Build Your Career with Us!
About Us.
Kirkland Capital Group is a founder-led commercial real estate investment platform built by operators, not allocators. We originate and manage short-term bridge loans with a singular focus on protecting capital and executing well across cycles.
Chris Carsley and Brock Freeman—and their families—are the largest investors in our fund, ensuring alignment is real, not rhetorical.
Fully Remote.
We are deliberately small, fully remote, and built around ownership. What matters here is output, judgment, and follow-through—not optics, hours logged, or bureaucracy. Every quarter, the entire team reviews company goals, individual ownership areas, what worked, what did not, and what we are changing next.
Transparent and Engaged.
Today, KCG operates a proven lending platform with deep broker relationships, an experienced in-house underwriting and LoanOps team, and documented execution across intake, underwriting, closing, and servicing. At the same time, we are expanding into originate-to-sell programs—creating a rare opportunity to help shape how institutional loan sale programs are designed, launched, and scaled. This is not a finished machine. It is a platform in the middle of being built, by people who intend to own the outcome.
Job Opening
Head of Originate‑to‑Sell Programs
Remote - location open but must work in a North American aligned time zone.The Role
The Head of Originate‑to‑Sell Programs owns the end‑to‑end success of KCG’s Originate‑to‑Sell (OTS) platform. This role is accountable for delivering a fully functioning, buyer-validated loan origination and sale engine—one that executes in the market, produces saleable loans at origination, and supports a clear path to repeatable, scalable volume. Success is measured by outcomes and execution.
Key Responsibilities
End-to-End OTS Program Ownership: Design, launch, and manage the originate-to-sell engine from inception through execution, building programs backward from institutional buyer requirements to ensure loans are saleable at origination rather than remediated post-close.
Buyer Development & Program Formation: Convert institutional buyer interest into durable, executable relationships by clarifying credit criteria, negotiating commercial terms, structuring program parameters, and sourcing alternative buyers as needed to support continuity and resilience of the loan sale platform.
Execution and Repeatability: Translate initial transactions into a repeatable, scalable operating model by pressure‑testing underwriting standards, documentation, operational handoffs, and controls—tightening the system to support increasing volume without operational friction or execution risk and ensuring it runs cleanly through the LoanOps Origination team as scale increases.
About You
This role is for someone who reads the above and thinks:
“I’ve already built or run an investor-aligned loan program end-to-end — and I’ve owned both the buyer relationship and the execution.”
This is not a role to learn originate‑to‑sell for the first time.
We are looking for someone who:
Has built or run investor-aligned loan programs with direct responsibility for buyer relationships and execution.
Understands secondary-market scalability at a practical level.
Thinks in systems, not tasks.
Is comfortable starting close to execution to earn leverage.
Communicates early, clearly, and without drama.
Treats ownership as non-negotiable.
Ideally, you have:
5–10+ years in real estate or mortgage lending.
2–5 years directly owning or operating secondary-market, correspondent lending, or whole-loan sale programs.
A strong understanding of underwriting, buyer criteria, and execution risk.
Comfort working in a remote, high-autonomy environment.
Compensation & Upside
This role is intentionally structured with meaningful upside.
Base (Security)
$85,000 – $100,000
Covers downside risk.
Filters for candidates confident in their ability to perform.
Keeps fixed costs aligned while the engine is being proven.
Performance Upside
Compensation is explicitly tied to OTS program success and repeatable execution.
This role is targeted to earn $400,000+ per year by the end of year two, assuming successful program formation and scale — not heroics or one‑off transactions.
No artificial ceiling exists as volume, buyers, and product breadth expand.
Other Benefits
Fully remote role with meaningful autonomy over how you work.
Small, high‑ownership team where your judgment materially shapes the platform.
Health care coverage.
Who You'll Work With
You will partner directly with KCG’s founders. This role has no layers and no proxies: we align on goals and constraints, then expect you to own execution.
Chris Carsley, Chief Investment Officer: Your counterpart on buyer strategy and economics. Chris pressure‑tests institutional fit, pricing, and long‑term scalability. He cares about whether a program works in the market, not whether it looks good on paper.
Brock Freeman, Chief Operating Officer: Your counterpart on execution and systems. Brock focuses on turning early deals into repeatable processes, hardening handoffs, and eliminating friction as volume scales. He will push for clarity, documentation, and operational leverage.
You will work closely with KCG’s LoanOps team to translate buyer criteria into executable reality. Early tension is expected — tightening underwriting, documentation, and process so loans are sale‑ready by design, not retrofitted after the fact. You will also collaborate with our TechOps & Automation Manager to use automation and AI as leverage as the platform scales.
Pre-Employment Background Check
All offers are contingent upon the candidate successfully passing a credit and criminal background check, consistent with the responsibilities and fiduciary nature of the role.
Before You Apply
If this role feels aligned after reading the description above, we recommend watching the short video below before applying.
How to Apply
We hire for ownership, not polish.
We start by reviewing résumés for direct, relevant experience building and running investor‑aligned loan programs. If there’s a potential fit, the next step is a text‑based interview directly with the Partners. This is where we evaluate judgment, decision‑making, and whether you’ve actually owned outcomes like this before.
From there, we move into live conversations focused on execution, tradeoffs, and scale. No tests. No theatrics. No proxy signals.
This role is not won through credentials or process compliance. It’s won by demonstrating real ownership and the ability to build something that works.
Send your résumé to ots@kirklandcapitalgroup.com. The email itself should serve as your cover letter—tell us what you’ve built and why this role fits.
If you’re looking for:
real ownership,
direct partnership with leadership,
a role where results matter more than optics,
…apply.
Kirkland Capital Group is an equal opportunity employer and makes hiring decisions based on merit.