The commercial real estate developer looked at our property management software demo and said: "This is impressive. I can see how this would transform our operations."
I got excited. We were six months into the sales cycle and finally had buy-in.
Then he said: "I'll bring this to our quarterly partners meeting in three months. If the partners approve, we'll need to evaluate it during our next development cycle, which starts in 18 months. Then we can discuss implementation."
My sales forecast said this deal would close in Q2. His timeline said Q4... two years from now.
That conversation taught me the fundamental reality of selling software to commercial real estate: everything moves slowly, relationships matter more than product features, and "fast" sales cycles are measured in years, not quarters.
CRE buyers don't rush technology decisions. They've been operating the same way for decades and see no reason to change quickly. They value stability, proven track records, and deep relationships over innovation and speed.
After burning through sales forecasts for 12 months because I treated CRE like SaaS sales, I rebuilt our GTM strategy around CRE timelines, relationship dynamics, and decision processes.
Revenue grew from $240K ARR to $4.6M ARR in 28 months by accepting that "slow is normal" and building our business around it instead of fighting it.
Here's how to build a successful PropTech business when your customers make decisions on timelines that seem absurd to software companies.
Why CRE Sales Cycles Take 18-24 Months (and That's Fast)
Standard enterprise SaaS sales cycle: 3-6 months from first contact to signed contract.
Commercial real estate sales cycle: 18-24 months (and we're talking about $200K-$500K annual deals, not $10M enterprise deployments).
When I asked CRE buyers why decisions took so long, I expected answers about budget approval or procurement complexity.
The real reasons had nothing to do with those factors:
Reason 1: CRE operates on development cycles, not fiscal quarters
Real estate developers plan in development cycles—the time from acquiring property to delivering completed projects.
Office development cycle: 24-36 months Multi-family development cycle: 18-24 months Industrial development cycle: 12-18 months
Technology decisions align with development cycles, not software sales cycles.
A developer explained: "We're starting a new office project in 2024. We'll evaluate property management software during planning in early 2023. We'll select software by mid-2023 for implementation when the building delivers in late 2024. Your timeline is 18 months minimum."
Reason 2: Partners make decisions by consensus, and partners don't meet weekly
Most CRE firms are structured as partnerships. Major decisions require partner consensus.
Partners don't meet weekly like SaaS executive teams. They meet quarterly (or less frequently for small partnerships).
Technology evaluation happens between partner meetings. Decisions happen during partner meetings.
This adds 3-6 months to any sales cycle regardless of how fast you move.
Reason 3: Existing systems work "good enough" so urgency doesn't exist
CRE firms run profitable operations with systems they've used for 10-20 years.
The systems are outdated, inefficient, and clunky. But they work.
In SaaS, "it could be better" creates urgency. In CRE, "it works" eliminates urgency.
Reason 4: CRE values stability over innovation
Technology failure in real estate can cost millions:
- Lost lease because tenant application wasn't processed
- Compliance failure resulting in regulatory penalties
- Financial reporting errors affecting investor relationships
- Property damage because maintenance requests weren't tracked
CRE firms won't rush technology decisions when failures have massive financial consequences.
We stopped trying to accelerate CRE sales cycles and started building our business model around 18-24 month timelines:
Business model adjustments:
- Pipeline built 24 months ahead of revenue recognition
- Sales forecasting on 18-month minimum cycles
- Sales comp plans that reward milestone progression, not just closes
- CAC budgets that account for 18-24 months of sales effort
- Cash reserves sufficient to survive long sales cycles
This acceptance of CRE timeline reality made our forecasts accurate and our operations sustainable.
The Relationship Currency That Matters More Than Product
I tried to sell CRE software like SaaS: feature demos, ROI calculators, competitive comparisons, urgency-based closes.
CRE buyers didn't respond.
A CRE executive told me: "I've been in this business for 30 years. I know everyone in this market. When I need a vendor, I call someone I've worked with before or someone a trusted colleague refers. I don't evaluate random companies with impressive demos."
CRE runs on relationships and reputation more than any other industry I've sold into.
The buyers we closed all came from:
Source 1: Existing CRE relationships (45% of deals)
Firms where we knew partners, had worked with them previously, or were referred by someone they trusted.
Source 2: Industry referrals (35% of deals)
Current customers referred us to their industry colleagues. "Talk to [Name] at [Firm]. I've known him for 20 years. Tell him I sent you."
Source 3: Industry events and associations (15% of deals)
Buyers we met at CRE conferences (NAIOP, ULI, ICSC) and built relationships with over 12-18 months.
Source 4: Cold outreach (5% of deals)
Almost none of our deals came from cold outreach, paid advertising, or marketing-generated leads.
This relationship-driven dynamic completely changed our GTM:
What we stopped:
- Paid advertising (CRE buyers don't click ads)
- SDR outreach (cold email doesn't work)
- Marketing automation (low conversion, wrong channel)
- Gated content and lead magnets (CRE buyers don't download whitepapers)
What we started:
- Industry event sponsorship and attendance (every major CRE conference)
- Relationship development with CRE industry leaders
- Customer advocacy and referral programs
- Personal introductions and warm handoffs
- Long-term relationship nurturing before any sales conversation
We measured success not by MQLs or pipeline created but by "relationship depth": how many CRE executives knew our team personally and would take a call if we reached out.
The Decision Committee That Never Appears on Org Charts
CRE firms have org charts like any company: partners, VPs, directors, managers.
But real CRE decisions aren't made by org chart hierarchy. They're made by informal power structures that outsiders can't see.
I'd identify the "decision maker" using standard sales qualification:
Who owns this decision? Who controls the budget? Who has authority to sign contracts?
Then I'd sell to that person.
Deals would stall mysteriously.
A CRE consultant explained: "You're selling to the named decision-maker. But in CRE, decisions are really made by kitchen cabinets—small groups of partners or senior executives who've worked together for decades. The official decision-maker can endorse your software, but if the kitchen cabinet doesn't approve, it won't happen."
The kitchen cabinet often included:
- Founding partners (even if semi-retired)
- Long-time COO or CFO (regardless of title)
- External advisors (accountants, attorneys) the firm has used for 20+ years
- Major investors in the firm's deals
These influencers didn't appear in our sales process until deals died because "the partners decided not to move forward."
We rebuilt our sales process to map informal power structures:
During discovery, we asked:
- "Who else should be involved in this evaluation?"
- "Whose opinion do the partners value on technology decisions?"
- "Who else has input even if they're not the formal decision-maker?"
- "Are there external advisors (accountants, attorneys) who review major vendor relationships?"
Then we:
- Met with all influencers, not just the named buyer
- Provided information packages for partners who wouldn't meet with us directly
- Facilitated conversations with their external advisors
- Built consensus across the informal decision network
This stakeholder mapping approach was time-intensive but dramatically reduced late-stage deal failures.
For PropTech companies managing complex stakeholder dynamics in CRE, platforms like Segment8 offer vertical-specific stakeholder mapping frameworks that help identify informal power structures beyond org charts.
The Proof Points CRE Buyers Actually Need
SaaS proof points: customer logos, ROI metrics, testimonials, analyst validation.
CRE proof points: specific deals they know about, people they know who use your software, visible presence in CRE community.
I showed CRE buyers our customer logos from well-known firms.
Response: "I've never heard of them. What markets are they in?"
Or: "I know that firm. But I don't know anyone there personally so I can't validate your claims."
CRE buyers want proof from people they know personally in their specific market segment.
Market segmentation in CRE:
- Office (Class A trophy, Class B/C, suburban)
- Industrial (logistics/warehouse, manufacturing, flex)
- Multi-family (luxury, mid-market, affordable)
- Retail (regional malls, strip centers, urban retail)
- Mixed-use and specialty (hotels, senior housing, student housing)
Each segment is its own ecosystem with its own networks.
A luxury multi-family developer doesn't care about industrial warehouse references. They want proof from other luxury multi-family developers they know.
We rebuilt our proof strategy:
Segment-specific case studies:
Instead of generic "CRE customer success," we created segment-specific stories:
- "How [Luxury Multi-Family Developer] uses our software across their 4,200-unit portfolio"
- "Office developer success story: Managing 2.1M SF across 8 Class A properties"
Local market validation:
For each target market (markets are geographic: Seattle CRE, Dallas CRE, DC Metro CRE), we secured 2-3 reference customers.
CRE is local. Buyers trust other CRE professionals in their market over national references.
Named references with permission to contact:
We built a reference program where customers agreed to take calls from prospects.
CRE buyers wanted to call references directly and have off-the-record conversations.
Visible industry presence:
We sponsored industry events, spoke at CRE conferences, published in CRE journals.
This visibility created "I've heard of you" credibility even before sales conversations.
The Pricing Model That Matches CRE Economics
SaaS pricing: per-user per-month subscription.
CRE rejects per-user pricing because users fluctuate based on development cycles.
A development firm might have:
- 8 employees during planning phases
- 25 employees during active construction
- 12 employees during lease-up
- 6 employees in property management phase
Per-user pricing creates budget uncertainty CRE firms won't accept.
We rebuilt pricing around CRE economics:
Pricing model: Per property or per square foot
Instead of per-user, we priced based on what's stable: properties under management or square footage.
Example pricing:
Office properties: $X per building or $Y per 100,000 SF annually Multi-family: $X per property or $Y per 100 units annually Industrial: $X per property or $Y per SF annually
Multi-year contracts with fixed pricing:
CRE firms budget on 3-5 year cycles tied to development projects.
We offered 3-5 year contracts with locked pricing:
- 3-year contract: $X per property annually (no price increases)
- 5-year contract: $X per property annually with 3% annual escalator (predictable)
Portfolio pricing with volume discounts:
CRE firms think in portfolios (collections of properties).
We offered portfolio pricing:
- 1-5 properties: $X per property
- 6-15 properties: 15% discount
- 16+ properties: 25% discount
This portfolio pricing matched how CRE firms thought about their businesses.
The Implementation Timeline That Matches Development Cycles
SaaS implementation: 30-60 days, aggressive go-live timelines.
CRE implementation timeline: align with development milestones.
I tried to implement our software on standard timelines: sign contract in Q1, implement in Q2, go-live by Q3.
CRE firms pushed back: "We're in the middle of construction. We can't implement new software until the building delivers and we transition to operations phase. That's 18 months from now."
CRE implementation must align with development or operational milestones:
New development implementation timeline:
Contract signed: During planning phase (18-24 months before building delivery)
System configuration: 6 months before building delivery
Staff training: 3 months before building delivery
Go-live: At building delivery or lease-up start
Acquisition implementation timeline:
Contract signed: During due diligence
Data migration: Between contract signing and closing
Staff training: 30 days before close
Go-live: At acquisition close
Existing portfolio implementation timeline:
Contract signed: Any time
Pilot: Single property for 90 days
Rollout: One property per quarter (slow, deliberate)
Complete implementation: 12-18 months for 15-property portfolio
We rebuilt implementation around these timelines:
- Contract terms included deferred go-live dates aligned with development milestones
- Implementation fees were milestone-based (not time-based)
- Revenue recognition aligned with actual usage, not contract signature
- Resource planning assumed 12-18 month implementation periods
This eliminated pressure to force "fast implementations" that CRE firms couldn't accommodate.
The Industry Events That Actually Matter
In SaaS, I'd attend tech conferences to generate pipeline.
In CRE, technology conferences are irrelevant. CRE industry conferences are essential.
CRE industry events that generated deals:
ULI (Urban Land Institute) conferences:
- Fall Meeting (largest annual CRE conference)
- Regional events throughout the year
- Industry council meetings
NAIOP (Commercial Real Estate Development Association):
- National conference
- Chapter events (local market gatherings)
Segment-specific conferences:
- NMHC (National Multi Housing Council) for multi-family
- ICSC (International Council of Shopping Centers) for retail
- CoreNet Global for corporate real estate
Local market events:
- CRE breakfast forums
- Market-specific association events
- Local CREW (Commercial Real Estate Women) chapters
We shifted our event strategy:
Stopped: Technology conferences like SaaStr, SaaStock, tech industry events
Started: Sponsoring and attending every major CRE industry conference
Budget reallocation:
- Previously: 70% digital marketing, 30% events
- New: 20% digital, 80% CRE industry events and sponsorships
Results:
- 60% of qualified pipeline came from CRE industry event connections
- Average deal size from event-sourced leads was 2.3x higher than other sources
- Close rate from industry events was 45% versus 18% from other sources
CRE buyers wanted to see us at their industry events. Presence signaled commitment to CRE, not just trying to sell software to whoever would buy.
The Multi-Year Sales Relationship That Becomes Partnership
In SaaS, sales reps close deals and hand off to customer success.
In CRE, sales relationships continue indefinitely after the close.
CRE executives expect ongoing relationships with vendors. The sales rep who closed the deal is expected to remain their primary contact even after implementation.
When we tried standard SaaS handoff (sales → customer success), customers felt abandoned:
"I built a relationship with [Sales Rep]. Now they handed me to someone I don't know. That's not how we work in real estate."
We restructured our account management:
Sales rep remains primary relationship:
Even after close, the sales rep who built the relationship maintains it:
- Quarterly business reviews
- Strategic planning sessions
- Expansion and upsell conversations
- Relationship development with other executives in the firm
Customer success supports implementation and operations:
CSM handles implementation, training, support, and product adoption.
But strategic relationship remains with sales rep.
Compensation structure:
Sales reps receive ongoing commission on account expansion and renewals because they maintain the relationship.
This isn't just comp structure—it's relationship continuity that CRE buyers expect.
What Worked: The Long-Cycle, High-ACV Business Model
After accepting that CRE sales cycles are 18-24 months and that relationships matter more than product, we rebuilt our entire business model:
Strategic shifts:
From: High-volume, short-cycle SaaS sales ($50K ACV, 3-month cycles)
To: Low-volume, long-cycle CRE sales ($400K ACV, 18-month cycles)
Business model:
- Target: 15-20 CRE deals per year (not 200 SaaS deals)
- Average ACV: $350K (versus $50K in SaaS)
- Sales team: 5 senior CRE-experienced reps (not 20 junior SaaS reps)
- CAC: $120K per customer (18 months of sales effort)
- LTV: $2.8M (8-year average customer lifetime, high retention)
- LTV:CAC ratio: 23:1 (exceptional, because retention is so high)
Team structure:
- Hired CRE industry veterans for sales team (former developers, brokers, operators)
- Eliminated SDR function entirely (doesn't work in relationship-driven CRE sales)
- Built customer success team with CRE operations experience
- Dedicated events and sponsorship manager for industry presence
Pipeline and forecasting:
- Built pipeline 24+ months ahead of revenue targets
- Forecasted based on relationship depth and deal stage, not time in pipeline
- Accepted that Q1 pipeline wouldn't close until Q3 next year
- Measured success by relationship development, not MQLs
The Uncomfortable Truth About PropTech for CRE
Commercial real estate doesn't operate like tech companies or even like most other industries.
Decisions are slow. Relationships matter more than product. Innovation is valued less than stability. Trust takes years to build.
PropTech companies that try to impose SaaS GTM models on CRE fail. PropTech companies that adapt to CRE dynamics succeed.
What doesn't work in CRE:
- Fast sales cycle expectations (sub-6 months)
- Product-led growth and self-service
- Cold outreach and SDR teams
- Per-user subscription pricing
- Fast implementation timelines
- Sales-to-CSM handoff model
- Digital marketing-led demand gen
What works:
- 18-24 month sales cycles accepted as normal
- Relationship-driven sales through industry presence
- CRE industry event sponsorship and networking
- Per-property or per-SF pricing with multi-year contracts
- Development-cycle-aligned implementation
- Sales rep maintains relationship post-close
- Industry referral and advocacy programs
- Segment-specific (office/industrial/multi-family) proof points
Building a PropTech business for CRE requires accepting that you're not building a typical SaaS company.
You're building a relationship-driven, long-cycle, high-ACV business that looks more like professional services than software.
Our results after rebuilding for CRE realities:
- Revenue: $240K → $4.6M ARR in 28 months
- Average ACV: $65K → $350K (moved upmarket to larger portfolios)
- Sales cycle: 4 months (failed SaaS approach) → 19 months (successful CRE approach)
- Close rate: 12% → 48% (relationship qualification improved dramatically)
- Customer count: 15 → 38 (low volume, high value)
- Net retention: 142% (portfolio expansion over time)
The PropTech companies winning in CRE are the ones that embrace CRE's unique culture, timelines, and relationship dynamics instead of trying to change them.
Move slowly. Build relationships. Think in years, not quarters.
That's how you win in commercial real estate.