Enterprise GTM Strategy: Why Lean B2B Teams Struggle with Enterprise Sales

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For most parts, I’ve worked closely with teams doing enterprise sales — from early-stage vertical SaaS startups running founder-led GTM to larger, IPO-bound companies relying on legacy relationships to win large accounts.

Over time, I’ve learned a few hard-earned lessons while setting up marketing programs for teams of vastly different sizes and maturity levels.

To those unfamiliar or new to this, enterprise sales refers to selling high-value, complex B2B solutions to large organizations — often with 2,000–5,000+ employees and annual revenue exceeding a billion dollars.

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What Makes Enterprise Sales So Hard

Despite what online playbooks and generic advice suggest, enterprise sales — where average contract value (ACV) is above $100K and deals span multiple years — typically involves:

• Long sales cycles (6–9 months or more)
• Multiple decision-makers — executive sponsors, economic buyers, technical evaluators, users, finance, legal, and procurement
• Complex buying and compliance processes — RFIs, RFPs, security and legal reviews, multi-round technical evaluations, and negotiations
• Customization and integrations with existing IT systems, plus dedicated account management to retain and grow each customer

Each of these elements can quietly become a pipeline killer.

Because executing enterprise GTM effectively requires:

• Serious budget and patience to stay the course
• A disciplined sales and marketing motion that can navigate bureaucracy as an “opportunity” matures into a “deal”
• An always-on rhythm of stakeholder mapping and relationship nurturing — across multiple accounts — without letting anything fall through the cracks

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Enterprise GTM Remains Under-Leveraged in Plain Sight

In reality, no matter how large or small the organization, enterprise GTM can remain dangerously under-leveraged in plain sight.

It often looks like this:

• Under-resourced setup: Even a minimum viable team is missing (no SDRs, one AE per territory), with limited in-house skills or marketing budget for visibility and communication.
• Multi-hatting and over-spread bandwidth: Founders or SDRs act as Swiss-army knives; or a single sales rep handles all verticals and territories.
• Weak GTM data pipeline: Sales tactics, account intel, and opportunity history live inside people’s heads or one-off campaigns — not in a CRM or dashboard. Many small to mid-sized GTM teams lack documentation, process discipline, or adoption, making sustained nurture impossible.
• Scattershot execution: Expecting consistent sales-qualified leads from sporadic, under-funded campaigns; running “stop-and-go” marketing; measuring ROI only by leads; skipping credibility building — the true backbone of enterprise sales success.

Fixing an under-leveraged GTM engine is not about hiring faster, running more campaigns, or attending more events.

It requires stepping back and reframing why the GTM system is breaking before diving into tactics.

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Root Causes of Enterprise GTM Failure

In my experience, the causes of an under-leveraged enterprise GTM strategy usually fall into two buckets:

1. Don’t Know What to Operationalize for Enterprise GTM Success

These teams lack the tacit knowledge of what needs to be done — and in what order — to make enterprise GTM work.

They learn on the fly from peers, advisors, and investors — doubling down on whatever earns a few conversations while dismissing everything else as noise.

Anything that generates short-term leads stays; everything else gets killed.
They jump from one campaign or channel to another, without ever building a repeatable sales and marketing process that can sustain 3–6 quarters for a single enterprise deal.

This is common among:

• Early-stage SaaS or automation startups moving upmarket without prior enterprise muscle memory
• Mid-sized companies that have won a few large accounts via leadership relationships and assume this model will scale — only to find it doesn’t work in new verticals or cold territories
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2. Know What to Operationalize But Not How to Execute It

These teams are slightly higher on the GTM maturity curve.

They’ve experienced some success with enterprise selling and are running tactical activations — events, campaigns, and partnerships.
However, they struggle to stitch these efforts into a coherent go-to-market framework that can scale across regions or industries without headcount and cost bloat.

For instance:

• A geographically dispersed field sales team attending events while a disconnected central marketing team lacks the ground context to support them effectively
• A “tiger team” within a larger company tasked with entering a new vertical (say, Global Capability Centers) but forced to design their GTM process from scratch with limited support from central marketing

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Before You Fix Enterprise GTM, Frame the Gap Clearly

There are countless reasons why enterprise GTM strategy feels difficult in lean setups — but the first step is framing the gap properly.

Ask yourself:

• Do we truly know what to operationalize — or are we reacting to noise?
• If we know the what, do we have the rhythm, systems, and GTM data backbone to sustain it?

Your answer determines whether the next campaign compounds or collapses under its own weight.

That clarity alone can prevent months of wasted effort — and it’s where building a scalable enterprise GTM system truly begins.

In the next post, we’ll look at some strategic foundations of enterprise GTM success — the principles that help lean B2B teams sell to large enterprises without losing focus or burning out.

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