For most start-ups operating across the world, the enterprise client is the ultimate feather in their cap.

Why?

The enterprise reflects larger and more consistent deals that can fuel additional revenue and growth streams. Imagine being able to close one or two deals that reflect multiple smaller deals in a month, knowing that this revenue is consistent for the foreseeable future. Combined with the boasting power of working with a leading Fortune 500 or Fortune 1000 company, you’re instantly provided with a significant amount of undeniable credibility that boost your presence in the enterprise space.

I’ve had the opportunity to meet with leaders of corporate innovation in the Canadian space since I moved to Toronto and have often discussed with them what start-ups could do better when selling to the enterprise. Combining this with my experience in designing and implementing enterprise sales tactics for multiple start-ups has enabled me to put together a list of what to consider while pursuing a lucrative enterprise deal.

Prepare for the Enterprise

No one can stress this enough. Ensure you are geared for the rigors of an enterprise client. Stress test your product, your platform and your team to make sure that you can and will deliver what your promise. Failing to do so will do significant damage to your brand and reputation in the market, slowing down your growth curve significantly. 

Organization

List out potential enterprise targets and design a ranking system specific to your objectives and business stage. This will help create a priority target list and a secondary target list that can augment your efforts should the need arise. Re-ranking the list every now and then provides you with a layered and flexible sales plan, shaped to your business needs. Criteria can range from deal time, deal size, product fit to even connections that can shorten your sales cycle.

Prepare for the Long Haul

Experience has taught me that this is easier said than done. I’ve seen deals with Fortune 50 companies close in 3 weeks with some deals taking over a year, only to fall apart at the last minute. Working an enterprise deal takes time and can be financially, emotionally and physically draining – but worth it at the end. It’s important to take a step back and evaluate how long you can last through a long sales cycle. It always helps to augment large enterprise deals with smaller, quick to close deals that bring in cash to keep the lights on.

Relevant Sales Tools

Customize everything. The product, your discovery calls and your demo. Small steps like using a target’s logo in your demo environment can go a long way in helping building relevance for the team. Design your pitch and demo to address known problems specific to either the company or the industry. Providing contextual use cases is far more effective rather than leaving the target to imagine their own use cases.

Identify Multiple Stakeholders

Build multiple internal advocates for your company within the target enterprise. Multiple advocates come in handy when there are cross-team decisions to be taken or even hedge your risks in the event of situations removing your one and only internal advocate out of the decision-making process. Enterprise sales consist of a lot of moving parts and having someone who can help you along way quickens the process, making it a lot less painful along the way.

Designate Decision Makers

Involving more than one person on a deal ensure that your team can divide the responsibilities associated with an enterprise deal. However, its equally important to have designated decision makers to ensure that any delays in the sales cycle are not from your end. I’ve seen start-ups take a significant amount of time to reach a decision only to consequently suffer setbacks in a deal. Think every decision through with your team but have on person who can provide the clarity and an executive decision when needed.

Pricing

Never undermine the perceived value of your product by under pricing your offering. Despite popular belief, the “cheapest price” doesn’t always go through. Although, it’s also important to be realistic and quote a price that can close a deal without getting too much red tape involved in the enterprise. Listen to your advocate on potential pricing and determine a level that makes sense to you but also to potential future deals once you’ve had a chance to prove yourself.