Outsourcing Operations with Jen Dillard | Ep 066

15 snips

Apr 22, 2025

Jen Dillard, team leader of the JDRE Team in Hood River, Oregon, and co-founder of Brick by Brick Collective, shares her journey of building a real estate business in a new market. She discusses the challenges of outsourcing operations, including the importance of effective communication and tailored strategies. Jen delves into lessons learned from staff hiring and the pain points of managing a growing team. She also offers insights on aligning team roles with community engagement to boost productivity and success in a competitive landscape.

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ANECDOTE

Losing Staff Forced A Reset

Two key in-house staff left voluntarily and Jen initially felt devastated and overwhelmed as she put all the hats back on.
That crisis revealed inefficiencies and pushed her to search for a better outsourced solution.

ADVICE

Outsource Before Rebuilding In-House

Evaluate cost and managerial overhead before re-hiring senior salaried roles; outsourcing can be cheaper and less taxing.
Jen tested virtual assistants then partnered with Boutique COO to offload operations and marketing in stages.

INSIGHT

Productizing Your Own Pain Point

Turning a personal operations solution into a product can create a new business offering for other teams.
Jen co-founded Brick by Brick Collective after building the outsourced support she needed.

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The JDRE Team was growing quickly in the relatively small and highly competitive market of Hood River, Oregon.

But when their Director of Operations and Marketing Manager separated from the organization, team leader Jen Dillard found herself back in a challenging, undesirable, and familiar spot - wearing all the hats and doing all the things, but none of them especially well.

Jen shares the process of getting operations and marketing back on track, as well as how she started her business from scratch after moving to a town where she knew no one, how to work with an outsourced operations team, and how she landed an exclusive builder relationship she’s servicing with her team.

Watch or listen to this conversation with Jen for:

- What is and isn’t coachable about drive, hunger, and passion, plus questions to ask to close that gap

- The path from property management and condo conversions in Seattle to starting over in a small market where she knew no one

- Why co-owning a brokerage didn’t work for her

- Three specific things she did to build a business in a brand new market (including one that was “like a Seinfeld episode”)

- How she started a team with an engaging coffee barista and when she finally added admin

- The wrong way to hire staff and the pain it can create

- Her options to rebuild operations after the departure of two key staff members

- How she turned her operations solution into a business of its own

- How communication, visibility, and strategy work when you outsource operations

- Which systems and process were especially helpful to outsource

- Two themes she’s hearing from team leaders via coaching and networking

- Why Hood River isn’t as much a second-home market as it was when she arrived

- How being “pleasantly persistent” landed her an exclusive relationship with a builder and how that opportunity plays out within her team

- Advice for agents thinking about starting a team or joining a team

At the end, hear about a “beautiful mess” and frivolous rewards. Also: “Go Hawks!”

EOS conversation mentioned in this episode:

- https://realestateteamos.com/episode/eos-principles-scale-faster-real-estate-harvey-yergin

Jen Dillard
- http://instagram.com/jendillard

Real Estate Team OS:

- https://www.realestateteamos.com

- https://linktr.ee/realestateteamos

- https://www.instagram.com/realestateteamos/