Tax Manager

Ashford Sky CPA; United States; Remote; USD 135,000 - 150,000; Full time

Benefits offered by this job

Health insurance

Unlimited PTO

Paid CPE

No timesheets

Fully remote with occasional in-person

Annual team offsite

Job summary

Ashford Sky CPA is hiring a Tax Manager to lead the U.S. tax team, review returns prepared by our Philippines staff with AI support, and own advanced tax pieces. You will train offshore teammates, shape playbooks for our AI system, and coordinate tax planning for owner-operators.

The role is fully remote from the U.S., with occasional in-person team offsites and ongoing collaboration with the founder. CPA required, 4–8 years tax experience preferred; M&A tax a plus.

Qualifications

• CPA certification with public accounting background.
• Strong in pass-throughs and business returns; M&A tax a plus.
• Experience with CCH Axcess is advantageous.

Responsibilities

• Review business and individual returns prepared by offshore team with AI support.
• Own technical tax pieces: 8594 allocations, structuring, elections, state nexus.
• Serve as primary tax contact for clients and coordinate with outside advisors.
• Train Philippines staff and help write AI playbooks and workflows.
• Provide tax planning and strategy calls for owner-operators.

Skills

CPA

Tax experience (4-8y)

Pass-throughs

M&A tax

CCH Axcess

AI-driven workflows

Remote collaboration

Leadership

Education

CPA certification

Tools

CCH Axcess

Job description

Ashford Sky is a founder-led CPA firm for people who buy and run small businesses. Our clients are acquisition entrepreneurs (searchers) and owner-operators. We cover the whole lifecycle (quality of earnings before close, tax structuring, then ongoing tax and accounting after).

We use AI to help us significantly in our firm. AI helps prepare the first draft of our tax returns and workpapers. AI also helps review them before a human does. We also have a "firm brain" where you can ask questions about any client (and it has all the context!) and an automated time tracker so you don't have to track your time. We're still building, and you'd be building it with us.

We've grown from 2 people to 7 in the last 12 months, and we're still growing. As the firm grows, this role grows with it. If you're interested in partnership or ownership, we'll help develop a plan for you.

The role

You'd be our tax manager and the only U.S. team member besides me (the founder). I worked at several accounting firms (including EY) and bought, ran, and sold my own business before starting the firm. Our tax and accounting team (five people) is based in the Philippines. They're sharp, and you'd be leading, reviewing, and training them.

What you'd do

• Review business and individual returns (1065, 1120-S, 1120, 1040) prepared by our Philippines team with help of AI
• Own the technical tax pieces - purchase price allocations (8594), structuring, entity elections, state nexus
• Be a primary tax contact for clients
• Train and coach our Philippines staff, and help write the playbooks our AI follows
• Help design our AI prep and review workflows
• Tax planning, projections, and strategy calls for owner-operators
• For a large multinational client, act as their outsourced tax department alongside me. You'd coordinate outside advisors on tax planning and strategy and learn the international side as you go. It feels like an in-house role, and the work runs year-round, not just tax season.

Who you are

• CPA with 4-8 years of tax experience, public accounting background
• Strong on pass-throughs and business returns. M&A tax experience is a big plus
• CCH Axcess experience is a huge plus (not required)
• You want to use AI every day and push it further
• Self-driven and comfortable working fully remote
• US-based: Based in the Central, Mountain, or Pacific time zone. Your late afternoon is our Philippines team's morning, and that overlap is where a lot of the collaboration happens.
• Good at working with an offshore team on a different time zone
• You like teaching and leading people
• You want to work directly with a founder and help build the firm

Compensation and benefits

• $135,000 - $150,000 per year base salary (DOE)
• Health insurance paid by the firm, up to $1,500/month, tax-free to you (you pick your own plan)
• 10% target bonus
• Fully remote, with some in-person time (annual team offsite with the whole team, plus trainings and trips with me, as required)
• Limited overtime - AI and good workflow planning keep it that way
• Unlimited PTO
• Paid CPE
• No timesheets. Our time tracking is automated, so you never fill one out

Shortlisted candidates will be asked for a quick, casual 2-3 minute video before a first call.