Multi-Year Deal Structuring

Define multi-year deal parameters in a spreadsheet: discount structure (e.g., 1-year full price, 2-year 10% discount, 3-year 20% discount), payment terms (annual prepay vs quarterly), expansion clauses (pricing for additional seats/usage), renewal terms.

Identify 3-5 opportunities in proposal stage where multi-year deals make sense (strong fit, large company, strategic importance, high expansion potential); prepare multi-year proposals.

Set pass threshold: propose multi-year terms to >=3 prospects and close >=1 multi-year deal (2+ years) within 2 weeks.

Position multi-year benefits to prospects: "Locking in pricing now protects you from future increases" (hedge against inflation), "Multi-year commitment unlocks priority support and early access to features" (added value), "Predictable annual spend simplifies budgeting" (CFO benefit).

Create pricing scenarios for prospects: Option A (1-year at $100K), Option B (2-year at $180K total = 10% savings), Option C (3-year at $240K total = 20% savings); show total savings and annual cost clearly.

Address objections: "What if our needs change?" → Include expansion clauses allowing seat/usage increases mid-contract. "What if we want to cancel?" → Offer annual payment terms (less risk than full prepay) or exit clauses after year 1.

Log multi-year proposals in Attio with fields for contract_length, total_contract_value, annual_discount, payment_terms, and outcome; track which terms close most often.

In PostHog, create events for multiyear_proposed and multiyear_closed with properties for deal length, discount, and TCV.

After 2 weeks, analyze: did >=1 multi-year deal close? What objections arose? What terms were most attractive? If multi-year deals close and TCV is >=1.8x annual deal, multi-year motion is working.

If threshold met, document multi-year positioning and pricing structure, then proceed to Baseline; otherwise refine discount levels, payment terms, or value positioning.