Bryan Ossa

I spent a year and a half as a Senior Product Manager at HubSpot, on the automation R&D team, building the tools companies use to run their operations. Before that, I worked in product at a tech startup, owned project and product delivery at an agency, and managed teams across several other industries. Across all of it, I kept seeing the same pattern: companies buy good software one decision at a time, and nobody configures it around how the business actually runs.

That's the work I do now at Cartographer Consulting, which I co-founded with Danielle Urban. We help product SaaS companies and supply chain operators, meaning freight brokers and 3PLs. On the SaaS side, the CRM holds the deal, the product holds the usage data, and finance runs renewals from a spreadsheet. On the supply chain side, a single load lives in four systems at once: the TMS has the details, the WMS has the pallet, HubSpot has the shipper, and accounting invoices whatever lands in its inbox. Either way, someone on the team becomes the human middleware, and the process lives in their head instead of in the system.

My process consists of three phases, in order. Orientation maps how work really flows today, including the spreadsheet someone updates every morning and the step that only works because one person remembers it. Cartography designs the future state: every handoff, every data flow, and what the system should escalate to a person instead of deciding alone. Exploration is where we build it with the client's team: HubSpot configured around their business, plus integrations, automations, and documented, repeatable processes that don't depend on tribal knowledge. I audit the systems and design the fix myself, so the person who finds the problem is the same person who solves it.

Bottom line — information/content is only valuable if it can be useful. It is always easier (and less time consuming) to do it right the first time. I'd rather give you the tools you make that happen now than step in 6 months down the road to help you fix something that could have been solved with a brief chat.

If your team is running on spreadsheets and tribal knowledge, I'm happy to talk it through.