contracts.
- Coordinate client onboarding and offboarding processes.
- Oversee the operational calendar, holiday closure planning, and internal communications.
Systems and Technology
- Work with our IT partner to expand automation across firm operations using Zapier, AI, and other tools.
- Lead evaluation and implementation of new systems as the firm grows.
- Manage AI policy implementation and technology guidelines in partnership with the CEO.
- Partner with IT on disaster recovery planning and system maintenance.
Client Experience
- Identify and implement improvements to client onboarding and communication processes.
- Design and execute the client feedback and survey strategy.
- Ensure cross-functional team workflows support a consistently excellent client experience.
- Coordinate client communications for tax law changes and important firm updates.
Finance
- Oversee and continuously improve Affinity’s internal financials: bookkeeping, AR/AP, payroll, and financial reporting.
- Build and manage the firm’s annual budget. Track KPIs and profitability metrics monthly.
- Maintain and update firm’s forecast monthly.
- Lead client pricing and billing strategy in partnership with the CEO.
This role is for someone who acts like an owner. Specifically:
- Owner mindset. You take ownership of outcomes, not tasks. You translate priorities into clear execution plans and you deliver.
- Acts with urgency. You move with urgency and a bias toward achievement. You do not wait to be told what needs doing.
- Sees problems before they are named. You proactively spot opportunities and challenges before they are formally defined.
- Operationally fluent. You have worked across HR, technology, finance, and client operations and are comfortable operating across all of them.
- Leads with genuine care. You build trust with teams, hold people accountable with respect, and create cultures where people want to stay.
- Clear communicator. You communicate openly and collaboratively, keeping others informed without overcomplicating things.
- Thrives in growth-stage environments. You are energized by ambiguity, not stalled by it.
Our Values
- We communicate directly and respectfully.
- We value progress over perfection.
- We support each other and step in when needed.
- We take our work seriously, but not ourselves.
- We are proactive, not reactive, for our team and our clients.
- We do meaningful work for clients we genuinely care about.
Required:
- 5+ years in an operations management or leadership role.
- Professional services industry experience (CPA firm, law firm, consulting, agency, or similar owner-led service business).
- 3+ years directly managing a team, including performance management and development conversations.
- Demonstrated financial management experience, including P&L ownership, budgeting, forecasting, and KPI tracking.
- Hands-on experience with workflow and project management tools such as Karbon, Asana, Monday.com, or equivalents.
- Familiarity with automation tools such as Zapier or equivalents.
- Strong organizational skills and the ability to manage across multiple functional areas simultaneously.
Nice to have:
- Experience in a CPA firm, accounting practice, or financial services environment.
- Familiarity with Karbon, QuickBooks Online, Xero, or similar accounting-specific platforms.
- Experience leveraging AI tools to improve operational efficiency.
We take hiring seriously because this role matters. Candidates should expect:
- Initial screening conversation with HR + Predictive Index Assessment.
- In-person conversation with the CEO + an operational case study.
- Final interviews with the leadership team.
- Reference checks.
Why Affinity
- Real authority and ownership over firm operations and finance.
- A CEO who values your perspective and gives you the space to lead.
- A team environment where people genuinely enjoy working together. Low ego, high support.
- A firm with 13 years of stability and a clear growth trajectory.
- Holiday soft-close between Christmas and New Year’s, quarterly team outings, flexible work-from-home policy, and a culture that values your time outside of work.