Overview
You're managing a team of 4-8 AEs selling AI automation to multifamily property management companies. You're coaching deals, hiring to support 2x growth, and ensuring your team hits their numbers while the company scales from category leader to dominant player. You're also likely carrying a small individual quota or working strategic accounts while building the team.
Role Snapshot
| Aspect | Details |
|---|---|
| Role Type | Player-coach Sales Manager (managing team + likely some individual contribution) |
| Sales Motion | Managing both inbound and outbound motions |
| Deal Complexity | Overseeing consultative to enterprise deals |
| Sales Cycle | 3-6 months (you're coaching through these cycles) |
| Deal Size | Your team closes $50K-250K ACV deals |
| Quota (est.) | $4-6M team quota annually, plus possible $500K-1M personal quota |
Company Context
Stage: Series C-D+ (523 employees, growing 2x YoY, recognized category leader)
Size: 523 employees
Growth: Aggressive hiring across all teams - you're building your team in a scaling environment
Market Position: Category leader competing against legacy platforms adding AI features
Leadership: Jeff Cooper just joined as Senior Sales Manager, suggesting rapid sales org expansion
GTM Reality
Your Team's Coverage:
- Managing mix of enterprise and mid-market AEs
- Coordinating with SDR team for pipeline generation
- Working with SEs on complex technical deals
- Partner with marketing on campaign strategy and lead quality
What You Own:
- Team quota attainment and forecast accuracy
- Hiring and ramping new AEs during growth phase
- Deal strategy and win rate improvement
- Competitive win/loss analysis
- Sales process and methodology evolution
Competitive Landscape
What Your Team Faces:
- Legacy property management software (Yardi, RealPage, Entrata) bundling AI features
- Commoditization pressure as "AI for property management" becomes crowded
- Long sales cycles with property management budget constraints
- Proving ROI against "just hire more people" mentality
Your Job: Coach reps through competitive situations, refine positioning, and improve win rates by sharing what's working across the team
What You'll Actually Do
Time Breakdown
Team Coaching (35%) | Hiring/Recruiting (25%) | Forecasting/Admin (20%) | Strategic Deals (20%)
Key Activities
- Deal reviews and coaching: You're in weekly 1:1s reviewing pipeline, helping reps navigate multi-stakeholder deals, strategizing how to get past stalled opportunities. You're teaching them how to sell operational transformation, not just software.
- Hiring to scale: You're interviewing AE candidates constantly, trying to find reps who can sell to operations leaders and handle 3-6 month cycles. You're building a team that can support doubling revenue again.
- Forecasting and pipeline management: You're in weekly forecast calls with leadership, defending your commit numbers, explaining why deals slipped, and pressure-testing your team's opportunities. You own the accuracy of your forecast.
- Strategic account involvement: You're jumping into larger deals ($250K+ or key accounts) to help close, doing executive alignment meetings, or navigating political situations your reps can't handle alone.
- Sales process improvement: You're analyzing what's working, where deals stall, and implementing changes to improve win rates and cycle time. You're making the playbook as the company scales.
The Honest Reality
What's Hard
- You're hiring aggressively during hypergrowth, which means some hires won't work out. Managing out underperformers while maintaining team morale is part of the job.
- Forecast pressure is real - you're on the hook for your team's number and leadership expects accuracy during rapid scaling. Deals slip and you have to explain why.
- Balancing coaching time with your own quota (if you have one) is a constant tension. Your team needs you but you also have deals to close.
- Property management sales cycles are unpredictable despite your best qualification. You'll have quarters where multiple deals slip and you miss the team number.
- You're building process and methodology while the company is growing - it's not clean and documented yet. You're figuring it out as you go.
- New manager dynamics: Jeff Cooper just joined at Senior level, so you're navigating a new leadership layer and potentially new expectations/processes.
What Success Looks Like
- Team hits 90-100%+ of quota consistently
- Hiring 2-3 productive AEs per quarter who ramp quickly
- Forecast accuracy within 10% of commit
- Win rate improvement quarter-over-quarter as team learns the market
- Retention of top performers despite competitive recruiting pressure
- Promotion to Senior Manager or Director as the org continues scaling
Who Your Team Sells To
Primary Buyers:
- Regional Property Managers (operational leaders)
- VPs of Operations (budget holders)
- CTOs/IT Directors (technical gatekeepers)
- C-suite at larger property management groups
Your Job: Train your team to navigate these stakeholders effectively, build business cases that resonate, and avoid getting stuck in single-threaded deals
Requirements
- 5-7 years B2B SaaS sales experience with 2-3 years as top-performing AE
- 1-2 years prior sales management/team lead experience (or ready for first management role if exceptionally strong IC)
- Track record closing consultative deals in $50K-250K range
- Experience coaching and developing sellers, not just managing them
- Comfortable with rapid hiring and scaling (this isn't a stable, optimized team - you're building it)
- Analytical approach to pipeline management and forecasting
- Property management or real estate software experience helpful but not required
- Willingness to carry individual quota while managing team