Senior Product Manager, AI-Driven Pro Workflows

Jobtailor; New York (NY); On-site; USD 140,000 - 200,000; Full time

Job summary

Jobtailor is seeking a Lead Product Manager in New York to drive product discovery, shape a long-term vision, and guide cross-functional teams through AI-driven product development.

You will balance hands-on delivery with strategic storytelling, test hypotheses, and focus on metrics that matter to small and medium-sized businesses. The role emphasizes rapid iteration, user delight, and durable competitive advantage.

Qualifications

• 8+ years of hands-on Product Management experience and/or Product leadership experience.
• Proven track record of leading R&D teams that deliver impactful results.
• Expert product discovery and analytical skills.
• Ability to tell a compelling story that drives alignment and inspires action.
• Exceptional collaboration skills; ability to quickly build trust with teams and customers.
• Passion for helping small and medium size businesses.
• Strong POV and demonstrated impact through building products in the age of AI.
• Active engagement with AI tools relevant to the role and continued AI fluency development.
• Secure, reliable, and consistent internet connection when approved to work from a non-office location.

Responsibilities

• Lead product discovery to understand customer problems and test risky assumptions.
• Create a long-term vision and strategy with durable competitive advantage.
• Build iteratively to prove hypotheses and test new concepts.
• Partner with Engineering, Design, and Data Science throughout product development.
• Rapidly execute and iterate with emphasis on user delight, impact, and learning.
• Take risks and make calculated tradeoffs.
• Balance hands-on building with strategic storytelling.
• Define, measure, and improve key product and business metrics.
• Improve foundational workflows including payroll task coordination, roles and permissions, and reports.
• Lead Workflows for Gusto Pro, a product built for accountants.

Skills

Product management

Product discovery

R&D leadership

AI tools

Collaboration

Storytelling

Tools

AI tools

Job description

Jobtailor is seeking a Lead Product Manager in New York to drive product discovery, shape a long-term vision, and guide cross-functional teams through AI-driven product development.

You will balance hands-on delivery with strategic storytelling, test hypotheses, and focus on metrics that matter to small and medium-sized businesses. The role emphasizes rapid iteration, user delight, and durable competitive advantage.