Chief of Staff

About Taxwire

Taxwire is building an AI-native global sales tax engine & managed service for finance teams. We handle sales tax and VAT from end to end for hundreds of mid-market companies and dozens of accounting / tax firms. We’ve raised ~$25M in venture capital from firms like Headline, XYZ, Vinyl, and dozens of CFOs, founders, and tax practitioners.

Indirect tax is high-stakes, fragmented, and unforgiving. Rules change constantly, vary by product and location, and create real financial risk when companies get them wrong.

We hire people with high ownership, strong judgment, and low ego. Everyone at Taxwire is expected to understand the customer, solve messy problems end to end, and build systems that scale. We move quickly because our customers depend on us to get it right.

Death and taxes are forever. If you want to operate in one of the largest markets in the world and sovle a massive, enduring problem with a team of people playing to win, Taxwire is the place to do it.

What you’ll do

Your job is simple: create leverage for the CEO and help Taxwire operate at a higher level as we scale.

You’ll work directly with Andrew, our CEO, on whatever problems are most important to the company at a given moment. Sometimes that means driving a strategic project from idea to completion. Sometimes it means standing up a new company process from scratch. Sometimes it means noticing something that isn’t working, figuring out why, and fixing it before anyone asks.

The scope will evolve as Taxwire grows, but initially you’ll:

• Create leverage for the CEO → Help Andrew spend more of his time on the things only he can do. Take important problems off his plate, own follow-ups, prepare for key decisions, and make sure priorities actually move forward.

• Drive high-priority special projects → Take ambiguous, cross-functional initiatives from “we should do this” to done. You’ll often work on problems that are important to the company but don’t fit neatly within any one function.

• Support Taxwire’s business operations from zero to one → We’re at the stage where many of the systems required to run the company are being built for the first time. You’ll help build them—and own them until they deserve a dedicated owner. Initially, that will include things like:

  • Owning our company financial model, forecasts, and operating plan.

  • Helping run recruiting across the company: sourcing, pipeline management, process, coordination, and generally making sure we hire great people quickly.

  • Building company reporting and helping us understand how we’re performing against our goals.

  • Improving the basic systems and processes we use to run the company as we scale.

• Own problems that don’t have an obvious owner → At a growing startup, important things constantly fall between functions. You’ll be one of the people we trust to pick them up, figure out what needs to happen, and drive them to completion.

• Make the company more operationally rigorous → Find places where we’re relying on manual work, tribal knowledge, or duct-taped processes and turn them into scalable systems. Build the operating cadence and infrastructure that lets Taxwire grow without adding unnecessary complexity.

Over time, the role should evolve with the company. Done well, you’ll become one of the CEO’s most trusted operators, take on increasingly important problems, and have the opportunity to grow into a Chief of Staff role or ownership of a major function within Taxwire.

What you need

• You’re a finisher. You take ownership of messy problems, figure out the right answer, and ship solutions without waiting for someone to tell you every step.

• You have unusually high agency. When you encounter something you don’t know how to do, your instinct is to figure it out—not wait for instructions.

• You’re comfortable with ambiguity. Startups don’t have perfect processes. You don’t need a manual. You write it.

• You can go from strategy to execution. You’re comfortable thinking through a problem with the CEO at 10,000 feet and then opening a spreadsheet, writing the memo, making the calls, or building the process yourself.

• You have good judgment. You know when to move fast, when to slow down, what actually matters, and when something needs to be escalated. You don’t confuse motion with progress.

• You’re quantitatively strong. You can build and maintain a financial model, are excellent in spreadsheets, and are comfortable using financial and operational data to make decisions.

• You’re an excellent communicator. You can write a clean memo, synthesize messy information, run a tight meeting, and explain complex topics simply.

• You’re low-ego and high-trust. You’ll work directly with the CEO and across nearly every function of the company. That means fast feedback loops, real responsibility, and zero time for posturing.

• You have at least 3–5 years of professional experience, ideally including time at a high-growth startup or another environment where you were expected to learn quickly and operate independently.

We care much more about slope, judgment, and demonstrated ability to get difficult things done than whether you’ve previously had “Strategy” or “Operations” in your title.

Why work at Taxwire

• You want to learn and achieve personal career growth on an extremely accelerated timeline.

• You want real responsibility rather than waiting years for someone to give it to you.

• You want to work directly with a founder and have meaningful exposure to how a fast-growing company is built.

• You want to win, both for yourself and the teammates depending on you.

• We have high standards and the work can be intense, but our team is kind and we give a fuck about each other.

• Our team is deeply credible and experienced within the industry we operate in.

• We’re tackling a massive, complex, global problem in a big market with strong signs of product-market fit, lots of happy customers, and momentum across the broader business.

• We’re well funded by respected institutional VCs and angels.

• Strong equity, competitive salary, and full benefits.

Why you shouldn’t work at Taxwire

• You don’t hold a high bar for excellence. You don’t play to win.

• You want a narrowly defined job where someone else decides what you should work on.

• You want structure, hand-holding, or a well-defined playbook.

• You’re uncomfortable being handed a problem you’ve never seen before and being expected to figure it out.

• You are uncomfortable with direct feedback.

• You’ve watched Whiplash and found its message too hardcore.

• You prefer optimizing mature systems over building things from zero to one.

• Early-stage ambiguity or fast iteration makes you uncomfortable.

• Being responsible for outcomes scares you.

Benefits

• Competitive salary

• Meaningful equity

• Company-covered benefits