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Head of Tax

About Sunset

Sunset helps tech startups shut down. We’re the 1-stop shop for dissolutions, handling all the legal, tax, and operational burdens that go into winding down. We make sure founders and investors avoid penalties, reduce liabilities, and can immediately move on to what's next.

In 1.5 years, we’ve helped over 175+ Venture-backed startups shut down, are generating millions in revenue, and raised $1.5M from some of the world’s best entrepreneurs and investors.

About the role

As the Head of Tax at Sunset, you’ll play a crucial role in managing all corporate tax related aspects that go into the shutdown process. This position will be responsible for overseeing the preparation and filing of all final federal and state tax returns, addressing tax-related questions and issues directly with our clients, and managing the withdrawal of our clients from foreign qualified states.

In this role, you’ll also be closely collaborating with the Customer Success Team and the product team to build scalable processes, track metrics, and improve our overall efficiency.

This role is for you if:

  • Expert in Corporate Tax Returns and Tax Laws: You have multiple years of experience working on corporate 1120 returns, have an active EA or CPA license, and can give tax advice during complex wind-downs and acquisitions.

  • Incredible Leader & Operator: You have a proven ability to build and manage a team all while streamlining tax processes and workflows

This role is not for you if:

  • Mission: You aren’t excited by Sunset’s mission of helping founders move on and support them in a very challenging time.

  • Early-Stage: You’re not interested in early-stage startups

  • NYC: You don’t live in NYC or want to move to NYC

  • Office: You don’t want to work in person, 5 days a week in Dumbo, Brooklyn

What success looks like in this role

  • Develop a deep understanding of common client pain points and challenges when it comes to tax and state related issues when winding-down

  • Communicate effectively with clients, legal counsel, and our own internal teams via email, slack, and phone — ensuring clear and timely updates throughout the dissolution process

  • Ability to prepare and file corporate tax returns on behalf of Sunset’s clients

  • Ability to build and manage a team of tax preparers and bookkeepers to help scale Sunset’s tax team

In the first 6 months, you’ll:

  • Learn: Immerse yourself in everything Sunset, our customers, and the dissolution process. You’ll gain a comprehensive knowledge of our products, services, and industry landscape.

  • Analyze: You’ll work with our existing tax preparers to learn what’s working and what areas can be improved in our processes

  • Own: You’ll start actively preparing and filing Sunset’s clients corporate 1120 tax returns.

  • Manage & Grow: Based on the team, growth, and data - you’ll create a hiring plan for how the team can properly scale and meet the demand

  • Culture: You’ll continue to build and cultivate an engaging, high-performing, and fun culture on the Tax Team.

  • Onboarding: You’ll have built an onboarding process and documentation for new tax preparers that join our team.

Benefits:

At Sunset, we believe in taking care of our team. Our comprehensive benefits package includes:

  • Health Coverage: We cover 100% of premiums for medical, dental, and vision insurance, offering the best and most comprehensive plans available.

  • Generous Time Off: Enjoy 20 days of Paid Time Off (PTO) per year, plus 8 company-wide holidays.

  • Office Setup Allowance: $500 allowance for your in-office desk setup, ensuring you have the tools you need to succeed.

What You Should Know About Head of Tax, Sunset

Join Sunset as the Head of Tax and play an essential role in our mission to assist tech startups in winding down effectively and with dignity. Sunset has grown rapidly, helping over 175 venture-backed startups navigate the complexities of dissolution, and now we're looking for a seasoned professional like you to ensure smooth tax-related procedures during this crucial transition. In this role, you will oversee all aspects of corporate tax returns, including the preparation and filing of final federal and state returns. You'll tackle tax questions directly with our clients and coordinate their withdrawal from foreign qualified states. Collaboration is key, and you'll work closely with our Customer Success and product teams to streamline operations, track key metrics, and boost efficiency. If you're well-versed in corporate tax laws and have a robust record of managing tax teams, you'll thrive here. At Sunset, we champion the journey of founders and believe in offering them the support they need during a challenging time. If you meet the qualifications and are excited about building a high-performing team culture while working in Dumbo, Brooklyn, we can't wait to meet you!

Frequently Asked Questions (FAQs) for Head of Tax Role at Sunset
What type of work environment can I expect as the Head of Tax at Sunset?

As the Head of Tax at Sunset, you can expect a collaborative work environment that values engagement and high performance. We work in-person five days a week at our office in Dumbo, Brooklyn, fostering communication and team building. Additionally, we offer a culture that prioritizes fun and support among team members while achieving professional goals.

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Common Interview Questions for Head of Tax
Can you describe your experience with corporate tax returns relevant to the Head of Tax position?

When answering this question, be sure to highlight specific experiences you've had with corporate 1120 returns. Discuss any complex cases you worked on, particularly those involving startups. Mention your familiarity with tax laws and how you have applied this knowledge in similar roles.

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How do you handle client communication during the dissolution process?

In your response, underline the importance of clear and timely communication. Describe your approach to keeping clients informed about tax matters and the dissolution process, including using tools like email and Slack effectively. Providing regular updates reassures clients and supports smoother transitions.

Join Rise to see the full answer
What methods do you employ to streamline tax processes and procedures?

Share specific methods you've used in the past, such as creating checklists, implementing software tools, or developing training programs for your team. Discuss how these strategies have improved efficiency and reduced errors in tax filings, demonstrating your ability to lead process improvements.

Join Rise to see the full answer
What challenges have you faced when managing a tax team, and how did you overcome them?

Be honest about past challenges, such as differing levels of expertise among team members or seasonal workloads. Discuss the steps you took to address these issues, such as providing additional training or redistributing workloads during peak seasons, showcasing your leadership skills.

Join Rise to see the full answer
How do you stay updated on changes in tax laws and regulations?

Explain the methods you use to keep abreast of developments in tax regulations, such as subscribing to industry newsletters, attending seminars, or networking with other tax professionals. Highlight your proactive approach in ensuring compliance and providing accurate advice to clients.

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What role does teamwork play in your approach to tax management?

Emphasize the importance of collaboration in tax management, particularly when working with cross-functional teams like Customer Success and product teams. Share examples of how you have fostered teamwork to achieve common goals, reinforce relationships, and improve overall client satisfaction.

Join Rise to see the full answer
Can you outline your approach to mentoring junior team members in tax preparation?

Discuss your belief in the importance of mentorship and how you create an encouraging environment for junior team members. Share your process for onboarding new hires and your personal approach to offering constructive feedback and continued learning opportunities in tax preparation.

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Describe a time when you had to provide tax advice during a complex wind-down situation.

Provide a specific example of a complex situation you've navigated in the past. Discuss the steps you took to analyze the tax implications and the advice you provided to ensure compliance and minimize penalties for your client. This showcases your expertise in handling challenging situations.

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What systems or tools have you implemented to enhance tax team performance?

Mention any software solutions, project management tools, or performance tracking systems you've implemented in previous roles. Explain how these tools have improved productivity, accuracy, or communication, making a positive impact on the tax team's efficiency.

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Why do you want to work for Sunset in the Head of Tax position?

Express your enthusiasm for Sunset's mission of supporting founders and tech startups in their winding-down process. Highlight your alignment with the company's goals and values, as well as your desire to contribute your expertise and leadership to a rapidly growing organization.

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Founded in 1898, Sunset Magazine has long covered all aspects of life in the Western United States, focusing in particular on travel, food & drink, home design, and gardening. Based in the Los Angeles area, Sunset is owned by the private equity fi...

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Full-time, on-site
DATE POSTED
March 15, 2025

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