I watched a VP of Sales nearly destroy a $50M ARR business because he refused to believe that selling to SMBs required a fundamentally different playbook than selling to enterprises.
He'd come from Oracle. Twenty years of enterprise deals, six-figure ACVs, year-long sales cycles. When he joined our mid-market SaaS company, he brought his enterprise playbook with him. Multi-threading into economic buyers. Extensive discovery. Custom ROI models. Executive briefings. The full enterprise toolkit.
It worked beautifully for our handful of enterprise deals. And it killed our SMB motion completely.
Our SMB reps couldn't get prospects to sit through 60-minute discovery calls. Small business owners didn't want to "multi-thread" into their two-person finance team. They definitely weren't interested in custom ROI models for a $3K annual product. Our conversion rates dropped 40% in three months.
The VP kept insisting the reps just needed better training. "These are fundamental sales skills," he'd say. "They work for any buyer." He was right about the fundamentals. And completely wrong about the execution.
Here's what I learned after running GTM across all three segments: the buying behaviors are so different across SMB, mid-market, and enterprise that using the same playbook is like using a speedboat manual to fly a plane. The basics might overlap, but the execution will get you killed.
Why Segment Strategy Actually Matters
Most GTM leaders know segments are different. They'll tell you SMBs move fast, enterprises move slow, mid-market is somewhere in between. Then they build one sales process and hope it flexes.
It doesn't flex. It breaks.
The failure mode isn't obvious at first. Your enterprise reps close deals using abbreviated versions of their playbook, and you think it's working. Your SMB reps stretch out sales cycles trying to execute multi-threading, and you blame them for being inefficient instead of recognizing the playbook is fundamentally misaligned.
I've seen this play out dozens of times. A company grows from SMB into mid-market and keeps their low-touch, product-led playbook. Suddenly their $50K deals take six months to close instead of two weeks because they're not equipped for committee-based buying. Or a company downmarkets from enterprise and watches their CAC explode because they're deploying $15K sales cycles for $8K ACVs.
The core problem isn't process—it's that buyer behavior changes so dramatically across segments that your entire GTM motion has to change with it.
SMB: Speed Wins Everything
The defining characteristic of SMB buying isn't budget constraints or small team sizes. It's urgency combined with authority concentration.
When I ran SMB GTM, our best customers made buying decisions in 72 hours. Not because they were impulsive—because they had acute pain, clear authority, and no organizational friction. The owner or department head had a problem, found a solution, and bought it. No committees, no multi-month evaluations, no procurement reviews.
This sounds like a dream until you realize it completely reshapes your entire GTM strategy.
Your product has to be instantly understandable. I don't mean simple—I mean a prospect needs to understand exactly what it does and why they need it within 60 seconds of landing on your site. Complex positioning kills SMB deals not because SMBs can't understand complexity, but because they won't invest the time to figure it out when they have eight other urgent problems competing for attention.
We had a feature that increased email deliverability by optimizing send times using ML. Enterprise customers loved the technical sophistication. SMB customers bounced because they couldn't quickly tell if we were an email tool, a marketing automation platform, or an analytics product. We changed the homepage headline from "AI-Powered Email Optimization" to "Get More Customers to Open Your Emails" and SMB conversions jumped 35%.
Your sales process has to match their decision speed. When an SMB prospect requests a demo, they're evaluating you against two competitors and making a decision by Friday. If your AE tries to book a discovery call for next week, then a demo for the week after, then a follow-up to discuss next steps, the prospect has already bought from someone else.
Our top SMB rep closed 60% of her deals on the first call. Not because she was pushy—because she understood that when an SMB prospect takes time to talk to you, they're ready to buy. The call was discovery, demo, objection handling, and close in 45 minutes. She'd ask "What made you start looking for a solution this week?" to uncover urgency, "Who else needs to weigh in on this?" to identify any committee risk, and "What would stop you from getting started today?" to surface objections early.
Enterprise reps hated this approach. It felt transactional and rushed. But for SMB buyers who'd already done their research and just needed to confirm the product worked, it was perfect.
Your pricing has to be transparent and simple. No "contact sales for pricing." No custom quotes. No tiered packaging with 15 features per tier that require a comparison spreadsheet to understand. SMB buyers want to see a price, calculate the ROI in their head, and decide.
We tested this by A/B testing our SMB pricing page. Version A had three tiers with detailed feature lists. Version B had three tiers with outcome-focused descriptions and a clear "Most Popular" badge on the middle tier. Version B converted 28% better. Then we added pricing transparency for our lowest tier and saw another 15% lift. SMB buyers weren't trying to optimize for the perfect feature set—they were trying to get to a decision quickly.
Mid-Market: Committee Choreography
Mid-market is where most GTM strategies fall apart because teams treat it like "bigger SMB" or "smaller enterprise." It's neither.
The defining characteristic of mid-market isn't company size or budget—it's committee-based buying without formal procurement processes. You're selling to multiple stakeholders who all have input, but there's no structured evaluation framework like enterprise. It's organized chaos.
I learned this the hard way on a $75K mid-market deal we should have won. We had a champion in marketing who loved the product. We did a great demo. Pricing worked. We thought we were golden.
Then the champion said "I need to get buy-in from sales and product before we can move forward." Our AE said "great, can you intro me?" The champion said "let me socialize it internally first."
We never heard from them again. What happened? The champion tried to sell it internally, sales had concerns about integration with their CRM, product asked questions about data security, and instead of coordinating a conversation to address these concerns, the whole deal died in Slack threads and hallway conversations.
We lost because we treated it like an SMB deal where the champion has unilateral authority. In mid-market, champions have influence but not authority. The decision happens through consensus, which means your job is to orchestrate that consensus, not just convince one person.
You need to multi-thread, but differently than enterprise. In enterprise, you multi-thread up to power and across to key stakeholders through formal meetings and structured processes. In mid-market, you multi-thread to prevent internal deal death through informal alignment.
Our best mid-market rep would ask champions: "Walk me through how decisions like this typically get made at your company. Who usually weighs in? What concerns come up?" Then she'd suggest: "Would it be helpful if I did a quick 15-minute call with your sales leader to address the CRM integration question? That way when you bring this up internally, you'll have concrete answers."
She wasn't trying to go around the champion—she was giving the champion ammunition to sell internally by addressing objections before they became deal-killers.
Your sales cycle will be longer than SMB but shouldn't require enterprise-level process. Mid-market deals take 4-12 weeks on average. Not because buyers need extensive evaluation, but because coordinating internal consensus takes time. Your job is to compress that time by reducing coordination friction.
We built a mid-market "alignment call" into our process. After the champion demo, we'd schedule a 30-minute call with all key stakeholders. Not a re-demo—a structured conversation where we'd ask each stakeholder what they needed to see to feel confident, surface concerns, and address them in real-time. This single call eliminated 80% of the back-and-forth that normally drags out mid-market deals.
Your pricing needs to balance transparency with flexibility. Mid-market buyers want to see pricing to understand if you're in budget. But they also expect some negotiation room because deals at this size often require CFO approval, and CFOs expect to negotiate.
We handled this with "starting at" pricing on our site and a clear escalation path. "Our Growth plan starts at $24K annually for up to 50 users. For larger teams or custom needs, we can build a tailored package." This gave prospects enough info to self-qualify while leaving room for deal shaping when we got into conversations.
Enterprise: Process is the Product
Enterprise buying is defined by one thing: risk mitigation through process. The larger the deal, the more career risk for everyone involved, which means decisions get distributed across formal evaluation processes designed to diffuse responsibility.
This fundamentally changes what you're selling. You're not just selling your product's value—you're selling your ability to navigate their buying process without creating risk for internal champions.
I worked on an enterprise deal where our champion was the VP of Engineering at a Fortune 500 company. He'd personally used our product at his previous company and loved it. We had a clear $500K business case. The product was obviously better than their current solution.
The deal took 13 months to close. Not because of indecision—because the buying process required security review, legal review, procurement negotiation, vendor onboarding, technical evaluation, pilot program, executive approval, and budget allocation across three fiscal cycles.
Our champion wasn't slow or bureaucratic. He was navigating an organizational system designed to prevent bad vendor decisions. Our job was to make his job easier.
You need a multi-threaded strategy that maps to their decision architecture. In SMB, you sell to the person with the pain and the budget. In mid-market, you sell to a champion who coordinates consensus. In enterprise, you sell to a buying committee with formal roles, and each role has different success criteria.
We built an enterprise playbook that mapped our activities to typical enterprise roles: technical evaluation (engineering), business case (finance), risk assessment (security/legal), change management (operations), and strategic alignment (executive sponsor). For each role, we had different collateral, different proof points, and different conversation frameworks.
Our best enterprise AE would literally draw out the org chart with our champion and ask: "Who owns each part of the evaluation? What does each person need to see to say yes? What would make them say no?" Then we'd build a plan to give each stakeholder exactly what they needed.
Your sales cycle is long, so you're selling momentum, not just outcomes. Enterprise deals take 9-18 months on average. That's long enough for champions to change roles, budgets to get reallocated, and priorities to shift. Your job is to create consistent forward progress so the deal maintains organizational momentum even when individual people lose interest.
We used "forcing functions"—events that required decisions and kept deals moving. Pilots with clear success metrics and end dates. Executive briefings scheduled in advance. POC timelines with milestone check-ins. These weren't sales tactics—they were project management tools that helped champions maintain internal momentum.
One deal stalled for three months because the champion got pulled into a different strategic initiative. We proposed a 30-day pilot with clear success criteria and a scheduled readout to the CTO. The champion agreed because it gave him a structured reason to re-engage. The pilot succeeded, and the CTO approved the deal based on the results. The forcing function rescued a deal that was effectively dead.
Your pricing is custom, but your packaging framework needs to be clear. Enterprise buyers expect custom pricing, but they still need a framework to understand what "good" looks like. If your pricing feels arbitrary, it creates risk.
We handled this with a modular packaging framework. Base platform + usage tier + add-on modules. Prospects could see the structure (which made it feel logical) while we had flexibility to customize based on their specific needs. We'd say "Most companies your size start with our Enterprise platform ($150K) plus Analytics ($50K) plus Premium Support ($25K)" which gave them an anchor while leaving room to adjust based on their requirements.
The Mistake Most Teams Make
The biggest mistake I see is companies trying to serve multiple segments with one GTM motion. They'll say "we're building repeatable process" or "we want consistency" but what they're really doing is forcing fundamentally different buyers through the same playbook.
You cannot sell to SMBs and enterprises with the same sales process. The buyer behaviors are too different. The decision timelines are incompatible. The value conversations aren't analogous.
If you're going to serve multiple segments, you need segment-specific playbooks. Different marketing, different sales processes, different pricing approaches, different success metrics. This feels inefficient until you realize that a "unified" playbook that converts at 8% across all segments is worse than segment-specific playbooks that convert at 25% for SMB, 18% for mid-market, and 12% for enterprise.
The teams that win across segments accept that GTM orchestration is complex. They build different engines for different buyers and resist the temptation to force false consistency. They know that speed wins SMB, coordination wins mid-market, and process navigation wins enterprise.
And they stop trying to use the same playbook for all three.