Founding Head of Product - cmdr

Help build the AI-native loan servicer.
Remote (U.S.) · Travel up to 25%

About cmdr

Servicing is the bedrock of lending. Every loan is serviced for its entire life. Someone collects the payments, tests the covenants, manages escrow, tracks insurance, spreads the borrower's financials and reports to investors. In the U.S., $5.1 trillion of commercial real estate debt needs servicing, and $1.5 trillion of it comes due in 2026 and 2027. Most of that work runs on platforms built in the 1980s and 1990s. Those platforms record what happened and leave everything else to people working from spreadsheets and inboxes. Covenant terms sit in PDFs that nobody re-reads until something goes wrong.

cmdr is building an AI-native loan servicer. We acquire servicers whole: their books, their people and their client relationships. Then we run every loan they hold on one live, sourced record. Our first acquisition, a commercial loan servicer with roughly $10 billion of loans under management, is in advanced discussions.

The record does the work that servicing depends on. We extract every term and covenant from the loan agreement, and every value carries the words it came from. AI reads, code computes, and a person confirms every exception. Each covenant becomes a tracked obligation: what the borrower owes, how often, what proves it, and the threshold. Obligations are checked as they happen, and a person is accountable for every decision. Agreement reading and human review run in production today.
The prize is larger than servicing. Servicing creates the live, sourced record that every other lending workflow runs on. We start with commercial real estate. Next comes underwriting and portfolio management on the same record, then private credit, auto, personal and student loans, and eventually finance beyond lending. We think autonomous finance starts here.

Why cmdr

• A growth model that compounds. We buy the servicer, not its clients. Every acquired book moves onto one platform, so improvements ship once, and what one book teaches, the next inherits.
• A working product on real loan files. Agreement reading and human review run in production, and we are building with lenders under NDA. You start with a working system and real books to run it on.
• A founder who has taken real estate public. Drew Sterrett, our founder and CEO, co-founded and led LEX, which took individual commercial buildings public through single-asset IPOs.
• Studio backing. Stackpoint, the Boston venture studio started by the co-founders of Notarize (now Proof) and Convene, committed our founding capital and is our operating partner. Its co-founders have created more than $2 billion in combined equity value. An institutional co-investment round is in progress.
• Real influence from day one. You will shape strategy, product, culture and execution from the start.

The role

This is not a typical "Head of Product" job. You will be Drew's partner in building the company. You will own the product vision and its prioritization, work alongside Drew on clients, fundraising and board meetings, and build the systems and rhythms that define how cmdr ships. The servicers we acquire keep running their own operations, and their teams do that work in cmdr. Each acquisition adds a new book and a new team to bring onto the product, and you own what they move onto.

We are looking for a company builder with a spike in product. That means someone who thinks about servicers, engineering bottlenecks, strategy and team quality without being asked. In a given week you might sit with an acquired servicing team while they review a lease amendment, review an eval set with engineers, map how a target servicer's book would move onto the platform, and cut a feature that was not earning its place.

What you'll drive

1. Product vision and strategy

• Own a long-term vision for the AI-native servicer and turn it into a focused near-term roadmap.
• Sequence the path from commercial real estate servicing to underwriting, portfolio management and new loan types, all on the same record.
• Decide what we will not build. Our first workflows are deliberately narrow, and holding that line is part of the job.
• Adjust quickly when a client, a document type or a regulatory requirement changes the picture.

2. The product servicers work in

• Own the human-in-the-loop product our servicing teams work in every day: the review surface, the exception queue and escalations. The servicers own the work and its service levels. You own the product they do it in.
• Design the split between agents and people. Agents handle the volume, servicers make the judgment calls, and every human correction shows what to automate next.
• Own the product side of moving an acquired servicer onto the platform: loan boarding, data migration from legacy systems, and the tools the team learns. Work with each servicer's leadership, who lead their team through the change. Make it faster and cheaper with each book.
• Make sure that nothing a client relies on drops during a transition.

3. Quality, evals and metrics

• Own the quality bar. Servicers and their clients act on what cmdr tells them, so accuracy is our license to operate.
• Work with engineering on evaluation: gold sets, grounding checks, and the review data that shows where extraction is wrong and why.
• Define and own the company's metrics, from loans per servicer and cost per loan down to how long an acquired book takes to board.
• Use the reasons behind servicer corrections to set the automation backlog. The operation generates its own roadmap, and you are the person who reads it.
• Work directly with engineers to understand constraints, unblock work, challenge assumptions, and cut scope when needed.

4. Clients, partners and acquisitions

• Own the product relationship with the lenders and investors whose loans we service. Their reporting requirements and trust are what each acquisition is worth.
• Run partnerships with lenders building with us: working sessions, workflow observation, the feedback loop into product, and conversion to commercial agreements.
• Support acquisition diligence with Drew: assess a target servicer's book, systems and workflows, and how quickly it can move onto the platform.
• Own pricing and packaging: per-loan economics, and the model that turns each point of automation into margin.
• Represent cmdr at the conferences and associations where lenders decide who to trust with their loans.

5. Company building beyond product

• Recruit across product, engineering and design.
• Work with each acquired servicer's leadership as their team adopts cmdr.
• Own investor materials and partner pitches with Drew.
• Model founder-level ownership: when something breaks, you own the fix.
• Run cmdr as an AI-native company, so a small team operates like a much larger one.

What you bring

Builder's range. You have been an early product leader or founder who worked past the edge of the job description. At this stage, product, operations and strategy are one job.

Operations-in-the-loop product experience. You have built a product that is a workflow run by both software and people. Lending, servicing, fintech operations, insurance or logistics all count, as does any other document-heavy domain where quality comes from a system rather than one heroic person. You know how to instrument human work and turn it into automation. You have migrated a team or a book of business onto a new system without losing what the old one held. Experience in CRE lending, servicing or asset management is a plus, not a requirement.

AI-native judgment. You use AI tools heavily in your own work. You have shipped LLM-powered features where a wrong answer had a real cost, and you have built or run the evals that caught those wrong answers. You know from experience where extraction does well, where it fails, and how to design the human backstop.

Engineering partnership. You go deep enough into architecture and data flows to challenge assumptions and make real tradeoffs. Engineers trust you because you understand their constraints and protect their focus.

Team leadership. You have built and led cross-functional teams of engineers, designers and operators, and kept them aligned on milestones. You have brought a team through a big change in how they work, and they trusted you on the other side of it. You explain tradeoffs directly, and people leave your meetings with more energy than they brought.

Commercial drive. You have run B2B sales or client relationships, or been a core part of that motion: building pipeline, keeping clients through change, setting pricing. Experience with acquisition diligence or post-merger integration is a strong plus. A room of lenders energizes you. You are ready to travel for it, with regular in-person time alongside Drew, our servicing teams, clients and the industry.

What makes this role unique

• A founding seat at an AI-native servicer with real books. Servicing touches every loan from closing to payoff, yet almost no one outside the industry has seen the work. The pressure is rising: 11.42% of CMBS loan balances are in special servicing, the most since 2013. You will run a product on live loans, not a pilot.
• A founder who has done it before as your partner. Drew built LEX on the boundary between real estate and capital markets. That gives cmdr credibility with servicers, lenders and investors from day one.
• Ownership of the product a servicing operation runs on. Acquired servicers keep running their books, and their daily work happens in what you build. This seat barely exists anywhere yet, and you would help define it.
• A measurable mission. Every correction a servicer no longer has to make shows up in the data, loan by loan and book by book.
• The Stackpoint ecosystem. You get a venture studio as operating partner, plus a portfolio of AI real estate companies building alongside you, several of them selling to the same lenders. That means shared engineering, operator networks, and other founders one message away.

Compensation and logistics

• Competitive salary calibrated for early-stage leadership.
• Meaningful equity with upside potential as we grow.
• Comprehensive health benefits.
• Location: flexible within the U.S. We operate remotely.
• Travel: up to 25%.

If you read this and want to own the product a servicing operation runs on, we'd like to talk.