How to succeed in enterprise sales

Corinna Erken
hellosignals
Published in
9 min readApr 7, 2021

Sluggish, time-consuming, and obscure. These three words are often associated with enterprise sales. Backlogs are frequently filled early in the year, (too) many people are involved in decision making and — on top of that — regulatory requirements often come into play, making corporate sales no fun for startups.

Unfortunately, there is no hidden secret to solve all these pains. However, with the following article, we want to support you in reflecting on your status-quo of enterprise sales, whether you are only just starting your corporate sales process or are already further down the road to make corporate sales as efficient and pleasant as possible.

Why? Because with the signals ecosystem, we combine the startup’s and corporate’s perspectives. As investors (signals Pre-Seed & signals VC), we understand the founders’ needs and have a genuine interest to support our startups to succeed in corporate sales as a means to scale their businesses. Besides, we are connecting SIGNAL IDUNA and startups with our signals Startup Client and therefore have a deep understanding of what enterprises need to cooperate with startups.

We have amassed our learnings and experiences and came up with three observations on how to sell to corporate clients.

…and never forget, if you do it well and succeed, corporate sales brings you a large user base, a strong reference client, tremendous scaling opportunities, and — last but not least — deep pockets!

PART 1: Really (!) know your customer

Everyone is not your customer — Seth Godin

Sounds too easy? Oh well, this is where the wheat is separated from the chaff, and it becomes clear who has really done their homework. From the corporate point of view, there is nothing more annoying than to learn that the startup that deems itself to be the perfect match for you has little or no information about your specific industry and company.

Wait — why exactly do you want “us” as customers again? And why exactly should “we” have the feeling that you are a trustworthy and competent partner after this meeting?

Yes, indeed — that doesn’t sound quite right. By all means, please do know your target audience before you go into a sales meeting. Only then will you stand a chance to go out successfully. So what does that mean exactly?

HOW

Before approaching customers, portray the target group and the specific company again as tangible as possible. Knowing your customer implies you have thought about the following questions:

1.What is the corporate’s pain point? Prepare a mission, not a vision pitch.

Talking to VCs, you have learned to paint your vision, the big picture. Most startups are excellent at explaining what added value their solution will bring in a couple of years. That is great but relatively irrelevant when selling to enterprise customers. Except for large tech giants, the majority of enterprises in Germany can look back on decades, sometimes even centuries of history. While this comes with strong brands and loyal customer bases, unfortunately, this often also reflects a lack of openness to new solutions, a workforce with little digital affinity, and an old IT infrastructure.

If you want to attract these companies as paying customers, they have to understand what they get from you now and not in five years! Which pain points are you solving? What KPIs of todays’ decision-makers can you meet so that they want to work with you? Use expert interviews and discovery calls with employees from different departments to acquire a deep understanding of the customer’s needs, pain points, and vision before entering into sales talks with decision-makers (a discovery call is not a sales call).

2. How can you support the decision-maker to reach his/her goals? Show that you have a plan.

Use cases are great to demonstrate that you understand and know the customer. The more tangible your product or service becomes, the more likely it will be purchased. Most corporations are not known for their speed of implementation, yet most executives are measured on this. Show them that they can move into implementation quickly with you. Don’t leave the customer guessing where you can support; show them the potential and make it crystal clear to the decision-maker how your solution solves his/her problem. If it makes sense, prepare more than one use case. They could, for example, differ depending on which department or unit would use your product. Use cases help to demonstrate the potential of your solution beyond the current possible status quo.

3. What language does the corporate speak? Adapt to his language!

Have you ever tried to sell something to a Japanese person without speaking Japanese? It seems completely absurd, yet this scenario happens regularly when corporations and startups meet. There are three types of languages you should therefore consider in enterprise sales:

  1. Mother tongue

Again, appointments with VCs differ from appointments with corporations. While calls with VCs are usually held in English as per default, this quickly becomes a disadvantage in enterprise sales. Don’t risk that the customer doesn’t see the added value in your product because of a language barrier — if you are not a native speaker (in whichever country), then get someone on board who can support you.

2. Industry / Function tongue

Based on whether you are selling an industry-specific product (e.g., underwriting tool) or a function-specific product that can be used in different industries (e.g., recruiting tool), you should have the right people on the product and sales team. Selling an underwriting product without deep insurance knowledge does not work in the same way as selling a recruiting tool without HR expertise. If the customer is supposed to take your solution seriously, you have to talk to him/her at eye level.

3. Corporate Slang

There is usually a very casual tone in the tech, startup, and VC environment. Everyone is on first-name terms, and English and “Denglish” are an integral part of startup jargon. Even if most corporations have adopted their language to a younger target group in recent years, you should still try to use as few “foreign startup words” as necessary in sales meetings. Here it helps to have someone in your sales team familiar with the corporate world’s abbreviations–because similarity leads to sympathy!

PART 2: Define and follow your path to success

„A goal without a plan is just a wish“ — Antoine de Saint-Exupery

In large corporations, it’s easy to lose track of the big picture; topics are re-located or de-prioritized. You won’t be able to change that. But it is a good idea to create a clear sales plan for yourself that gives you a foothold and can guide the corporate as well.

HOW

Step 1: Define success

Know what you want from the customer. What is your desired scenario? Are there any no-gos? What requirements (e.g., timing, minimum purchase amount) must be met so that the conversations are exciting for you?

Step 2: Set and demand clear expectations

If you are aware of your goals and expectations, communicate them at the beginning of the sales process. Don’t be afraid and ask the customer to share their goals and expectations. Avoid long conversations with people who find it exciting to speak with startups but have no interest or authority to buy your solution. Transparent expectation management ensures that the work and time invested on both sides are worthwhile.

Step 3: In or out

If you notice the expectations or mindset do not match, do not be afraid to de-prioritize or distance yourself from the customer. Maybe he will be an exciting customer at a later stage but apparently not at this point in time. Hence you should focus on other customers!

If the conversations do go well, then steer the rudder and get the big fish!

  1. Always know the next step.

Make the collaboration as concrete as possible. Always propose and fix specific next steps and follow up on them so that the decision-maker doesn’t lose sight of you — even if he/she has tons of work to do.

2. Make working with you easy

Make it as easy as possible to work with you. Create a project plan that shows at a glance what steps will be taken, when they will be implemented, and which human and financial resources are needed.

3. The deal is about the details

Many corporates start the partnership with a pilot or a smaller order volume. That makes sense for them for many reasons — who likes to marry a blind date?! For you, this can be an advantage as pilots usually involve less complicated and lengthy ordering processes.

Though, before you start collaborating, make sure it won’t be a “pilot to death” by defining clear KPIs. Measurable goals will show the success of your solution. Clear agreements should also be made regarding compensation. Depending on how much you “need” the customer, you may offer a special price initially. However, make sure there is a consensus on the cost for a roll-out or a larger order amount. Whether written down or not, don’t launch a pilot unless you are sure that the customer will be able to roll out your solution if the pilot is successful. You should know the customer’s big vision (see expectation management).

PART 3: Execute the basics

„Success is neither magical nor mysterious. Success is the natural consequence of consistently applying the basic fundamentals.“ (Jim Rohn)

Basics are key! That doesn’t sound super profound. Yet, at least half of the startups we are talking to with the signals Startup Client could do much better (not just early-stage startups without sales employees).

WHY

Being outstanding is about having a fantastic product — yes indeed — but it is also about executing the basics! Let’s go through this from a corporate perspective to highlight the importance:

If you’ve decided on the right customer group and got the chance to present your product to a corporate client — that’s great as this constitutes the first step. But (!) that’s really only the first step! Even if you do have a solution that alleviates the pain and financial & human resources are available — you can take it for granted that the corporate will also take a closer look at your competitors. Why?

Well, corporates usually want a long-term partnership rather than a short-term adventure — which is great if you actually become the long-term partner! To find the ideal match, the corporate, of course, compares different players and their offers. On top of that, another simple but yet often forgotten reason is compliance. Above certain purchase amounts, corporates are obliged to obtain several bids for compliance and competitive reasons. Hence, the corporate will try to absorb all available information and impressions about your — and everyone else’s — product, company, and working ethos to make an informed decision.

That’s why you have to differentiate yourself from the competition — not only with your product but also with the basics. Show that you are committed to going above and beyond for your client. How well you perform in the beginning will be a precursor of how well you perform in the long run. So, make sure the corporate understands that you are not only an innovative but also a reliable and trustworthy partner to work with.

HOW

Just a couple of basics to consider

  • Be on time and make sure your technical setup works. Many corporates use older tools than you do — prepare and make sure you can join in time and provide a demo.
  • Join important meetings as a team.
  • Have a sales deck handy. Make it as easy as possible for internal stakeholders to spread your message and become your internal ambassador.
  • Be thorough with your language. Make sure to have a founder or sales manager who speaks the corporate’s language (sector-specific and native speaker, see tip 1)
  • Avoid careless mistakes. To err is human, but typos in a deck and misspelling the corporate’s name is a no-go. Make sure you always double-check — you may only have a single shot!

Summing up, corporate sales is sometimes sluggish, time-consuming, and obscure. And yet, as a startup, there are things you can do to play your cards right. Successful teams often don’t differ from less successful teams in having a fundamentally better product or team. Most of the time, they are just significantly better at highlighting their strengths in a customer-specific way. They spend enough time getting to know their client, stringently guiding through the sales process, and convincing the customer with their executive power.

In the end, never forget: enterprise sales is a marathon, not a sprint! Maintain your stamina and keep pushing your chances.

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