Overview
You're selling loan management software to private lenders, land sellers, and note investors who are currently tracking loans in spreadsheets or outdated systems. You'll do everything from cold outreach to demo to close at a 9-person company, which means you're both the sales team and the person figuring out what works.
Role Snapshot
| Aspect | Details |
|---|---|
| Role Type | Full-cycle AE (self-sourcing + closing) |
| Sales Motion | Outbound-heavy with some inbound trial conversions |
| Deal Complexity | Transactional to light consultative |
| Sales Cycle | 2-6 weeks |
| Deal Size | $500-3K/year (based on typical loan management SaaS pricing) |
| Quota (est.) | $15-25K MRR/quarter |
Company Context
Stage: Pre-seed / Bootstrap (no funding data found)
Size: 9 employees
Growth: Actively hiring for first sales role, signals early GTM build-out
Market Position: Niche player in private lending software - competing against spreadsheets and generic loan servicing tools
GTM Reality
Pipeline Sources:
- 70% Outbound - You're finding private lenders through LinkedIn, industry forums, land investor groups, and cold calling
- 20% Inbound - Free trial signups from website (30-day trial on all plans means some hand-raisers)
- 10% Word-of-mouth/Referrals from early customers
SDR/AE Structure: No SDR support. You're doing your own prospecting, qualification, demo, and close.
SE Support: No dedicated SE. You're doing your own demos (product is relatively straightforward - loan tracking and payment collection).
Competitive Landscape
Main Competitors: Generic loan servicing platforms, LoanPro, Nortridge, custom-built internal systems, Excel spreadsheets (the real competitor)
How They Differentiate: Purpose-built for private lenders specifically (not banks), integrated payments, borrower portal, configurable to different loan types
Common Objections: "I already have a system that works" (spreadsheet), price sensitivity from smaller lenders, reluctance to change existing workflows, questions about security/compliance
Win Themes: Automation over manual tracking, professional borrower experience, time savings on payment collection and reporting
What You'll Actually Do
Time Breakdown
Prospecting (40%) | Active Deals (30%) | Product Demos (20%) | Internal (10%)
Key Activities
- Cold Outreach: Finding private lenders on LinkedIn, in real estate investor forums, and at land investing groups. Sending personalized emails and LinkedIn messages. Most won't respond. You're trying to book 8-12 discovery calls per week.
- Product Demos: Walking prospects through the platform - showing loan setup, payment tracking, borrower portal, and reporting. Demos are 30-45 minutes. You'll do the same demo multiple times per day.
- Trial Follow-up: Chasing free trial users who signed up but aren't active. Most trial users don't convert without nudging. You're calling and emailing to get them to actually use the platform.
- Closing: Negotiating pricing (which is mostly fixed but you have some discretion), handling procurement (usually simple with small businesses), getting contracts signed. Deals are small enough that you can close multiple per week when pipeline is healthy.
The Honest Reality
What's Hard
- You're educating a market that doesn't know they need this yet. Many private lenders are fine with Excel and don't see the problem until you show them.
- Small company means limited brand recognition. You're selling against "who are you?" skepticism constantly.
- You'll build your own lists, write your own sequences, and figure out messaging through trial and error. No proven playbook exists yet.
- Deals are small, so you need volume. Missing a week of activity directly impacts your month.
- You're probably the only sales person, which means no one to strategize with or learn from day-to-day.
What Success Looks Like
- Booking 8-12 qualified discovery calls per week from cold outreach
- Converting 30-40% of trials to paid customers
- Closing 6-10 new customers per month at $100-250 MRR each
- Building a referral engine - getting happy customers to introduce you to other lenders in their network
Who You're Selling To
Primary Buyers:
- Private lenders (individuals or small firms managing 10-100+ loans)
- Land sellers offering seller financing
- Note investors who buy and service debt
What They Care About:
- Time savings vs manual tracking in spreadsheets
- Professional borrower experience (portal for payments and statements)
- Accurate reporting for taxes and cash flow management
- Security and reliability of payment processing
- Price - these are often solo operators or small shops watching costs closely
Requirements
- 1-3 years in B2B sales (preferably SaaS or fintech)
- Comfortable with full-cycle sales - prospecting through close
- Self-directed - you'll be building territory and process from scratch
- Coachable and scrappy - things will change as the company figures out product-market fit
- Willing to work at a 9-person company (no corporate structure, limited resources, everyone does everything)
- Understanding of lending/finance concepts helpful but not required