Director of Product
About The Position
BigTime is building a next-generation, AI-native professional services automation platform intended to automate the back-office process from quote to cash. The Director of Product will lead product management, with most of their time focused on this new platform, including roadmap development, release sequencing, scope decisions, and the product managers responsible for each area. The initiative is the company’s largest investment and receives close attention from the board. The role also owns the roadmap for BigTime Delivery, the platform used by existing customers. A dedicated team handles day-to-day work, while the Director provides judgment on priorities, fixes, and when to stop investing in particular work. The Director will lead and develop the product management team, establish expectations for product work, and oversee specifications used in the company’s spec-driven development process. They will work directly with customers, including leading the Customer Advisory Board, maintaining executive relationships at major accounts, conducting discovery and win/loss research, and supporting sales opportunities where roadmap decisions matter. The role partners closely with Engineering to maintain a shared roadmap queue and coordinate product managers with engineering tech leads from shaping through release. It also aligns Support, Implementation, Forward Deployed Engineering, Customer Experience, Marketing, and Finance on upcoming product work. The position is based in Chicago on a hybrid schedule, with direct reports outside Chicago, a protected overlap window with teams in Poland, and periodic travel to Poland, customers, advisory board sessions, and industry events.
Requirements
- At least 8 years of product management experience for Director level, or 10 or more years for Senior Director level.
- At least three years of experience managing product managers.
- B2B SaaS experience with a product that has substantial operational or financial depth.
- Experience building something new at a company with existing customers to protect, such as a replatform, migration, or net-new product running alongside an existing product.
- Uses AI in their own work for analysis across sources, prototyping, and drafting product documents.
- Has shipped AI or agent capability in a real product.
- Comfortable engaging with customers at the executive level, including in difficult conversations.
- Experience managing people in other time zones.
- Ability to align Sales, Support, Implementation, and Marketing without directly managing those teams.
- Experience developing product managers.
- Authorized to work in the United States.
Nice To Haves
- Background in professional services automation (PSA), ERP, accounting, or financial software.
- Experience with cohort-based customer migrations, including parity and reconciliation work.
- Experience working with engineering and design teams in Central or Eastern Europe.
Responsibilities
- Own the new platform roadmap, including release sequencing, scope decisions, customer migration timing, and written rationale for product priorities.
- Use pipeline data, product usage, customer research, and win/loss analysis to inform prioritization.
- Lead, hire, and coach the product management team and establish standards for product work.
- Own product specifications for a spec-driven development process in which specifications feed agentic building directly.
- Lead the Customer Advisory Board and maintain executive relationships at the company’s largest accounts, including unhappy customers.
- Conduct customer discovery and win/loss work to inform the roadmap.
- Support sales opportunities where roadmap decisions affect deal outcomes.
- Partner with Engineering leadership on a shared roadmap queue and ensure PMs work with engineering tech leads from shaping through release.
- Coordinate with Support, Implementation, Forward Deployed Engineering, Customer Experience, Marketing, and Finance so teams understand upcoming product work.
- Own the BigTime Delivery roadmap, including decisions about fixes, priorities, when to stop, and when work needs engineering time planned for the new platform.
- Work with distributed direct reports and maintain effective coordination with teams in Poland.
- Travel periodically to Poland, customers, advisory board sessions, and industry events.
Benefits
- Competitive benefits package
- May be eligible for bonuses
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What This Job Offers
Job Type
Full-time
Career Level
Director
Education Level
No Education Listed
