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Real Estate Inside Sales, Training, CRM Management and Consulting

The Skills and Systems That Turn Your Agents Into Consistent Closers

25 years building the pipelines, training the agents and running the CRMs to drive Production and Revenue.

For Team Leaders and Brokers Serious about Scaling

25+
Years Experience
40K+
Leads Managed
50+
Transactions — Year One
About Cheryl Sileo

The Inside Sales Expert Real Estate Teams Trust to Scale.

Cheryl grew up in Westchester county New York. She obtained a BA in psychology from IONA College in New Rochelle, NY. She raised her two awesome sons in North Carolina where she has called home for the past 22 years.

Her career spans the full spectrum of real estate - from high volume production and luxury corporate relocation in Westchester county, NY to high volume residential sales in the Carolinas.

She discovered along the way that her true passion lies in teaching agents the communication skills and daily habits that fuel success in real estate. She also thrives on building systems, implementing them effectively, and optimizing processes for continuous improvement. As the daughter of an English teacher and a systems analyst, she naturally absorbed both human‑centered communication and structured analytical thinking, making her uniquely skilled at helping agents blend strong interpersonal skills with the technical tools that support and scale their business.

What We Do

Four Ways to Elevate
Your Team's Performance

Agent Training

Individual and team training built around what actually converts leads — prospecting habits, dialogue frameworks, and daily workflow systems that agents use consistently.

Prospecting training and discipline
Dialogue and script coaching
Lead conversion techniques
Follow-up strategy and systems
Business development coaching

CRM Management

Full setup, organization, and ongoing management of BoomTown and Market Leader CRM platforms. Every lead properly statused, every opportunity captured, every drip running.

BoomTown and Market Leader setup
Lead status and pipeline organization
e-Alerts, drip campaigns, and automations
Agent onboarding and CRM training
Ongoing system management

Pipeline & Lead Nurturing

Strategic oversight of the full lead lifecycle — from first contact to closed transaction. Ensures every opportunity in the CRM is being worked, not just sitting there aging.

Initial lead contact and qualification
Long-term nurture strategy
Top opportunity identification and tracking
Past client reactivation campaigns
Pond and shark tank management

Accountability & KPI Programs

Structured accountability programs that translate activity into measurable outcomes. Agents know exactly what is expected, tracked, and reported — and why it matters to the team.

KPI tracking, reporting, and analysis
Goal-setting frameworks (monthly, quarterly, annual)
Minimum performance standards
Recruiting support and agent retention
Team performance consulting
"

Real production does not happen without real systems. The CRM is the engine. Training is the fuel. Accountability is what keeps it running.

Cheryl Sileo — Superior Inside Sales and Systems
Client Testimonials

What Team Leaders and Agents Say.

Cheryl has worked with some of the top-ranked real estate teams in the country. Here is what their leaders and agents say.

Top RE/MAX Team
★★★★★

When I first met Cheryl she was the only girl on a top Remax team of nine aggressive door to door meat-selling-turned-real-estate guys. We were competitive. So was she. She gave us a run for our money. Some months she even beat all of us out for first place. She was a relentless prospector. She can tell you some funny stories about deals that we did together, as she was double and triple booked most weekends with buyers coming in from other states TO BUY. Fast forward a few years later to when I had my own Remax team and had just purchased Boomtown. I knew I needed Cheryl. I mean she was the queen of conversion, systems and driving revenue. There was no one better to help take the team to the next level.

Cheryl played a major role in helping us scale and elevate performance. She's a true team player and a "big picture" thinker who helps bring vision to life.

PN
Patrick Nooney
Founder & Team Leader, The Premier Team RE/MAX Executive — Ranked #5 RE/MAX Team Nationwide
★★★★★

As team leaders of one of the top RE/MAX teams in the country, we understood how critical it is to have the right people in the right roles. Having Cheryl lead our BoomTown CRM was a major advantage.

She didn't just manage the system—she owned it.

Cheryl built out the platform, onboarded every agent, and created a scalable strategy that allowed our 25-agent team to maximize every opportunity. She became the engine behind our lead conversion.

She handled initial lead contact, tracked opportunities, and held agents accountable—driving real results, not just activity.

One of her greatest strengths was helping agents create early wins, building confidence and momentum across the team.

We never had to worry about our CRM. Cheryl ensured every opportunity was captured, nurtured, and converted.

She was an invaluable asset who brought structure, results, and energy to everything she did. I highly recommend her without hesitation.

JL
Jeff Lynch
Team Leader, The Premier Team RE/MAX Executive — Ranked #5 RE/MAX Team Nationwide
★★★★★

As the Director of Operations for the Premiere Team, the #5 RE/MAX Team in the Nation, I oversee and manage numerous agents, staff members, and systems. I'm often referred to as "The Glue" that keeps everything running smoothly. When our Team Leaders shared that Cheryl would be implementing and leading our BoomTown system, I was genuinely thrilled. Knowing Cheryl was in charge gave me complete confidence that this critical system would be handled with excellence and require very little oversight from me.

My office was right next to hers, so I frequently heard her on the phone throughout the day speaking with both leads and agents. She was always upbeat, positive, and encouraging—often laughing and bringing great energy to every conversation. Agents regularly stopped by her office just to say hello, ask a quick question, or update her on a client she had initially connected with. She truly enjoyed hearing their stories and following their progress.

I remember one time I found a contract sitting on the printer and said the buyer's name out loud. Without hesitation, Cheryl immediately told me which of our 25 agents was working with that client. I told her it was incredible that our entire BoomTown account seemed to live in her brain.

Cheryl is deeply passionate about teaching agents and helping them succeed. Her knowledge, energy, and genuine desire to see others grow make her an incredible asset to any team.

CS
Courtney Scott
Senior Vice President & Director of Operations, The Premier Team RE/MAX Executive — Ranked #5 Nationwide
★★★★★

Meeting Cheryl was a turning point in my career. I began working with her as my ISA and business development trainer, and from day one, it was clear she was exceptional. Our team brought her in to lead inside sales and train agents on prospecting and CRM management—but what she delivered went far beyond expectations.

I can say without hesitation that my business would not be where it is today without Cheryl.

She has a rare, natural ability to connect with people and turn simple conversations into meaningful opportunities. What truly sets her apart, though, is her ability to teach. She doesn't just train—you feel inspired, challenged, and driven to grow.

Cheryl helped me build a strong foundation by showing me how to effectively manage my CRM and develop consistent, income-producing habits. She holds you accountable in the best possible way and pushes you to reach a level you didn't think was possible.

Because of her, I became more confident, more disciplined, and far more successful.

Cheryl is truly elite at what she does. Her impact isn't just measurable—it's transformational. If you have the opportunity to work with her, take it. It will change your business and your trajectory. I cannot recommend her highly enough.

AM
Abreyon Moses
Crosson & Co. Brokered by eXp Realty
★★★★★

I had the privilege of working alongside Cheryl, where she served as both a mentor and an inside sales agent. I met her when I was brand new to the real estate industry, and she immediately made a significant impact on my professional development.

Cheryl was instrumental in building a strong foundation—not just for me, but for our entire team.

One of the most valuable parts of working with her was observing how she handled calls and having her listen in on mine. Her feedback was always constructive, insightful, and delivered in a positive, encouraging way that made learning both effective and enjoyable.

She has a unique ability to break down personality types and teach you how to adapt in real time—knowing when to push a conversation forward and when to step back. That skill alone has had a lasting impact on how I communicate and convert opportunities today.

Working with Cheryl was an incredible experience, and I'm truly grateful for the time I spent learning from her.

Cheryl made an immediate and lasting impact on my career. I highly recommend her.

FR
Fadi Rishmawi
New Homes Sales Consultant, Starlight Homes
★★★★★

The day I hired Cheryl, I had received 251 resumes for an inside sales position. I read hers, picked up the phone, and hired her on the spot.

She checked every box—licensed, experienced, professional, articulate—and she didn't need training! She already had a strong command of real estate sales and the BoomTown CRM I relied on to manage my seller database.

As a high-end, high-volume listing agent with very high standards, I knew from our first conversation that Cheryl was different. She operates independently, communicates confidently with high-net-worth clients, and executes at a high level without supervision.

She managed my BoomTown account in just two hours a day—and nothing ever fell through the cracks. Even working remotely, we operated at a high level for years. That level of trust is rare.

Cheryl is exceptional at lead conversion and CRM management. It's rare to find someone with her level of skill, discipline, and work ethic. I genuinely enjoyed working with her—I highly recommend her.

KS
Kati Spaniak
Lead of Terra Lux Homes / brokered by EXP Realty — Northbrook, Illinois & Naples Florida
★★★★★

Cheryl is truly one of the best. I had never done inside sales before joining Crosson & Co. brokered by eXp Realty, and she took the time to teach me the fundamentals while allowing me to learn by watching a true expert in action.

Her ability to keep people engaged and uncover their needs through conversation is incredibly impressive. She didn't just teach me what questions to ask—she showed me how and when to ask them, which made all the difference.

I've since transitioned into primarily inside and virtual sales for a home builder, and much of my success is directly tied to Cheryl's training.

Her deep understanding of how to quickly build rapport and guide conversations is unmatched.

You truly couldn't find a better person to add to your team. I highly recommend her.

LP
Lauren Piner
New Home Sales Consultant, Century Complete Homes
Relevant Experience

Every position built directly on the skills she now teaches. This is not coaching theory — it is lived experience at a high level.

Real Estate Agent
The Foundation
CS Realty & Relocation — Westchester County, NY

Specialized in luxury and corporate relocation. Worked with high level international executives in Westchester County, NY. Built strong landlord and seller relationships. She was expertly mentored by the broker/owner of this boutique brokerage. He taught her how to keep it simple. He tracked her KPIs for 10 years. She knew exactly how many people she had to talk to per day to make x amount of dollars per year. It was here that she learned and developed the prospecting, time blocking, daily income producing activities and lead conversion fundamentals that form the foundation of the training she delivers today.

Real Estate Broker
Remax Metro — Charlotte, NC

Cheryl moved to a different state. She didn't know anyone so she needed to figure out lead gen. She applied all that she had been taught by her mentor in NY. She prospected for hours every day. Before she knew it she had 38 deals pending. They all closed.

Inside Sales Agent, Database Organization and Business Development
Wilkinson & Associates, ERA — Charlotte, NC

Organized and optimized a 52,000 lead CRM. Converted under utilized data into a high performing sales pipeline, which helped establish the foundation for a call center supporting hundreds of agents. Exceeded first year goal of 50+ units for existing database leads.

Inside Sales, System Implementation and Business Development
The Premier Team, Remax Executive — Charlotte, NC

Implemented and managed Boomtown CRM for a 25 agent top ReMax team. Trained agents on lead conversion, prospecting, pipeline and CRM management. Developed systems enabling agents to close 2+ deals per month consistently. Became a key recruiting advantage cited by joining agents.

Inside Sales and CRM Management
Kati Spaniak, eXp Realty

Spent two hours a day doing virtual inside sales for a top producing, luxury listing agent. Managed the seller pipeline and gently led them through the sales funnel. When she wasn't doing follow ups, last visits or top opps she was hunting for and finding business within the database. Persevered through Covid and helped pretty much sell out the database. Many of the clients were empty nesters, so they decided to sell their primary residence in Illinois and move to their secondary residence in Florida or Arizona.

Inside Sales Agent, Business Development, CRM Management and Trainer
Crosson & Co., Remax Professionals — Florence, SC

Organized a 40,000+ lead Boomtown CRM, converting stagnant leads into active opportunities. Provided ongoing training and accountability to agents for lead conversion, prospecting, pipeline and CRM management. Developed systems to teach and support agents to close 2–4 deals per month consistently.

The Foundation

Experience Built in the
Field, Not a Classroom

Every system Cheryl teaches, she has run. Every script she coaches, she has used on live calls. From luxury relocation in New York to managing 40,000+ leads for top-ranked teams in the Carolinas, her career is the curriculum.

When she trains your agents, she is not reading from a manual — she is drawing from decades of real production across multiple platforms, markets, and team structures.

How It Works

Three Steps to a Functioning System

Every engagement starts with understanding where you are, then building toward where you need to be.

1

Book a Free Call

A 30-minute no-obligation consultation. You walk through your current CRM setup, agent structure, and lead system. Cheryl identifies the gaps and maps out what needs to change.

2

Assessment & Plan

A full review of your BoomTown or Market Leader account, your team's prospecting habits, and your KPI tracking. A clear plan is built — specific to your team size, your goals, and your lead sources.

3

Implementation

Training starts, CRM gets structured, and accountability systems go live. Results are tracked from day one. No theory, no generic playbooks — only what your specific team needs to produce.

FAQ — Superior Inside Sales and Systems
Common Questions

Before You Book

Everything you need to know before the consultation — answered directly, without the runaround.

BoomTown and Market Leader are the primary platforms. That said, the systems, training frameworks, and accountability structures Cheryl builds are transferable to most CRM environments. The first consultation is the right place to discuss your specific setup.
Cheryl has worked with single-agent setups up to 25-agent teams, including one of the top-five RE/MAX teams in the country. The approach scales. Whether you have three agents or thirty, the fundamentals of CRM management, lead conversion, and agent accountability apply the same way.
All services are delivered fully remote. Cheryl is based in Indian Trail, NC, but works with teams nationwide. Remote delivery has no impact on the depth of training or the accountability structure — most engagements run entirely via Zoom and screen-share sessions.
It is a real working conversation, not a sales call. In 30 minutes you will walk through your current CRM setup, how leads are distributed, what your agents' prospecting habits look like, and where the conversion drop-offs are happening. You leave with a clear picture of what is and is not working, regardless of whether you proceed.
CRM organisation and lead pipeline cleanup produce visible changes within the first two to four weeks. Agent training outcomes depend on consistency of practice — teams that commit to the daily workflow and accountability structures typically see measurable lead conversion improvements within the first 60 to 90 days.
Both options exist. Some clients engage Cheryl for a defined training block or CRM setup project. Others bring her in on an ongoing basis to manage the CRM, run agent accountability, and provide continuous coaching. The right structure depends on your team's needs and is decided during the assessment phase.
Common Questions

Before You Book

BoomTown and Market Leader are the primary platforms. That said, the systems, training frameworks, and accountability structures Cheryl builds are transferable to most CRM environments. The first consultation is the right place to discuss your specific setup.
Cheryl has worked with single-agent setups up to 25-agent teams, including one of the top-five RE/MAX teams in the country. The approach scales. Whether you have three agents or thirty, the fundamentals of CRM management, lead conversion, and agent accountability apply the same way.
All services are delivered fully remote. Cheryl is based in Indian Trail, NC, but works with teams nationwide. Remote delivery has no impact on the depth of training or the accountability structure — most engagements run entirely via Zoom and screen-share sessions.
It is a real working conversation, not a sales call. In 30 minutes you will walk through your current CRM setup, how leads are distributed, what your agents' prospecting habits look like, and where the conversion drop-offs are happening. You leave with a clear picture of what is and is not working, regardless of whether you proceed.
CRM organisation and lead pipeline cleanup produce visible changes within the first two to four weeks. Agent training outcomes depend on consistency of practice — teams that commit to the daily workflow and accountability structures typically see measurable lead conversion improvements within the first 60 to 90 days.
Both options exist. Some clients engage Cheryl for a defined training block or CRM setup project. Others bring her in on an ongoing basis to manage the CRM, run agent accountability, and provide continuous coaching. The right structure depends on your team's needs and is decided during the assessment phase.
Book Your
Free Call

Select a time directly from Cheryl's calendar. The call is 30 minutes. Bring your CRM situation, your team structure, and your production goals.

Team & Brokerage
Intake Questionnaire

These 24 questions give Cheryl the context she needs before the call. The more detail you provide, the more specific and useful the consultation will be. There are no wrong answers — this is a diagnostic, not a test.

Book a Consultation

Let's Talk About
Your Team

The free 30-minute consultation is where it starts. No pitch, no pressure. You tell Cheryl where your team is today and she tells you exactly what she sees and what it would take to change it.

Indian Trail, NC — Serving teams nationwide remotely

Book Your Free 30-Minute Consultation

Select a time that works for you. The calendar below will let you book directly — no back and forth needed.

Or reach out directly by phone or email to book a time.

Before the call

You'll be asked to complete a short pre-consultation questionnaire covering your current CRM setup, lead volume, team structure, and goals. This ensures the 30 minutes is spent on what matters to your specific situation, not background questions.

Ready to Start

Your Agents Have the Leads.
Now Give Them the System.

Real production does not happen without real systems. Book the consultation and find out exactly what your team needs.

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