Director of Product

BigTime Software•Chicago, IL

1d•Hybrid

About The Position

BigTime is building a next-generation, AI-native professional services automation (PSA) 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 the new platform. They will own its roadmap, release sequencing, scope decisions, and the product managers responsible for each area. They will also own the roadmap for BigTime Delivery, the existing platform, while a dedicated team manages its day-to-day work. The role includes setting product priorities using pipeline data, product usage, customer research, and win/loss analysis; hiring and coaching the product management team; and maintaining a high standard for specifications used in the company's spec-driven development process. The Director will lead the Customer Advisory Board, maintain executive relationships with major accounts, conduct discovery and win/loss work, and participate in sales opportunities where the roadmap is consequential. The Director will work closely with Engineering leadership and product managers to coordinate a shared roadmap queue and guide work from shaping through release. They will also coordinate with Support, Implementation, Forward Deployed Engineering, Customer Experience, Marketing, and Finance. The position is based in Chicago on a hybrid schedule and is not remote. The role includes direct reports outside Chicago, a protected time window to collaborate with teams in Poland, and periodic travel to Poland, customers, advisory board sessions, and industry events. Applicants must be authorized to work in the United States.

Requirements

At least 8 years of product management experience for Director level; at least 10 years for Senior Director level.
At least three years of experience managing product managers.
B2B SaaS experience with a product involving substantial operational or financial complexity.
Experience building something new at a company with existing customers to protect, such as a replatform, migration, or net-new product 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 and can demonstrate what they built.
Comfortable engaging with customers at the executive level, including in difficult conversations.
Experience managing people in other time zones.
Able to align Sales, Support, Implementation, and Marketing without directly managing those teams.
Experience developing product managers.
Must be authorized to work in the United States.

Nice To Haves

Background in 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, release sequencing, scope decisions, customer migration timing, and written rationale for product decisions.
Set priorities using pipeline data, product usage, customer research, and win/loss analysis.
Lead, hire, and coach the product management team and establish standards for its work.
Oversee product specifications for a spec-driven development process in which specifications feed agentic building directly.
Lead the Customer Advisory Board and maintain executive relationships with major accounts, including dissatisfied customers.
Conduct customer discovery and win/loss analysis to inform the roadmap.
Participate in sales opportunities where roadmap decisions may affect the outcome.
Partner with Engineering leadership to maintain a shared roadmap queue and guide product managers and engineering tech leads from shaping through release.
Coordinate product communication and work with Support, Implementation, Forward Deployed Engineering, Customer Experience, Marketing, and Finance.
Own the BigTime Delivery roadmap, deciding what to fix, when to address it, and when to stop, including decisions that may draw engineering capacity from the new platform.
Build the work week around the protected collaboration window with Poland-based teams and travel periodically to Poland, customers, advisory board sessions, and industry events.