Flexible Leasing for Hospitality Operators

Overview

Guesst Software is a real estate and fintech platform that automates percentage rent calculations, track lease breakpoints and provide real-time visibility for both operators and property owners.

I led go-to-market strategy and positioning for Guesst within the hospitality ecosystem, focusing on translating complex lease structures into real-time operational clarity for restaurant operators.

The Problem

Percentage rent agreements create ongoing friction for operators:

Manual and delayed sales reporting
No real-time visibility into lease breakpoints
Administrative burden across multiple locations
Fragmented communication between tenants and landlords

A hurdle to vSMB's acquiring brick & mortar presence and growing location is expensive leases.

Insight

The challenge to flexible leasing is operational visibility into real-time sales and contractual obligations.

Operators need continuous clarity on financial exposure.

GTM Approach

1. POS Integration Narrative

Framed integration with Toast POS as foundational:

“Sales data already exists in your POS. Guesst turns it into lease flexibility.”

2. Core Value Messaging

Simplified GTM around three outcomes:

Automated percentage rent calculations based on real sales data
Elimination of manual reporting to property owners
Daily visibility into lease breakpoints and financial standing

Outcome

The GTM strategy positioned Guesst as a flexible financial layer linking POS system to real estate security.

It clarified adoption for operators, reduced perceived complexity and strengthened the narrative for multi-location hospitality groups managing varied lease structures.