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Who is Aiwyn and what do we do?


Aiwyn is the fastest-growing software company serving the accounting profession. Founded in 2020, we now work with 100+ of the largest CPA firms in the world. Our “Job to be done”: speed up cash flow, save Partner time, & deliver best-in-class client experiences. We do this by automating day-to-day firm operations with our Practice Automation solutions. Aiwyn is led by serial entrepreneurs with multiple exits and funded by a Top 10 fintech VC.


To learn more, visit our website


Who Are You?


As our Senior Product Manager for Calculation Systems & Regulatory Innovation, you'll lead the development of our core computational capabilities and regulatory solutions - the fundamental components that power our entire platform. This role offers a unique chance to leverage AI to build products that will revolutionize an industry. You'll help solve a genuine market pain point, collaborating with diverse perspectives to build something transformative, taking true ownership of critical systems, and contributing to our collective success.


Key Responsibilities:
  • Market & User Representation: Serve as the voice of the customer, deeply understanding professional service workflows, pain points, and needs
  • Hands-on Product Development: Work directly with engineering and design in daily collaboration, from virtual whiteboarding sessions to code reviews
  • Product Architecture: Drive the roadmap for our core calculation systems, handling complex rules and compliance requirements
  • Regulatory Innovation: Lead product strategy for achieving and maintaining necessary certifications while pioneering streamlined approaches
  • SME Collaboration: Design validation workflows and tools that enable professional services experts to efficiently validate AI-generated calculations and rules
  • AI/ML Integration: Partner with our AI team to guide the development of machine learning capabilities
  • Data-Driven Optimization: Use product analytics to measure effectiveness of validation tools and calculations, driving continuous improvement
  • Quality Assurance: Create tools that enable efficient validation, testing, and quality assurance of system outputs
  • Customer Research: Conduct regular interviews and feedback sessions with users to validate solutions and identify opportunities


Qualifications:
  • 5+ years of product management experience, with at least 2 years working on technical products
  • Experience with AI/ML or data-centric products, including familiarity with machine learning concepts and applications
  • Strong data analysis skills and experience using product analytics to drive decision-making
  • Experience leading complex product initiatives from conception through launch
  • Strong technical aptitude with the ability to partner effectively with engineering teams
  • Excellent communication skills with the ability to translate between technical and business domains
  • Track record of collaborating with subject matter experts and stakeholders
  • Experience building internal tools and systems (preferred)
  • Background in fintech, compliance software, or regulated industries (preferred)
  • Remote work experience with demonstrated ability to collaborate effectively in distributed teams


Benefits and Perks:
  • The big-picture value proposition of this role is simple: join us, and you'll be paid competitively to have freedom in solving worthwhile, challenging problems alongside other A-players at a fast growing SaaS startup led by an experienced and successful co-founding team with industry experience.

Other benefits include:
  • Adventure travel stipend - you receive a $1,000 travel reimbursement on your work anniversary each year. We encourage our team to recharge and explore the world beyond their home office walls.
  • Remote, work-from-anywhere culture
  • Flexible PTO
  • World Class health benefits - we believe in fostering flourishing teams by providing benefits that go beyond the usual standards - Health, vision, dental, HSA/FSA, and mental health support.
  • Stock options - every Full Time Employee has ownership in Aiwyn's future and success.
  • 401(k) matching


Our Values:
  • Trust - We champion transparency, welcome differing perspectives, uphold accountability, and trust that others have good intentions
  • Courage - We have the courage to take calculated risks and embrace change, knowing what worked in the past won’t always work in the future
  • Impact - Rooted in determination and innovation, we chase extraordinary outcomes and impactful results
  • Relentlessness - We approach challenges with an unwavering resolve, never settling for mediocrity, and always striving to surpass expectations


Learn more about Aiwyn:


Aiwyn is an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to age, ancestry, color, family or medical care leave, gender identity or expression, genetic information, marital status, medical condition, national origin, physical or mental disability, political affiliation, protected veteran status, race, religion, sex (including pregnancy), sexual orientation, or any other characteristic protected by applicable laws, regulations and ordinances.


Candidate information will be treated in accordance with our CCPA privacy notice which can be found here: https://www.aiwyn.ai/ccpa

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What You Should Know About Senior Product Manager, Aiwyn

Are you ready to take on an exciting role as a Senior Product Manager at Aiwyn? Aiwyn, a fast-growing software company revolutionizing the accounting profession, is seeking your expertise to lead the development of our core calculation systems and regulatory innovation. Since our inception in 2020, we've quickly expanded to support over 100 of the largest CPA firms in the world, focused on automating essential firm operations for improved cash flow and client experiences. In this position, you'll be the voice of the customer, working closely with engineering and design teams to ensure our products address real market pain points. You'll be at the forefront of integrating AI capabilities, driving the roadmap for complex systems while ensuring regulatory compliance. Your keen understanding of professional services workflows and strong collaboration skills will be essential as you engage with subject matter experts to validate and optimize tools for efficiency. If you're a seasoned product manager with a knack for AI/ML or data-centric solutions, Aiwyn offers a competitive compensation package, flexibility to work from anywhere, and unique benefits like an adventure travel stipend to enrich your life beyond the office. Join our passionate team, and let’s make a lasting impact together!

Frequently Asked Questions (FAQs) for Senior Product Manager Role at Aiwyn
What are the key responsibilities of a Senior Product Manager at Aiwyn?

As a Senior Product Manager at Aiwyn, your responsibilities will include serving as the voice of the customer, collaborating with engineering and design on product development, driving the roadmap for core calculation systems, leading regulatory innovation efforts, and integrating AI/ML capabilities into our products. You'll also conduct user interviews to gather feedback and refine our offerings.

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What qualifications are required for the Senior Product Manager position at Aiwyn?

To qualify for the Senior Product Manager role at Aiwyn, candidates should have at least 5 years of product management experience, with 2 years specifically focused on technical products. Familiarity with AI/ML technologies, strong data analysis skills, and a history of leading complex product initiatives from conception to launch are essential. Experience in fintech or regulated industries is preferred.

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How does Aiwyn foster a collaborative remote work environment for the Senior Product Manager role?

Aiwyn promotes a culture of collaboration among remote teams through daily engagement features like virtual whiteboarding sessions, regular feedback loops, and open communication channels. We trust our team members to work independently while ensuring they have the resources and support to succeed in a distributed environment.

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What opportunities for professional growth exist for Senior Product Managers at Aiwyn?

At Aiwyn, Senior Product Managers not only lead significant product initiatives but also have access to continuous learning opportunities in the fast-evolving tech landscape. With a focus on innovation, we encourage our team to explore new technologies and methodologies, ensuring professional development is central to your career with us.

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What benefits does Aiwyn offer to its Senior Product Managers?

Senior Product Managers at Aiwyn enjoy an array of competitive benefits, including flexible PTO, world-class health benefits, stock options for ownership in our future success, and a yearly $1,000 adventure travel stipend to recharge and explore beyond work. We believe in supporting our team for both personal and professional well-being.

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Common Interview Questions for Senior Product Manager
Can you describe your experience with product management in AI/ML-focused products?

When answering this question, focus on specific projects where you've successfully integrated AI or machine learning into product development. Highlight your understanding of these technologies, how you collaborated with technical teams, and the positive outcomes achieved through these initiatives.

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What strategies do you use to gather and prioritize user requirements?

Discuss your approach to user research, such as conducting interviews, surveys, or usability tests. Explain how you analyze and synthesize findings into prioritized requirements that align with company goals and user needs.

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How do you balance technical and business considerations when managing a product?

Describe your method for collaborating with engineering teams while keeping business objectives in focus. Emphasize your communication skills and ability to convey technical complexities to stakeholders who may not have a technical background.

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What is your approach to managing complex product roadmaps?

Share your experience with creating and maintaining product roadmaps that strike a balance between long-term strategic goals and immediate user needs. Discuss any tools you've utilized for tracking progress and optimizing workflows.

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How do you ensure compliance with industry regulations in your product management work?

Explain your well-defined process for staying updated on regulatory changes and integrating compliance considerations early in the product development lifecycle to mitigate risks effectively.

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Can you share an example of a successful product launch you managed?

When responding, provide a detailed account of your role in a specific product launch. Highlight challenges faced, strategies employed for a successful launch, and the results, including metrics that showcase the product’s impact.

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What tools do you use for product analytics and decision-making?

Discuss specific analytics tools you've utilized to measure the effectiveness of a product, how you interpret the data to inform decisions, and how that data-driven approach improves user experiences.

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How do you handle feedback from users during the product development process?

Describe how you actively seek out and embrace user feedback as a vital component of your development process. Discuss methods for gathering feedback and how you translate this input into actionable improvements.

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How do you work with cross-functional teams to deliver products successfully?

Share your experience in collaborating with various teams, such as engineering, design, and marketing. Discuss your communication practices and how you resolve conflicts and align different perspectives towards a common goal.

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What are the most critical metrics you track for product success?

Discuss the key performance indicators you regard as vital for assessing product success—be it user engagement, conversion rates, or retention metrics. Explain how you leverage these metrics to guide future developments.

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DATE POSTED
April 21, 2025

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