Pro Serv Podcast by Collective 54 Episode 231 - Moving Up-Market: How to Win and Keep Enterprise Clients
Aug 22, 2025
Explore how boutique firms can transition from small to enterprise clients, with insights from industry veterans. Discover strategic approaches for engaging Fortune 500 companies, including building trust and nurturing multi-threaded relationships. Learn how smaller firms can stand out by being impeccable and addressing executive needs effectively. Dive into strategies for entering the competitive Fortune 100 market, focusing on client confidence and risk mitigation. Plus, hear personal stories on the importance of relationships for career growth.
AI Snips
Chapters
Transcript
Sell To A System, Not A Single Buyer
- Selling to enterprise means navigating a system of stakeholders, not just pitching a solution.
- Map incentives and risks across the buyer ecosystem before you assume a single yes equals a win.
Plan For Long Sales Cycles
- Prepare for a much longer sales cycle and delays from legal and procurement.
- Consider starting work before MSA execution when the risk is calculated to get your foot in the door.
Make Procurement A Priority
- Treat procurement as a gatekeeper and be ready with onboarding, compliance, and security docs.
- Show flexibility and avoid heavy redlines to demonstrate you're easy to work with.