Founder Mode is a weekly newsletter for builders—whether it’s startups, systems, or personal
growth. It’s about finding your flow, balancing health, wealth, and productivity, and tackling
challenges with focus and curiosity. Each week, you’ll gain actionable insights and fresh
perspectives to help you think like a founder and build what matters most.
Negotiating vendor contracts goes beyond cutting costs. It's about flexibility, leverage, and protecting your company's interests. Many teams lack structure in dealing with vendors. This leads to mistakes in selecting, evaluating, negotiating, and implementing them. You can turn these talks into a competitive advantage with the right approach.
Key Areas in Vendor Negotiations
1. Common Process & Pitfalls Most companies have an unstructured process. They identify a need, assign a lead, and evaluate vendors without rigor. Common mistakes include:
Rushing to buy without understanding real needs. Many times, vendors will sell features or functionality you don't need. Vendors may try to control the pace of the deal or order flow.
Focusing on features over fit (like scalability and hidden costs). You must know how the solution scales in cost as usage and users grow.
Accepting vendor terms without negotiating or picking apart contracts. Everything is negotiable.
Ignoring performance tracking after implementation. You must continue to hold vendors to a high standard even after the deal closes. Keep an issue list, as this will come in helpful during renewals.
How to Fix These Issues:
Define "must-haves" vs. "nice-to-haves" from the start. Always ask for some added functionality or higher-tier pricing. i.e., Ask for quotes for 100, 1000, and 5000 users, even if you only have 200. This will show you the available discounts. Then, push for the 1000 or 5000 pricing at the 200-user tier.
Ask for data about scalability, performance, SLAs, and total cost. This is key to learning where you can try to push back or reduce costs later.
Track ROI and renegotiate based on results. Create and track data on the vendor's value. Use it to resist price hikes or ask for renewal discounts.
Assume you can always walk away. In the past, I've let deals lapse or expire to put extra pressure on the vendor to "win back" the deal. Rarely, a SaaS vendor will disable or turn off the software.
2. Key Contract Clauses Negotiation is where you can gain or lose value. Important areas to cover:
Contract Term: Push for a shorter term. Avoid auto-renewals or negotiate 30-90 day exit clauses. Only add back longer terms at the end and only if there are significant discounts.
Rate Caps & Discounts: Cap rate increases, secure growth incentives, and volume discounts.
Performance Penalties: Include penalties for delays or unmet SLAs. When a vendor is unwilling to include fee refunds when they miss their SLAs this could be a red flag.
Logo/Marketing Use: Remove clauses allowing the vendor to use your logo or data. Again, only add back at the end if it comes with a significant price decrease.
Exit Strategy: Ensure you can export your data if you leave and have easy well defined ways to end the contract. Ideally, remove any auto-renewal language.
3. Building Leverage Creating leverage means introducing competition and staying in control:
Pilot Programs: Negotiate extended trials to test the tool before committing.
Competitive Quotes: Always compare quotes, especially from aggressive new startups.
Bundle Deals: When possible, combine services from the same vendor for volume discounts. Many large companies have multiple contracts with the same vendor. Combining them can save a lot of money.
Talk to the boss: Negotiate with senior sales reps or decision-makers. If the head of sales or CEO isn't deciding your deal, you haven't reached the highest possible discount. To get to this level, you typically have to say "no" a lot to the sales rep or let the deal drag on or appear lost to the vendor.
Be slow to reply: Make it a habit to never take live meetings, phone calls or texts from the sales rep. Force all communication to be over email and then be slow reply. This frustates sales reps as they prefer to talk live to "get a feel" for the deal and eek out more understanding of where they stand. When you do reply always try to include an ask so they have homework to do on your behalf.
My SaaS Negotiation Playbook
Here’s the approach I use —and you can adapt it, too:
Adopt the "Software Costs $0" Mindset: Vendors depend on recurring revenue. So, they'll often bend to keep your business. Always assume the first price is inflated. These days, the 'hard' costs to run most software are basically zero. AI software is an exception to this but you can assume the lowest token rates or offer to use your own AI API key. This removes the cost but gives you more direct control over AI usage.
Ask for More: Always ask for additional discounts, upgrades, or extended trials. Even if they say no, you’ve lost nothing.
Create Competition: Let vendors know you’re considering alternatives. Ask, “What can you offer that [Competitor] can’t?”. ALWAYS get at least one other quote or bid for any vendor project.
Anchor Low: Start negotiations with a bold but reasonable offer. Ask for a discount or state the price that will close the deal. This gives the sales team the ability to say "Yes."
Find Your Leverage: If you're a fast-growing startup or a "logo" customer, you can be valuable to the vendor. This can increase your partnership's value. If you can sign the deal quickly, the end of the month or quarter is a good time to ask for an extra discount.
Toolbox Demo
Here's a quick Loom I recorded showing one way in which I do quick comparative vendor searches. I also include the steps I take using ChatGPT to dive deep into contracts.
Next time you negotiate, think of it as designing a system. Every clause you challenge, quote you compare, and question you ask builds leverage. Contracts are more than agreements. They're a chance to create flexibility, protect growth, and keep costs predictable. Was this helpful? Hit reply and let me know other tips you've used or if you have suggestions for additonal topics like this.
Kevin Henrikson leads engineering for Microsoft Outlook iOS/Android. Previously, he co-founded Acompli and ran engineering prior to an acquisition by Microsoft in 2014 for $200M. Before Acompli, he was an
Entrepreneur-in-Residence for Redpoint Ventures, a venture capital firm for early stage technology companies.
Founder Mode is a weekly newsletter for builders—whether it’s startups, systems, or personal
growth. It’s about finding your flow, balancing health, wealth, and productivity, and tackling
challenges with focus and curiosity. Each week, you’ll gain actionable insights and fresh
perspectives to help you think like a founder and build what matters most.