Enterprise Sales Guide Summary

Many B2B startups initially focus on selling to startups and SMBs. Once the product is ready, they try to go upmarket.

For the past two years, Relate has been building a simple CRM and targeting startups. In the second half of last year, we started to see customers with more complex needs, which led us to expand our product offerings to a full-stack revenue platform for larger teams.

We had many lost deals before closing our first five-figure deal. After that, closing the next five-figure deals became easier.

We organized our internal playbook for enterprise sales for B2B startups. Other B2B startups with similar backgrounds can use this to accelerate their enterprise sales.

This post is a quick summary of our enterprise sales guide. For details, see the Relate team's Enterprise Sales Guide.

What is Enterprise Sales?

Key characteristics of Enterprise sales include:

1. Long-term contracts (1 year or more).
2. Larger deal size (ACV)
3. Complex sales process
4. Requires building relationships with various customer-side stakeholders.
5. Requires understanding of the customer's business problems and work process, including decision-making.

Enterprise sales isn't just about explaining key features. It's about emphasizing the value you can deliver by solving the customer's key business problems.

Why is enterprise sales important for B2B sales teams?

Enterprise sales may not be essential for every B2B sales team due to its long sales cycle and complex process. However, there are compelling reasons enterprise sales benefit B2B teams.

1. Large deal sizes (ACV) and revenue opportunities
2. Opportunities for long-term relationships
3. Builds brand credibility

Through enterprise sales, B2B teams can close larger deals, upsell and cross-sell through relationship building, and enhance brand credibility through logo acquisition. So, why isn't everyone doing enterprise sales?

Because Enterprise sales is challenging.

Why is enterprise sales challenging?

Enterprise sales are more time-consuming and complex than SMB sales. They involve longer cycles, often taking months to close compared to weeks for smaller deals.

This requires engaging multiple stakeholders across various departments, from end-users to decision-makers and support teams.

Success in enterprise sales hinges on understanding and addressing the diverse needs and agendas of all stakeholders rather than focusing solely on decision-makers.

Enterprise sales step 1: Prospecting

When prospecting for enterprise customers, first focus on getting these right.

1. Focus on your ICP: Maintain a high standard for qualifying whether they are ICPs or not.
2. Multi-threading: Contact multiple stakeholders simultaneously to understand the prospect's org chart, key business goals or issues for decision-makers, and decision-making processes, etc.
3. Initial discovery call: The purpose of an initial discovery call is to validate a sales opportunity and gather information for further sales efforts.
4. Focus on value, not features, during product demos: If you're doing a product demo, don't just showcase the product. Demonstrate enough to make them think you can solve their problem.
5. Be patient and follow up consistently: Enterprise sales don't close with a single contact or meeting, so follow up appropriately.

Enterprise sales step 2: Closing

To close enterprise opportunities, you need:

1. More discovery calls and product demos: In enterprise sales, discovery is not a one-and-done task but an ongoing process. They should continue to understand the needs of various stakeholders, their decision-making processes, and more.
2. Identify and support champions: Quickly identify and support champions advocating for the sales team within the customer organization.
3. Proposals and pilots: Proposals are all about addressing the customer's critical problems and demonstrating the value. If customers want to test your product, consider a pilot - but with a clear purpose and plan.
4. Competition and objection handling: In enterprise sales, dealing with competition and objections is inevitable.
5. Security review: Delay the IT/security team review as much as possible to ensure quick product adoption and sales team efficiency.
6. Negotiations and contracts: Understand the purchasing process, negotiate, and sign contracts to find reasonable terms for both parties. Avoid unreasonable terms and prioritize long-term customer success.
7. Utilize a mutual action plan: A mutual action plan can help the sales team and customer collaborate during the product adoption process. The plan should define clear goals, decision-making processes, milestones, timelines, roles, resources, communication plans, and success criteria.

Enterprise sales step 3: Onboarding & customer success

Closing an enterprise deal is just the beginning. Successful onboarding and ongoing customer success are crucial for long-term growth.

1. Understanding the customer’s workflow: Before onboarding, identify the customer’s workflow that your product will impact. This understanding is critical for SaaS products.
2. Data migration and setup: Assisting with data migration and setup provides a good onboarding experience and allows users to see the product’s value from day 1.
3. Onboarding meetings and training sessions: Your onboarding meetings should focus on showing customers how your product solves their needs, not just introducing features. Consider segmenting onboarding meetings for different user groups to customize the experience.
4. Regular follow-ups: In a SaaS, retaining existing customers is crucial for recurring revenue. When customer satisfaction and product improvements align, you can generate larger revenue through upsells and cross-sells.

Enterprise sales FAQs for startups

Here are common questions startups have when selling to enterprises.

1. When can a startup start selling to enterprises?

Enterprise sales is about solving big problems, not just showcasing features. You can win enterprise deals even without a fully developed product. Focus on the customer's main business challenge and how you'll solve it. Be clear about what you can deliver now and what you'll develop soon (aim for under 90 days). Communicate openly and agree on timelines with the customer throughout the process.

2. What if I can't meet all the customer's requirements at once?

Skilled sales reps should conduct a thorough discovery call to prioritize the customer's requirements and eliminate unnecessary ones: evaluate critical requirements based on the customer's willingness to pay.

When a feature requires further development, the sales rep must ensure clear communication between the product team and the customer.

3. Communicating with the product team

When a startup closes an enterprise deal, immediate communication with the product team is crucial. Here's what they'll need to know:

• The customer’s core problem
• The problem context
• The customer's proposed solution or requirements
• For multiple problems/requirements, their relative importance and priority; identifying any "deal breakers"
• Implementation timeline

Case study: Our first five-figure deal

Check out this post if you'd like to see how Relate closed our first five-figure deal started from outbound.

How Relate closed the first five-figure deal through outbound sales - Ch. 6 - Relate Enterprise Sales Guide

Here’s a case study on the Relate team’s first enterprise deal. It details the process from prospecting to closing the deal and onboarding.

Relate Enterprise Sales Guide