Many B2B founders are lured into selling to Enterprise before they are ready. Big contracts and flashy logos draw them in, yet early-stage startups waste time and money trying to create a new sales strategy. 

Enterprises, defined not just by size but by the complexity of their organizational structures and decision-making processes, demand a tailored approach that differs markedly from strategies employed for smaller market segments. This article and video delve into the essential strategies for engaging with enterprise clients effectively—from adjusting sales tactics and fostering robust relationships to executing a rigorous discovery process and customizing solutions. We'll explore how to navigate the intricate and often lengthy cycles of enterprise sales, ensuring your business is poised to meet these large-scale clients' high expectations and specific needs.

This presentation (video below) will explore the intricate details of transitioning to the enterprise segment.

Make sure you understand the enterprise segment

• Define what 'enterprise' means for your company, considering factors like employee count, revenue potential, or organizational complexity. This definition can (and probably should!) evolve. 

• Recognize that enterprise decision-making and purchasing processes differ significantly from smaller segments – adjust your expectations accordingly and don’t let the longer cycles frustrate you. 

Adapt your sales strategies for your enterprise needs

• Selling to enterprise differs significantly from selling downmarket. Be prepared for longer sales cycles and larger buying committees who will expect you to adapt to their processes

• Adjust your approach to accommodate more formal and rigorous procurement and legal review processes typical of enterprise deals.

  Focus on relationship-building

• Engage with multiple stakeholders across the enterprise, including technical buyers, user buyers, and economic buyers. Know who owns the budget and make sure they get included in the conversation early! 

• Find your champion(s) and use them creatively to understand the hurdles that need to be overcome for the deal to get done. Maybe it’s about learning the client’s internal jargon so you can speak the budget owner’s language in the meeting.

Discovery, discovery, discovery

• Don’t make the mistake of thinking that discovery ends after the initial meeting. Implement thorough discovery at every stage of the sales journey, from initial contact to post-sale.

• Unpeel the onion. Dig deep into uncovering the team’s different pain points – not just the explicit needs but also the implicit challenges and internal dynamics -  so you can understand what you could do to ease them.

• Make sure to ask about timeframes and budget allocations so you can accurately forecast when that revenue could realistically come in. Never assume you know if you haven’t asked!

Customize and personalize solutions

• Enterprise clients will often expect a certain level of product customization to fit their needs and integrate smoothly into their existing systems – show flexibility and readiness to adapt to those expectations. 

Prepare for intensive negotiations

• Expect enterprise negotiations to be detailed and time-consuming, often focusing on specific clauses or terms.

• Equip your team with the necessary skills and legal support to handle these negotiations smoothly – often that means commercial lawyers who can handle the redline! 

Remember that timing is everything

• Determine the optimal timing for engaging with enterprise clients based on your company’s readiness and market conditions.

• Ensure your organization is prepared for the demands of enterprise sales -  including compliance, legal readiness, and resource allocation – before going after that type of whale. For some companies, this process can take years. 

Leverage your data

• Use sales intelligence tools and CRM systems to record your enterprise client interactions accurately. Then, make sure to use this data to manage your enterprise relationships seamlessly. 

Align sales and marketing efforts:

• Ensure that marketing and sales are tightly integrated, using consistent language and strategies tailored to the enterprise market.

• Consistently leverage feedback from sales interactions to refine your marketing strategies and product development loops.

Iterate and learn as you go

• Consider establishing pilot programs with enterprise clients to test and refine your approach before a full rollout. Pilots can mean different things depending on your needs, so don’t be afraid to get creative with them! 

• Use every interaction as an opportunity to collect feedback and use it to create scalable strategies that can be adjusted as your enterprise sales grow.

• Leverage automation to complete lengthy Enterprise RFPs and security docs. 

More tips on selling to the enterprise:

- Cracking the Code: How to Win an Enterprise RFP

- Establishing a Demand Gen Function for an Enterprise Sale

- Top Takeaways on Early-Stage B2B Marketing

Check out the whole presentation below!