Start Small, Win Big: Mastering the Art of Selling to Enterprise Clients

In the last twelve months, the economic landscape has been filled with challenges—from market volatility and inflation to increased competition for venture capital. Small and growing businesses face an uphill battle, especially B2B startups aiming to secure deals with large enterprises.

As someone who's been in the CIO and CTO seats at several large companies, I empathize with founders and know firsthand how difficult it can be to navigate these deals. In this article, I'll share five insights that can serve as your compass when you're trying to make that first pivotal enterprise sale.

1. Understand Your Customer Inside And Out
Effective selling begins with thorough research. Don't just skim the surface—deep-dive into your target enterprise.  Who is their Ideal Customer Profile (ICP)? What pain point(s) are they trying to solve? Where are they on the innovation adoption curve (early adopter vs. laggard)? Who are the key decision makers and budget holders? Ask pointed questions about their needs, available budget, and timelines. Aim to offer solutions that fulfill a "must-have" need. "Nice-to-haves" rarely lead to closed deals.

2. Get Acquainted with the Due Diligence Process Early
Selling to a large enterprise often means navigating a labyrinth of evaluation procedures. Due diligence will likely include everything from product and technology assessments, to information security and financial reviews, to complex legal agreements (e.g., NDA, MSA, SOW). If you're dealing with a regulated industry, there will be additional steps in the process led by Compliance. Acquaint yourself with these processes as early as possible, understand the criteria they'll use to evaluate your business, and prepare for each step of the process.

3. Cultivate an Expansive Support System of Decision Makers
It’s too common of a story. A startup that spent over a year trying to secure an enterprise client is suddenly stuck at a standstill when their company sponsor or advocate moves into a new role or leaves the company. Enterprises are notorious for frequent restructuring and leadership shifts. Therefore, foster relationships with multiple stakeholders who are not only enthusiastic about your product but are also key company decision makers!

4. Execute a Meticulously-Planned Pilot
Often an enterprise will want to pilot your solution before deciding to sign a deal. This stage is your chance to showcase the real-world efficacy of your solution. To ensure your pilot is successful, plan meticulously by timeboxing, defining your success metrics upfront, and ensuring both parties have skin in the game. Clear and timely communication is key. I am also a believer in paid pilots even if for a nominal fee. Your team’s time is valuable. A potential client should be willing to pay for the resources and time required to organize and execute a 6-week pilot, for example.

5. After the Deal: The Importance of a Seamless Implementation
Founders are ready to celebrate when they’ve finally signed a Master Service Agreement (MSA) and secured a new enterprise client. It is a huge milestone but the journey has just begun. Now it’s time to deploy your solution effectively, offer exceptional post-sale customer support and retain the client long-term. Usually an MSA lays out the terms of the business agreement but is not a commitment to implement the solution. Discuss and plan the implementation strategy early and focus on how to remove implementation friction. For example, if you are relying on the client’s tech team to build an interface, convert data, or stand up a testing instance, you may encounter long delays. Can your team take on or automate some of these tech tasks? Can you implement your service in phases to expedite ROI? Lastly, build a relationship with key users. Developing an internal community of advocates will help reaffirm the “can’t live without this” mentality and retain your enterprise client’s business year over year.

Breaking into enterprise sales is not for the faint-hearted, especially for early-stage startups. However, many companies have cracked the code and laid the foundation for their business’s success with lucrative enterprise deals. You can succeed if you have a solution that meets a large company’s needs and you are prepared to work through their due diligence process.

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More about Beth Devin, HearstLab Co-Lead
Prior to her current position at HearstLab, Beth held significant roles as a Chief Information Officer (CIO), CTO, and Managing Director at established enterprises such as Citi, Silicon Valley Bank, Charles Schwab, and Turner Broadcasting. She holds a BS in Computer Science from San Francisco State University and is an International Women's Forum (IWF) Leadership fellow. Beyond her day job, she serves as a board member and chairs the Program Committee of the IWF Northern California chapter.