How to Speed Up Sales Deal Cycles

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?

An eye-opening observation about strategic SaaS deals: Transformation deals don’t have to take 18 months. Here's how to cut big deal sales cycles by 50%: 1/ Create a distinct point of view for your industry (Discovery) Most sellers fail to articulate a broad vision for the industry they work in and focus on what their company does. That will drastically limit your deal size. Instead, become a “performance curator” using your existing largest customers. Leverage their facts and stories to paint a clear picture of the big vision in their space and generate authentic curiosity. This will help with gathering meaningful data during Discovery and move you faster to the Insights stage. 2/ Actively collaborate with the prospect on how to change (Insights) Most sellers take way too long to get to the Insights stage, if it all. They think closing a deal is solely about teaching and persuading, rather than collaborating and co-designing something together. After gathering and receiving the prospect’s data, now will be the time when you bring together their change drivers and your subject matter experts (SMEs). I found the best way to do this is set up a design session, or what’s known as a “Lighthouse Workshop.” The goal of the session is to suspend limiting beliefs and get out of status-quo thinking. This is where both sides can open up on how to ideally tackle big problems and go after “moonshot” ideas.” 3/ Drive home why the prospect needs to change now (Accelerate) After too much time passes on working a large deal, most sellers get frustrated and deal-fatigued. This is when they get sloppy, succumb to the pressures of their management, and default to discounting to try to accelerate deal closure. That leads to an erosion of trust and quickly devaluing your solution. Instead, after completing a successful design session together where you architected the ideal way to operate, develop a narrative proposal and business case to secure (or create) budget. Make sure both executive sponsors (yours and theirs) sign off on it before it gets positioned inside their org. Both sides should have their hands on the proposal, ensuring it includes their specific terminology, initiatives, and realistic KPIs. This will help you accelerate closing the deal without compromising your reputation or cutting costs unnecessarily. If you're struggling to close large transformation deals within a calendar year, these are 3 great ways to enhance your approach. And remember this mantra at all times: "Less, but better." You already know quality is better than quantity at this level of sales... But are you truly living it? Those at the top are. 🐝

Why Your Salesforce Approval Process Is Killing Your Deals (And How We Fixed It) Your 6-step approval process isn't making deals safer, it's killing them while your competition closes in hours, not days. I recently analyzed a client's "robust" quote approval process: -7 approval steps -14-day average cycle time -40% of deals lost to competitors during approvals -Customer frustration at all-time high The shocking truth about multi-step approvals: 1. They create false security - More approvers doesn't mean better decisions—it means diluted accountability. Nobody takes ownership when everyone shares responsibility. 2. They extend your sales cycle - Aberdeen research shows contracting bottlenecks contribute up to 18% of the enterprise sales cycle. Just a one-day slowdown costs $80,000 in lost revenue. 3. They kill momentum - When sales reps chase multiple approvals, they spend precious selling time on admin tasks, leaving deals vulnerable to competition. 4. They make you lose to faster competitors - Research across 1,000 B2B companies found businesses with streamlined processes respond in just 2 hours and 14 minutes, compared to over 29 hours for companies with complex approval chains. The Fix We Implemented in Salesforce: 1. Automated pricing rules for standard scenarios (70% of deals) 2. Reduced approval steps from 7 to 2 for non-standard deals 3. Built guardrails using Flow Builder to enforce parameters 4. Added real-time visibility dashboards for leadership confidence The Results Were Immediate: -Quote approval time: 14 days to 4 hours -Win rate increased 35% -Zero pricing compliance issues -Sales team confidence restored -By optimizing approval routing, contract cycle time was reduced by over 50%, allowing reps to focus on what matters most, closing deals and finding new opportunities. Key Learning: Over-engineering approval processes doesn't reduce risk, it creates it. What about you? What's the most unnecessary approval step slowing down your sales cycle? #SalesforceConsulting #SalesProductivity #SalesProcess #SalesVelocity

“Speed doesn’t just impress buyers. It changes how they think.” I was supporting a deal with a government agency in India. After months of slow movement, one of our AEs decided to change pace. Instead of waiting days to reply to follow-up questions, she started responding within 30 minutes. Instead of booking calls a week out, she offered same-day options. Instead of letting the buyer’s process set the tempo, she respectfully started dictating rhythm. Something shifted. The buyer’s team — previously unhurried — began mirroring that pace. Questions came faster. Decisions followed more quickly. Procurement even escalated approvals internally to stay in sync. ✅ What happened? We triggered urgency. Not by pressuring the buyer — but by resetting their internal tempo. Speed changed the emotional texture of the deal from “eventual project” to “active initiative.” ✅ What we did systematically: – Rebuilt our MAP (mutual action plan) with tighter next steps and weekly internal follow-ups – Used short email recaps post-meeting to clarify alignment – Trained reps to end every call with a same-day or next-day scheduling option – Flagged every unanswered email internally within 12 hours for follow-up 🎯 Behavioral psychology at work: – Temporal Contagion: People mirror perceived urgency – Momentum Bias: Once in motion, inertia helps keep deals alive – Availability Heuristic: Fast responses feel more valuable, more reliable, and more urgent Speed isn’t just about “being helpful.” It influences how buyers prioritize you in their mental stack of decisions. And in complex B2B deals, staying top-of-mind is half the battle. 📌 If you want faster deals, act like it’s already urgent — and watch your buyer catch up. 📥 Follow me for more insights. Repost if this resonated.

Your sales cycle is quietly preventing you from scaling. I've worked with 3 companies and one little tweak gets results like this: 1. From 109 days to 74 days 2. From 35 days to 29 days 3. From 16 days to 7 days What's the tweak? You're gonna laugh... It's asking for next steps tomorrow, instead of next week. Most reps do something like this, "Hey Mark, sounds like you are interested. I'm happy to set up a call to go through pricing. How's next week sound? Tuesday work?" If it's Wednesday, that means you just added 7 days to your sales cycle bc of when you asked for the next meeting. All the companies above just changed to something like this, "Mark, can I share what helped my customers make a confident decision? We get your VP of Pricing on a call and go through an exec demo and walk through pricing. Does tomorrow work?" How many people agree to tomorrow? Not many. How many people suggest just a day or two after tomorrow? Almost all of them. So if it's Wed, and we get them to agree to a meeting on Friday by asking for one on Thursday, then we just cut 4 days off our sales cycle compared to booking on Tuesday by asking for next week. If you have 5-7 meetings per deal...that's deals winning about a month faster. It's not rocket science. It's not hard. Other benefits: - build more momentum bc of less time between convos - not as much rehashing and repeating things bc it's fresh on their minds - you test urgency in deals - you get used to an uncomfortable ask, which makes other ones easier - you can run more deals in the same period of time = more commissions But don't start this tomorrow....start this TODAY!

What’s the fastest way to compress your sales cycle when selling large deals to Enterprise accounts? Here's what you DON'T do: - meet with department heads - demo your product and get them excited - have them attempt to sell upstream Instead, try using my Yo-yo sales framework. Here’s what it looks like. Step #1: Connect with power first, understand the most important problem(s) they need to solve, why they want to change, and the costs of not changing.If it’s a problem you can help solve, get their sponsorship for your discovery process. Ghost write a note they can send to their team to begin discovery Step #2: Meet with their department heads, get the real deal on what their day to day challenges look like, and grab some quotes which capture their biggest pain points. Seek to understand, not sell. Dig deep - understand the people, processes, and steps involved in doing the painful things which you can help improve or automate. Step #3: Package everything you’ve uncovered into an Executive Summary and Business Case and deliver back to Exec Sponsor and their team. Demo only what’s relevant. Close. Power compresses deals. This insight was key to me becoming the number one AE at Salesforce. It's how I went from averaging $240K/year my first four years to averaging $720K my final four years (including two years cracking 7 figures). Want to learn my process for closing huge enterprise deals? Tune-in to my full conversation on the 30 Minutes to President's Club podcast. Listen here: https://lnkd.in/gCJ4x7HZ