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Salary: USD 200,000 - 250,000 / annual
BigTime is a PSA (Professional Services Automation) platform serving thousands of consulting, IT services, and engineering firms. The company is building a next-generation, AI-native platform from the ground up—an autonomous back office where agents handle the entire quote-to-cash workflow: scoping, pricing, staffing, time and expense capture, revenue recognition, invoicing, and payment collection. Today, firms manage these processes manually across disconnected tools. BigTime has a unique competitive advantage: years of project history from thousands of existing customers to train against.
As Director of Product, you will lead the product management team with primary focus on the new platform—the company's largest investment with board-level visibility. You will own the roadmap, release sequencing, and scope decisions for both the new platform and BigTime Delivery (the existing customer platform). You will manage the PM team, including hiring and coaching. You will drive spec-driven development, working closely with engineering leadership to maintain a shared roadmap queue. Your PMs will pair with tech leads from shaping through release.
Key responsibilities include: defining and defending the roadmap based on pipeline data, product usage, customer research, and win/loss analysis; managing the product management team; running the Customer Advisory Board and maintaining executive relationships at major accounts (including difficult conversations); conducting discovery and win/loss analysis; supporting sales on deals where roadmap decisions are critical; coordinating across engineering, support, implementation, forward-deployed engineering, CX, marketing, and finance; and making judgment calls on what gets fixed in BigTime Delivery and when to stop.
You will be based in Chicago on a hybrid schedule with regular office presence. Much of engineering and UX design is in Poland; you will protect the Poland overlap window and build your week around it. You will have direct reports outside Chicago. Periodic travel to Poland, customers, advisory board sessions, and industry events is expected. Decisions are documented rather than settled informally.
REQUIREMENTS:
- 8+ years in product management (10+ for Senior Director level)
- At least 3 years managing PMs
- B2B SaaS experience on a product with real operational or financial depth
- Proven experience building something new at a company with existing customers to protect (replatform, migration, or net new product alongside existing offering)
- Comfortable with executive-level customer conversations, including difficult ones
- Experience managing people across time zones and aligning cross-functional teams (sales, support, implementation, marketing) without direct authority
- Track record developing PMs
- Use of AI in your own work (analysis, prototyping, drafting product documents)
- Shipped AI or agent capability in a real product
NICE TO HAVE:
- PSA, ERP, accounting, or financial software background
- Experience with cohort-based customer migrations and parity/reconciliation work
- Experience working with engineering and design teams in Central or Eastern Europe
