SENIOR TAX MANAGER WITH PATHWAY TO FIRM LEADERSHIP

Location: Northern Virginia / Greater Washington, D.C. (Hybrid: 2–3 days/week in-person)

Type: Full-time

Compensation: Highly competitive salary + performance bonuses + pathway to equity

WHAT IS CHERRYWOOD ADVISORS?

Cherrywood Advisors is a modern accounting and advisory firm built for the next generation of professionals and clients. We’re not just another CPA firm—we’re on a mission to reimagine what it means to work in and with an accounting firm.

Led by a high-integrity founder who is super fun to work with (if I do say so myself!), who also has deep experience building and scaling an organization, we are well-resourced and ready to invest in the right people, the right systems, and the right tools.

Our goals are bold but grounded:‍

1. TO CREATE THE SINGLE BEST PLACE TO WORK ANYWHERE.

We believe work should be meaningful, intellectually stimulating, and surrounded by people you genuinely enjoy. But it should also be sustainable. We respect life outside of work, offer true flexibility, pay well, share profit with the whole team, and avoid burnout culture.

2. TO DELIVER EXTRAORDINARY RESULTS FOR OUR CLIENTS.

Whether it’s a business owner looking to scale with clarity or a family navigating wealth planning, we aim to make a meaningful, lasting impact on our community by serving clients with excellence

We’re building something special - a place where smart, compassionate professionals can thrive and help others do the same.

WHERE WE’RE HEADED: OUR STRATEGY

This is truly a chance to get in on the ground floor.

We’re just getting started – we currently only have two clients that are producing $180k in annual revenue – but we are planning to grow aggressively over the next five years with a goal to reach $5 million in annual revenue by the end of 2030.

Our growth strategy is focused, well-funded, and centers on three core pillars:

1. ACQUIRING LOCAL CPA PRACTICES

We aim to acquire small, owner-operated tax firms from retiring CPAs in Northern Virginia/Greater DMV—ideally solo practitioners or firms with 1–5 person teams. We want to give those CPAs a dignified exit and their clients and teams a new, high-integrity home where they’ll continue to thrive.

2. EXPANDING SERVICE LINES

We’re starting with tax but we are building beyond tax. Our vision includes a robust wealth management offering for individuals and a fully outsourced back office (CAS) function for business owners. Over time, we’ll expand into other high-value services that help our clients run stronger, smarter, more profitable operations.

3. ORGANIC CLIENT GROWTH

As we earn a reputation for delivering outstanding service with a human touch, we expect to grow organically through referrals and focused strategic marketing to niche business industries and segments

This is a build opportunity — to shape a firm’s future with the support, funding, and leadership vision already in place. If you’ve ever wanted to help build the kind of firm you’ve always wished existed, I’d love to meet you.

ABOUT THE ROLE

We’re hiring our first Senior Tax Manager—a pivotal leadership role with three core responsibilities:

1. LEAD THE TAX TEAM AND DELIVER EXCEPTIONAL WORK

You’ll be the inaugural “pod leader,” responsible for overseeing the day-to-day delivery of tax and bookkeeping services across a growing client base. You’ll ensure high-quality, timely work while cultivating strong clients relationships and leading a growing team.

2. HELP US WIN AND INTEGRATE NEW FIRMS

You will give retiring CPAs confidence and peace of mind that Cherrywood is the right home for their clients and team. You’ll be a key player in our growththrough-acquisition strategy, helping ensure a smooth transition and a high-trust relationship with new clients and new staff from day one.

3. BUILD THE SYSTEMS OF THE FUTURE

You’ll work directly with me to design and refine the org structure, workflows, tech stack, and operational infrastructure that we will use to scale. If you’ve ever dreamed of doing it better, here’s your shot to build from scratch.

YOU MIGHT BE A GREAT FIT IF…

• You read the core values on our website and think “That sounds like me!”
• You’re leading a tax and accounting delivery team at your firm but you have hit a ceiling - until that partner ahead of you retires you have run out of upward mobility and opportunities to grow.
• You are a top talent and emerging leader at your firm, but you have a growing family and 80-hour weeks just aren’t your idea of a good time any more. Plus you’re looking ahead to what it is like to be a partner and realizing you don’t actually want that life.
• You’ve always dreamed of going out on your own and building your own firm, but were concerned about the lack of a stable paycheck and the pressure and administrative headaches of leading your own business.
• You thrive in dynamic environments and want to help build something—not just execute someone else’s playbook.
• You’ve got the gravitas to impress and instill confidence in the owners of acquisition target firms and their clients.
• You’re hands-on and entrepreneurial—ready to get your hands dirty, solve problems, and build alongside others.
• You love the idea of true work-life balance, high compensation, and the chance to grow into a firm-level leader (and eventually an equity partner).
• You’re emotionally intelligent and know how to integrate new team members and clients with empathy and tact.
• You live in Northern Virginia / D.C. or are excited to relocate, and want to be part of a hybridinperson team culture.
• Optional Bonus points: If you have experience with government contracting and DCAA compliance and fluency with, Deltek, PROCAS and/or Unanet

WHAT WE OFFER

• Competitive base pay with opportunities for additional incentive compensation
• Pathway to equity and firm leadership
• Hybrid flexibility with 2–3 days per week in-person (Northern VA / D.C.)
• Strong support systems—no clunky legacy software or bloated bureaucracy
• Smart, thoughtful teammates who care about the work and about each other
• The chance to build a great firm, not just work at one

APPLY NOW

If you’re an experienced tax leader who’s ready to do the best work of your career—and help build the firm you’ve always wanted to work for—I’d love to hear from you.