Brett Weber

Account Executive

Funnel Leasing

Account ExecutiveOutbound HeavyConsultative
Deal Size: $30-150K ACV
Sales Cycle: 3-6 months
Posted by Brett Weber•

Overview

You sell Funnel's AI-infused CRM and automation platform to multifamily property management companies—the people who manage apartment complexes. You're talking to operations directors, IT managers, and sometimes VPs who currently use a patchwork of tools (or spreadsheets) to track leads, communicate with renters, and manage properties. Most of your time is spent educating buyers on what's possible, navigating multiple stakeholders, and waiting on procurement cycles.


Role Snapshot

AspectDetails
Role TypeFull-cycle AE (self-sourcing + closing)
Sales MotionOutbound-heavy with some inbound
Deal ComplexityConsultative to Enterprise
Sales Cycle3-6 months
Deal Size$30-150K ACV (estimate based on CRM category)
Quota (est.)$400-600K/year

Company Context

Stage: Late-stage (173 employees, established product)

Size: 173 employees

Growth: VP of Sales just hired to build out a new team—suggests either expansion into new market segments or rebuilding sales function

Market Position: Challenger in the multifamily property management software space—competing against legacy PMSs (Property Management Systems) and newer point solutions


GTM Reality

Pipeline Sources:

  • 30% Inbound - mostly from existing customers referring sister properties or competitors within portfolio companies. Some content marketing leads but quality varies wildly
  • 60% Outbound - cold calling property management companies, LinkedIn outreach to ops directors, conference networking at multifamily trade shows (NMHC, Apartmentalize)
  • 10% Partners - referrals from property management system integrations and consultant relationships

SDR/AE Structure: Likely self-sourcing initially since VP is building the team from scratch. May add SDRs later but expect to do your own prospecting for the first 6-12 months.

SE Support: Probably shared SE pool or product specialists for demos—this is technical enough (CRM integration, AI features, contact center setup) that you won't solo all technical conversations.


Competitive Landscape

Main Competitors: Legacy property management systems with built-in CRMs (Yardi, RealPage), point solutions for leasing (Knock, Rent Dynamics), general CRMs like Salesforce that companies try to customize

How They Differentiate: AI automation for responding to renter inquiries across channels (email/chat/SMS/voice), multifamily-specific CRM built for the leasing workflow (not adapted from another industry), non-profit mission angle (HOME initiative around equitable housing)

Common Objections:

  • "We already have a CRM built into our PMS"
  • "Our team is comfortable with the current process"
  • "Integration risk with our existing tech stack"
  • "Budget already allocated to other initiatives"

Win Themes: ROI from lead response automation, better renter experience leading to higher conversion and retention, consolidating multiple tools into one platform, AI handling routine inquiries so staff can focus on complex issues


What You'll Actually Do

Time Breakdown

Prospecting (35%) | Active Deals (40%) | Internal (25%)

Key Activities

  • Prospecting Property Management Companies: Research portfolio companies that manage 500+ units, find the operations or marketing director on LinkedIn, cold call/email to book discovery calls. Lots of gatekeepers. Most property management companies don't have sophisticated buying processes, so you're often creating urgency where none exists.

  • Discovery and Multi-Stakeholder Demos: First call is with whoever you got on the phone (often a leasing manager). Then you need to loop in IT for integration questions, operations for workflow approval, and finance for budget. You'll do the same demo 3-4 times per deal to different audiences. Lots of "let me get back to you" and scheduling coordination.

  • Navigating Long Approval Cycles: Even after everyone agrees they want it, deals sit in procurement or budget committee review for weeks. You're chasing for updates, sending ROI justification docs, and trying to keep champions engaged. Many deals slip quarters because "they decided to revisit in next year's budget."

  • Building Custom Business Cases: Every property management company thinks their workflow is unique. You'll spend time documenting their current process, calculating time savings from automation, and building ROI models. A lot of spreadsheet work and Loom videos showing how Funnel would work for their specific use case.


The Honest Reality

What's Hard

  • Prospect inertia is massive: Most property management companies have been doing things the same way for years. Even when they acknowledge problems with their current process, getting them to actually change is like pushing a boulder uphill. "We'll think about it" means "no" 80% of the time.

  • Long cycles with lots of dead time: You'll have 15-20 deals in pipeline where you're just waiting. Waiting for the IT team to review security docs. Waiting for the budget meeting. Waiting for them to finish busy season. You can't force it faster, but you're still accountable for the number.

  • Multi-stakeholder politics you can't control: Your champion in operations loves you, but IT doesn't trust new vendors, or finance says budget is frozen. You'll lose deals not because your product isn't good, but because internal politics killed momentum and you have no visibility or influence over it.

What Success Looks Like

  • Booking 8-12 qualified discovery calls per month (companies with 500+ units, budget authority in the room, active pain with current process)
  • Carrying a pipeline of 15-20 active opportunities worth $2-4M to hit $500K annual quota
  • Closing 1-2 deals per quarter, with larger deals ($100K+) taking 6+ months and requiring executive sponsor involvement

Who You're Selling To

Primary Buyers:

  • Director/VP of Operations at property management companies (the person responsible for occupancy rates and operational efficiency)
  • VP of Marketing (the person trying to improve lead conversion and renter experience)
  • IT Director (has to approve integration with their PMS and ensure data security)

What They Care About:

  • Improving lead-to-lease conversion rates (fewer prospects slipping through cracks)
  • Reducing time staff spends on repetitive inquiries ("What's your pet policy?" x 1000)
  • Better visibility into leasing pipeline across their portfolio
  • Integration risk—they've been burned by software that promised easy integration and wasn't
  • Training burden—their leasing teams have high turnover and limited tech sophistication

Requirements

  • 3-5 years closing B2B software deals, ideally in prop-tech, real estate tech, or vertical SaaS
  • Comfortable with consultative selling—these aren't transactional deals, you're diagnosing workflow problems and prescribing solutions
  • Self-starter who can build pipeline from scratch without SDR support
  • Experience navigating multi-stakeholder deals where you don't control the timeline
  • Willingness to travel occasionally for conferences and on-site demos (multifamily is relationship-driven)
  • Bonus: familiarity with property management, real estate, or CRM/marketing automation categories