Negotiation Strategies for Startups

Negotiation tactics we used to decrease our SaaS spend by 30% in the last year: It’s amazing to me how much room there is in SaaS pricing. The price is not the price is not the price. You can always negotiate, and there are often loopholes that can save you a ton of money. Here are some of them: - Cancel the renewal before the negotiation. We send cancellation notices to our biggest opportunity negotiations months in advance, and tell them that we will only renew upon having a new deal. Often, account reps can provide special discounts for “at risk” clients. - Get your usage data. We always dig through our data before a negotiation. If our usage is lower than expected, we use that as leverage. For example, our hiring has gone down by about 60% post-ZIRP, but we still paid the same annual price for our applicant tracking system. We showed them the data and made it clear the software wasn’t worth what we were paying. - Be nice. Honestly, sometimes I get frustrated because I know I’m getting the runaround. Every time I do, it backfires. When I’m on my A-game, I’m nice - I tell them I love their software, it is useful, but we just don’t have as much of a need right now. It’s not you, it’s me. I do tell the truth, though, so they know I’m genuine with my praise and critiques. - Compare their costs to other options. There are 3 different types of comparisons: 1) direct competitors. Just call them and get a quote. 2) indirect competitors. Oftentimes another company offers a “basic” version of the software you’re using, so you can use that as leverage: “we don’t need an applicant tracking system because we already pay for Notion”. 3) budget competitors. Compare the pricing of x subscription with y subscription. We regularly compare unrelated products and say: you are the 2nd highest cost product we use, even though you aren’t the 2nd most valuable to us. - Ask 3x. You almost always have to negotiate at least three times to get the best deal. It doesn’t work with every company, but most account reps have latitude and at some point you’re not worth their time. Take advantage and just make sure you press multiple times in a row instead of taking the first offer. I’m surprised at how often we get our way in these negotiations. Sometimes I step in as the founder, but now my team has watched this playbook and gets the same results on their own. You don’t need to be a founder or a business unit leader to do this: act like an owner and make sure your company isn’t wasting money!

To Salespeople Who Are Negotiating Q4 Deals: Here's 3 steps for the ultimate "win-win" (and stop deals from falling apart) ⬇️ BACKGROUND: 90% of salespeople play negotiation “whack a mole.” Your buyer asks for a concession. You give it, assuming it will close the deal. But all you did was “feed the dragon.” “That was easy,” your buyer thinks. They're now emboldened to ask for more. Here’s what the top 10% highest paid sellers do instead: 1. Uncover ALL “Asks” Before To One. Your buyer just asked for a discount? Great. Now put your head in a straight jacket. Don’t nod and say yes. Don’t shake your head and say no. Instead ask this: “Let’s say that issue was resolved and we found a win-win. What additional ‘asks’ would you or your team have before we move forward?” If they say "nothing," proceed. But chances are, there are other issues: - billing terms - free services - payment timelines Your job is to see the forest for the trees. Understand EVERYTHING they’re asking for. Not just one individual ask. Otherwise, you'll win the battle but lose the war. 2. Uncover the Underlying Need. Got all the “asks” out on the table? Perfect. Now figure out WHY they’re asking for them. What underlying need are they trying to meet? There might be a better way of addressing it. There was once two men “negotiating” over an orange. As one of them was about to cut it in half so they could share it, one guy asked: “Wait, why do you want the orange?” Turns out, one guy wanted to eat it. The other guy wanted the peel for his beer brewing. Both got 100% of what they wanted instead of only 50%. All because one guy asked the question. Do the same with your buyers. 3. Uncover the SERIES of Next Steps. Ok. You’ve got the “asks” on the table. You understand the WHY. One last step before it’s time to negotiate: Uncover the series of steps between agreeing on the issues, and signature. After summarizing their asks, say this: “Let’s say we found a way to agree on all of the above. What series of steps would you and anyone else on your team still need to take before we move forward together?” If their answer is “nothing,” proceed. But. Half the time… They answer with something like: “Well, we still need to get our CXO bought in on the business case.” That tells me one thing: You still have SELLING to do! Not NEGOTIATING! In that situation, you can negotiate until you’re blue in the face. But it still won’t close the deal. Rule of thumb: A successful negotiation should close the deal. If it doesn’t? If there are other steps to still take AFTERWARD? You’re negotiating too early. Get the selling steps out of the way first. Then come back to the “negotiation table.” Otherwise? You're signing up for TWO negotiation cycles. Ok. That’s all for today, Did you learn something? If so, let me know in the comments with a “yes!” And if you have a question? Let me know that too.

I recently closed a six-figure deal with an enterprise client. While most deals this size take 6-8 months, I closed this one in under 60 days. Here's exactly how I did it: When selling to an enterprise company, it's easy to get trapped in long deal cycles. To avoid this from always happening, here are the 4 steps I take to expedite my enterprise closing process: 1. Subject Matter Expertise Plays    Most sellers pitch products. We pitch proven expertise in their space. This shifted the entire conversation from "vendor" to "expert." • Pitched as an industry expert, not influencer • Showed proven processes from our team  • Focused on vertical expertise vs following Expertise beats influence every time. 2. Multi-Threading     Instead of focusing on one champion, I built relationships across the organization. Each stakeholder had different things that made this a win for them. • Built relationships with seven key stakeholders • Sent a recap email to each buying department so everyone knew what was going on • Had notes for each department's goals and why they wanted to win Throughout the deal, I always asked who would feel left out if they weren't involved. Every time I found a new person, I made it a point to meet them. That means more allies for the deal to sell internally. 3. Weekly Momentum Building    Most deals need more momentum. That's why I keep the energy high. • Sent weekly videos to keep my POC informed • Highlighted each stakeholder's priorities • Highlighted work we were doing along the way Momentum beats perfection. 4. Procurement Fast Track This is where deals typically go to die. Not today my friends. This is where the party starts. As soon as I get introduced to procurement, I ask for a quick 15-minute call so I can quickly text edits as my lawyer goes back and forth. • Asked for concerns up front • Built solutions into proposal • Asked what do you people typically redline when they approach you Being proactive beats being reactive every time. Because doing the little things well will always yield great results. P.S. Have a favorite step?

Stop dreading tough talks. Master them with these 21 phrases instead: I once snapped when a colleague questioned my timeline. My defensive reaction created a week of tension. That day I realized emotional responses solve nothing. They only create new problems. We've all been there: Feeling defensive Reacting without thinking Watching a simple disagreement turn into a lasting conflict But I've learned the shift from reactive to constructive changes everything ✨ 21 ways smart people handle difficult conversations: 1) Lead with Curiosity ↳ "Tell me more about your perspective on this" ↳ Questions defuse tension faster than statements 2) Name the Energy ↳ "I notice there's tension here, let's address it" ↳ Acknowledgment creates safety 3) Find Common Ground ↳ "We both want what's best for the project" ↳ Alignment before action 4) Set Clear Expectations ↳ "Here's what I need, what do you need?" ↳ Clarity prevents future conflict 5) Pause the Escalation ↳ "Let's take a step back and break this down" ↳ Breathing room creates solutions 6) Mirror Their Language ↳ Use their exact key words when responding ↳ Matching builds instant connection 7) Acknowledge Impact ↳ "I see how this affects your priorities" ↳ Understanding beats defense 8) Own Your Part ↳ "Here's where I could have done better" ↳ Accountability creates trust 9) Focus Forward ↳ "How can we prevent this next time?" ↳ Solutions beat blame 10) Check Understanding ↳ "Here's what I'm hearing - am I getting it right?" ↳ Clarity prevents escalation 11) Create Space ↳ "Let's revisit this when we're both fresh" ↳ Time transforms tension 12) Stay on Topic ↳ "Let's focus on solving this specific issue" ↳ Boundaries keep talks productive 13) Express Confidence ↳ "I know we can figure this out together" ↳ Belief shifts energy 14) Share Context ↳ "Here's what led to my decision" ↳ Understanding reduces resistance 15) Invite Solutions ↳ "What ideas do you have for this?" ↳ Collaboration beats control 16) Set Timelines ↳ "When should we check in on this?" ↳ Structure creates safety 17) Validate Concerns ↳ "That's a legitimate worry - let's address it" ↳ Recognition reduces defense 18) Stay Factual ↳ "Here's what the data shows us" ↳ Evidence beats emotion 19) Close with Action ↳ "Let's clarify next steps together" ↳ Progress prevents repeat issues 20) Follow Through ↳ "As we discussed, here's what I've done" ↳ Action builds credibility 21) Document Growth ↳ "Here's how we'll work differently now" ↳ Learning beats repeating Difficult conversations aren't obstacles to success. They're the moments where true connection happens ✨ Which strategy will you try in your next challenging conversation? -- ♻️ Repost to help your network transform difficult conversations into opportunities 🔔 Follow Dr. Carolyn Frost for more practical tools to succeed with confidence

My #1 tip in negotiation is to make the other person feel like they've won by giving the illusion of choice. I really can't believe how powerful this has been for me personally, professionally & for my sales team. BACKGROUND: I've noticed something over & over again in any negotiation - people feel good when they have control. No one likes to feel out of control or that their fate is not in their own hands. So when I go toe-to-toe with a colleague, a prospect or my mother I think about how I can make them feel like they're in control by letting them choose the outcome. Only the outcomes they're choosing between, are options I presented to them because I'm cool with any of the outcomes. EXAMPLE 1: Here's an example. Let's say I quote the prospect a $20k deal and they push back for $15k. I know I won't go below $17.5k so I say: --- Hey - I've taken this back to my team since I know a more affordable service is important for you given your budget. You're really crushing me on the negotiation so I know I need to meet you halfway. I'm excited to share a few different options we came up with and I need your help deciding which is the best one for you so you can feel really good about this deal: (1) $20k deal with the 13th month free (2) $18k deal where you do a case study with us (3) $17.5k deal but it's a two-year commitment --- Prospect now has the illusion of choice. And always expect a good negotiator to collapse your choices by asking for the cheapest one with no strings attached. I know they're going to counter with $17.5k, one-year deal which I expect and am ok with. EXAMPLE 2: Second example, attached, is me negotiating yesterday with a LinkedIn Social Selling coach I just signed with (I've never tried one but think I could use one). My highest willingness to pay was $10k cash for 3 months. Just like in the first example I gave 3 options for the illusion of choice. They countered, collapsing my options to $10k + the references. Smart move and a tad beyond what I wanted but I signed and we both walk away feeling good. I'm amusing myself writing this because this new coach will both hate & love this post ;) #negotiation #saas #tips

Negotiations don’t go wrong—they start wrong. Through my experience, I can often tell within the first 30 minutes whether a negotiation will take a collaborative or positional direction. The early signals—the tone, structure, and mindset of the parties—set the course for either value creation or value extraction. Too often, negotiations begin with adversarial positioning, where each side stakes out demands, focuses on "winning," and sees concessions as the primary path to agreement. This zero-sum mentality is where most negotiations start wrong. The problem isn’t what happens later—it’s how we approach the process from the outset. Do you negotiate how to negotiate before you start negotiating? This is a game-changer. Before discussing numbers or terms, set the stage for success. Consider opening with: "I am here today to help you reduce your risk, cost, and liabilities while improving your profits. Would you be interested in having me assist you with this?" This shifts the conversation from position-based bargaining to problem-solving and mutual value creation. SMARTnership® negotiation flips the traditional approach. Instead of defaulting to competitive bargaining, it starts by identifying asymmetric values, trust currency, and hidden gains that can turn the negotiation into a collaborative value-maximizing process. The real difference lies in: ✔ Mindset: Are we here to protect our own turf or explore mutual benefit?  ✔ Communication: Is the focus on claiming or creating value?  ✔ Trust: Is there openness to share real needs, costs, and priorities? If the first 30 minutes are spent staking positions, debating individual gains, or withholding critical information, the negotiation is already off track. But if we establish transparency, mutual benefit, and creative problem-solving early on, we unlock the hidden potential of the deal. Next time you step into a negotiation, ask yourself: Are we starting right? #Negotiation #SMARTnership #ValueCreation #TrustCurrency Tarek Amine Tine Anneberg Francis Goh, FSIArb, FCIArb Francisco Cosme Gražvydas Jukna Juan Manuel García P. Darryl Legault World Commerce & Contracting BMI Executive Institute #negotiationtraining Daniel McLuskie

The biggest founder lesson I’ve learned through fundraising and hiring: you can tell a lot about someone by how they negotiate. Whether it’s a VC, a hire, or an advisor—those early conversations reveal how they show up when it matters. There’s a fine line between advocating for yourself and staying grounded. Between pushing for what you need and keeping the bigger picture in mind—the company, the mission, the team. I’ve made plenty of mistakes: countering too aggressively, starting with offers that felt off (to both parties). But over time, I’ve realized negotiation isn’t a transaction; it’s the start of a relationship. At Yoodli, we look for people who are transparent, prepared, and assume we’ll figure it out together. We try to do the same. It’s not about you winning - it’s about alignment. Both parties should feel like they've "won" I actually love when someone asks why behind an offer. It shows thoughtfulness and trust. And we owe it to them to explain our thinking with clarity. Negotiation isn’t a battle, it’s day zero. And it sets the tone for everything that follows.

Deal or No Deal? Have you ever found yourself in a negotiation where the person you were negotiating with was the "good cop" and the "bad cop" was never directly involved in the conversations? I find this convenient trick to be one that many leaders use to avoid direct conflict in having the tough conversations around deal terms. It's so much easier to blame the CEO or the Board or the Owner who aren't ever in the room. But here’s the thing—if the decision-maker is never actually present, are you even negotiating with the right person? I’ve seen this tactic used time and time again to delay, deflect, or pressure the other party into accepting less favorable terms. It creates an artificial power dynamic where the “good cop” seems reasonable while the unseen “bad cop” remains an immovable force in the background. So how do you handle it? 1.  𝗖𝗮𝗹𝗹 𝗶𝘁 𝗼𝘂𝘁. Politely ask, “What would it take to get the real decision-maker in the room?” If they keep dodging, you know where you stand. 2.  𝗦𝗲𝘁 𝗯𝗼𝘂𝗻𝗱𝗮𝗿𝗶𝗲𝘀. If you’re negotiating with someone who doesn’t have full authority, clarify that your final concessions won’t be made until you’re speaking with the right person. 3.  𝗟𝗲𝘃𝗲𝗿𝗮𝗴𝗲 𝘁𝗵𝗲 𝗱𝗲𝗹𝗮𝘆. If they’re playing the “bad cop is unavailable” game, take your time too. Don’t let them rush you into bad terms while they hide behind hierarchy. At the end of the day, real deals get done when both sides come to the table prepared to make real decisions. If you find yourself negotiating with someone who always needs to “check with someone else,” you might not have a real deal on the table—just a runaround. Deal or no deal? You decide. #scalingwellness

𝐓𝐫𝐮𝐬𝐭 𝐢𝐬𝐧’𝐭 𝐛𝐮𝐢𝐥𝐭 𝐢𝐧 𝐜𝐨𝐧𝐭𝐫𝐚𝐜𝐭𝐬. 𝐈𝐭’𝐬 𝐛𝐮𝐢𝐥𝐭 𝐢𝐧 𝐫𝐞𝐥𝐚𝐭𝐢𝐨𝐧𝐬𝐡𝐢𝐩𝐬 𝐚𝐧𝐝 𝐜𝐫𝐞𝐚𝐭𝐢𝐧𝐠 𝐬𝐚𝐟𝐞𝐭𝐲. We once had to shut down four city blocks in downtown Phoenix for a private Macklemore concert. On the surface, it sounds like logistics. In reality, it was about trust. It took a month meeting with city departments, knocking on doors, and listening to city employees who mostly wanted to help the public, get a paycheck and benefits, plus not lose their job. Each had their own concerns: safety, traffic, liability or what would their boss do to them. Instead of pushing my agenda, I focused on their pain points and showed that I understood what mattered to them.  After the month of planning, we started at 2:15 the morning of the concert, to set up - they would not let us close the roads, then I convinced them it was okay, after the bars closed. That’s how you move big, complicated projects forward. Not with pressure. Not with shortcuts, instead - by giving people confidence that you see them, hear them, and will protect their interests (if nothing else, that they won’t get fired, their kids will be okay and life will be good). The principle is simple. 𝐈𝐟 𝐩𝐞𝐨𝐩𝐥𝐞 𝐟𝐞𝐞𝐥 𝐬𝐚𝐟𝐞 𝐚𝐧𝐝 𝐫𝐞𝐬𝐩𝐞𝐜𝐭𝐞𝐝, 𝐭𝐡𝐞𝐲’𝐥𝐥 𝐨𝐩𝐞𝐧 𝐝𝐨𝐨𝐫𝐬. 𝐈𝐟 𝐭𝐡𝐞𝐲 𝐟𝐞𝐞𝐥 𝐢𝐠𝐧𝐨𝐫𝐞𝐝 𝐨𝐫 𝐮𝐧𝐬𝐚𝐟𝐞, 𝐭𝐡𝐞𝐲’𝐥𝐥 𝐜𝐥𝐨𝐬𝐞 𝐭𝐡𝐞𝐦. Whether you’re closing a deal, running a campaign, or trying to get four blocks of a city to shut down, the foundation is the same: trust built through listening. What’s one way you’ve built trust in a tough negotiation? #Trust #Negotiation #DealMaking #TILTTheRoom #MediaLaw #Macklemore Christopher Voss Kwame Christian, Esq., M.A. Alexandra Carter Dr. Robert Cialdini Scott Tillema

Negotiation best practices that would’ve saved me a ton of commission as a new AE: 1. Expect them to ask for a discount. Every savvy buyer is going to tell you that you're too expensive.  Knowing that it's coming can help you from getting shook. -- 2. NO unilateral concessions. Giving something (discount, something custom, free seats) without getting something in return (timeline to sign, longer term, reference) is the number 1 way to lose all your leverage. -- 3. It’s okay to tell your prospect what you want. One of the biggest lessons I learned from The Transparency Sale. Tell your buyer that they CAN get a discount if they give you something in return (longer term, sign by X date, etc) -- 4. Never send pricing over email. Always try to walk 'em through it live. If you really can’t, record a video reviewing the proposal so you can include your context & voice with the price. -- 5. Don’t let what YOU make affect your pricing confidence. Just because YOU make $75K/year doesn’t mean quoting $150K should throw you in a tizzy.  B2B pricing is just on a different scale than your personal budget. -- 6. Say the price, then stop talking. I used to literally bring a cup of water with me onto sales calls to take a sip of after I said the price as a way to force myself to stop talking. -- 7. Always get the full ask before going to your VP. Make them put ALL their requests on the table. It's a quicker, cleaner way to end the negotiation. Things get really messy if you only handle asks one at a time. --- What else would you add here?