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Written By:Ken Mocabee
Published on

Challenges of Selling to Mid-Market and Enterprise: Going to Market

Corporate Sales Meeting

In my previous blogs on selling to mid-Market companies and bigger, we addressed the challenges with your product offering, and how to get your product ready, and how to address your company being too new and small. In Part 3 I’m going to talk about how you go to market, and some strategies for selling to those larger corporate clients.

One of the primary challenges in going to market, especially with large corporate clients, is navigating the complex and lengthy sales cycles that can delay revenue and strain resources. To address this, key strategies include using a Beachhead Market approach to gradually build momentum, effectively engaging stakeholders, maintaining a professional appearance, and being prepared to manage requests for custom solutions. 

Note that this isn’t a full tutorial on Enterprise sales – there are enormous resources online for that. Instead, this is an overview of the things that small companies need to do and be aware of when preparing to sell to larger companies.

Sales Cycles are Longer

This one can be very hard to deal with because startups and new product teams are looking for traction as soon as possible, and selling to larger companies requires patience and a commitment to process. If you are expecting a quick close, you are likely going to be disappointed.

At this level it can take many months or even years to close a sale. This means you have to plan not only on building your foundation over time, but you have to have the funding to get to that finish line, which might be several years away.

All good things to those who wait

Scale Gracefully with a Beachhead Market Strategy

Small companies that try to dive into the deep end of the pool often drown. Onboarding, support, supply chains, customizations, and many other services are not easy to scale up instantly.

If your goal is to sell to larger companies, you might need to work into it gradually and ratchet up the companies you onboard. A beachhead market strategy can really help you do that. Beachhead markets are smaller niche submarkets to the larger market you are eventually targeting. It can be a great way to establish yourself, generate revenue, and prepare for the whales.

Know the Stakeholders

As the companies get larger so does the number of people involved in the deal. For smaller companies, the decision maker is usually easier to get to. You might be talking to a founder or the CEO, and their green light is all you need. But larger companies will have many players who will put you through your paces.

You need to not only know who they are, but what motivates them. What they expect from you, and what will either kill the deal, or get you through to the next round. That means you need to know their vetting process inside and out, and be prepared to counter objections, and to build trust.

Here’s a pain point we have seen many times - the people you are initially selling to often don’t make the final decision. Getting a “we would totally buy that if you built it” is exciting, but it’s far from a firm commitment. It’s a good signal, no doubt, but if they recommend your solution to their leadership, that’s when the vetting process, and the hard work, starts.

The key is to identify all of those stakeholders prior to going to market and learn the dynamics of selling to them. Engage early before you are ready to make a sale, and make sure you understand their specific requirements and vendor criteria such as company size, years in business, etc.

Look the Part

The time to improve your branding, website, and anything else that might make you look small is now. And, it’s not just about looking bigger, it’s about having your act together and being ready. Here are a few things that help you look like you belong in the ring:

Branding

Branding

Your brand says a lot about who you are, and what you stand for. That Fiverr logo might be OK for a scrappy startup, but it might not be when going to the big show.

Your Product

Website

Your website is often the first touchpoint with your company, and it’s where you need to look like you have your act together. It doesn’t have to be elaborate or cost a fortune, but it needs to be professional and look great.

Content Creation

Content

Your content is more than marketing, it’s how you communicate who you are and what you care about. Create a content plan and create new blog posts, case studies, white papers, articles, and videos on a regular basis. If you need help doing this, get it.

Contracts

Agreements & Contracts

Your agreements and contracts can’t be “bush” at this level! What got by for small clients won’t fly for larger companies that have their own legal counsel. Make your proposals, MSAs, SoWs and other documents professional and get input from your legal counsel. Expect their legal counsel to pick apart your contracts and plan to go through multiple rounds of changes. Be prepared to spend the money on legal fees, too. You don’t want to go into a bad agreement that you will regret later.

Your Company

Sales & Marketing Collateral

Create presentations and documents for information that stakeholders will certainly want such as processes, policies, procedures, and architecture, and have them ready to deliver when requested. For example, security is always important. Create a packet that includes documentation, prior audits, certifications, etc.

Be Prepared for Customized Solution Requests

Large companies will indeed ask you for custom solutions that might be challenging or problematic. You’ll need to weigh the costs and benefits of doing those things. Some might be easy, such as a set of reports or a one-off systems integration. Others might be bigger like custom features, or an on-premises installation.

In technology that can seem to be straightforward because you can add custom features to your main product if they have broad appeal. But, if they are too narrow to be attractive to any other companies, you now have a fork in your product and have 2 versions to support and keep updated.

And make sure you have contracts in place that make it worthwhile. If your SaaS solution is typically month to month, you don’t want to spend hundreds of hours on a custom solution only to have the client walk away early. The commitment goes both ways.

Summary

Early-stage companies face a lot of challenges when selling to mid-market and larger companies. You have to plan accordingly and do the foundational work that gets you there over time. You can’t force it; you have to know the rules and play the game the right way. 

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Developing great digital products is our passion. Not sure how to start that journey? Let us help you find the right path. Schedule a free 1-hour consultation with our team. At the end we’ll deliver a Project Brief that will help you to crystalize your vision.

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