Enterprise x Startup Collaboration: Lessons from Both Sides of the Table

There are two fundamental truths that I’ve come to recognize over the course of my career working at both massive enterprises and startups alike.

1. Enterprises need to work with startups to evolve and innovate and;
2. Startups need to work with enterprises for validation and scale

So, if these two things are true, why can it be so challenging for enterprises and startups to be good partners to one another? As someone who has had the opportunity to play for both teams, I like to think that I can bring a unique perspective to this question. As the first sales hire at a VC backed startup in NYC, I was perplexed by the vast internal procedures, long decision-making processes, and extensive timelines that I often ran into at large enterprises. It wasn’t until I joined E*TRADE a few years back to lead their startup mission that I developed a deeper understanding of and empathy for the incumbent.

Given that collaboration is essential but recognizing that it can also be difficult, how can startups collaborate with enterprises while making sure that they use their time and resources most effectively and efficiently? Here are the key learnings that I’ve gathered over the years for founders.

Build relationships intentionally and spend time wisely

One of the most important things that you can do as a startup is to be very clear, specific, and upfront about your current goals. What types of people (e.g. title, role, business unit) are you looking to meet with inside of the enterprise? Are you looking for early feedback, beta or PoC users, enterprise customers? Having been an advocate for startups within an enterprise, it makes my job much easier if a startup is specific about who and what they are looking for so that I can help facilitate the right introductions and relationships internally. Make it easy for your initial contact at the company by clearly articulating your goals so that introductions can be made to the right people and meetings can be set up with the proper context.

If you’re a startup that has overwhelming inbound interest from enterprises, that’s certainly a good problem to have. But it’s also important to be selective about where you spend your time and resources. Even corporates with the best of intentions may work with a startup longer than they should when they don’t have the need, budget, or executive sponsorship. If you realize that an opportunity isn’t going anywhere, it is perfectly okay to step back and say that you’ll revisit next quarter or next year when the commitment from the enterprise is real.

Meeting etiquette and preparation matters

It feels outrageous to talk about what goes into making a meeting successful but the reality is that meetings are truly an art form that not everyone takes the time to master. For better or for worse, impressions really do matter when you’re a startup that is meeting with a potential enterprise client/partner/advisor for the first time. There have been some amazing startups that I’ve put in front of enterprise execs and stakeholders that couldn’t secure a second meeting so I can’t emphasize the following guidance enough.

1. Set up a prep call

Do you understand what the purpose of the meeting is, what the expectations are, who the audience is? If you don’t, ask. There is a big difference between a casual 1:1 chat and a formal presentation to a group of executives and you need to know what you’re walking into to be able to prepare appropriately. As a frequent champion on the enterprise side, I am always happy to do a 15 minute prep call or answer questions over email to help set a founder up for success prior to a meeting with executive stakeholders. I’d argue that most champions would be willing to do the same because ultimately, the success of that meeting is a direct reflection on that champion who has brokered the meeting or introduction.

2. Minimize slides and get to the demo

When it comes to content, I’ve found that slides are rarely powerful. The best enterprise presentations typically use the minimum amount of slides (<7 usually) needed to set up the product demo. Enterprises want to understand the gap that you’ve identified, the pain point you’re solving for, your unique value proposition and why you are well positioned to solve for it. Ideally, you want to get to the product demonstration as quickly as possible so that the audience can think through what use cases might be applicable to them. From there, the presentation can evolve into more of a discussion. Finally, don’t forget to be prescriptive about a potential path forward and next steps. The best presentations usually include a very straightforward slide with suggested next steps and action items. Even if the corporate doesn’t agree with the next steps that you’ve laid out, it opens the door for you to flip the script and ask what their proposed next steps would ideally look like.

3. Keep it professional

The last thing that I’ll say in regards to meetings is that professionalism really does matter and the little things do count. If you’re going into a new office for the first time (if in person meetings are a thing again one day…), give yourself plenty of time to find the building and anticipate that checking in at security will take at least 15 minutes more than you think it will. Test out the conference line ahead of time and if it is one that you haven’t used before, make sure you understand the content sharing functionality. Log into the meeting a couple of minutes early if you’re able to. Make sure that you do some high level research about the company and that you’re up to speed on any recent or current events. Send over an agenda before hand and follow up the same day. The reality is, corporates can be apprehensive to work with startups because many of them are so risk adverse; don’t give them a reason not to work with you because you weren’t professional.

Over communicate for alignment

Nothing is more exciting than when you get that green light from a corporate that they want to move forward with your company. The single most important thing that both sides can do to ensure success of the engagement is make sure that you are aligned and over communicate about goals and expectations. Is this a use case that is high priority and solves for a business need at the corporate? On the flip side, is this a use case that the startup knows (or anticipates) that they can execute on and deliver a powerful business case? If the engagement involves a new or exploratory use case for the startup, the corporate should know this upfront so that they can decide if the engagement makes sense to pursue and expectations can be set appropriately.

It is also important for both sides to be transparent with one another about timelines and how decisions are made. Corporates should be upfront with you about their procurement, legal, and InfoSec processes and the associated realistic timeline. If they aren’t, you have the right to ask. It is equally as important to align on the value of the engagement. Startups need to clearly define value and the measures of success for a PoC up front. Then, make sure that the corporate is committed to putting in the time, resources, and budget required to derive that value. When I was on the startup side, we would put together a document for every PoC customer outlining the timeline, decision makers, processes, metrics for success, communication preferences and schedules. Sometimes I’m sure that it felt like overkill to our enterprise customers to have to go through that whole document with us. That said, it always helped ensure that we were on the same page, kept us on track, and held both sides accountable.

Respect, but challenge, the power dynamic

There often exists a power dynamic between enterprises and startups. At the end of the day, enterprises have the brand names and more importantly, they have capital which often gives them the upper hand in these collaborations. But enterprises need what startups have to offer, innovative products and business models that are solving for pain points that they have or that their customers have.

Enterprise sales cycles can be long and frustrating at times, especially when it comes to the amount of stakeholders that you’ll have to meet with and the procurement processes. The reality is that these internal processes exist for a reason (enterprises need structure to survive) and you’ll have to be flexible to a certain degree in order to move the engagement forward. But know that for every meeting you take, you have reserved the right to ask for something in return that helps you to move the relationships or engagement forward, like an update on the InfoSec process or feedback from a specific stakeholder.

One thing that many startups forget is that you have just as much of a right to walk away from an enterprise as they do to you. It’s hard to walk away from a big name enterprise that you are really eager to work with but it’s important to recognize when you are putting in time and effort that isn’t reciprocated or the use case just isn’t a good fit. At the end of the day, a startup’s most valuable resource is time and you have to make the best decision around where to spend your team’s energy.

With that being said, walking away from an active conversation or engagement doesn’t have to mean the end of the relationship. I’ve found it to be very effective when founders will still check in on a quarterly basis, include me on investor updates, or send over articles that they think might be relevant. More often than not, a corporate engagement doesn’t move forward because of timing but you never know when circumstances (e.g. people, priorities, budget) may change so it’s worth staying in touch.

Put yourself in the other person’s shoes

Finally, one of the things that I think we can all do better on is having empathy for the folks sitting on the other side of the table.

Startups: Recognize that enterprises want and need to work with startups in order to embrace new technologies, new products, and new business models. Internal processes don’t exist solely to make your job selling into them difficult; these processes exist to maintain and protect the integrity of their infrastructure. Don’t forget that enterprises will always have internal dynamics going on in the background that may not be apparent to you. Sometimes a lack of progress or even a “no” actually has nothing to do with you or your product. Having been most recently on the enterprise side, I have a newfound appreciation for big companies. I have a lot of respect for enterprises that have managed to survive over the years and recognize that they need to continue to evolve to stay alive.

Enterprises: Embrace the uncomfortableness that sometimes comes from working with an early stage startup. Startups are supposed to be chaotic, they are building the rocket ship while simultaneously flying it. Know that they aren’t trying to rush you into making a big decision or trying to bypass your internal processes, they’re just eager to find ways to work with you and prove themselves. Startups can be incredibly agile and can be flexible in terms of meeting your enterprise’s needs and processes. When you’re at an enterprise, you typically don’t think about your company’s survival on a daily basis but a startup’s very existence relies on them constantly growing, adapting, and scaling.

At the end of the day, putting yourself in the shoes of the person sitting across the (virtual) table from you, is everything. Be the partner that you would want to work with if you were the other person. And maybe it is actually just as simple as that.

Founders and enterprise folks — would love to hear your thoughts and feedback on your own experiences!