How to Sell into an Enterprise as a Startup

Breaking into the enterprise market is one of the biggest inflection points for a startup. It’s where your sales cycle gets longer, your buying group gets bigger, and your marketing needs to grow up fast.

Most founders make one of two mistakes:

1. Trying to sell too low (getting stuck in mid-level demos that never convert).

2. Or selling too high too early (without user validation or ROI proof).

The right approach isn’t either/or, it’s a dual strategy: top-down and bottom-up working in sync.

1. Understand the Enterprise Buying Group 

Enterprise deals don’t happen in isolation. You’re selling into a committee of decision-makers, each with their own incentives and influence.

The average B2B purchase today involves 6–10 stakeholders across finance, ops, IT, and the business unit. Your job is to influence the group, not just the “lead contact.”

Start by mapping four types of roles:

• Influencer: Shapes internal opinions (e.g., FP&A Manager).

• Decision Maker: Owns the strategic decision (e.g., COO).

• Budget Owner: Signs the contract (e.g., CFO).

• User: Validates usability and product fit (e.g., Finance Analyst).

This is where ABM (Account-Based Marketing) becomes your foundation, not a campaign, but an organisational lens for go-to-market.

2. When to Lead with Bottom-Up Momentum

The bottom-up approach works when your product can prove value through usage. If your product helps individuals or teams work faster, collaborate better, or automate repetitive work, start here.

Use this play if:

• You have strong product-led growth (PLG) mechanics.

• Adoption is simple (no complex integrations).

• You can land small, expand fast.

Your targets: Users and influencers.

 Example: A startup offering workflow automation tools could target finance teams directly through community content, tutorials, and free trials. Once internal champions start using it, you’ve created pull, internal advocacy that brings you into executive conversations organically.

Tactic: Track internal usage signals and share adoption data in your next meeting with leadership, nothing builds trust like user evidence.

3. When to Lead with Top-Down Authority

When your product impacts multiple departments, risk, or compliance, you must start higher. Here, adoption depends on executive sponsorship, especially in regulated industries or data-heavy environments.

Use this play if:

• The ROI is strategic (cost reduction, compliance, security).

• The buying cycle involves procurement or IT.

• You need cross-functional alignment to succeed.

Your targets: Decision makers and budget owners.

 Example: Selling a spend optimisation tool? The CFO and COO will care about financial visibility, risk, and total cost of ownership.

You’ll need a business case, not a demo. Show how your product improves margins, forecasting accuracy, or working capital.

Tactic: Bring numbers to the table. Use calculators, benchmark data, and projections that translate product value into financial outcomes.

4. How to Influence a Complex Buying Cycle

The key to enterprise sales is sequencing your influence. Each persona requires different proof points at different times.

Orchestration tip: The CFO needs confidence, the user needs clarity, and the influencer needs credibility. ABM lets you deliver that message to each, consistently and contextually.

5. How to Create an ABM Campaign as a Startup

ABM doesn’t require a $200K tech stack, it requires focus. Here’s a lean, proven structure I use with early-stage founders breaking into enterprise accounts:

Step 1. Identify your top 25 target accounts. Use firmographic data (industry, headcount, funding, tech stack). Tools like Apollo, Clay, or ZoomInfo can help.

Step 2. Map the buying group. Find 3–5 contacts per account across finance, ops, and IT using LinkedIn Sales Navigator.

Step 3. Craft a unified narrative. Create one “enterprise story”, then personalise it by persona.

• CFO → ROI & risk

• COO → efficiency & scalability

• FP&A → automation & accuracy

• Users → ease of use & value

Step 4. Orchestrate multi-channel touchpoints.

• LinkedIn ads (for brand exposure)

• Email sequences (for tailored messaging)

• Events / webinars (for trust-building)

• Personalised DMs (for direct impact)

Get Creative with the C-suite! send a personalised box to get their attention. 

I was once running an ABM campaign, 1:1, to influence an RFP (request for proposal). To reach the CEO I found out from my sales rep that he drove his kids to school every morning. I rented the billboard space outside the school for 2 weeks (only costs me £2000) and created a personalised campaign message relevant to the RFP, highlighting how our product achieved 40% uplift. We won that RFP. 

Step 5. Measure engagement at the account level. Track engagement by account penetration, not just leads, how many stakeholders are aware, engaged, and responding?

6. How to Automate the ABM Process (with or without Budget)

If you have budget:

• 6sense / Demandbase /Seam AI → end-to-end ABM automation

• Mutiny + HubSpot + Clay → personalised website + data enrichment + smart outreach

• ChatGPT / Jasper / Writer → persona-specific content and sales copy generation

• Gong / Lavender / Apollo → insight extraction + message optimisation

If you’re resource-constrained:

• Use LinkedIn lists + Zapier + Airtable to track engagement manually.

• Create AI-assisted personalisation using GPT prompts:

• Repurpose your top-performing founder posts into 1:1 outreach assets.

• Record personal Loom videos showing ROI impact in 60 seconds.

Start with the mindset, not the martech. ABM is about precision, empathy, and persistence, not just automation.

7. The Growth Mindset That Wins Enterprise Deals

Selling into enterprise is a discipline. It’s not a single campaign, but a rhythm, one that balances bottom-up product validation with top-down executive alignment.

The winning formula:

Land with value, expand with proof, and sustain with partnership.

For founders selling into large accounts, ABM isn’t just a marketing tactic, it’s the architecture of enterprise growth.