The RoleYou will lead our product management team, and most of your time goes to the new platform. The roadmap, the release sequencing, the scope decisions, and the PMs who own each piece of it. It is the biggest investment the company has made and the board follows it closely.
You will also own the roadmap for BigTime Delivery, the platform our existing customers use today. It is the smaller part of the job and a dedicated team runs the day to day. What we need from you is the judgment on what gets fixed, in what order, and when we stop.
What You Will Own- The roadmap. What ships in which release, what gets cut, which customers migrate when, and the written case for all of it. Priority gets argued from pipeline data, product usage, customer research, and win and loss analysis, rather than whoever asks most often.
- The product management team. Hiring, coaching, and the standard for the work.
- Specifications. We use spec-driven development, so the spec feeds the agentic build directly.
- Customers. You will run our Customer Advisory Board, hold executive relationships at our largest accounts including the unhappy ones, and do the discovery and win and loss work behind the roadmap yourself. Sales will pull you into deals where the roadmap decides the outcome. This is a real share of your week.
- The cross-functional loop. Engineering is the closest partner, where you and their leadership run one roadmap queue and your PMs pair with their tech leads from shaping through release. Support, Implementation, Forward Deployed Engineering, CX, Marketing, and Finance each need something different from you, and all of them need to know what is coming before a customer does.
- BigTime Delivery. Not the day to day, but the calls on what we fix and when we stop, including when it needs engineering time the new platform was counting on.
What We Are Looking For- 8+ years in product management for the Director level, 10+ for Senior Director, including at least three years managing PMs.
- B2B SaaS experience on a product with real operational or financial depth.
- You have built something new at a company that already had customers to protect. A replatform, a migration, or a net new product running alongside an existing one. Tell us what went wrong and what went well.
- You use AI in your own work for analysis across sources, prototyping, and drafting product documents, and you have shipped AI or agent capability in a real product. Show us what you have built.
- You are comfortable in front of customers at the executive level, including when the conversation is difficult.
- You have managed people in other time zones, and you can get Sales, Support, Implementation, and Marketing pulling in the same direction without managing any of them.
- You have developed PMs.
Nice to Have- PSA, ERP, accounting, or financial software background.
- Cohort-based customer migrations, including the parity and reconciliation work.
- Experience working with engineering and design teams in Central or Eastern Europe.
Location and How We Work- Chicago, hybrid. You will be based here and in the office on a hybrid schedule. This is not a remote role.
- Much of our engineering and most of our UX design sit in Poland. You will have direct reports outside Chicago. Decisions get written down instead of settled in a hallway, the Poland overlap window is protected, and you will build your week around it.
- Periodic travel to Poland, plus customers, advisory board sessions, and industry events.
The expected salary for this position ranges from $200,000 to $250,000 annually. The actual salary will be determined on an individualized basis, taking into account a wide range of factors including, but not limited to, relevant skills, experience, education, and, where applicable, licenses or certifications held. In addition to base salary and a competitive benefits package, this position may be eligible for additional types of compensation such as bonuses. 
