A Game Plan From a Friend
Adriann, Let’s Talk
I put this together for you because I’ve been thinking about your situation — and honestly, I think you’re in a stronger position than you realize. You’ve got 20 years of experience, a Georgetown degree, and relationships that people can’t buy. This isn’t a setback. This is a setup for something better.
Real Talk
Here’s What I See
Look, I’ve built a career on understanding people — nursing, psychology, economics, an MBA, even some law school. I’ve learned to read situations. And here’s what I see when I look at your resume:
You’re not a job seeker. You’re the person organizations are looking for.
You’ve managed $1.7 million budgets. You’ve tracked legislation across all 50 states. You’ve advised the Mayor’s office on housing policy. You’ve built coalitions that actually moved the needle. That combination? It’s rare. And it’s valuable.
I’ve been in situations where things didn’t go the way I expected. The Army taught me that setbacks are just setups for comebacks. You’ve got everything you need — now it’s about positioning yourself right and letting the market see what I already see.
Your Arsenal
What You Bring to the Table
Let me break down what makes you valuable — because I don’t think you’re giving yourself enough credit:
Legislative Intelligence
You’ve tracked hundreds of bills a year. You know how policy actually moves — not theory, but practice. That’s experience money can’t buy.
High Demand
Political Relationships
You’ve got connections from city hall to Congress. Lauren Underwood’s advisory council. The Mayor’s office. Civic Federation. That network is gold.
Irreplaceable
Budget & Team Leadership
$1.7M budget. Team of five. That’s not just advocacy — that’s running a business unit. You’ve got P&L accountability on your resume.
Executive-Level
National Scope
You tracked legislation in all 50 states at NAR. That national perspective sets you apart from people who’ve only worked locally.
Differentiator
The Georgetown Credential
That Master of Real Estate from Georgetown? One of the best programs in the country. Combined with your MPA, you’ve got both the policy and business chops.
Top Tier
Mobilization Skills
200% increase in advocacy participation at CCIM. You don’t just talk — you get people to move. That’s the hardest skill to develop.
Rare
Strategic Positioning
Where You Should Be Aiming
Based on everything you’ve built, these are the four lanes where you’ll have the most impact — and the most leverage. Don’t settle for anything below this level. You’ve earned it.
VP of Government Affairs
Major developer, REIT, or corporation that needs policy leadership
Executive Director
Housing nonprofit or community development organization
Chief of Staff / Policy Director
City, county, or state government — housing or economic development
Principal / Partner Track
Government affairs or lobbying firm with real estate practice
Don’t be the first one to throw out a number. When they ask, say: “I’m targeting roles in the $175,000 to $225,000 range depending on total compensation and scope.” You’ve got 20 years of experience — don’t leave money on the table.
Target Organizations
Places That Need You
I put together a list of organizations in Illinois that either need someone like you now — or will soon. Prioritize based on where you’ve got the warmest connections.
🏛️ Government & Quasi-Government
You’ve already advised the Mayor’s office. That makes you an insider for city roles. These offer stability and real policy impact.
- City of Chicago — Dept. of Planning & Development
- City of Chicago — Housing Commissioner’s Office
- Illinois Housing Development Authority (IHDA)
- Cook County Bureau of Economic Development
- Chicago Housing Authority (CHA)
- Metropolitan Planning Council
🏢 Trade Associations
You know this world inside and out. Your experience at Illinois REALTORS translates directly to any of these.
- BOMA Chicago — Building Owners & Managers
- Chicagoland Apartment Association
- Illinois Bankers Association
- Home Builders Association of Greater Chicago
- Midwest Real Estate Data (MRED)
- Illinois Chamber of Commerce
🤝 Nonprofits & CDFIs
Mission-driven work with real budgets and policy influence. Your Mercy Housing volunteer work and housing expertise make you a perfect fit.
- NHS Chicago — I can make an intro here
- LISC Chicago
- Enterprise Community Partners
- Chicago Community Trust
- Mercy Housing — They already know you
- Community Investment Corporation (CIC)
🏗️ Private Sector — Real Estate
Big developers need government affairs leadership as regulations get more complex. Your Georgetown degree gives you instant credibility with C-suite folks.
- Sterling Bay
- Related Midwest
- JDL Development
- Lendlease
- JLL — Government & Public Affairs
- CBRE — Public Policy
- Cushman & Wakefield
💼 Consulting & Lobbying
Partner-track roles where your relationships become your equity. These firms will value your ability to bring in clients.
- Strategies 360
- Foley & Lardner — Government Affairs
- Locke Lord — Public Policy
- Res Publica Group
- Barnes & Thornburg
🏥 Corporate Government Affairs
Big companies with Illinois HQs need state and local government affairs pros. Great comp, great benefits.
- United Airlines — Chicago HQ
- Walgreens Boots Alliance — Deerfield
- Advocate Health / Northwestern Medicine
- ComEd / Exelon
- BMO Harris Bank
- Abbvie — North Chicago
- Peoples Energy — Beto knows Maria Bocanegra (law school) — call her
The Playbook
Your 30-Day Game Plan
Here’s what I know from being in real estate: the best opportunities don’t come from job boards. They come from conversations. Your job for the next 30 days is to activate your network and let people know you’re available. Most roles at your level get filled before they’re ever posted.
Foundation & Inner Circle
- Write your 60-second story: what happened, what you’re looking for, what you bring. Keep it positive and forward-looking.
- Update LinkedIn: “Government Affairs Executive | Housing & Real Estate Policy | Open to Opportunities”
- Make a list of your “personal board of directors” — 5-7 people who will go to bat for you. Call each one.
- Create a target list of 40 specific people (not organizations) you want to talk to
- Let Congresswoman Underwood’s office know — they’ll want to help
Network Activation
- Reach out to 5-7 people per day — coffee, calls, LinkedIn messages. Just start talking.
- Reconnect with your NAR colleagues — they see the national market
- Touch base with your Civic Federation contacts — those folks are connected
- Schedule 2-3 informational meetings with leaders at target organizations
- Track everything: Name, Org, Date, Next Step
Get Visible
- Go to one industry event — ULI, BOMA, Civic Federation. Be seen.
- Connect with 2-3 executive recruiters who specialize in government affairs or nonprofit leadership
- Look for board opportunities — a strategic board seat can open doors
- Follow up on all your Week 2 conversations: “Who else should I be talking to?”
- Pay attention to where you’re getting energy. Double down there.
Convert to Opportunities
- Apply to 3-5 posted positions that match your profile — but only at the right level
- Ask for warm introductions to hiring managers at your top targets
- Prep hard for interviews: research deeply, prepare smart questions, practice your story
- When offers come, negotiate. Don’t just accept the first number.
- Trust your gut on culture — a wrong fit at a good title is still a wrong fit
Watch Out
Mistakes to Avoid
I’ve seen good people hurt their search by making these mistakes. Don’t be one of them.
⚠️ Spraying Applications Everywhere
Mass applying signals desperation. Be selective. Go after roles that actually fit — quality over quantity.
⚠️ Selling Yourself Short
Don’t lowball your salary expectations out of fear. You’ve got 20 years. Price yourself accordingly.
⚠️ Talking Negatively About Illinois REALTORS
Even if you’re frustrated, don’t go there. Focus on what you’re building next, not what happened before.
⚠️ Jumping at the First Offer
I know it’s tempting to just be done with the search. But take your time. 30-60 days is normal at your level.
⚠️ Ignoring Culture Fit
A fancy title means nothing if you’re miserable. Ask hard questions about leadership and team dynamics.
⚠️ Going Dark
Stay visible. Post on LinkedIn occasionally. Go to events. Silence makes people wonder what’s wrong.
When They Ask “Tell Me About Yourself”
“I’m a government affairs executive with nearly 20 years of experience in housing and real estate policy. I’ve led legislative strategy at the state and national level, built coalitions that actually moved policy, managed multi-million dollar budgets, and advised elected officials from city hall to Congress. I’m now looking for a senior leadership role where I can have real strategic impact — whether that’s in the public sector, a mission-driven organization, or a company that needs sophisticated government affairs leadership.”
Say it with confidence. Make eye contact. Then stop talking and let them ask questions. You’re the expert they need — let them feel that.
You’ve Got This, Adriann
I’ve watched you work for years. You’re sharp, you’re connected, and you know your stuff. This isn’t the end of anything — it’s the beginning of your next chapter.
Go get it. And if you need anything — an intro, a sounding board, someone to practice with — I’m here. That’s what friends are for.
— Beto
Roberto “Beto” Montaño
Managing Broker, M.B.A.
Engel & Völkers Chicago
P.S. Whatever you need, you got a guy! 💪 #CallBeto